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.

Great STARTER HOME in EDGARTOWN! The house itself was modular built BRAND NEW just under 7 years ago, so everything is plum, level, well insulated and updated. Featuring 2 beds and 2 baths on the first level, with a unfinished full walk-out basement and unfinished upstairs office space. Lots of room to spread out inside. Just under 1/4 acre lot near Edgartown Vineyard Haven Road, only a 5 minute drive to downtown Edgartown and only 5 miles from South Beach. Despite the turn-key nature of this house and parcel, the property is being sold as is.

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.

READY TO BUILD: MODERN LUXE RETREAT WITH POOL. Create your signature island home with this unique ready-to-build opportunity. This expansive half-acre lot is one of the last remaining vacant parcels in the sought-after Edgartown Estates area -- and included in the offering are full architectural plans by Lauren and Nate Morgan, the husband-and-wife design team at Morgan Studio, showcasing a custom modern, chic and stylish 3,674-square-foot home with a pool. There is an approved 3-bedroom septic design featuring advanced treatment, ensuring a seamless transition from vision to reality as you build your new home. Edgartown Estates is ideally situated to provide convenient access to the pristine shores of Katama/South Beach and charming Edgartown Village. Don't miss this exceptional opportunity to build a home that reflects your style and sophistication in one of Edgartown's most desirable neighborhoods. Note: Architectural plans attached; buyer to obtain building permit,.

Edgartown opportunity—Finish off the seller's vision or create your own masterpiece! With over an acre of land, there is plenty of room to expand. Only two miles from lively downtown Edgartown, you get the privacy, beauty, and feel of the up-island without the commute. The lot can support a house, guest house, garage, and pool. Please no drive-bys.

Sited on a pleasantly landscaped lot in sought-after Edgartown Estates, this desirable Katama location is equidistant between the Village and South Beach, with easy access to the bike path and proximity to Morning Glory Farm. 87 Schoolhouse Road is a charming gem with two large primary suites, loads of natural sunlight, a cathedral-ceiling living room, and slider doors off the kitchen to a patio for outdoor enjoyment. This pristine move-in ready home with a full basement and AC has been loving maintained with many updates including a new roof, shingling, a new furnace, new irrigation and professional landscpaing. This fabulous offering enjoys all the components of a Vineyard dream home. Being sold furnished this property is not to be missed!

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.

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.

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”.

Ocean views - Nestled on a quiet corner lot, this classic beach house offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain. It is only 1.5 miles to South Beach and just under 2 miles to the heart of Edgartown village. The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus an 2 additional bedrooms and full bathroom. For 30 years the property has been a generational meeting place for the owners, their family, and friends, and now they are passing the baton on to its future owners. Enjoy it “as is” or put your vision to work to create a brand new Katama beach house to make your own memories.

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!

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.

Experience luxury living at 1 Marchants Path, a spacious and modern home with classic coastal charm in downtown Edgartown. BRAND NEW hardwood flooring in the expansive primary suite and hardwood throughout. Boasting spacious living areas, a gourmet kitchen with stainless appliances and Quartz countertops and island eat-in. Beautifully appointed outdoor living perfect for relaxation, covered Mahogany deck with Teak furnishings and two outdoor showers. Detached artist shed. Attached one-car garage. Conforming 1/2 acre parcel with connected town wastewater allow for expansion with approvals. Located near Edgartown beaches, shops, and dining, this home offers unmatched convenience and privacy.

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.

EDGARTOWN - NEW CONSTRUCTION with POOL - 6 Bedrooms...in Two Structures.....Plus a 31'6" x 14' heated saltwater pool! 5 Bedroom Main House with 4.5 Bathrooms. Detached 1 bedroom w/Full Bathroom over a Two (2) car garage. Main house has a lovely open floor plan with a large kitchen w/Bosch® Stainless Steel Appliances, beautiful Soapstone Island and Carrara Marble counters, a dining room, additional breakfast area and a living room w/fireplace flanked by built in shelves. Living area leads through French Doors to a large mahogany deck, that continues the length of the rear of the house and incorporates a private deck outside the ground floor private suite! Step off the deck directly onto the patio surrounding the saltwater pool and custom outdoor wood burning Fireplace! Lovely hardscape and dramatic landscaping. Back inside, Four more bedrooms upstairs, two (2) are private suites, plus two (2) guest rooms that share a full bathroom. DETACHED BEDROOM: 368 sq.ft. One bedroom with a FULL PRIVATE BATH, which is the Sixth (6th) Bedroom and Fourth (4th) Suite, a 'getaway space', over a two car Garage. Garage has potential for expansion to become and ADU - Accessory Dwelling Unit - with appropriate permits and approvals. Minutes to Farm Neck Sanctuary, short distance to Sengekontacket Pond and Downtown Edgartown, quick trip to Farm Neck Golf or Edgartown Golf. DAYS ON MARKET INCLUDE BUILDING PERIOD.

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.

Located at the end of Sweetened Water Farm, on nearly 5-acres, lies this property with incredible and expansive views across open fields to the horse pasture and barn. There is a 5-bedroom, 3-bath main house featuring an open floor plan, a screened porch and spacious deck. Additionally, there is a 6-stall horse barn with a large one-bedroom apartment above. The peaceful and quiet setting is complimented with stone walls, gardens and large expanses of manicured lawns. This is a very special offering which is in great condition and wonderful as it stands, but could be reimagined to create an extraordinary family compound in a country setting, all within minutes to downtown Edgartown.

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.

Situated just steps from South Beach and Norton Point, 5 Dunes Road offers an unbeatable location and unlimited possibilities. This unique property features a total of 7 bedrooms, including a 3-bedroom main house, a 3-bedroom guest house, and a detached oversized two-car garage with an additional bedroom above. The thoughtful layout of the two homes allows for a variety of rental and living options. Whether you choose to rent the homes out together or separately, both guests and owners will enjoy ample privacy. The expansive private lot enhances the potential of this Katama compound, providing plenty of space for outdoor activities, gatherings, or even the opportunity to expand and create your dream retreat. Come experience seaside living in Edgartown’s premier location.

This custom Gambrel-style home sits high atop Manaca Hill on Chappaquiddick Island with views of Edgartown Harbor and Katama Bay. The first-floor features hardwood floors throughout, tall ceilings and lots of windows to maximize the views. Enjoy the spacious open kitchen with top of the line appliances, a large center island and soapstone countertops. Perfect for entertaining, the area opens up to a sunny living room with fireplace and French doors leading out to the terrace. A formal dining room, laundry room, powder room and den with custom woodwork complete the first floor. All three-bedroom suites are on the second floor with luxurious private baths. The large, screened porch with fireplace and lounge seating is the perfect spot for morning coffee or a glass of wine before dinner. You will have the pleasure of spending your day on the private association beach just a short walk from the house, and the Chappy Ferry is also nearby for a quick run into Edgartown Village.

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*

The Katama General Store, fondly known as the "Heartbeat of Katama," has been a beloved community landmark on Martha’s Vineyard since 1995. Reestablished with a new building in 2017, this store is ideally located just a half-mile from historic downtown Edgartown and close to South Beach, making it a vital stop for locals and tourists alike. Offering a fully equipped commercial kitchen and modern retail space with over 2,000 square feet on the ground level featuring a vaulted ceiling and abundant natural light. The upper and main levels offer bright, spacious prep, office and storage space. The property also offers extensive outdoor amenities, including a covered 1,800 square-foot wraparound porch and 4,300 square-foot landscaped picnic event area with 25 dedicated parking spaces. This property combines historic charm with robust operational capability. This property is a true community hub, offering local produce, gourmet foods, and specialty items, and serving as a gathering place for the Edgartown area. The opportunity also includes a seasonal wine and beer license that is transferable to the new owner upon approval from the Town of Edgartown, adding further value for expanding the business's offerings. This sale includes all commercial equipment, fixtures, and furnishings, creating a seamless path for the next owner to continue building on the Katama General Store's 22-year legacy. Own a piece of Martha’s Vineyard history with a property poised for continued growth, community engagement, and connection.

The Katama General Store, fondly known as the "Heartbeat of Katama," has been a beloved community landmark on Martha’s Vineyard since 1995. Reestablished with a new building in 2017, this store is ideally located just a half-mile from historic downtown Edgartown and close to South Beach, making it a vital stop for locals and tourists alike. Offering a fully equipped commercial kitchen and modern retail space with over 2,000 square feet on the ground level featuring a vaulted ceiling and abundant natural light. The upper and main levels offer bright, spacious prep, office and storage space. The property also offers extensive outdoor amenities, including a covered 1,800 square-foot wraparound porch and 4,300 square-foot landscaped picnic event area with 25 dedicated parking spaces. This property combines historic charm with robust operational capability. This property is a true community hub, offering local produce, gourmet foods, and specialty items, and serving as a gathering place for the Edgartown area. The opportunity also includes a seasonal wine and beer license that is transferable to the new owner upon approval from the Town of Edgartown, adding further value for expanding the business's offerings. This sale includes all commercial equipment, fixtures, and furnishings, creating a seamless path for the next owner to continue building on the Katama General Store's 22-year legacy. Own a piece of Martha’s Vineyard history with a property poised for continued growth, community engagement, and connection.

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.

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 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!

CASUAL ELEGANCE ON KATAMA BAY. Welcome to 25 Lelands Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappaquiddick. This magnificent home, nestled at the end of a private winding drive on 16.4 private acres, offers over 7,200 square feet of living space, designed for the ultimate luxury of spending treasured time with family and friends. As you step inside, you'll be greeted by the warmth of four wood-burning fireplaces, handsome hardwood and painted floors, custom millwork and built-ins, a spacious screened porch and more! The rooftop widow's walk provides breathtaking 360-degree views, while the sparkling blue waters of Katama Bay can be seen and enjoyed from most every room in the house This welcoming retreat features six bedrooms, all with en suite baths, including an exquisite three-room Owner's Suite with en suite bath, adjoining den/office, sweeping water views, and a private second-floor deck. Additionally, there is a three-room Family Suite on the second floor, complete with its own private living area and kitchenette. The combined screened and covered porch, which extends nearly the full length of the home and overlooks Katama Bay, is a defining feature of the property, providing ample space for al fresco summer meals, reading, playing games, or simply soaking in the brilliant evening sunsets. With over 320 feet of frontage on Katama Bay, this home offers ample opportunities for sailing, boating, paddleboarding, fishing, and clamming. Embrace the tranquility of life on Chappy, surrounded by sand dunes, tidal ponds and grassland habitats, with access to miles of unspoiled beaches and nature trails. There is an attached 3-bay garage for storing all your recreational gear including your island car, watercraft, bicycles, beach equipment and fishing gear! The home was designed by architect Patrick Ahearn and is being offered turnkey, including hand-selected furnishings and accessories by interior designer Jon Hattaway of MJ Berries Design in Boston, adding objects and vibrant colors that delight the eye in every room. Enjoy this beautiful property as-is or bring your own design style and create your signature coastal haven. Discover the perfect blend of casual elegance and serene waterfront living at this stunning Chappy waterfront retreat on Katama Bay.

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 captain’s home built in 1850 lies on a double sized lot with expansive views of Edgartown Lighthouse and the entrance to the harbor. The home went through a full renovation years ago, updating the kitchen, bathrooms, opening up the floor plan and freshening all surfaces, while maintaining much of the original historic features. The street level of the home features an open floor plan with kitchen, family room, dining and living room, all which open up to an enormous exterior deck and enjoying incredible views. The second floor features a master suite with private bath and three additional bedrooms sharing two baths. There is a finished, cathedral ceiling third floor that could be used as additional bedrooms or recreational usages. The lower level offers two additional bedrooms, a full bath, living area and laundry. There is a guest house set on the lower lawn offering one bedroom, a full bath, living room with kitchenette and a charming, covered porch with direct views of the harbor. The property offers ample parking, beautiful landscaping and a huge front lawn which stretches to the harbors edge with sandy shoreline and a deep-water pier. A very rare opportunity to acquire a significant waterfront home on Edgartown’s inner harbor and with an exclusive North Water Street address.

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.