A rare opportunity to own 7.7 acres on the beautiful and sought-after island of Chappaquiddick. This wooded parcel offers exceptional privacy, natural contours, and the quiet, untouched landscape that defines Chappy living. Preliminary information suggests there is potential upland area to support the creation of a custom island retreat, with possible capacity for 4–6 bedrooms subject to final engineering, wetlands delineation, septic design, permitting, and all required approvals. A percolation test has been completed with favorable results based on available non-wetland acreage. With significant acreage, exceptional privacy, and the timeless natural landscape of Chappaquiddick, this offering represents a unique opportunity for a buyer willing to complete the necessary permitting, engineering, and due diligence to realize the potential of a remarkable island property.

CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an enhanced system and proper approvals. Also included in the sale is the owner's share of the Calebs Beach Corporation, giving you access to the sandy beach on the outer harbor.

This home is walk in ready to enjoy while you let your imagination go to work for this ideal property. Located a short walk along the bike path to Post Office square you will find this quiet location is perfect. You feel the old Vineyard charm along this peaceful lane. This represents the best entry way into Edgartown Real Estate today so do not let this opportunity pass you by. A 3rd bedroom maybe an option here and seller will work with you to help with the process.

Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently located near town amenities, beaches, bike paths, a public fitness facility, veterinary services, shopping, the airport, restaurants, and other island services. Buyer is responsible for conducting all due diligence regarding intended use, permitting requirements, and development of the property.

OPPORTUNITY ABOUNDS: This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer (see notes below) creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the benefits of in-town living while building new in a highly desirable neighborhood. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designed for comfortable island living. A hallway leads to the primary bedroom with private bath, along with two additional bedrooms that share a full bath. The lower level includes a spacious family room plus additional unfinished space with potential for expanded living quarters, guest accommodations, or a recreation area. Set on a private half-acre lot, the property offers both privacy and ample outdoor space to relax after a day at the beach. Its convenient location and versatile layout make it appealing for both seasonal and year-round living. Property is being sold as is. Estate rules apply. Sale may be subject to probate approval and court confirmation. Please see comments below.

OPPORTUNITY KNOCKS: Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat, while building value in a sought-after location. A fantastic opportunity to customize, restore, and make it your own. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

CONTEMPORARY ISLAND RETREAT. As a smart opportunity for Vineyard buyers seeking a low-maintenance Island home close to Edgartown Village, this contemporary home offers easy access to shopping, services, and the bicycle path connecting the three down-Island towns. Whether used as a year-round residence, seasonal getaway or potential vacation rental, the setting and layout make it easy to enjoy the best of Island living. The home offers a comfortable open-concept living and dining area, an efficient kitchen, and a welcoming living room with a wood-burning fireplace. Outdoor living is a highlight, with multiple spaces to relax and gather, including a south-facing front deck for dining or lounging, a newer rear deck for grilling and outdoor meals, and a second-floor balcony that is ideal for morning coffee. The natural, low-maintenance landscaping means less upkeep and more time to enjoy the Vineyard. A detached Party/Game Shed with French doors opens to the backyard and firepit area, adding flexible bonus space for entertaining, working remotely, or creating a fun hangout after a day at the beach or in-town!

Well-maintained three-bedroom, two-bath home set on a quiet road in a convenient Edgartown location. The property is bordered by more than 100 acres of conservation land, offering a peaceful setting and added privacy while remaining close to Edgartown Village, beaches, bike paths, and everyday amenities. The home features comfortable living and dining spaces along with a beautifully updated kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances. Three bedrooms and two full bathrooms provide a practical layout, while the full basement offers plenty of additional storage and utility space. A well-cared-for Edgartown home with a quiet setting, conservation land in its backyard, and easy access to everything the area has to offer.

CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Chappaquiddick Community Center, the Ferry, Wasque Beach, and Quammox Preserve with its public access to Katama Bay, this property is perfectly positioned to enjoy the best of Chappy. Abutting conservation land, with the Cross Chappy Trail and Pocha Pond Reservation just outside your door, it offers direct access to some of the island's most treasured natural landscapes. The home's efficient floor plan features a first-floor bedroom, open living spaces, and a cozy sunroom, creating the perfect retreat to enjoy all that Chappaquiddick has to offer today, while providing outstanding opportunities for future expansion.

Imagine creating your own Vineyard retreat on this almost half-acre parcel, ideally located within walking distance to downtown Edgartown. This property offers the opportunity to build a custom home within a designated building envelope, while a protected no-build area provides an added sense of privacy and separation from the neighboring property. The thoughtful placement of the building envelope allows you to envision a home that takes advantage of the property while preserving a natural buffer around it.

Dodgers Hole - Delightful contemporary cape style home, centrally located, suitable for seasonal or year-round use. The privately sited half acre lot features a first floor primary bedroom with en-suite bath, a light filled eat-in kitchen, central A/C, full unfinished basement, a detached 18'x24' shed/garage, with a large rear deck and generous outdoor shower compliment the property. A four bedroom septic design affords expansion potential. Offered 'turn-key' with a solid repeat rental history!

LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own family compound including all the popular requests such as a 3-car garage, pool and pool house. The oversized lots are connected to town water and town sewer and all have an established building/development envelope. Substantial new construction homes are up on surrounding lots 1, 2, and 5. Lot 4, which is 1.57-acres, is currently being offered and is ready for your design concept.

Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed space. The full basement could be finished off for additional living areas. Plenty of room to grow on this property if garage, guest house, pool or more square footage is wanted, this lot offers the space.

Tucked into a quiet neighborhood and surrounded by mature trees, this home sits elevated on a 0.84-acre lot. With an open floorplan, the kitchen, dining, and living areas flow comfortably together, enhanced by vaulted ceilings, a stone gas fireplace, and French doors that bring in abundant natural light and provide easy access to the outdoors. A custom-designed open staircase serves as a focal point, leading to a primary loft-style suite on the second floor. Two traditional guest bedrooms and a full bath are conveniently located on the main level, creating a flexible and comfortable layout. The walk-out lower level offers significant additional potential, with multiple finished spaces and two full baths that can be configured to suit a variety of needs from guest accommodations to recreation areas or home office. A spacious slate patio is ideal for morning coffee or summer grilling. Already connected to town water and sewer, the property has the added advantage of supporting up to seven bedrooms, offering exciting possibilities for future expansion or reconfiguration.

Set at the end of a cul-de-sac, this property offers a peaceful setting on .71 acres, with easy access to more than 25 acres of Land Bank conservation land. Morning Glory Farm is just a short distance away, offering a wonderful connection to the seasonal beauty and character of the Island. The bike path, Edgartown Village, and South Beach are also nearby, providing an easy balance of privacy and convenience. Filled with natural light, the post-and-beam home features a spacious kitchen with a large center island, walk-in pantry, and garden access. The dining area opens to a generous deck, while the sunken living room features cathedral ceilings, a floor-to-ceiling brick fireplace, and views of the surrounding landscape. A first-floor bedroom and full bath offer flexibility for guests. Upstairs, the primary suite includes a half bath, along with two additional bedrooms and a full bath. Established gardens, an outdoor shower, and expansive decking extend the living space outdoors. A basement provides additional storage and overflow space. Town sewer allows for expansion to as many as seven bedrooms, offering meaningful future potential in a private and well-connected Edgartown setting.

Two complete homes on one acre in Edgartown's Smith Hollow neighborhood — a rare find. Set at the end of a paved cul-de-sac, the property gives each house its own septic system, its own landscaped yard, and enough separation for real privacy. The main house has four bedrooms and two baths, along with a basement and a drive-under garage. The guest house features three bedrooms, two baths, a full basement, and laundry. With a solid rental history already in place, this is a chance to get two houses for the price of one.

Discover this turnkey Edgartown home in a prime location near downtown dining and shopping, Edgartown Golf Club, and popular beaches. The refreshed interior features modern flooring, modern LED lighting, bathroom, and a bright kitchen with dark green granite countertops, tall windows, and a vaulted ceiling. All bedrooms have private en suite full baths, with two bedrooms on each floor. A sunroom opens to the deck and spacious backyard, offering room to relax or entertain. The home has town water and sewer and is being sold turnkey. Easy to show. This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed. Owner occupants are those buyers that will occupy the property as their principal residence within 60 days of closing and will maintain their occupancy for at least 1 year. These buyers are required to sign an Owner Occupant Certification as part of the contract. An investor, trust, vacation or part-time residence, or purchasing for another person will be considered an Investor and are not eligible for First Look. Investors are welcomed to make offers the initial 30 DOM, but will not be countered until day 31. Neither seller or listing agent make any representations as to the accuracy of any information contained herein. Buyer/buyer agent must conduct their own due diligence, verification(s) and research and are relying solely on the results thereof. NO DISCLOSURES. All offers to be submitted by the buyer's agent only through propoffers.com. Buyer Agent or Transaction Broker to pay $200.00 plus tax at closing. *IMPORTANT:* Any seller requests and offer terms need to be written under offer comments in the offer submission section — if you do not input the comments it may NOT be seen by seller. Please be advised that any offers on this property require a minimum Earnest Money Deposit of 1% of the Purchase Price or $1,000. Cash offers require 10% EMD. BUYER/BUYER AGENT to obtain all finals, verify utilities. * ALL offers must have POF for CASH offers and Lender PQ's for Financed offers. Cash offers require 10% EMD. Rehab Offers must have one rehab bid in hand pre-offer, no exceptions. Under FinCEN's new RRE Rule, transfers will be subject to reporting when buyers use entities or trusts to take title to residential real estate, when the transaction is all cash, privately financed or HELOC- Photos have been edited for brightness and color.

Tucked at the end of a quiet cul-de-sac in the desirable Island Grove neighborhood of Edgartown, this charming three-bedroom, (plus bonus space and 6 bedroom sewer capacity), two-bathroom residence offers a private setting, association amenities and excellent proximity to Edgartown Village and Katama Beach. Located on arguably one of the most desirable lots in Island Grove and surrounded by conservation land, this half acre lot benefits from peaceful woodland views and has a direct pathway to the association tennis and pickle ball courts. The property has been recently connected to town sewer, with the potential for expansion to SIX BEDROOMS subject to Board of Health confirmation and approval. In addition to the sewer connection, the home benefits from having several significant upgrades including new roof, new windows, and mini-split air conditioning. The main level features a double-height living room with south-facing windows and French doors opening to a generous sun deck and lawn—an inviting setting for summer entertaining and relaxed outdoor living. A wood stove adds warmth and character for cozy fall and winter evenings. The well-equipped kitchen flows comfortably into the dining area, while two spacious bedrooms and a full bath complete the main level. Upstairs you will find the private primary suite with balcony overlooking the yard, and full bathroom, plus bonus loft room which makes a great office, den or additional guest space. On the lower level is a finished bonus room, laundry area and plenty of storage. With its exceptional setting, desirable Island Grove location, recent improvements, expansion potential, and strong rental history, this property presents an appealing opportunity to enjoy immediately while offering the flexibility to enhance and expand over time.

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN HUXFORD COTTAGE, Unit 94 at 131 N Water Street in Edgartown, a 730-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after a restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a microwave, and refrigerator/freezer. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Huxford Cottage, Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

Set on a quiet cud-de-sac by the State Forest, in Dodger's Hole, amidst lovely landscaped grounds with stonework defining a circular driveway & parking, with lovely mature plantings. This spacious, well maintained home offers very comfortable living with significant upgrades. Large living room with vaulted ceilings, abundant natural light from multiple windows and skylights and a wood burning fireplace, creates a wonderful gathering space. The thoughtfully designed floor plan includes three bedrooms, two with ensuite bathrooms, one suite up and one on the ground floor, along with a third bedroom and third full bathroom with laundry. The kitchen has been updated, white cabinets, quartz countertops, island, stainless steel appliances, and pantry, with convenient access to dining area and outdoor living spaces. Central air with hard wood floors through out. Upstairs there's a very bright, expansive loft overlooking the living area, providing additional flexibility for a family room, home office, recreation space or overflow accommodations. Numerous improvements represent a substantial investment in the property, including a newer roof with 35 year architectural shingles, five replacement VELUX skylights, landscaping and stonework. A large mahogany deck, outdoor shower and lovely private yard provides plenty of room for outdoor dining, entertaining & relaxation. Enormous unfinished basement, offering exceptional storage, potential for additional finished living space, subject to applicable approvals. The property is served by a four (4) bedroom septic system, providing capacity for a potential fourth bedroom. Additional possibilities include an Accessory Dwelling Unit or, subject to applicable zoning and permitting requirements, a Guest House. With its generous interior spaces, extensive improvements, attractive outdoor amenities and opportunities for future expansion, this property offers a compelling combination of immediate enjoyment and long term versatility. Wonderful for year round living. Also be a terrific rental property. Contents may be purchased separately. MOVE IN READY!

Imagine owning your own beach house on Martha’s Vineyard, ready for summer fun. Perched atop a rise that captures sweeping views over the property, floods interiors with natural light, and opens to a spectacular night sky, this furnished move-in-ready home delivers the Vineyard lifestyle you've been imagining — with room for everyone. Over 2,600 square feet (not including the walk-out basement) unfold across four levels, beginning with a dramatic 30-foot vaulted foyer bathed in sunlight. The fully renovated chef's kitchen features Sub-Zero paneled refrigerator, luxury stainless steel appliances, and stone counters, opening onto a favorite gathering place in the heart of the home - a custom banquette with built-in window seats that easily seats 10. A formal dining room, oak floors, a wood-burning stone fireplace once featured in Architectural Digest, and a view-facing living room with balcony set the tone for effortless entertaining. The primary suite features a walk-in closet and en-suite bath, complete with a sunken tub and double vanity. Two additional bedrooms share a full bath. A sculptural spiral staircase rises to a loft lounge with glass doors to a private balcony — perfect for stargazing or savoring the serene setting — plus two bonus rooms for overflow guests. The walk-out lower level(an additional 900 s/f not included in the s/f), with custom stained concrete floors and new Andersen French doors, adapts easily as a lounge, home office, or gym. Overall, the home is well-maintained, lightly used, with regular renovations and upgrades, including a HydroViv water filter system. The expansion potential is exceptional: a sewer connection option allows growth to seven bedrooms, with room for a guest house, pool, and pool house. Seller is offering $25,000 at closing for the sewer tie-in. There is flex space within the existing floor plan ready for additional bedrooms. Minutes to Vineyard Golf Club, Morning Glory Farm, South Beach, Edgartown Village, and scenic bike paths.

A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between. Gather around the custom firepit under a canopy of stars, soak in the sauna and cold plunge after a day on the water, or simply unwind on the porch as the island quiets down around you. The three-bedroom main house offers warm, open living spaces, while the two-bedroom guest house — with its covered porch, back deck, and outdoor shower — keeps guests close but comfortably their own. Recent renovations include extensive landscaping, new features, exterior paint, select Vineyard Decorators furniture, plus stainless steel appliances. Move-in ready and offered turnkey with few exclusions for immediate enjoyment. Everything here is geared toward living well outdoors. An oversized garage with furnished loft space provides room for the gear and the gang. Chappy's beaches, hiking trails, Slip Away Farm, and the Community Center are all just minutes away — but with a place this special, you may never want to leave. Offered turnkey with no rentals in place - ready for summer fun!

Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm. Built in an era when homes were crafted with artistry and intention, this distinctive post-and-beam residence blends warmth, character, and enduring craftsmanship. The spacious 4-bedroom, 3-bath home features soaring cathedral ceilings, wide pine floors, a mudroom with built-in storage cubbies, and a generous office/media/playroom complete with custom desks and bookcases. Sun-filled living spaces feel both open and inviting, while a striking brick fireplace anchors the living room — the perfect gathering place after a day at the beach. The property also includes a charming guest cottage, outdoor shower, and large shingled shed, all thoughtfully positioned within a beautifully private setting abutting conservation land. Expansive front and rear decks invite outdoor living, entertaining, and quiet moments immersed in the natural beauty of Chappaquiddick. Thoughtfully updated for comfortable year-round living, the home includes central heating and air conditioning, a whole-house water filtration system, heated mudroom and bathroom floors and energy-efficient solar panels that help keep annual utility costs remarkably low. Located just three miles from the heart of Edgartown, the property is a short walk to Katama Bay, where kayaks and sailboats may be stored, and only 1.5 miles from the pristine shores of Wasque and East Beach. Property Highlights * Distinctive post-and-beam architecture * 4 bedrooms | 3 bathrooms * Separate one-bedroom guest cottage with outdoor shower * Large shingled storage shed * Sprinkler system * Private lot abutting conservation land * Spacious yard with exceptional privacy

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick’s most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird’s-eye views capture the natural beauty that surrounds you. Thoughtfully renovated throughout, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality—an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres of pristine conservation land, featuring scenic trails, abundant wildlife, and direct ocean beach access. Whether you’re seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque delivers it all. With an impressive rental history and consistent bookings during both summer and shoulder seasons, it stands out as a premier opportunity in today’s market. This home is more than just an address—it’s the essence of Chappy living.

Close to South Beach! Close to Katama Airpark and nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a garage underneath. The guest house is an A-frame home. Conveniently located just off the bike path, and only a mile to the desirable South Beach, the location doesn’t get much better than this. Property is being sold “as is”. Buyer is responsible for the research on how to make this pre-existing, non-conforming property conform to today’s building and zoning requirements.

Introducing this rare opportunity to acquire one or two buildable parcels in a prime Katama neighborhood. Located within a newly created four-lot subdivision, now referred to as 1 & 3 Jane's Way, these two conforming half-acre lots offer an exceptional setting for new construction, just minutes from South Beach and Edgartown Village. Each lot has been approved for up to 4 bedrooms and approved septic plans are included for ease and convenience to a buyer. Town water is available to each lot and underground utilities are installed. Offered individually or together, the properties provide buyers with flexibility to create a custom Island residence or secure both parcels for the potential development of a private family compound. The size of the lots, new construction potential, and a sought-after Katama location makes this an especially compelling opportunity in today’s Edgartown market. *Advertising photo is for promotional purposes only and is virtually enhanced. Please see engineered plan for actual lots lines.

Introducing this rare opportunity to acquire one or two buildable parcels in a prime Katama neighborhood. Located within a newly created four-lot subdivision, now referred to as 1 & 3 Jane's Way, these two conforming half-acre lots offer an exceptional setting for new construction, just minutes from South Beach and Edgartown Village. Each lot has been approved for up to 4 bedrooms and approved septic plans are included for ease and convenience to a buyer. Town water is available to each lot and underground utilities are installed. Offered individually or together, the properties provide buyers with flexibility to create a custom Island residence or secure both parcels for the potential development of a private family compound. The size of the lots, new construction potential, and a sought-after Katama location makes this an especially compelling opportunity in today’s Edgartown market. *Advertising photo is for promotional purposes only and is virtually enhanced. Please see engineered plan for actual lots lines.

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN ROWLEY COTTAGE, Unit 62 at 131 N Water Street in Edgartown, a 895-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after an extensive restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a cooktop, microwave, and refrigerator/freezer. Both bedrooms are well proportioned, and the two full bathrooms are designed for everyday ease. An outdoor shower enhances the coastal lifestyle. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Rowley Cottage, Unit 62 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with strong rental history!

Located on Upper Main Street in Edgartown’s BII zoning district, this versatile property is currently home to Lucky Hank’s restaurant. Set on a desirable lot with a large private parking area, and in a coveted high-visibility location. The building offers a turnkey restaurant space and thriving business complete with a fully equipped commercial kitchen on the first floor. Upstairs, you’ll find one bedroom with an ensuite full bathroom, currently being used as the office. There is also an additional room being used for restaurant storage. With the flexibility to convert the property back to residential use, if desired, this is a rare opportunity in a prime location that should not be overlooked! Showings are on Mondays when the restaurant is closed.

COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming, sailing, and relaxing with friends or family are just a few of the daily dalliances of time spent on Chappy. There is simply no better place to relax and unwind.

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

WATERVIEWS of Sengenotacket when you pull out of the driveway at 77 SIXTH STREET NORTH, EDGARTOWN. NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2027; just in time to bring in the 2027 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with seating for four. The kitchen sports Bosch appliances, an island with a built in drawer microwave, quartz countertops and an easy layout for cooking and entertaining. The kitchen then opens to a separate dining room. A half bath off the living room and a first floor primary bedroom with a luxurious private bath completes the first floor. The second floor offers a second living room and two guest bedrooms, each with their own bath. The plot is large enough to support a future detached garage. Come and enjoy! The pictures are of a similar home that was built.

Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortable year-round living. At the heart of the home is a beautifully remodeled kitchen, completed in 2023 and designed to be part of daily life rather than separate from it. From here, the home unfolds into a spacious living room warmed by a propane fireplace, a formal dining room and a separate sitting room—giving family and guests the increasingly rare luxury of having both places to come together and places to retreat. Three large bedrooms provide comfortable private quarters, while an open loft creates another flexible destination for working, reading, watching a movie or simply escaping the activity downstairs. Below, a substantial unfinished basement with high ceilings and both interior and exterior access provides exceptional storage and flexibility for the future. Summer living extends naturally outdoors. A generous back deck overlooks the wooded acre-plus setting, offering a private place for morning coffee, long dinners and evenings under the Vineyard sky. And after a day spent at the beach, there is perhaps no more quintessentially Island pleasure than coming home to an outdoor shower. Beyond the property, Woodhaven offers something increasingly difficult to find: a neighborhood setting surrounded by nature with access to trails connecting the Manuel F. Correllus State Forest - opening miles of the Island for walking, running and biking. Private without being isolated, spacious without feeling overwhelming, and thoughtfully updated where it matters most, 10 Woodhaven Drive offers a relaxed approach to Edgartown living—and a home designed to be enjoyed well beyond the summer season.

Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main house offers a comfortable and inviting interior, highlighted by a bay window and a spacious open kitchen and dining area with granite countertops, custom cabinetry, and direct access to the deck. A sunken living room offers separation while maintaining an open flow. The main level includes a primary bedroom and an additional bedroom, while the second floor offers a third bedroom, a full bathroom, and flexible living space. The finished lower level offers approximately 790 sq ft of additional finished space, including a recreation area, den, and full bathroom, along with approximately 525 sq ft of unfinished storage. Outdoor living is equally inviting, with a deck off the kitchen leading to the heated pool and patio. The space includes a pool house with half bath, an outdoor shower, and ample room for dining and lounging, surrounded by hydrangeas. There is ample yard space behind both the main house and guest house, ideal for games, outdoor entertaining, or simply enjoying the privacy and natural setting. The guest house, built in 2011, is thoughtfully separated from the main house by its own private driveway and mature landscape screening. It features a spacious living area, a main-level bedroom, and additional finished space upstairs, along with full bathrooms on both levels. There is also a half bath with laundry, a one-car garage, and a full basement. At the end of 21st Street you’ll find direct access to over 150 acres within the Caroline Tuthill Preserve, as well as the Boulevard landing on Sengekontacket Pond — perfect for kayaking, paddle boarding, or boating. Edgartown Village is approximately 1.5 miles away. A unique opportunity with an established rental history — details upon request. Furniture available for separate purchase.

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN COLLINS COTTAGE, Unit 22 at 131 N Water Street in Edgartown, a 960-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after a restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a microwave, and refrigerator/freezer. Both bedrooms are well proportioned, and the two full bathrooms are designed for everyday ease. An in-unit washer and dryer add to the practicality of the home and an outdoor shower enhances the coastal lifestyle. The building features an elevator for effortless entry to your unit. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Collins Cottage, Unit 22 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

Coastal Luxury Meets Versatility in Edgartown Welcome to a rare opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a sprawling one-acre plot with a stunning detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, sun-drenched living room featuring a wall of glass sliders that erase the boundary between indoor and outdoor living. The gourmet kitchen is a chef’s dream, boasting premium Bosch appliances, a large quartz-topped island with casual seating for four, and a sleek, hidden microwave drawer, all perfectly arranged for entertaining.  The first floor hosts a serene primary suite with a luxurious private bath. Upstairs, you’ll find a cozy second living room and two spacious guest suites, each with private baths. The property includes a 900 sq ft detached accessory dwelling, complete with full kitchen, bath, and bedroom. With one acre of land, this property is poised for a future pool or private oasis. Ready for your 2026 occupancy!  Note: This property is subject to M.G.L. Chapter 40A Section 6 of the Affordable Homes Act: Single-family residence not to exceed 1,850 sq ft of heated living area, min. 3 bedrooms, no short-term rentals.

Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy access to town and the beach. Neighboring Wilson's Landing opens the door to the Edgartown Great Pond, where kayaking, paddleboarding, and quiet days on the water await. With 8 bedrooms possible and the option to add a guest house, the potential here is considerable. This is one of two parcels for sale.

Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore. Neighboring Wilson’s Landing provides water access to the Edgartown Great Pond for kayaking, paddleboarding, and other activities. With 8 bedrooms possible and the potential to build a guest house, the development options here are many. Whether you envision a family compound, a retreat with room for extended family and friends, or a legacy property designed to be enjoyed for generations, this land provides the canvas. This is one of two parcels for sale.

Just a block off Main St, Winter Street grew alongside Edgartown's 19th Century maritime and whaling boom. In the mid 2010's local business owners began transforming the corridor, and affectionally dubbed Winter Street the "Left Bank" of Edgartown in comparison to Paris's famous boutique shopping district. This retail condo is one of the the prettiest shops in Edgartown with 2000+ square footage. It has a front row on Winter Street with wonderful display windows that attract attention from auto passengers and pedestrians alike. The space has been extensively renovated with built-ins which help display myriad types of merchandise from clothing and accessories to furniture, books, and house wares. In addition to the retail space, the upstairs offers a full bathroom and office, while the full dry basement is ideal for storing inventory. This is a wonderful opportunity to own a retail space in downtown Edgartown, which is widely considered highly prestigious and places you among the most exclusive markets on the East Coast. This beautiful store is available to rent starting in January 2027!

A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence, this .66 acre property features two side-by-side cottages dating back to the 1940s and captures the relaxed character of an earlier Vineyard. The larger cottage is a quintessential Vineyard retreat with beautiful direct waterviews from the Main living areas, dining area and porch. Upstairs, a sitting area and small upper deck provide exceptional views across Sengekontacket Pond to State Beach extending out towards Cape Cod. The porch and the spacious lush side yard with lawn and lovely plantings, offer an inviting setting for morning coffee, summer dinners, entertaining, or simply enjoying the changing light and activity on the water. The larger cottage has an established rental history. An attractive option for seasonal rental income. The second smaller cottage offer the opportunity for a new owner to renovate and make the space their own as additional living space, a guest cottage or studio, subject to applicable approvals. Another compelling option is to explore removing the cottages and combining the existing square footage together with a percentage of additional square footage as allowed, to create one larger residence to take full advantage of this extraordinary waterfront setting. Any renovations, expansion or redevelopment would be subject to all applicable approvals and zoning regulations. Additionally, just a stone's throw away, the nearby boat landing provides convenient access to the pond, with openings into the Nantucket Sound, for launching kayaks, paddleboards and trailered boats. putting one of the Vineyard's most beautiful waterways practically at your doorstep. With two cottages, acreage, established rental history, convenient boating access and remarkable views.#49 The Boulevard offers a special opportunity to enjoy a classic Vineyard property today while imagining and planning its possibilities for the future.

Nestled on a private 1.7-acre parcel in the peaceful Bold Meadow neighborhood, this classic expanded Cape offers a perfect blend of comfort, space, and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from all that Edgartown has to offer. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a wood-burning fireplace and a separate TV/family room. The well-appointed kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar for casual dining. An eat-in area opens through sliding glass doors to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, two guest bedrooms share a full bath, while a loft above the two-car garage provides flexible bonus space, currently used as an artist’s studio. The home is served by a four-bedroom septic system, with the potential to expand to six bedrooms subject to Board of Health approval and installation of an enhanced system. With easy access to nearby bike paths, pristine beaches, and the shops and restaurants of downtown Edgartown, this property offers an exceptional combination of location, privacy, and lifestyle.

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN HUXFORD COTTAGE, Unit 96 at 131 N Water Street in Edgartown, a 1061-square-foot, three-bedroom, three-bath, second & third floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after a restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a cooktop, microwave, and refrigerator/freezer. An in-unit washer and dryer add to the practicality of the home. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Huxford Cottage, Unit 96 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

Tucked in the heart of Katama, this classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a seamless blend of comfort and classic Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a welcoming sitting area. Sliders lead to a spacious mahogany deck—ideal for outdoor dining and relaxing after a day at the beach. This level also includes an additional family room, a generously sized bedroom with access to a private terrace and a full bath. Upstairs, the entire third floor is dedicated to the primary suite, a peaceful retreat with vaulted, beamed ceilings and walls of glass that flood the space with natural light. The en suite bath features a sleek glass shower, completing the quiet atmosphere. On the first floor, you’ll find a third bedroom, a large bath with laundry, and an additional living area with direct access to a covered porch. Set on a generous 0.7-acre lot, the property includes the must-have outdoor shower. The property also boasts a strong rental history and is an island favorite, making it appealing as both an investment and as a personal getaway.

OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a quick stroll to South Beach. The home features vaulted ceilings, two first floor bedroom en-suites, each with it’s own private bath and a central lounge area to enjoy. The second, primary floor, opens to a bright, light filled living space where the kitchen, dining and living room area flow into each other with ease. From the living and dining area outdoor decking offers al fresco dining and lounging. Ascend to the top floor where you are met with a full floor primary suite with a private lounge leading to a private exterior deck, a bedroom with an inviting window seat and a luxurious bathroom with vaulted ceiling and soaking tub. This home comes fully furnished, a true turn-key experience. Come and enjoy!

Perched atop the highest point on Chappaquiddick, this private compound truly has it all, while still being a short distance from Chappy favorites including the Community Center, Beach Club, Ferry, and Slip Away Farm. Designed for both relaxation and recreation, the property offers endless ways to enjoy time with family and friends. Spend the afternoon on the sports courts, cool off at the pool, or relax on one of the expansive porches or patios. The guest house provides additional space and privacy. The pool house, complete with a half bath and kitchenette, makes entertaining effortless, with everything you need close at hand. A separate gym and game room offer even more ways to stay active or unwind, whatever the weather. With a strong rental history, the property also presents an excellent investment opportunity, while its generous amenities and multiple living spaces make it an ideal generational home to be enjoyed for years to come.

Katama at its best ~ WITH A POOL! Set in one of Martha’s Vineyard’s most coveted locations, 21 Vickers Street is a classic beach home with an effortless connection to everything that makes Katama so special. Just one mile from South Beach. With the bike path, Katama General Store, and Edgartown Village close by, this updated, move-in-ready home puts the best of the Island within easy reach. A newly installed pool and expansive yard create a private setting for summer days and long afternoons outdoors. Inside, the kitchen features an inviting banquet dining area and opens to a spacious cathedral-ceilinged family room with sliders to the back deck, outdoor shower, pool, and yard. A separate living room provides another gathering space, while a first-floor bedroom and full bath offer flexibility for family and guests. Upstairs, two generous bedrooms share a full bath. The full basement provides ample storage for bicycles, beach chairs, paddleboards, and all the essentials of Vineyard life. With the ability to tie into town sewer for up to six bedrooms, the property also offers exciting possibilities for the future. The very best of Katama comes together here with a coveted location, a classic Vineyard home, and an easy way to enjoy everything that makes summer on Martha’s Vineyard so special. Sale is contingent on seller finding another home.

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach and Edgartown Village. Featuring a custom guesthouse built in 2018, with solid rental history and is outfitted with modern amenities. With a 6-bedroom septic system in place, there’s ample opportunity to build a main house or additional structures, pending necessary town approvals. Expansion to 8 bedrooms possible with septic upgrade. This unique opportunity allows the developer to enjoy Edgartown now while envisioning the full potential.

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach and Edgartown Village. Featuring a custom guesthouse built in 2018, with solid rental history and is outfitted with modern amenities. With a 6-bedroom septic system in place, there’s ample opportunity to build a main house or additional structures, pending necessary town approvals. Expansion to 8 bedrooms possible with septic upgrade. This unique opportunity allows the developer to enjoy Edgartown now while envisioning the full potential.

Perfectly situated just moments from the bike path, Edgartown Village, and South Beach, this exceptional Edgartown compound offers the best of Vineyard living. The main house is filled with warmth and character, featuring soaring ceilings, exposed beams, and an inviting open living area centered around a custom stone fireplace. Thoughtfully designed and perfectly sited for privacy, the Casita offers a comfortable and welcoming retreat for family and guests. Beautifully manicured grounds and gardens overlook the picturesque fields of Morning Glory Farm, creating a serene backdrop and a true sense of tranquility. With town sewer available, the property offers the potential for additional bedrooms, providing even greater flexibility for future expansion. A rare opportunity to own a distinctive island compound in one of Edgartown's most convenient and desirable locations!

COASTAL CONTEMPORARY IN KATAMA. An exceptional Katama retreat, this beautiful coastal contemporary offers a refined expression of island living, thoughtfully designed for both casually elegant entertaining and effortless summer relaxation. Set on beautifully landscaped grounds between Edgartown Village and South Beach, this custom-built residence pairs sophisticated architecture with an inviting sense of ease. The centerpiece of the home is a spectacular two-story Great Room, where dramatic volume, abundant natural light, and a gas fireplace create an impressive yet comfortable gathering space. The open living and dining areas extend naturally to a generous screened porch, blurring the distinction between indoor and outdoor living and providing an ideal setting for everything from morning coffee to sunset dinners. The beautifully appointed eat-in kitchen combines custom cabinetry with all-new appliances, offering both exceptional functionality and understated elegance. A private primary suite occupies the main level, while the second floor features a spacious guest suite and an adjoining open living and recreation space overlooking the great room. A recent second-floor expansion adds more than 200 square feet of beautifully integrated living space, further enhancing the home's generous proportions. The outdoor spaces are equally compelling. Expansive, professionally landscaped grounds offer exceptional privacy and ample room for a future pool, while a handsome stone terrace with a private hot tub creates an intimate setting for evenings beneath the stars. The screened porch and outdoor living areas invite a relaxed rhythm of Vineyard life, with room to gather, dine, entertain, and simply enjoy the beauty of Katama. Additional amenities include central air conditioning, a full unfinished basement offering significant potential for additional living or recreational space, and a two-car garage with abundant storage for everything that comes with island living. Beautifully conceived and exceptionally well maintained, 26 Pulpit Lane offers the rare combination of architectural presence, modern comfort, generous outdoor space, and an enviable Katama location—a sophisticated Martha’s Vineyard residence designed to be enjoyed for generations.

A compelling opportunity to acquire raw land in Edgartown with exceptional development potential. Lots 4B and 4C based on the plot plan provided, each offer the potential for a five-bedroom residence, ADU/guest house, pool, and pool cabana, providing the flexibility to create a substantial Martha’s Vineyard property from the ground up. With multiple possibilities for residential and recreational amenities, these parcels offer a unique opportunity for buyers, builders, or investors looking to bring their vision to life in Edgartown. Subject to applicable approvals. No drive-bys, appointments only

CHAPPAQUIDDICK - Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to ½ mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding, and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your backyard. An exceptional opportunity to create more than just a home, but cherished memories for generations to come.

Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence with three levels of living space, a charming two-bedroom guest house, pool house, pool, spa, stone patios, lush gardens, and multiple outdoor entertaining areas. Step into the main residence through a welcoming screened-in porch with dual entries. The main foyer leads to a light-filled great room, the heart of the home, featuring custom built-ins, a fireplace flanked by French doors, and sweeping views of the stone patio, pool, and gardens. The gourmet kitchen is open to the great room and features a central island, access to a mudroom, and a half bath. The formal dining area is complete with a wall of French doors that leads to the outside. Nearby, a first-floor bedroom currently serves as a richly appointed library, with custom built-ins, a compass rose medallion, and a bay window overlooking the back gardens. The first-floor primary suite is a private retreat, accessed through its own hallway with a built-in home office. The bedroom features a bay window, and the ensuite bath includes a soaking tub. Upstairs, a cozy lounge anchors two bedrooms and a full bath. An unfinished bonus room offers potential for expansion or serves as ample storage. The partially finished lower level includes a playroom with custom built-in seating and shelves, a second home office/lounge area, and a walk-in cedar closet. Unfinished areas provide more storage. The Outdoor Living: From the great room and dining room, step onto an expansive stone patio bordered by classic Vineyard stone walls. Multiple seating areas invite entertaining or peaceful relaxation, all with views of the pool, spa, and manicured gardens. The Guest House: The two-bedroom guest house offers complete privacy, with its own driveway, garden entrance, outdoor shower, and patio. The open-concept living space features a cathedral ceiling, French doors, and an eat-in kitchen. One bedroom is on the main level, alongside a full bath and laundry, while the second bedroom is upstairs. This guest house boasts a strong rental history. This unique Vineyard compound offers timeless elegance, privacy, and a stellar location, perfect as a year-round residence, summer retreat, or investment opportunity.

Set in the heart of Katama, this exceptional 5.5-acre building lot offers a rare opportunity to create a private island retreat surrounded by nature and conservation land. The property is bordered by 87 acres of Sheriffs Meadow conservation land and an additional 75 acres of town-owned land, providing an extraordinary sense of privacy and protected open space. Located in a well-established Katama neighborhood, the property captures the essence of the island lifestyle, with the sights, sounds, and salt air of the Atlantic Ocean close by. Just minutes from South Beach and Wilson’s Landing, easily enjoy swimming, boating, fishing, and long summer days by the water. A remarkable opportunity to build in one of the Vineyard’s most coveted settings, with expansive protected land and the beauty of Katama all around.

PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot can afford up to 4 bedrooms and has the potential to subdivide with proper permitting (see proposed plan in documents), offering versetility and an exceptional canvas for your estate planning vision. Positioned at the end of a private drive, on an elevated parcel amid a neighborhood of distinguished new homes. The original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Possibility of a fourth-bedroom with proper permitting and approvals. Ideally situated just minutes from Edgartown Village, with Katama and South Beach only a short distance away, the location blends convenience with coastal appeal. Dual access from Pease Point Road and Mill Hill enhances the property’s versatility. We have this listing presented as both a Land Listing and a Single Family depending on what your longer term goals may be.

PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot can afford up to 4 bedrooms and has the potential to subdivide with proper permitting (see proposed plan in documents), offering versetility and an exceptional canvas for your estate planning vision. Positioned at the end of a private drive, on an elevated parcel amid a neighborhood of distinguished new homes. The original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Possibility of a fourth-bedroom with proper permitting and approvals. Ideally situated just minutes from Edgartown Village, with Katama and South Beach only a short distance away, the location blends convenience with coastal appeal. Dual access from Pease Point Road and Mill Hill enhances the property’s versatility. We have this listing presented as both a Land Listing and a Single Family depending on what your longer term goals may be.

Rare opportunity to own a prominent commercial property on Main Street in the heart of downtown Edgartown. The first floor offers approximately 1,300 square feet of open retail space with excellent visibility on one of Martha’s Vineyard’s premier shopping streets. The second floor includes a two-bedroom apartment together with substantial climate-controlled inventory and storage space. The third floor offers additional storage potential. This well-maintained historic building has successfully accommodated both seasonal and year-round retail operations and offers a unique opportunity for a retailer seeking long-term control of a prime Edgartown location.

Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses. Private guest quarters above the detached oversized garage offer additional comfortable accommodations. Sweetened Water Farm combines the tranquility of an up-island location with the convenience of being just moments from the boutiques, restaurants, and harbor of downtown Edgartown. A home for all generations in a setting like no other.

Tucked into a quiet corner of Chappaquiddick, with protected views of Nantucket Sound and abutting the Pocha Pond Reservation and miles of endless hiking trails, this beautifully crafted custom home offers a rare combination of privacy, natural beauty, and effortless island living. The home is defined by a sense of casual elegance, with dramatic soaring ceilings and a striking prism skylight that fills the interior with warmth and natural light. An expansive, open living area is anchored by a floor-to-ceiling, double-sided fieldstone fireplace, creating a welcoming gathering space with a strong connection to the surrounding landscape. A remarkable two-story screened porch captures the water views and extends the living space outdoors, with a comfortable gathering area on the first level and a charming sleeping porch above. Four generously sized bedrooms, each with its own ensuite bath, offer privacy and comfort, with two enjoying water views. A finished lower level and oversized attached garage provide ample space for beach, boating, and fishing gear. Close to the ocean beaches of Wasque, yet within easy reach of downtown Edgartown, the property offers the best of Chappaquiddick, quiet, natural, and wonderfully removed, while still connected to everything the island has to offer. A cherished home in a truly special setting, ready for its next chapter.

A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above — a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-to-month under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and ready for its next owner: roughly 1,253 sq. ft. of office with high efficiency heat pump heat & A/C, plus 1,148 sq. ft. of garage and storage. Ample on-site parking with 25 designated spaces and a loading dock for your business needs. Owned solar installed in 2018 conveys with the property, and the current owners have put significant capital improvements into the building since 2017 — electrical, roof, solar, integrated fire & security systems, mechanical systems, and irrigation system. This property has a long history of permitted commercial use well before these owners. The Edgartown Zoning Board of Appeals granted a special permit in 2016 for the operation of a small-scale business in a residential neighborhood, and that permit predates the current owners' purchase. A buyer will need approval from the Zoning Board to continue commercial operations.

A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above — a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-to-month under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and ready for its next owner: roughly 1,253 sq. ft. of office with high efficiency heat pump heat & A/C, plus 1,148 sq. ft. of garage and storage. Ample on-site parking with 25 designated spaces and a loading dock for your business needs. Owned solar installed in 2018 conveys with the property, and the current owners have put significant capital improvements into the building since 2017 — electrical, roof, solar, integrated fire & security systems, mechanical systems, and irrigation system. This property has a long history of permitted commercial use well before these owners. The Edgartown Zoning Board of Appeals granted a special permit in 2016 for the operation of a small-scale business in a residential neighborhood, and that permit predates the current owners' purchase. A buyer will need approval from the Zoning Board to continue commercial operations.

Nestled within Edgartown’s coveted Katama/Island Grove enclave, 32 Martha’s Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophistication—rich with architectural intention, bathed in natural light, and thoughtfully composed for both intimate daily living and memorable entertaining. Set on .5 acres, the home unfolds across approximately 3,594 square feet, with an additional 2,300+ square feet of high-ceilinged, unfinished basement space offering extraordinary future potential. Cathedral ceilings, refined millwork, and expansive windows throughout create an atmosphere of lightness and luxury. A soaring, cathedral-height entryway immediately captivates, framed by striking two-story windows that draw the eye through the home to the serene, professionally landscaped backyard beyond. The foyer’s scale and natural light set the tone for the residence’s modern, airy aesthetic. The open-concept kitchen, dining, and living areas form an inviting central gathering space anchored by a warm gas fireplace and illuminated by windows on both sides. The gourmet kitchen is a true showpiece, featuring Thermador appliances, an expansive center island, and exceptional craftsmanship. It opens to a deep, walk-in pantry and a beautifully designed entertaining area complete with a sink, Zephyr beverage refrigerator, generous shelving, and abundant storage—functioning perfectly as a wet bar when hosting family and friends. Just beyond, a stunning screened porch extends the living space outdoors, offering a wood-burning fireplace and direct access to the stone patio and level backyard. With ample room for recreation and the potential for a future pool, the property invites endless enjoyment. With commanding curb appeal, flexible expansion opportunities, and abundant outdoor space, 32 Martha’s Road stands as an exceptional offering in one of Edgartown’s most desirable neighborhoods. Beautifully conceived, crafted with care, and designed with intention, this modern farmhouse is ready to be made uniquely your own—a rare opportunity to enjoy Vineyard living at its most refined.

Ideally situated just one-half mile from historic downtown Edgartown on the main access road to South Beach, the Katama General Store presents a rare opportunity to acquire a premier commercial property in one of Martha's Vineyard's most desirable locations. Set on 0.67 acres, the property features a newly constructed building completed in 2017, offering exceptional turn-key condition. The thoughtfully designed space includes a fully equipped commercial kitchen, expansive retail area, immaculate food preparation space, office, and ample storage, making it well-suited for a variety of retail and food service operations. The property's outdoor amenities further enhance its appeal, highlighted by an impressive 1,800 sq. ft. wraparound porch and approximately 4,300 sq. ft. of outdoor space for special events. An additional benefit is 25 dedicated on-site parking spaces, providing convenience for customers and staff alike. Renowned for its selection of local produce, gourmet foods, and specialty items, the Katama General Store has established itself as a beloved destination for both residents and visitors. The offering also includes a seasonal beer and wine license, transferable upon approval by the Town of Edgartown, creating additional opportunities for future business growth and expanded operations. The Katama General Store represents a truly unique opportunity to own an iconic, turnkey commercial property in a highly visible and sought-after Martha's Vineyard location.

ONE MILE FROM HISTORIC EDGARTOWN VILLAGE; Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with free standing columns, a granite entry step, mahogany decking and shiplapped ceiling. Attention to architectural detail presents at moment one. The welcoming expansive entry foyer presents your eye with an oversized lounge area to the right and a spectacular great room ahead. The great room offers a soaring cathedral ceiling and a rear wall of two story windows with a gas fireplace that is wrapped with a shiplap surround, very stunning! The great room opens to the dining room which features a wall of sliding glass doors overlooking the outdoor entertaining and pool area. The dining room flows into the large gourmet kitchen which features a kitchen island that can seat four. From the dining and kitchen area there is easy access to the smartly designed mudroom which offers a half bath, large pantry, and laundry area. Off the mudroom area is a large outdoor shower with quick access to the heated saltwater pool. The first floor hosts the primary bedroom with a luxurious bathroom featuring a soaking tub, oversized tile and glass shower, a two sink vanity and a private toilet area. Three custom built closets are found in this primary bedroom en-suite offering plenty of storage, a closet for linens, a closet for accessories and an oversized walk-in closet. The second floor offers three guest rooms and two large luxurious bathrooms, one with a soaking tub, both with glamorous showers. The exterior of the home, with its mature trees, cobblestone and pea stone driveway show off the homes architecture and is framed by its landscape. In the rear yard you experience privacy in the 14 x 30 ft. salt water heated pool that is surrounded by bluestone and professional landscaping. From the dining area, the mudroom and first floor primary bedroom you can access the rear yard onto a custom built deck, all overlooking the private pool area. A very wise and welcoming design!

This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft of private Atlantic beachfront. Unparalleled beauty, expansive fields and horse pastures and the rare opportunity to walk, bike or golfcart directly to the 19 acres of private Atlantic Ocean Beach owned together with the other landowners inside the farm. All of these features along with being a short drive to downtown Edgartown, make this a very special opportunity.

COASTAL LUXURY IN KATAMA — EXCEPTIONAL LIVING NEAR SOUTH BEACH. Set in one of Katama’s most coveted locations, where the sound of the ocean drifts in and South Beach is within easy reach, this distinctive coastal contemporary was thoughtfully designed to maximize natural light, energy efficiency, and long-term flexibility. The reverse-style floor plan places the main gathering spaces on the upper level, where abundant windows bathe the interiors in sunlight and frame distant views across the lower reaches of Katama Bay. The open-concept Living, Dining, and Kitchen areas flow seamlessly together, creating an inviting setting for both relaxed Vineyard living and effortless entertaining. At the heart of the home, the oversized Chef’s Kitchen opens directly onto a spacious porch designed for outdoor dining, gathering, and lounging, while two additional porches further extend the living space. The upper porch also enjoys seasonal views of the Edgartown fireworks, and nearby Fisherman’s Wharf and the public boat landing provide convenient access to Katama Bay and Edgartown Harbor. The home features four light-filled en suite bedrooms, each with a private bath and spacious shower. The generous Primary Suite includes dual oversized closets, a walk-in shower, and a private water closet. On the first floor, a bright and versatile bonus room offers flexible use as a Den, In-Home Gym, yoga studio, or additional guest space, with sliding glass doors for privacy, its own porch, and an adjacent half bath. Future accessibility was also incorporated into the original design with a fully framed, wired, and mechanically prepared elevator shaft, allowing for the potential installation of an elevator with minimal disruption. Offered turnkey with indoor and outdoor furnishings and an established rental history, the property is equally compelling as a personal Vineyard retreat, an income-producing investment, or a combination of both. The property also offers room for a future swimming pool and detached garage, subject to local approvals. Thoughtfully conceived for entertaining, sustainability, accessibility, and lasting enjoyment, this exceptional Katama residence presents a rare opportunity just moments from South Beach.

Set on over an acre of beautifully landscaped grounds, this estate offers a rare combination of privacy, refined living, and exceptional proximity to all that makes Martha’s Vineyard special. Bordering Land Bank conservation land and overlooking the picturesque fields of Morning Glory Farm, the property enjoys a peaceful pastoral setting with vibrant flower gardens and expansive outdoor living spaces. Just moments from the bike path, Downtown Edgartown, and South Beach, this exceptional compound offers the best of both worlds. With more than 4,000 square feet of living space across the main house, guest house, and detached garage with office above, there is ample room for both gathering and privacy. The recently renovated four-bedroom main residence is thoughtfully designed for comfortable living and entertaining. A dramatic living room with vaulted ceilings and a gas fireplace opens through sliding doors to an expansive deck overlooking the pool and outdoor kitchen. The dining room features soaring cathedral ceilings and direct deck access, while the beautifully renovated modern kitchen offers generous space for entertaining. A cozy den just off the kitchen provides a quiet retreat. The second floor is dedicated to the private primary suite with a renovated bath, while the lower level offers three additional bedrooms and two full bathrooms. The newly built two-bedroom guest house delivers an equally inviting experience, with cathedral ceilings accented by exposed beams, a modern kitchen, a spacious living room, a full bathroom, and laundry. Outdoor living is at the heart of this remarkable property. A heated infinity-edge pool and spa create a resort-like atmosphere, surrounded by beautifully manicured grounds and gardens with views across the working fields of Morning Glory Farm. A detached garage with an office and half bath above provides a versatile space for work or quiet retreat, complemented by an additional garage attached to the main house. Combining exceptional privacy, multiple living spaces and stunning farm views, 29 Llewellyn Way is a distinctive Vineyard compound designed for effortless year-round living and unforgettable summer gatherings.

Exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom. The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

Refined New Construction in Katama. Introducing the fourth custom built residence in the new Somerset development. This exceptional new construction represents a sophisticated interpretation of modern Martha’s Vineyard living. With nearly 3,500 sq ft, the beautifully appointed 4-bedroom, 4.5 bath residence features light-filled interiors, 10’ ceilings, gracious living spaces and clean architectural lines equally suited to relaxed summer living and year-round enjoyment. Two covered porches, an attached 2-car garage and additional space in the unfinished basement enhances the offering. The property offers the added opportunity to create an outdoor oasis, with ample room for a future pool, allowing the next owner to complete the setting with a a pool house, patio, and outdoor entertaining area tailored to their vision. Designed with the Vineyard lifestyle in mind, the home sits in close proximity to the Field Club, the bike path, and the spectacular shoreline of South Beach, while the shops, restaurants, galleries, and charm of historic downtown Edgartown and the picturesque harbor are just minutes away.

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows seamlessly throughout the home. Offering 10 well-appointed rooms, the residence features six bedrooms, four full bathrooms, and two powder rooms. The gourmet kitchen opens to the spacious living and dining areas, creating an inviting gathering space that extends through French doors to a generous bluestone patio. The beautifully landscaped yard is highlighted by a private, thoughtfully sited swimming pool, providing a peaceful outdoor retreat perfect for relaxing or entertaining.

Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

BEACH PLUM MEADOWS: ARCHITECTURAL KATAMA COMPOUND NEAR SOUTH BEACH. Set on more than 1.6 acres in the coveted Beach Plum Meadows enclave, this distinctive property combines classic coastal architecture, private compound living, and distant views across the Katama plains to the Atlantic Ocean—all less than one mile from South Beach. The gambrel-style Main House features three light-filled levels anchored by a dramatic Great Room with soaring vaulted ceilings, gas fireplace, and sliding glass doors opening to an expansive screened porch and two south-facing decks. A third-floor crow’s nest offers an ideal office or private retreat, with access to an elevated deck showcasing sweeping views toward the ocean. The open kitchen features a large center island, granite countertops, stainless appliances, and seamless flow to the dining and living areas. Four bedrooms are distributed across the compound, including two en suite primary bedrooms in the Main House and a private Carriage House suite with vaulted ceilings, gas fireplace, kitchenette, and full bath. Outdoors, a pergola-covered deck, established gardens, hydrangeas, mature landscaping, and sweeping lawn create an inviting summer setting, with ample space for a future pool, subject to approvals. Offering privacy, versatility, and easy access to South Beach and downtown Edgartown, this exceptional property captures the essence of the Katama lifestyle.

Situated down a long private driveway, this renovated 3.5-acre Katama estate offers a rare opportunity to acquire a turnkey property with a deep-water dock slip on Katama Bay. Impeccably executed throughout, the estate showcases exceptional craftsmanship, distinctive materials, top-of-the-line appliances, and an impressive array of amenities. Highlights include a finished lower level, expansive heated pool, three-car garage, neighborhood tennis and pickleball courts, first-floor primary bedroom, double-sided stone fireplace, and park-like grounds. For buyers seeking additional possibilities, information provided by the Edgartown Board of Health indicates that the property may support up to 15 bedrooms, subject to all applicable approvals, permitting, and regulations. Buyers and their agents are encouraged to independently verify all potential bedroom counts and development possibilities with the Edgartown Board of Health and other applicable authorities. 16 Witchwood Ln is the epitome of luxury, set in one of the most exclusive areas on Martha’s Vineyard.

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed new construction by Morgan Studio, a husband-and-wife–led boutique design firm. A turn-key offering for elevated indoor-outdoor living, the residence features soaring ceilings, a fluid floor plan with multiple gathering spaces, abundant natural light through oversized windows, and exceptional materials and finishes throughout. Every detail has been carefully considered in this modern interpretation of the Vineyard summer house. The layout centers on a private interior courtyard, envisioned as an edible garden, accessible from multiple points of the lower level. The centerpiece of the living spaces is a cathedral-ceiling great room with a wood-burning fireplace that opens to both the courtyard on one side and a 20’ by 40’ heated gunite swimming pool on the other. The great room also opens naturally into the kitchen, which features a large center island of patagonia tiffany stone, a breakfast nook, and a dedicated butler’s pantry. Bedrooms are strategically situated in separate wings, all with private bathrooms, each one uniquely designed. The primary suite is a true spa-like retreat, complete with a custom circular skylit shower and wall-to-wall travertine. The fully finished basement offers a bright, recreational space with impressive 10’ ceilings. A custom furniture package is available upon request for a truly effortless, fully turn-key purchase. Located on sunny land near Crocker Drive, the property offers convenient access to South Beach, all of Katama, and an easy connection to downtown Edgartown. An exceptional new construction opportunity in the heart of Katama.

Nestled in an enviable Katama setting, this masterfully designed shingle-style farmhouse compound epitomizes the peak of casual Vineyard luxury across a manicured coastal landscape. From the sprawling covered entry porch, the front door opens into an impeccably choreographed layout where a grand entry hall flows seamlessly into an expansive great room, an elegant formal dining space and a dedicated sunroom that bathes the main level in natural light. At the heart of the home is a true culinary haven—a premier chef’s kitchen anchored by a massive center island, supported by a walk-in pantry, and flanked by a quiet, professional study. Offering unparalleled versatility for multi-generational living, the main level also features a completely self-contained guest suite featuring its own private full bath and customized dual walk-in closets. A practical transition through the spacious mudroom reveals access to the attached two-car garage equipped with additional dedicated storage. Ascending to the second level, the sanctuary-like owner’s suite serves as a private retreat, boasting a secluded viewing balcony, an opulent master grand bath, and distinct his-and-hers walk-in closets. This upper story also accommodates two additional family bedrooms with a shared full bath, a central family area, and a large laundry room, all overlooking an airy, double-height stairwell corridor. Bridged elegantly by a spectacular outdoor roof deck is an entirely separate, fully autonomous upper guest wing configured with an independent living space, a private bedroom, a full bath and its own private balcony—perfectly framing views of the resort-style backyard oasis below, which features a premium inground gunite pool, a heated spa and endless outdoor space to entertain and enjoy. Schedule your private tour today!

This traditionally styled residence offers exceptional quality and craftsmanship in a coveted Edgartown location, situated on a corner lot just blocks from downtown and the harborfront. Thoughtfully designed for both elegant entertaining and relaxed island living, the home features beautifully proportioned interiors that flow seamlessly from one space to the next. The inviting front foyer opens to a gracious living room with fireplace and French doors leading to a deep, covered porch complete with its own fireplace. The 1st floor continues to a private den with fireplace, while the dining room and spacious kitchen/family room complete the main living spaces. Abundant windows and French doors throughout the 1st floor provide an effortless connection to the covered porch and the beautifully landscaped grounds. The 2nd floor offers 4 well-appointed bedrooms and 3 full baths providing comfortable accommodations, with most bedrooms offering access to private 2nd-floor decks. The finished lower level adds a 5th bedroom with en-suite bath, along with a TV area and billiards room. Numerous window wells bring natural light to this inviting additional living space. Outside, mature plantings, established gardens, and thoughtfully designed outdoor spaces create a private and serene setting. The property features a swimming pool, jacuzzi, entertaining patio with grill area, large outdoor shower, and lushly landscaped rear yard. An attached one-car garage adds convenience. Offered turnkey, this exceptional property combines timeless architecture, superior construction, sophisticated amenities, and a prime location within easy reach of all that Edgartown has to offer.

This truly remarkable Chappaquiddick property offers a rare opportunity to step back in time and experience the quintessential character of Martha’s Vineyard. The original historic home, built in 1892, is distinguished by its signature four-story tower with 270-degree water views and gracious wraparound porch. The main house features a spacious open living room with fireplace, dining room, kitchen with pantry, and comfortable TV room. A ground-floor bedroom and bath provide convenient access to a generous outdoor shower and jacuzzi. The 2nd, 3rd, and 4th floors feature six additional bedrooms, 2.5 baths, and office. The feeling throughout the home is wonderfully timeless, combining historic charm and architectural character with fresh surfaces and updated mechanical systems. Two charming guest cottages provide 3 additional bedrooms and a shared bath. A newly built, traditionally styled barn adds further versatility, while a private clay (Har-Tru) tennis court and storage shed create an exceptional setting for summer recreation. Set on 4.73 acres of beautiful lawns and wildflower-filled pastures, the property is framed by mature trees and enjoys spectacular water views in multiple directions. Every element, from the historic main house and charming cottages to the barn, tennis court, and expansive grounds, contributes to an extraordinary sense of place. Complimenting the entire property is deeded private beach access to Katama Bay as well as a mooring. This is a truly special and one-of-a-kind Chappaquiddick property, where history, natural beauty, and timeless Martha’s Vineyard living come together in a remarkable way.

Great Potential with Pond & Beach Access ~ Set on ten private wooded acres in the Boldwater community, this unique property combines privacy, flexibility, and exceptional potential. It includes a beautifully appointed guest house ready to enjoy, plus an approximately 5,400 sq. ft. structure offering the opportunity to create a custom main residence with a swimming pool. Owners enjoy deeded access to Edgartown Great Pond and a private Atlantic Ocean beach, all while being ideally located only 13 minutes to Edgartown Village or Martha's Vineyard Airport. The property may also be purchased with a waterfront residence in Boldwater, creating a rare opportunity for a private family compound. Whether purchased on its own or as part of a larger estate, this is an increasingly rare Martha's Vineyard offering with outstanding space, privacy, and long-term potential. FYI: First photo shows deeded pond access close-by to access the barrier beach on the south shore.

TIMELESS ARCHITECT-DESIGNED KATAMA RETREAT MADE FOR SUMMER LIVING. At the end of a long private drive, tucked into a quiet 1.5-acre setting near South Beach, this Patrick Ahearn-designed Katama estate feels like a true Vineyard retreat . . . elegant, relaxed, and made for gathering. The home brings Ahearn’s award-winning coastal architecture to life with style, sophistication, and luxury throughout this jewel-box designed property. Vaulted ceilings, custom shiplap paneling, custom millwork, antique rough-hewn beams, Rubio Monocoat floors, plus high-end fixtures, and luxurious finishes create a home that feels both newly built and instantly timeless. The spacious Great Room is anchored by a floor-to-ceiling gas stone fireplace, perfect for cozy nights during the island's shoulder seasons and for holiday gatherings. At the heart of the home is the Gourmet Cook’s Kitchen, designed not just for cooking, but for connection. Open on three sides to the Living Room, Dining Room, and Family Room, it naturally draws everyone together — for morning coffee around the island, long dinners after the beach, or easy summer evenings that move seamlessly from indoors to out. A Butler’s Pantry off the Dining Room adds both function and polish for entertaining. French doors open to the screened porch, offering a quiet, shaded retreat for morning coffee, an afternoon break from the sun, or a breezy lunch between swims. The outdoor living area carries the home’s sense of ease into the evening, with a PebbleTec-finished gunite pool, built-in whirlpool spa, bluestone patio, outdoor shower, and a pergola-covered lounge with a wood-burning fireplace. It is the kind of setting that naturally draws everyone back together after dinner — fireside, relaxed, and lingering under the Vineyard sky. The home offers four en suite bedrooms, including a serene Primary Suite with vaulted ceilings, a walk-in closet, spa-inspired bath, and direct access to the pool area. An attached two-bay garage adds ease, while the full unfinished basement offers exceptional future potential for a Media Room, Game Room, in-house gym, Wine Cellar, or additional lifestyle space. Private, beautifully crafted, and deeply connected to its Katama setting, this is a rare Martha’s Vineyard home designed for true island living: beach days, shared meals, quiet mornings, and effortless summer nights.

A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200 square feet of beautifully appointed living space created for the ultimate luxury: treasured time with family and friends. Inside, the home exudes warmth and sophistication with four wood-burning fireplaces, handsome hardwood and painted floors, custom millwork, built-ins, inviting gathering spaces, and sweeping views of Katama Bay from nearly every room. A rooftop widow’s walk crowns the home, offering breathtaking 360-degree vistas across the bay, dunes, tidal ponds, and surrounding grasslands. One of the home’s most captivating features is the expansive screened and covered porch, extending nearly the full length of the house and overlooking the sparkling waters of Katama Bay. It is an idyllic setting for relaxed summer dinners, quiet afternoons with a book, lively games, or simply taking in the brilliant evening sunsets. With more than 320 feet of Katama Bay frontage, the property invites a true waterfront lifestyle, with exceptional opportunities for sailing, boating, paddleboarding, fishing, and clamming. Beyond the shoreline, Chappaquiddick offers a rare sense of peace and privacy, with miles of unspoiled beaches, nature trails, sand dunes, tidal ponds, and protected habitats to explore. An attached three-bay garage provides ample storage for an island car, watercraft, bicycles, beach gear, fishing equipment, and every essential for life by the water. Offered turnkey, the home includes hand-selected furnishings and accessories by interior designer Jon Hattaway of MJ Berries Design in Boston, whose vibrant colors, curated objects, and artful details bring character and delight to every room. Enjoy the property exactly as it is, or make it your own and create a signature coastal haven. At once elegant, welcoming, and deeply connected to its extraordinary setting, this private Katama Bay retreat is designed for effortless waterfront living.

Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.

Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized windows, wonderful craftsmanship throughout and the home that offers 7 bedrooms, all with private baths. The 2-story living room features a massive stone fireplace, balconies that look down from the second floor and a grand 20 ft. diameter circular staircase. There is a huge gourmet kitchen, dining room, lower-level gym, media room and recreation area, are nicely arranged on the over 8,000 sq. ft. of living space. There is a large parking courtyard, a 3-car garage and swimming pool, all amidst a lush backdrop of manicured landscaping and mature perimeter vegetation. This incredible newly offered neighborhood is located less than a mile to town in one direction and same distance to the white sandy beach at the bend-in-the-road in the other. A very special property due for completion this fall and ready to enjoy.

An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galleries, and restaurants of downtown Edgartown. Expansive lawns, mature landscaping, and a substantial swimming pool create a setting more often associated with properties well beyond the Village center, offering remarkable space for outdoor living, entertaining, and generations of summer gatherings. At the heart of the property is a distinguished five-bedroom, five-bath residence encompassing more than 3,100 square feet. Rich in authentic Vineyard character, the home is attributed to Frederick Baylies Jr., builder of Edgartown’s iconic Old Whaling Church, lending architectural significance to an already exceptional property. Yet it is the combination of land, location, and lifestyle that truly distinguishes 14 Thayer Street. Opportunities to own this level of acreage and privacy within Edgartown Village are exceedingly limited, making this a compelling chance to acquire a true in-town estate in one of Martha’s Vineyard’s most coveted settings.

Thirty-eight (38 acres) of available land in Edgartown! This is a truly extraordinary and increasingly rare opportunity to own thirty-eight (38) acres of contiguous land in Edgartown. Come create a landmark estate or private compound in one of Edgartown’s most sought-after locations. Perfectly positioned between the charm of Edgartown Historic Village and the sweeping sands of South Beach and moments from Edgartown Great Pond. This premier parcel offers an unparalleled setting for a world-class residential retreat. The property’s scale and configuration present exceptional development potential, the creation of a substantial main residence complemented by guest accommodations, recreational amenities, and expansive outdoor living spaces. Whether envisioned as a generational compound or a singular statement estate, the land provides the flexibility to bring a sophisticated vision to life. Surrounded by prestigious homes and natural Vineyard beauty, the setting offers both privacy and proximity, close to harbor access, Edgartown Great Pond, fine dining, boutiques, and some of the island’s most celebrated beaches. Opportunities of this caliber, combining estate-scale potential with such a coveted location, are exceedingly rare and highly prized. An offering of this distinction is seldom available. This is an exceptional canvas for the discerning buyer seeking to establish a lasting presence in Edgartown.

Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion, the property remains just minutes from the charm and sophistication of downtown Edgartown. The six-bedroom main residence is a masterclass in timeless design and effortless elegance. Grand yet inviting, the home offers beautifully proportioned living and dining spaces, a thoughtfully designed chef’s kitchen and a sweeping screened porch, all oriented to capture wonderful views across the pool and out to Vineyard Sound. Every room is infused with natural light and a sense of understated luxury. The grounds are nothing short of spectacular, a curated landscape of mature plantings, expansive stone terraces, and romantic pergolas draped in cascading wisteria. At the heart of the property, a stunning pool and lounge area create a private resort-like setting, ideal for both intimate relaxation and sophisticated, large-scale entertaining. A separate carriage/guest house with full amenities offers flexible accommodations for guests or staff. This is more than a home; it is a rare and irreplaceable offering, a legacy property in one of the island’s most coveted coastal settings.

Unique opportunity to purchase two adjoining lots at 211 Upper Main Street and 26 Curtis Lane in Downtown Edgartown. 211 Upper Main St., Edgartown is a 15 bedrooms, 18 full baths, 2 half baths building with two large artist/fitness studios attached. It is in the B1 Commercial zoning district. Each bedroom includes an en-suite bathroom. Spacious kitchen and dining area. The kitchen/dining area includes: 2 refrigerators and 4 freezer drawers, A 5-burner gas stove and oven, 2 dishwashers, 1 microwave. Spacious living room: including 2 sofas and 1 coffee table, finished basement (2,000 square feet), Basement includes: 10 washer/dryers, 1 television and DVD player, 2 small rehearsal rooms, Complimentary Wi-Fi, Outdoor deck with picnic tables. 26 Curtis Lane is an exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom. The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill. Two more adjacent lots with parking and a yard are also available for purchase upon request.

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the bedroom and office located in the tower are stunning. 23 THAYER STREET is an extremely rare vacant lot in the heart of the Starbuck Neck neighborhood. With well over a third of an acre of land, the lot will comfortably accommodate a 5-bedroom house with guesthouse and pool.

Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown’s historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. A rare combination of scale, craftsmanship, and location. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana—an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location.

This stunning custom-built waterfront estate offers sweeping views of Edgartown Harbor and exceptional craftsmanship throughout. Set on a private Chappaquiddick compound, the property features a beautifully designed main house, a separate one-bedroom guest house, a pool and spa, and expansive outdoor living spaces perfect for entertaining. Inside, warm wood finishes complement the home's comfortable scale, while the gourmet kitchen, spacious living room with a stone fireplace, and walls of windows showcase the spectacular harbor views. The second floor includes two queen suites, a bunkroom, and breathtaking water views from nearly every room. The finished lower level features a home theater and recreation room. A private path leads to the property's beach and deep-water dock, while a barn across the meadow offers a fitness center, guest suite, and basketball court. Cruise to Main Street Edgartown by skiff or take the nearby Chappy Ferry. This exceptional waterfront retreat offers the perfect blend of privacy, luxury, and island living.

Experience the timeless beauty of Martha's Vineyard from this luxurious waterfront retreat where the landscape feels so effortlessly connected to daily life. This property embodies understated luxury and timeless design, featuring a meticulously crafted stone residence and guest house. The setting overlooking Edgartown Great Pond has a sandy pond beach and deeded access to the pristine Atlantic Ocean Beach. Ospreys and redtail hawks soar overhead in this naturalized setting that is only 13 minutes to Edgartown village or the MV airport, yet a world away. This is a rare combination of privacy and proximity. An opportunity to own one of the Vineyard’s most distinctive properties. The home was thoughtfully designed to embrace its exceptional surroundings; the residence is filled with natural light and enjoys beautiful water views. Custom floor to ceiling sliding doors invite the outside in. Spacious interiors flow easily to inviting outdoor living spaces, enhanced by a swimming pool, walking paths, blueberry grove and a half basketball court. Timeless architecture and extraordinary ambiance combine to create a peaceful sanctuary. A place to reconnect with nature and experience Martha's Vineyard as it has long been known by those who call it home. 16’ Duxbury Dory with trailer and motor are included with the house, allowing you to explore the great pond and easily access Atlantic Ocean beach rights only 15 minutes away. Simply the Best! If you need more space close-by for family and friends please check out 4 Jacobs Neck, owned by the same family and currently available! Please call listing broker for details.

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined modern luxury. Just moments from Edgartown Harbor and the island’s premier dining and shopping, the property spans two lots and features an exceptional compound with 10 bedrooms and 14 baths. Designed for both elegant entertaining and comfortable everyday living, the main residence showcases refined architectural details and modern technology throughout. Beautiful oak floors run across the home, complemented by sophisticated hardware, premium appliances, and walls finished in classic nickel board. A gracious living room with fireplace opens to a patio with retractable screens, creating effortless indoor-outdoor flow. The chef’s kitchen is impeccably appointed with dual dishwashers, a plumbed Miele coffee bar, refrigerator drawers, and a wine refrigerator. A custom brass and glass bar, complete with an ice maker and refrigerated drawers, can easily convert into a secondary kitchen. Two private bedrooms with en-suite tile baths anchor opposite wings of the main level, offering privacy and balance. The main floor also includes a secondary living room with a gas fireplace, an elegant dining room wrapped in seagrass wallpaper, a generous walk-in pantry, and a spacious mudroom. Upstairs, a spectacular primary suite serves as a retreat with a private balcony and two spa-inspired full baths. Three additional en-suite guest rooms and a spacious laundry room complete the second floor. The third level features a charming nautical-themed bunk room with four built-in beds and a full bath. The finished lower level includes two bedrooms with en-suite baths, a media room, wine cellar, and additional laundry. Beyond the main house is a beautifully finished two-car garage with brick floors and wood-paneled walls. The carriage house above offers a private guest suite with a balcony overlooking the pool. Lush hydrangeas surround a resort-style pool and spa, complemented by a built-in grill, firepit, and a fully equipped cabana with kitchenette, half bath, laundry, and climate control. This Edgartown estate offers rare privacy, scale, and sophistication just steps from Main Street. An iconic Martha’s Vineyard property reimagined for modern coastal living.