Great location, this vacant 1.44-acre lot is located on a quiet street with direct access to the bike path and proximity to State Beach, and just minutes to town for shopping, dining, and enjoying all the activities and amenities of Edgartown Village. The wooded parcel will support 2 bedrooms with a NitRoe 2ks Enhanced Septic System. The lot has been staked, and perc tested, and the septic design has been approved by the Edgartown Board of Health. The property is in the NHESP zone and the NHESP study has been completed. The seller is in the process of installing the well. Don’t miss this exceptional opportunity.

Nestled among the trees near the Sengekontacket Pond, this distinctive contemporary home offers privacy while being conveniently close to Downtown Edgartown and the picturesque trails at Felix Neck Sanctuary. Designed by architect Robert Orr, this multi-level residence showcases unique architectural details and striking angled ceilings. The main living area is bathed in natural light, surrounded by expansive windows, and features a charming brick fireplace. The eat-in kitchen boasts stainless steel appliances, an exposed brick backdrop, and opens to a spacious deck—perfect for outdoor dining and entertaining. The primary bedroom suite is a bright and inviting retreat, complete with a private bath. A comfortable guest bedroom and a convenient powder room complete the main level. Upstairs, you'll find a sun-filled office with a distinctive curved wall of windows and access to another lovely deck. This move-in-ready home has seen recent updates, including improved insulation, new siding, and roof, ensuring comfort and peace of mind for years to come.

KATAMA CONDOMINIUM IN MEETINGHOUSE VILLAGE - A bright and sunny center unit with an open floor plan, vaulted ceilings, skylights, and windows that fill the space with natural light. This home is in excellent condition, showing the pride of ownership. The wide-open kitchen with a breakfast bar offers a wonderful space for cooking and entertaining. Accommodations include a first-floor bedroom with a full bath and a second-floor primary suite. Outside, you will find a private back deck, beautiful garden and open lawn. The newly appointed Association swimming pool is close by. Located in the highly desirable Katama area, this home sits less than two miles from South Beach and even closer to Edgartown Great Pond. This private community is a hidden gem, ideal for year-round living, a vacation home, or a rental investment.

Island Grove Building Lot - A highly desirable Edgartown location near Morning Glory Farm, the Village, and South Beach. The 1/2 acre parcel is conforming in nature, allowing for maximum development. With approval for 6 bedrooms with sewer tie-in, the opportunities are endless! A great opportunity to get into this terrific community.

Edgartown: Stylish 3-bedroom 2 bath home with inviting and charming floor plan integrates comfort and function. Cathedral ceilings with skylight and 2 sets of sliders providing natural light and a bright open floor plan. Updated kitchen with breakfast bar and dining area. 1st Floor bedroom. Full bathroom and spacious living room perfect for gatherings and relaxing. There is a laundry room off the kitchen. The 2nd floor layout has 2 more bedrooms with a shared full bathroom and a flex area perfect for office or study. Peace of mind and easy living comes with the long list of completed major improvements which include, new windows, siding, roof, hot water heater, refrigerator, flooring, interior fully painted, 4 mini splits, solar panels and fire alarm system. Plus the home is being offered fully furnished! This sweet location is convenient to Bike path and Bus routes . As is Morning Glory Farm. Adjacent is access to Tar Klin Path with it's many points of access to trails of the State Forest and Pennywise Path Preserve. South Beach and the village of Edgartown are also just a short scenic bike ride away. This opportunity is ideal for buyers looking for year round, vacation and or rental income. BONUS: Title V capacity provides for the addition of a 4th bedroom with proper permits. Corner lot on .69 acres is a nice chunk of property highlighting expansion opportunities!

Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living room is open to the tiled eat-in kitchen area and the hallway leads to a pantry, full bathroom and two first floor bedrooms. The second floor offers a full bathroom and two generously sized bedrooms. The interior has been completely painted and sparkles brand new with new paint on ceilings, walls, windows, doors, baseboard heaters, and all trim. Brand new carpeting in the first-floor hallway and bedrooms. Do not miss the opportunity to purchase this great investment!

Tucked away in a quiet, wooded setting on picturesque Chappaquiddick, this charming three-bedroom Cape offers a peaceful island retreat. Designed for laid-back living, the home features a cheerful and versatile floor plan with generous indoor and outdoor spaces. The star of the show? A sprawling screened-in porch with a cozy wood-burning fireplace—perfect for summer nights or crisp fall evenings. The backyard is a private oasis, backing up to conservation land for lasting serenity. Direct access to the nearby walking trails means adventure is right outside your door. Less than a mile away, the calm, swimmable waters of Katama Bay beckon, ideal for paddling, picnicking, and memory-making. Whether you're seeking a peaceful escape or a fun-filled summer basecamp, this lovingly maintained home is move-in ready and waiting to welcome you.

Mattakesett units continue to be in high demand and #B2 is the only unit currently on the market! Take advantage of all the Winnetu Resort amenities and a robust rental program which covers your fees and provides great revenue! This unit offers abundant views of the farm fields out front, open common space next to and behind, and is a short walk or bike to South Beach! There are 3 bedrooms, 2.5 baths and the bonus of a finished loft. With over 1,400 sq ft of living space this is one of the larger units. The outdoor rear deck offers additional space for dining or relaxing after a day at the beach. These units are seasonal, closed down in mid-November and re-opened starting in mid-April. This unit is being offered fully furnished. Available to be shown now, but will be limited to Thursdays, rental turnover day, starting in late May.

Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy access to all island amenities, including beaches, bike paths, state forests, and public transportation. Step inside to discover a bright and airy first floor, adorned with hardwood floors and a cozy fireplace. The spacious eat-in kitchen boasts stainless steel appliances and granite countertops, complemented by a slider leading to a sprawling deck overlooking manicured landscaping and gardens. On the first floor, you'll find a convenient bathroom and one bedroom, while the second floor hosts a generously sized primary bedroom with abundant natural light and a skylight. Two additional bedrooms and another full bathroom complete the second level, offering ample space for family and guests. Adding to the allure of this home is the expansive basement, spanning 890 sq. ft. and providing endless possibilities for storage, recreation, or future expansion. Don't miss out on the opportunity to make this exceptional Edgartown property your own.

In the heart of Katama, close to south beach and all that the area has to offer, is this traditional 3 bedroom cape with updates. The bright kitchen and dining area offer a modern space, perfect for entertaining. A vaulted ceiling makes the living room light and bright. Three bedrooms, two up and one down, share bathrooms on each level. An outdoor shower, screened porch and outdoor decks make the indoor / outdoor transition comfortable. This property has an excellent rental history, or make it your island getaway or year round home. Offered turnkey, As Is.

EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well cared for neighborhood with over 70 acres of association common land. The property provides room to grow with a 6 bedroom septic system in the ground, and the lot has an open, sunny and bright feel to it. Surrounding gardens delight with a series of perennials, which bloom through spring and summer. The location is convenient to a variety of desirable amenities. Long Point Beach and Wildlife Preserve, numerous Lank Bank conservation trails, Black Sheep Gourmet, The Fish House, MV Airport, Vineyard Golf Club and Morning Glory Farm are all nearby. Walks, hikes and bike rides await your exploration. With options galore, it's easy to envision your Martha's Vineyard lifestyle starting here!

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.

TURN KEY READY 37 Knoll Drive, nestled in the heart of Katama, on a quiet sandy road, This charming 3-bedroom, 2 full bath home offers 1,232 square feet of cozy living space, including 520 S.F. of finished basement. Located on a generous 16,552 square foot lot. This home is offered "turn key" move in or rent out ready. ( 1 exception Dining Rm Table) Step inside to discover an open living and dining area, complete with an original wood-burning fireplace and a delightful bow window that fills the space with natural light. Oak floors throughout this home. The kitchen boasts stainless steel appliances & sleek stone counters and opens onto a deck that leads to your private backyard—perfect for summer barbecues or a quiet morning coffee. The primary bedroom features a full en-suite bath, while two additional bedrooms share a separate full bath. Wood floors and paneling add warmth and character throughout the home, and central A/C ensures comfort on those hot summer beach days. Recent updates include a freshly painted interior in 2025, a new roof in 2020, & renovated baths with new fixtures in 2015. The finished 520 S.F. area of the basement, completed in 2019, offers a fantastic space to watch the game or get some work done using the space as a home office. Located just a short bike ride from the Katama Kitchen, Katama Store and beautiful South Beach. This beach home is perfectly positioned for enjoying all that the Katama area has to offer. Just a 25-minute bike ride or a 5-minute drive to Edgartown's vibrant main street. This is a fantastic opportunity for both year-round living or rental income (rental history available). Don't miss out on this gem in a neighborhood of beautifully renovated homes. Town water runs in front of this property on Knoll Drive. Possible expansion of an additional bedroom with upgraded septic & town water. Edgartown approvals would be necessary. Title 5 passed on the existing Septic.

This incredibly charming Katama Cape Cod-style home that has been completely refreshed top to bottom! An updated kitchen with high-end appliances, including a wine fridge, two brand new bathrooms, central AC, new heating system, and a new second floor deck are just some of the improvements. There are two bedrooms, one on each floor. The second floor has a comfortable lounge area, and a cozy loft accessed with a ladder to provides a bonus sleeping area for teenagers or storage space. The primary bedroom has sliding doors leading to a new sundeck and the full bath is complete with a Victoria & Albert deep soaking tub. A finished lower level adds to the living space whether using as a kid's playroom, exercise, or office. The grounds are landscaped, and the pale blue shutters and window boxes are picture perfect. A small private yard, shed, and outdoor shower complete the offering. Located in the heart of Katama near the Field Club, it is a quick ride to South Beach or downtown. Offered partially furnished and ready for you to enjoy and/or rent this summer!

Nestled in the prestigious Majors Cove community, this lovingly maintained home offers the perfect blend of comfort, style, and Vineyard charm. Enjoy access to exceptional amenities, including tennis courts, a boat launch ideal for kayaking to State Beach, and proximity to the bike path for easy access to Edgartown, Oak Bluffs, and Vineyard Haven. Set on a pleasantly landscaped lot, this inviting home is filled with natural light. The heart of the home is the cathedral-ceiling living room, centered around a classic wood-burning fireplace ~ an inviting space for gatherings year-round. The open kitchen and dining area seamlessly connect to a spacious new deck, offering an ideal setting for outdoor entertaining or quiet relaxation. A convenient mudroom with laundry sits just off the dining area and provides direct access to the attached garage. Two comfortable bedrooms and a full bathroom complete the main level. The upper level is devoted entirely to the private primary suite. This serene retreat features a generous bedroom, a dressing area, a walk-in closet, and a full bath complete with a soaking tub and separate shower. Additional highlights include a full basement and the quintessential Vineyard outdoor shower. Offered furnished, this property is your opportunity to enjoy the very best of Island life.

Discover this exquisite, contemporary home nestled in the heart of Edgartown's Smith Hollow, conveniently located just off the bike path and mere minutes from the lively Edgartown Village. Situated in a welcoming, family-oriented neighborhood, this stylish residence boasts a bright and airy open floor plan. The Great Room captivates with its soaring cathedral wood ceiling and robust timber accent trusses, creating a striking centerpiece for the home. Thoughtfully designed, the efficient kitchen offers generous cabinet storage and ample counter space, making it a pleasure to cook and entertain. Adjacent to the dining area, a spacious screened-in porch leads to a vast private deck, perfect for hosting gatherings or enjoying quiet moments outdoors. The home features two first-floor en-suites, each with private bathrooms and walk-in closets for added convenience. Additionally, two more bedrooms share a third full bathroom, along with a half-bath for guest use.For climate control, the Great Room and two guest bedrooms are equipped with forced hot water central air, while the primary en-suites feature heat pump mini-splits. Recent updates include a new roof installed in 2023, complete interior and exterior painting (over 38 gallons), and new trim and ceiling fans. Furnishings can be negotiated for interested buyers. This property is a true gem, offering both comfort and style in a prime location.

This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first floor has hardwood flooring throughout, and the living room is open to the kitchen area. A separate formal dining area is adjacent to the kitchen with a full bathroom located in between. The primary bedroom has a vaulted ceiling, tiled bathroom with an air bubble jet tub, double sinks, and large walk-in closet. The second floor has four generous size carpeted bedrooms and a full bathroom. The lower level is partially finished creating additional living space to enjoy and can easily become a home theater room. The laundry room is in the basement area with a sink and storage cabinets. House is equipped with a central vacuum system. Many recent updates include a new roof 2025, new furnace in 2023, AZEK exterior trim and deck railings. Yard area has an installed irrigation system that is maintained annually. Currently a five-bedroom dwelling with a septic design for six bedrooms. A great investment property for year-round living or rental income.

Simply enchanting! The setting is picturesque with a pond, towering trees and flowering shrubbery, privately tucked away yet less than 1¼ mile to the Edgartown Village. The existing home is set at the edge of the pond and is awaiting reimagination and renovation. Parcel will support 5 bedrooms once connected to municipal sewer. Structures are being sold “as is”.

Welcome to this charming post and beam-style home, privately located at the end of a cul-de-sac on .71 acres with proximity to over 50 acres of Land Bank and Sheriff's Meadow land with multiple trails and paths. Conveniently located to the bike path, Morning Glory Farm, the heart of Edgartown, and Meetinghouse Way, with direct access to South Beach, the location is ideal. The floor plan was designed to bathe in natural light, creating a relaxing and inviting atmosphere. The first floor features a fabulous kitchen for the accomplished chef with a large island, desk space, and a walk-in pantry with direct access to the garden. The dining room enjoys a gorgeous enamel pellet stove and sliders to the expansive deck for outdoor entertaining. The sunken cathedral-ceiling living boasts a stunning floor-to-ceiling brick fireplace with remarkable sunlight and sliders to the deck. The first-floor bedroom is at the back of the house, adjacent to the full bath. The large primary suite with den/office space and a half bath is on the second floor, and two additional bedrooms and a full bath complete this floor. The basement offers room for storage and overflow. Outside, enjoy the pleasant front yard, spacious deck, gardens, and outdoor shower in the back. Town sewer connection permits expansion of up to 7 bedrooms. Come and experience this Vineyard retreat with unparalleled privacy, ready for immediate enjoyment.

New Construction! This newly built clean three-bedroom three-and-a-half-bathroom home in Edgartown offers a modern open concept design ideal for entertaining. The updated fresh kitchen features stainless steel appliances functional island with new induction oven and functional farmers sink. Beautiful flawless hardwood flooring throughout the home. Upstairs are two spacious bedrooms each with their own private ensuite bathroom with convenient laundry area in the hallway. The finished basement adds additional 960SF of living area with high ceilings multiple egress windows giving bountiful natural light with another large modern full bath. Lower level has interior and exterior access with a separate entrance to the backyard. The home includes an updated nitrogen septic system and owned solar panels! Situated on a large lot with access from both 13th and 14th Street there is potential for an additional structure or pool with Town approval. This newly built house is ready for you to enjoy!!!

This recently constructed home conveniently sits in the center of Edgartown close to Sengekontacket Pond. With 3 bedrooms, 3.5 baths, bright and sunny living areas, and a very spacious and finished lower level, this property is well-designed. Featuring hardwood floors throughout, the open concept on the first floor has modern kitchen with a center island and stainless appliances, a dining area and comfortable living room. There are two spacious bedroom on the second floor, both with ensuite baths. The finished basement has high ceilings, lots of natural light, a full bath, storage space, and a private entrance - a terrific rentable option! The solar panels will be sure to provide low electric bills. The yard has new plantings with irrigation, a MicroFast septic system, and a gravel driveway. This long lot includes additional, undeveloped space to increase the size of the yard, or seek approval to add a rear driveway from 14th Street, a pool or garage.

Set on a beautifully landscaped half-acre in Katama, this thoughtfully reimagined ranch is just a short bike ride to South Beach or downtown Edgartown. The main house features 2 bedrooms, 1.5 baths, and a bright, open layout with a fully renovated kitchen (2020) showcasing quartz countertops, stainless appliances, and a serene coastal palette. The full bath was tastefully updated in 2024 with modern, high-end finishes. The home is also supported by a 4-bedroom septic system, offering flexibility for future expansion or guest accommodations. A partially finished lower level in the main house adds approximately 550 sq ft of bonus living space — perfect for guest overflow, a playroom, or home office. Outdoor living is a highlight — enjoy a screened porch, a sun-drenched back deck, and a picturesque pergola patio, ideal for gatherings or quiet island mornings. A separate, handcrafted post-and-beam barn built in 2014 offers a flexible guest retreat. The 450 sq ft loft glows with exposed beams and natural woodwork, while the 720 sq ft lower level includes manufactured wood flooring and a built-in bar for effortless entertaining. All of this is nestled among mature trees and lush green lawn, offering privacy, charm, and true Vineyard living. Please see the full list of upgrades attached to the listing. A pre-listing home inspection is available upon request. Owners are in residence — no drive-bys, and advanced notice for showings is preferred

Enjoy the convenience of Dark Woods, a quiet neighborhood in an ideal location close to the Village, bike path, beaches, and 27 acres of Sheriff’s Meadow conservation land. This property has been meticulously maintained and is ready for your immediate enjoyment. Sited on a pleasant .77-acre lot, the property offers expansive space with a floor plan that is perfect for entertaining. The first floor features a fabulous living room with a gas fireplace and a formal dining room. Overlooking a private backyard is the open eat-in kitchen with direct access to a 2-tiered deck with a hot tub and outdoor shower, where you will spend much of your time entertaining. The bar/pantry is between the dining room and kitchen, and a laundry room is off the kitchen. If you are looking for a place to retreat, enjoy the bonus space above the 2-car garage. The primary ensuite occupies the right side of the second floor and enjoys a newly renovated bathroom with great natural light. Two large guest bedrooms and another newly renovated bathroom complete this floor. The lower level enjoys an ensuite walk-out bedroom, a living and dining area, a wet bar, and a full bath. The home is connected to town water and sewer, with the ability to expand to 7 bedrooms. Being sold furnished and ready for immediate occupancy, this highly coveted Dark Woods neighborhood offering is a home you don't want to miss! The listing agent is related to the seller.

EDGARTOWN HISTORIC DISTRICT - Terrific opportunity for an INVESTOR and HOMEOWNER alike to have an in town House and Guest house on this size lot in wonderful part of Town, on a lovely Street. Two cottages - One at the front and one at the rear of lot. Yard and parking for each cottage. Room to have a beadevelop the yard and the property in general. Presently a three (3) bedroom lot but Town Sewer is available on Norton Street and once connected FOUR (4) Bedrooms will be allowed. Off Street Parking. Walk to the Harbor, Edgartown Yacht Club, Restaurants, Stores. Many possibilities to enhance!! Tenants in place, but easy to show with reasonable notice. Shared driveway. Being sold in "As Is" condition.

Upon entering through the charming side door, you're welcomed into a beautifully screened sun porch – the perfect spot to relax and soak in the surroundings. This inviting space leads to a sprawling, light-filled chef’s kitchen, designed for both culinary creativity and social gatherings. Adjacent to the kitchen, a warm and welcoming living room awaits, featuring a convenient half bath and access to a cozy first-floor bedroom. Just to the right, you’ll discover a second ensuite bedroom, offering both comfort and privacy for guests or family. From the hallway, a staircase leads to the upper level, where two additional, spacious bedrooms each come with their own well-appointed bathrooms, creating a serene and private retreat. A second door off the living room opens to the lower level, where you’re greeted by a partially finished entertainment haven, complete with a pool table – an ideal space for relaxation and recreation. Further down the hall, to the left, is the media room, a cozy setting perfect for movie nights. Across from the media room, you’ll find a convenient half bath that leads into a laundry room with direct access to the backyard, blending functionality and convenience seamlessly.

PRIME 1.5 ACRE BUILDING LOT IN EDGARTOWN - Seize this opportunity to design and build your very own signature estate in Katama including the possibility of a Main House, Guest House, Garage, Pool, and more! This conforming, R-20 prime building parcel will support EIGHT BEDROOMS (8) with a standard Title 5 septic system. Nestled in an area of fine homes and ideally located on the edge of famed Katama, just 4 minutes to Main Street in Edgartown. PLEASE NOTE: Locus shown in first photo is approximate. Refer to attached documents for complete survey.

Located at the end of a quiet cul de sac, just half a mile to the top of Main Street, is this 4-bedroom home with a separate studio guest apartment, office, and heated 2-car garage with 10-ft doors. There is also an unfinished full basement. The living space is in excellent condition with a combination of hardwood, carpet, and tile floors. This light and bright home could be a reliable income producer or might be appropriate for the buyer who needs space for guests or employee housing. There is a 10.14 kilowatt rooftop solar array installed by South Mountain Company.

Welcome to a stunning blend of contemporary elegance and charm nestled in the heart of Edgartown. This exquisite water view residence offers 3 spacious bedrooms and 4 luxurious bathrooms, encompassing a generous amount of meticulously designed living space. The luxurious and versatile interior boasts a modern, move-in ready design, with a gourmet kitchen and recently renovated spaces. Whether you're seeking a private retreat, a space to entertain or an investment property, this home caters to all your needs. Additional amenities include a spacious garage with studio above that is perfect for extra guests; and a charming outdoor living space with a stone patio. Property is a short walk over to the public boat launch!

Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious floor plan offers four bedrooms and four full bathrooms, complemented by two powder rooms and a fully finished lower level for additional entertainment. Separate guest quarters above the garage provide visitors with their own private retreat, featuring a dedicated living room, convenient wet bar, and private deck. Outdoors, a mahogany deck overlooks beautifully landscaped gardens, with an outdoor shower perfect for post-beach rinses before alfresco dining under the stars. Conveniently located just a short distance from downtown Edgartown's acclaimed restaurants, boutiques, and harbor, this property offers a quintessential Vineyard experience and an established rental history.

Welcome to 24 Dark Woods Road, a beautifully maintained 3-bedroom, 3.5-bath Contemporary Colonial nestled in an upscale, tranquil neighborhood. This spacious residence abuts acres of Sheriffs Meadow conservation land, offering miles of trails, serene pond views and peaceful privacy at the end of a quiet road, yet is just a mile from the beach and closer to Edgartown Village. This association prides itself in complementing and maintaining the natural surroundings. Step into the entryway to a sunlit, front-facing kitchen featuring granite countertops, custom cabinetry and coordinated built-in desk. The open-concept living room boasts soaring ceilings, a commodious dining area and a wall of sliders leading out to a backyard deck perfect for outdoor living and future expansion. The first-floor primary bedroom with ensuite bath, second bedroom, full bath and study, provide convenience and comfort. An open stairway leads to the second floor with a balcony overlooking the living room, where you'll discover a cozy versatile den, a large third bedroom, full bath and a bright office space. Thoughtful design elements include a central vacuum system, ample storage and energy-efficient features including solar panels and a modern heat pump system, backed by an oil heating option. Additional unfinished space on the second level as well as over the garage. The lush, irrigated yard and welcoming front hydrangea garden complete this idyllic offering. With potential for expansion to 6 bedrooms, a spacious basement, and an EV-ready garage, this home is a rare find. Offered mostly furnished, it’s ready for you to make it your own.

Welcome to this inviting 4 bedroom home, with a pool, perched on the neighborhood hilltop. This tri-level cape offers an eat in kitchen featuring light green granite countertops, a Viking gas range, a double basin sink, a built in banquette and views of the front covered porch and beautifully hardscaped rear yard. The primary level presents with a living room, a separate bar area offering a wine refrigerator and dishwasher, a full bathroom and primary bedroom, which has private access to the outdoor pool and entertaining area. The second floor sports two sizable bedrooms and a full bath. The lower, entry level, greets you with a large lounge area with t.v. and sitting area, a bedroom, a full bath and a laundry area. An added benefit is the attached storage area on the first level that currently operates as a home gym. A 8 x 19 foot salt water heated pool is surrounded by professionally designed hardscape and landscape, including evening accent lighting. The technical details of the home include an electric car charging station and a rooftop solar array. This home has a strong rental history. It comes turnkey, with most furnishings remaining. A true gem of an offering. A must see in person.

COASTAL RETREAT IN KATAMA. Located in the heart of Katama, with the iconic Katama Airfield and the sandy shores of South Beach nearby, this contemporary coastal retreat is ideal for enjoying all the best of Katama. The reverse-style contemporary features a sunny, open-designed floor plan with vaulted ceilings that seamlessly combine an inviting Living Room with gas fireplace, a Game Room with custom built-ins, a spacious Dining Room with seating for eight -- plus an attractive cook's Kitchen with stainless appliances, granite counters and counter seating. The living space opens onto two second-story decks that are ideal for entertaining or relaxation, which enjoy sounds of the ocean and gentle summer breezes. The property is being offered furnished, providing a turnkey opportunity and seamless move-in experience. This property not only offers an exceptional living experience but also includes a solid rental history and $60,000+ in current gross rentals for Summer 2025 -- plus available peak weeks for a buyer to rent OR use themselves. Make this coastal gem your own and enjoy the unique Katama lifestyle that it offers.

WATERFRONT CHARMER ON SENGEKONTACKET POND. Perfectly perched on the shoreline of Sengekontacket Pond and surrounded by stone walls, lush perennial gardens, a cobblestone courtyard and expansive water views, this charming contemporary cottage blends all the best of island and waterfront living. As you step inside, you'll be greeted by a bright and airy open living space featuring an casual dining area and a well-appointed kitchen. The all-white interior is beautifully accented by warm hardwood floors and vaulted ceilings, illuminated by skylights and enhanced by the comfort of air conditioning and ceiling fans. Three sets of sliding glass doors extend the living space onto a spacious mahogany deck, perfect for savoring the breathtaking water views. The first floor hosts two inviting bedrooms and a stylish full bathroom complete with tub/shower and a convenient laundry area. An open staircase ascends to a second-floor balcony, leading to a stunning primary bedroom suite. Here, French doors open to reveal a sanctuary with vaulted ceilings, a luxurious full bath with another glass walk-in shower, and, of course, those mesmerizing water views. Designed for seamless indoor-outdoor living, this home offers magnificent vistas across Sengekontacket Pond, stretching all the way to State Beach. Stone steps from the backyard lead directly into the pond, where you can enjoy boating, kayaking, and paddleboarding, with the potential for your own private mooring. This property is a unique investment opportunity, offered fully furnished and boasting an impressive rental history, ($120,000+/year average) and over $80,000 in current bookings for Summer 2025. Whether you're seeking a tranquil retreat or an income-generating asset, this waterfront charmer is ready to fulfill your dreams of island living. Don't miss the chance to make this your very own slice of paradise.

WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the traditional US Open colors. The court is lined for tennis as well as two full pickleball courts with portable nets. Game on! All of this is set upon three acres of private, expansive land with distant WATER VIEWS! The estate is spectacularly located on Sampson Hill, being the highest elevation on Chappaquiddick. The location is convenient to the Chappy ferry, the Chappy Community Center, Slip Away Farm, the hiking trails on Land Bank properties and the beaches. A true gem of a location! This Chappy Compound has been meticulously grown and maintained over the years through architectural design, professional decorating and professional landscaping. The Workout & Game Barn was recently constructed in 2022. It has a light airy feeling with its cathedral ceiling, light colored wood and abundance of natural light streaming into its interior space. An interior barn door separates the space into two work out areas. The architecturally designed Guest House was constructed in 2018 with year round living as an option. It was designed with an open floor plan and an abundance of outdoor living spaces to make this Guest House live large. The fun Pool House sports a wooden beamed cathedral ceiling with a large open lounge area, kitchenette and bath, overlooking the Pool and Workout & Game Barn. The interplay between the Workout & Game Barn, Pool House, Pool and abutting Tennis and Pickleball Courts makes this Chappy Compound fun and playful! Strong Rental History.

PRIME 5-ACRE LOT - R20 ZONE EDGARTOWN Introducing a rare opportunity to own a piece of the island (currently two parcels) close to all Edgartown has to offer. This spectacular level lot is situated along Edgartown Road and provides the perfect setting to create a private retreat or a potential subdivision. The property borders the Triangle area of Edgartown, with ease of access to public transportation routes. Ideally located just minutes from beautiful beaches, boutique shops, and world-class dining. Please note, that perc tests and utilities are the buyer's responsibility. Don't let this extraordinary opportunity to build slip away!

Discover this private Katama retreat, perfectly situated on over 3 acres of forested and landscaped grounds. Located just a mile from Edgartown Great Pond and a little over 2 miles from both South Beach and Edgartown Village, this contemporary guesthouse offers the ultimate island escape. Built in 2018, it boasts a proven rental history and is outfitted with every modern amenity. With a 6-bedroom septic system already in place, there’s ample opportunity to expand by adding a main house or additional structures, pending necessary town approvals. Enjoy now while envisioning its full potential!

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.

Here is the Edgartown compound you've been waiting for - a 5-bedroom main house, 2-bedroom guest house, and elevated swimming pool area located on 1.5 acres. Next door there is 25 acres of conservation land. The property is barely 2/10s of a mile to Morning Glory Farm, and just a mile and a half to the village on the bike path. The house combines island country charm with modern amenities - honey pine floors, Douglas fir beams, and shiplap pine ceilings are among the custom details. The spacious kitchen has just undergone a renovation that includes new appliances and countertops. The guest house is in classic beach cottage style with open floor plan and cathedral ceilings. Get ready to make memories here. Sitting out and enjoying dinner beneath the stars on a balmy summer evening will be a highlight. The backyard is its own oasis with its centerpiece being an elevated pool with mahogany decking. With an acre and a half of land there is plenty of space to install other amenities your family might desire - Bocce court, firepit, the list is long. This property could be your family's Martha's Vineyard escape, and it can also be a healthy source of rental income to offset your expenses. Right now the property generates over $100,000 in rental income annually - close soon and the money is yours!

Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper’s Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha’s Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The Lightkeeper’s Inn, this historic Inn was said to be home to Henry Lyman Thomas, one of the last lightkeepers of the Edgartown Lighthouse. The property is unique in that it offers onsite parking, which is a rarity on Martha’s Vineyard. Currently operated as an Inn, this property may be converted to a single family residence with the required proper permitting and approvals. It is conveniently located close to Edgartown Ferry, Edgartown Lighthouse, and minutes from N. Water Street, which offers shopping and restaurants.

This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, is flooded with light, open to breezes, and marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with an expansive breakfast island, dining room, and living room with a gas fireplace. Sliders from the living room open to the heated pool and hot tub surrounded by granite pavers. The kitchen shares a view of the pond and Nantucket Sound through the wall of windows and sliders in the dining room out to the deck, a perfect spot for outdoor dining. A wine cooler in the dining room has a pass-through space above it to the adjacent family room. The open floor plan lets the cook connect with family and guests. Beyond the kitchen, accessed through a sliding barn door, is a cleverly placed office with built-in bookshelves and sliders to the deck. A pantry, half bath, laundry, and another mudroom adjacent to the outdoor shower complete the first floor. The views of Sengekontacket and Nantucket Sound become more dramatic on the second and third floors. There are 4 bedrooms on the second floor, including 2 primary suites, all with vaulted shiplap ceilings, as well as a den and a shared bath. The den and one of the suites have private decks that capture the essence of the views. A second sliding barn door opens to the den, creating a private primary wing at the front of the house. An outstanding spiral staircase provides access to the fabulous “Lookout Lounge,” where you will enjoy exceptional views inside and outside on 2 decks. The professionally landscaped yard includes a perennial garden, mature trees and shrubs, and a rolling lawn with a fire pit. It’s only steps away from the hiking trails of Felix Neck Wildlife Sanctuary, a short trip to the town landing, and an easy drive or bike ride to downtown Edgartown. With ample spaces for relaxation, entertainment, and multiple living areas, this home is the perfect Vineyard experience.

This beautifully renovated Katama retreat combines refined design, luxurious amenities, and thoughtfully crafted spaces. The main house features three bedrooms, including a peaceful primary suite with private deck access, a second en-suite bedroom, and a cozy bunkroom. The octagonal living room, skylit dining room with a gas fireplace, and a chef’s kitchen with quartz counters and high-end appliances create inviting spaces for relaxation and entertaining. The second floor is home to a state-of-the-art theater room, designed for an unparalleled viewing experience. A 4K projector and 110-inch acoustically transparent screen deliver vivid visuals, while the built-in sound system surrounds you with dynamic audio. This versatile space can also serve as a family room for games and gatherings. With additional room for a home office, plus the convenience of a powder room, it’s an ideal multipurpose area that adapts to your needs. The detached guest retreat offers a private bedroom, a comfortable sitting area, and a full en-suite bath. Guests can enjoy movie nights with their own theater projector and automated screen, all set under soaring cathedral ceilings. A standout feature is the newly constructed exercise studio, complete with a 14-foot Endless Performance Pool, a fully equipped gym area, and a convenient half bath. Outside, the expansive bluestone patio is perfect for al fresco dining or relaxing in the hot tub. The professionally landscaped grounds, mature gardens, and spacious lawn provide privacy and tranquility. There’s also an attached heated storage room plus a separate shed, ideal for housing beach gear, bikes, and recreational equipment. With its versatile layout, premium finishes, and proximity to South Beach, this Katama property is a sophisticated retreat, designed for effortless, year-round living.

A private Edgartown home in the distinguished Boldwater neighborhood on Martha's Vineyard. This property is spread over 8.5 acres of pristine land and fruit trees and includes a 4 bedroom/3.5 bathroom main house and a 1 car garage. A winding drive leads from the road to the main residence which features a generous first floor plan with an open living room with a brick fireplace, dining room, and a kitchen with doors leading out to a welcoming screened porch. This home features a primary bedroom suite and a guest bedroom suite on the first level. Two additional guest bedrooms complete second floor. The exclusive Boldwater Association offers tennis courts, a boat landing on the Edgartown Great Pond, and a private South Shore sandy Atlantic Ocean beach. The Edgartown Great Pond is great for kayaking, paddling and boating.

This historic commercial property, built in 1790, is ideally situated in the vibrant heart of Downtown Edgartown. Currently functioning as a blend of retail and residential units, it presents remarkable opportunities for diverse ventures. The property combines exceptional Main Street frontage with a large open lot that abuts Edgartown’s primary downtown commons, the Village Green. Whether you aspire to establish your own business or take advantage of the rental market, this property offers an exceptional chance for both ownership and investment that should not be overlooked.

NEWER CONSTRUCTION, with POOL, 1/2 mile from the heart of EDGARTOWN VILLAGE! LOCATION, LOCATION! Approx. 3,500 square feet of open living space. The Great Room has a dramatic Two Story wall of windows which surround a gas fireplace and overlooks a 14 x 30 foot in ground, heated, saltwater pool which is surrounded by bluestone hardscape. In addition to the dramatic Great Room there is a first floor study, a first floor primary-en-suite, a mud room and separate laundry area. The Gourmet Kitchen, with it’s central island, opens to the dining room which flows into the Great Room. The second floor offers a second primary-en-suite, as well as two additional guest bedrooms which share a full bath. The plot can have up to SIX BEDROOMS, a future guest house and/or a future detached bedroom. The home comes partially furnished. Stellar location, only a 1/2 mile to the heart of Edgartown Village. The property is also close to the Library, Girls/Boys Club, public tennis courts, public playscape and the bike path. SHOWINGS START APRIL 6TH.

Coveted Down Harbor! This 3-bedroom 2-bath home sits in the Down Harbor association in a prime Katama location. This charming home is an entertainer's delight with a spacious yard, a large deck, an outdoor kitchen, pool, and recently built pool house with 2 outdoor showers, 1/2 bath and a storage shed. This home features vaulted ceilings, exposed beams, and a bright kitchen with a breakfast bar open to the dining area. The living room is bathed in natural light with 2 oversized sliding doors to the deck overlooking the pool and outdoor kitchen. A bonus loft offers additional living space. The current homeowners have gone through the approval process for an attached garage with room above, for a maximum bedroom count of 4 on the property. Enjoy exclusive homeowner rights to the association's private beach, dock and mooring field, all rare and desirable amenities. Located between downtown Edgartown and South Beach, this property is perfect for beach lovers and outdoor enthusiasts looking for a retreat with easy access to biking and walking paths. Don't miss out on this prime coastal living opportunity! *Offered fully furnished, less a few owner exclusions*

NEW CONSTRUCTION: REIMAGINED ISLAND LIVING AT SOMERSET. Construction for 4 Somerset Lane is currently underway with a targeted completion date of spring, 2025. Somerset is an exclusive five-home luxury enclave perfectly located between Edgartown Village and South Beach -- and developed by Stanmar, owners of the Winnetu Oceanside Resort. This curated home has been perfectly designed for entertaining, peaceful relaxation, working from home -- and features spacious living spaces conducive to hosting and entertaining family and friends. The home sites have been designed to maximize outdoor living and entertaining around a spacious and private yard with expansive lawns and room for an in-ground pool, pool house/cabana and outdoor fire pit. The beautifully designed interiors will feature a fresh coastal style and will evoke a sense of casual island living and barefoot elegance. **ABOUT THIS HOME***: This smartly-designed luxury residence will include 3,643-square feet of finished interior living space -- with an additional 887 square feet of outdoor living spaces, including a spacious covered portico and second-floor screened porch -- for a combined total of over 4,530 square feet. Somerset offers a one-of-a-kind opportunity to own in premiere Katama location, with easy access to Edgartown Village, The Field Club -- as well as the bicycle path and South Beach.

Village dreams come true… STUNNINGLY CRAFTED, **this four-bedroom five bath property in Edgartown Village with Garage is truly a rare find! Situated on a corner lot just two blocks north of Main Street and two blocks from the Harbor, it features walking convenience and luxury in one package. Main and second floors combine over 3,400 square feet of spacious, elegant living. The partially finished lower level abounds with an additional 1891 sf, opening even more possibilities for unique customization to suit any lifestyle. Three of the four bedrooms are en suite with all four quarters well separated, adding wonderful privacy from the next. The show-stopping central staircase with its grandeur and contour adds a touch of elegance to the home, complemented perfectly by the warmth and sophistication of the maple inlay flooring, which is comfortably radiant heated throughout all three floors. Despite its proximity to the bustling village life, the thoughtful sound-proof design allows for quiet relaxation when desired. The abundance of French doors not only brings in natural light but also seamlessly connects indoor and outdoor living spaces, enhancing the overall inviting atmosphere of the home. Overall, this superb Edgartown Village property offers exceptional location with a unique blend of charm and elegance, making it a wonderful investment for those seeking a truly special home in the highly desirable Village of Edgartown.

This newly built traditionally styled Greek Reival home offers a wonderful open floor plan with refreshing interior design, all presented in excellent condition. The first floor front foyer, leads to the well-appointed kitchen with high-end appliances and large island. A dining area and living room with fireplace, all with an abundance of natural light. There are French doors leading to a covered porch with stone fireplace, all of which overlooks the exquisitely landscaped rear yard and patios. The second floor offers a spacious primary suite with sundeck and two additional ensuite bedrooms. The finished lower level offers two additional bedrooms with shared bath, a comfortable sitting room with TV and large laundry area. There is a detached barn to the rear of the property with a spacious deck that could be used for a number of usages, an outdoor shower and parking for 4-cars. All of the these mentioned on a quiet street just blocks to the downtown Historic District.

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.

This stately Greek Revival home lies on beautiful Fuller Street and a short walk to the beach. This 5-bedroom / 5.5-bath home features a beautiful foyer with arches and paneling leading past a grand staircase to a beautiful family room, kitchen and screened porch overlooking the backyard. There is an ensuite ground first floor bedroom and office off the hall as well as a side mudroom entry and interior access to the one-car garage. The second-floor features three bedrooms, two of which share a bath, laundry room in addition to a large primary bedroom with fireplace, luxurious bath and walk in closet. The 3rd floor offers a large room with water views that could be used for a number of purposes, with a full bath. The lower level offers a TV sitting room, large gym with wet bar, a second laundry room and door to exterior pool area. The rear yard offers a built in grill, swimming pool and pool house complimenting the nicely landscaped grounds, 2-car brick parking area and all located just a short walk to Fuller Street beach, the harbor and downtown.

Spectacular 20.8 acre Boldwater Association waterfront estate on Edgartown Great Pond with breathtaking views over 1,000 ft wide low brushy pond front terrain and across the 3/4 mile wide Lyles Bay, dreamy Swan Neck Point, the 1.5 mile wide main pond and barrier beach to the ocean beyond. The handful of well pruned trees on the property enhance the water views. The sophisticated and charming quality house was built by Andrew Flake, arguably the finest Vineyard builder over the last 40 years. Mark Hutker created an innovative design with an arc shape nautical theme so every room faces the water. The 3 second floor bedrooms enjoy large balconies and the first floor primary bedroom with separate sitting area opens to a nice deck and quiet garden sanctuary. The hand made luxury kitchen cabinetry and extensive woodworking were done by Smallbone, a British Company noted for time honored design and craftsmanship. Adding to this estate, reflecting decades of careful planning and development, is a lovely private pool and pool house, 4 room guest suite over the garage with large balcony, two stone wall enclosed specimen fruit tree meadows, a large field circled by a grand stone wall, an idyllic lily pond and 2 miles of private trails. Keep boats and small craft on your mooring at waters edge for a short trip to the 3,000 ft Boldwater private barrier beach. Boldwater is 38 homesites on 450 acres with 150 acres of conservation and abuts approximately 1,500 of additional conservation land and a few large estate. A most remarkable rural area convenient to town and the airport. (14.4 abutting acres with grand meadow on 3 Jacobs Neck Rd is available for purchase separately)

This distinguished Edgartown Great Pond compound presents an exceptional collection of features and amenities. Situated within a highly desirable, secluded enclave on Turkeyland Cove, the 4.8-acre property includes two residences, a bespoke private in-ground swimming pool, approximately 400 feet of waterfront, outstanding water views, and a private beach lot on the Atlantic Ocean. The principal dwelling offers four bedrooms, exquisite craftsmanship throughout, and a unique setting right along the water. The secondary residence was constructed in 2010 and spans 2,556 square feet, featuring two bedrooms, a three-car attached garage, and a full basement. The buildings are harmoniously integrated with meticulously designed plantings, landscape, and custom-built fencing and gates. The pool area provides a secluded oasis, with an L-shaped gunite swimming pool nicely complemented by two adjacent outbuildings. Expansive lawns gently slope towards the waterfront, and boat access to the Atlantic beach is readily available from the property shoreline. Held by the same owner for over three decades, this property represents an unparalleled opportunity.

This one of a kind property is extremely private, yet only 12 minutes to the airport or Edgartown Village. The 10+ acre parcel is bordered on two sides by Sheriff's Meadow Conservation land and miles of walking trails nearby. The dwellings and other structures are meticulously crafted and offer a range of possibilities. The "guest house" is 2300 sq ft with finished basement and loft space. The "barn" encompasses an 1,832 sq ft two bedroom, three and one-half bath apartment with fireplace, a 1,730 sq ft loft space with full bath, a multiple car garage with Tesla charger, and equipment room with counter and sink. The garage, loft and equipment room have red pine wall paneling. There is an exceptional 800 sq ft greenhouse and many other amenities are too numerous to list. This unique property is part of the Boldwater Association a sought after private enclave with use of the association tennis courts and deeded pond and Atlantic Ocean beach access across Edgartown Great Pond. The "barn" was built in such a way that it could be converted to an expansive single family home with a pool. This is a very special property with loads of potential. Call for a private showing of this one of a kind opportunity! FYI: First photo shows deeded pond access close-by to access the barrier beach on the south shore.

This classic New England home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room offers a serene retreat with ample natural light. The main living area is thoughtfully designed with an open concept layout, creating an ideal space for entertaining. A cozy fireplace and large windows enhance the ambiance, providing both warmth and captivating views of the lush surroundings. The french doors open to a deck overlooking the manicured lawn. A state-of-the-art media room, complete with comfortable seating, a large screen, and high-quality audio visual equipment. It's the perfect spot for movie nights, game days, or simply relaxing with friends and family along with a wine cellar just steps away. The carriage house features a three-car garage, providing ample space for your vehicles and storage needs including a large one bedroom and bath upstairs. Katama Bay View Road is located adjacent to Sheriffs Meadow Conservation land and public access to Katama Bay. Conveniently located near South Beach, one of Martha's Vineyard's most beautiful and sought-after beaches.

Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and custom cabinetry. The five spacious bedrooms are thoughtfully positioned throughout the home, providing unparalleled privacy and comfort. The main house features four private bedrooms with three full bathrooms and private balconies. The fifth bedroom is housed over the detached two-car garage. The detached two-car garage not only provides ample storage for vehicles but also features a private one-bedroom suite above, perfect for accommodating guests or serving as a tranquil home office space. The meticulously landscaped grounds are a true masterpiece, featuring a sparkling pool surrounded by a flagstone patio complete with an outdoor dining area and fire pit, making indoor and outdoor living seamless. This property offers both tranquility and convenience. Just moments away from the charming shops and restaurants of downtown Edgartown, and a short distance from the island's pristine beaches. A well rounded offering that should not be overlooked!

Located on prestigious Fuller Street, half a block from Fuller Street Beach lies this classically styled home. The home features an amazing family room/kitchen with an abundance of retractable glass doors facing the pool area and 2 fireplaces. There is a dining room, office, den and ground floor bedroom with private bath. The second-floor features two large en suite guest rooms and a cathedral ceiling primary bedroom with fireplace, walk in closet and expansive deck. The third floor offers a large multipurpose room with full bath. The lower level offers a game room, media room, powder room and additional bedroom with full bath. The grounds are meticulously landscaped and feature a pool, pool house with fireplace, exterior kitchen, dining pavilion and single car garage. All of the above is offered in excellent condition and tastefully decorated.

Uncover unparalleled Martha’s Vineyard opulence within a sprawling 9.8-acre estate. Immerse yourself in the timeless elegance and meticulous craftsmanship of the 7-bedroom | 10-bathroom main home, designed by the renowned architect, Robert A.M. Stern. From the grand foyer to the post & beam living room, each detail exudes sophistication. Revel in the warmth of multiple fireplaces and experience culinary delights in the superbly designed gourmet kitchen. This residence is a luminous haven, where natural light steals the spotlight. Step outside and discover a remarkable pool and pool house with a fully-equipped gym, sauna, and massage room. Located in the exclusive Boldwater Association, residents enjoy, tennis, pickleball, a boat landing, and a private Atlantic Ocean beach. An additional 11.97 acres is available separately.

Spectacular 35 acre Boldwater Association waterfront estate on Edgartown Great Pond with breathtaking views over 1,000 ft wide low brushy pond front terrain and across the 3/4 mile wide Lyles Bay, dreamy Swan Neck Point, the 1 1/2 mile wide main pond and barrier beach to the ocean beyond. The handful of well pruned trees on the property enhance the water views. The sophisticated and charming quality house was built by Andrew Flake, arguably the finest Vineyard builder over the last 40 years. Mark Hutker created an innovative design with an arc shape nautical theme so every room faces the water. The 3 second floor bedrooms enjoy large balconies and the first floor primary bedroom opens to a nice deck and quiet garden sanctuary. The handmade luxury kitchen cabinetry and extensive woodworking were done by Smallbone, a British Company noted for time honored design and craftsmanship. Adding to this estate, reflecting decades of careful planning and development, is a lovely private pool and pool house, 4 room guest suite over the garage with large deck, two stone wall enclosed specimen fruit tree meadows, a large field circled by a grand stone wall, a idyllic lily pond and two miles of private trails. Last but not least, are 14+ subdividable acres. Keep boats and small craft on your mooring at waters edge for a short trip to the 3,000 ft Boldwater private beach. Boldwater is 38 homesites on 450 acres with 150 acres of conservation and abuts approx. 1,500 acres of conservation lands and a few large estates. A most remarkable rural area convenient to town and the airport. (** The 20.8 acre 32 Boldwater Road waterfront property can be purchased without the abutting 14+ acres at 3 Jacobs Neck Road for $8,550,000)

NEW CONSTRUCTION - COMPLETED. POND FRONT on WINTUCKET COVE. The epitome of Luxury Living, yet understated. 6,343 sq.ft., 7 Bed, 9 Bath home, w/16 x 42 saltwater heated pool, 2 car garage & a dramatic over sized screened porch w/11ft high ceilings. Discover a beautiful Vineyard oasis on 9.2 acres of land on the South Shore w/346ft of shoreline. An expansive property, merging traditional & contemporary design, creating a warm, streamlined, elegant home. Huge living room w/fireplace flanked by two inviting alcoves for lounging/reading. Wall of glass doors leads to patio, yard, pool & down to a boardwalk on the Cove. Gourmet Kitchen w/large island, Quartz Counters, Thermador stainless appliances w/professional stove. Scullery w/additional fridge, dishwasher & sink. Quartz island w/contrasting cabinets which seats 6 comfortably. Adjacent dining room, with views towards the water, complete w/custom serving hutch. Hallway to oversized screened porch w/wood burning fireplace, or to a very bright Bonus Room w/multiple windows & doors leading to mahogany deck that directs you to the Gunite POOL & SPA. At the opposite end of the house, Ground Floor Primary Bedroom w/ensuite including soaking tub, shower, private outdoor shower enclosure & private deck. Upstairs you'll find another large suite w/private deck facing the water, WIC, writing area & huge bathroom w/double vanities. Two more guest suites nearby each w/private bathroom. Wonderful media room w/sumptuous seating & views over Wintucket Cove. Special reading nook on the way to super mahogany deck overlooking the pool, yard & Wintucket Cove. A 5th Private Suite finishes off this wing w/its own WIC & full private bathroom. Heading towards the 'East Wing', two guest bedrooms w/shared bathroom & a second laundry. A second staircase brings you down to a wonderful built-in mudroom, storage area & powder room. Mudroom leads to a huge very bright two car garage w/Tesla Charger & numerous windows. Expansion Possibilities included adding a Guest House, an accessory dwelling unit. Enjoy Swimming, Boating, Kayaking, Paddle boarding on Edgartown Great Pond, continue to Land Bank Beach, Atlantic Ocean & South Beach. Drive to Morning Glory Farm, Airport, Vineyard Golf & Downtown Edgartown. Potential Family Compound! Beautifully Furnished, contents may be purchased separately. Additional photos will be added!

This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive views of the South Shore. There are 5 suites all with luxurious bathrooms, closets, and private garden terraces. Additionally, there is an attached carriage house with 3 additional bedrooms, a billiards room and exercise room. The grounds offer a large, stunning pool, a 12 person Jacuzzi, outdoor kitchen, and parking courtyard. There is a high level of finish throughout, a whole house Lutron control system and advanced audio/video. Herring Creek Farm offers direct access to private South Shore beach and over 150 acres of conserved land.

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The main level features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscaped outdoor patio, ideal for al fresco dining and relaxation. Beyond the patio, a lush lawn and manicured gardens surround an impressive 42' x 18' swimming pool, creating a true outdoor oasis. The second level houses four spacious bedrooms, including a luxurious primary suite with an office, ensuite bath, and a private deck overlooking the pool. The third floor offers a large sleeping area with six twin beds, a full bath, a game area, and French doors leading to a sun-drenched deck. Perfect for family living or hosting guests, this home combines historic character with the finest modern conveniences. Located on North Water Street, this light-filled property is an exceptional opportunity to own a one-of-a-kind retreat in one of Edgartown’s most desirable locations.

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.

Move-In Ready – CONSTRUCTION COMPLETE - This 8-bedroom, 7.5-bath generational home, completed in 2025, is now fully furnished and move-in ready. The property includes a 6-bedroom, 5.5-bath main residence, seamlessly blending timeless elegance with modern comfort, along with a 1-bedroom, 1-bath guest house featuring its own kitchen, and a 2-car carriage house with a 1-bedroom, 1-bath living quarters. The private backyard oasis is designed for relaxation and entertainment, boasting a 16' x 32' saltwater pool and spa complemented with a pool cabana. This thoughtfully curated property is being offered fully furnished, ensuring effortless enjoyment from day one. While the window treatments for the main house are not pictured, they are included. Please note that the reported days on market reflect the construction and finishing period, and the certificates of occupancy have been issued. The property features a total gross square footage of 8,607 SF. This is a once-in-a-lifetime opportunity to own a truly extraordinary property in one of Edgartown's most desirable locations.

Exquisite Waterfront Retreat - A rare opportunity to purchase a meticulously crafted 5,600 square-foot stone main house and 900 square-foot stone guesthouse with pool in a naturalized wooded setting. This extraordinary compound redefines the conventions of traditional Vineyard architecture in the most charming and sophisticated of ways. The house was sited to offer views of Edgartown Great Pond and distant ocean views from almost every room and possesses a delightful mix of contemporary and modern features, such as geothermal and solar panels. The houses sit on nine acres of beautiful waterfront with 800 feet of sandy pond beach frontage. A 16’ Duxbury Dory with trailer in excellent condition included with the house, allowing you to explore the great pond and easily access Atlantic Ocean beach rights only 15 minutes away. In a private though convenient location only 12 minutes to the airport or Edgartown Village. This property may be purchased with 4 Jacobs Neck, if you need more space close-by for family and friends! Please call listing broker for details.