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

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56 North Summer Street

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SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and connection to the outdoors. 

The main living spaces are both dramatic and inviting, with high ceilings, skylights, and walls of glass that frame the ever-changing water views. A central staircase and classic columns define the space, with a decorative stone fireplace providing a natural focal point and warmth. 

A true chef’s kitchen is equipped with stainless steel appliances, expansive stone counter space, custom cabinetry and an oversized island. A wet bar featuring a beverage refrigerator and ice maker enhances the entertaining flow, while a more casual dining area provides a comfortable setting for hosting. 

The home includes three spacious ensuite bedrooms. The primary suite is privately situated and enjoys water views, direct access to the pool terrace, and a luxurious bath with soaking tub, double vanity, and glass-enclosed shower. Two additional en suite bedrooms are located on the second level, along with an open sitting area that overlooks the main living room below. Designed with entertaining in mind, the lower level features a billiards/game room, den, bonus room, kitchenette, wine storage, and flexible room for a gym or additional use. 

Outdoor living is a highlight of this fabulous property, with a heated pool and spa set within a bluestone terrace, and an outdoor kitchen area ready for your custom design and choice of appliances. This space is perfect under the open sky with multiple areas for lounging. The calm Lagoon waters are just steps away and offer ideal conditions for swimming, paddling, boating, and clamming, with the ability to secure a mooring. The Lagoon is known for some of the best steamers, littlenecks, and cherry stones on the Island. In fact, there is a huge clam bed in the Lagoon right behind the house off the private beach. 

Offered furnished, with a proven strong rental history, this property also enjoys a 2-car garage and is a rare offering combining privacy, comfort, and exceptional waterfront living.

385 Barnes Road

12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed  ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short  bike ride to the lighthouse.

12 Lobsterville Road

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

23 Calebs Common Lane

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 3,800 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.

62 North Summer Street

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 square feet of gracious living space.

The sunny, light-filled main house showcases an open kitchen and living area anchored by a striking central fireplace—ideal for both everyday year-round living and entertaining. An expanded primary suite wing includes a spacious primary bedroom, full bath, bright office, half bath, and dedicated laundry. A second-story space offers flexibility as an art studio, office, or media room.  A classic three-season living room invites relaxed enjoyment of the surrounding landscape, including distant winter waterviews.

Well-suited for compound living, the property is perfect for the equestrian and includes a guest house, horse barn, fenced pastureland, garage, and an old boat shed—providing exceptional flexibility for family, guests, and a wide range of outdoor pursuits. Deeded access to Chilmark Pond and South Shore Beach offers a rare opportunity to enjoy swimming, kayaking, and some of the Island’s most beautiful and unspoiled coastline. This property has a seven-bedroom septic, full solar, and abuts acres of conservation land.


Ideally located in the heart of Chilmark, the property is just minutes from Alley’s Store, Lucy Vincent Beach, Chilmark Tavern, Beetlebung Farm, the Chilmark Store, and more—perfectly capturing the essence of the Chilmark lifestyle and the very best of Vineyard living.

205 South Road

Introducing 3 Somerset Lane, one of 4 newly built residences in an exclusive new enclave in the heart of Katama.  This beautifully crafted new construction home, built by respected Island builder Adam Moran Construction, showcases nearly 4,000 square feet of thoughtfully designed living space, executed with the highest level of detail, craftsmanship, and timeless Vineyard style. The residence features 4 bedrooms and 5.5 baths, with elevated interiors designed for both comfort and sophisticated entertaining. Light-filled living spaces flow seamlessly throughout the home, complemented by high-end finishes and architectural details that reflect the quality and reputation of both the builder and the developer. Outdoor living will be equally inviting with a heated 16x32 Gunite pool and open-air cabana currently underway with a target completion date of July 1st to enjoy this summer!  The property also offers a spacious unfinished basement, providing the opportunity to create additional living spaces such as a recreation room, home theater, fitness studio, etc. An attached two-car garage adds convenience and functionality, completing this exceptional offering. Ideally situated between Edgartown Village and South Beach, Somerset provides easy access to the Field Club, the island’s finest dining, shops, harbor activities, and one of Martha’s Vineyard’s most beloved beaches. A rare opportunity to own new construction in a premier location. 

*Cover photo has been enhanced to show the property in bloom in the summer season.

3 Somerset Lane

Stunning waterview living with an active view that will never disappoint. Wake up every morning to breathtaking 180 degree water views in this beautifully appointed 4-bedroom, 3-bath coastal retreat. Perfectly situated to capture sunrise to sunset vistas, this home offers a blend of summer vibes with year-round living amenities. Step inside to find an open-concept living space filled with natural light,  lofty ceilings, and windows that frame the water views from all angles. The kitchen is clean, open and well designed with a large island—ideal for entertaining. The spacious primary suite has a full bath and private office which opens to the screened-in porch. On the main living level, there are two additional bedrooms that share a full bath.  The lower level is partially finished with a living area with ocean views, doors to the lawn and outdoor shower as well as a bedroom and full bath.
Enjoy morning coffee with ocean breezes and relaxing evenings watching the sun set while on this expansive deck or screened-in porch.
Whether you're looking for a year-round residence or a beachy summer escape, this property delivers ultimate waterviews with a current, clean home ready to be enjoyed. Don’t miss the chance to own one of the area's most desirable water view homes in a most impressive setting.

370 Lighthouse  Road

A rare opportunity to create your dream Vineyard estate in a unique setting with the rural feel of up-Island and the easy convenience of, and proximity to, Edgartown Village. Just a 1/2 mile walk, bike or drive to the top of Lower Main Street, the vacant lot rests on a private, dirt road off prestigious Planting Field Way.  The 1.79 acre, wooded lot has been partially cleared for an ideal building site, set on a level expanse about halfway up a gradual hill, providing additional privacy, quiet, and beautiful views. Rolling out in front and below are conservation wetlands (which can never be developed) in the foreground with glimpses of Eel Pond and Nantucket Sound in the near distance.  Access from both Lenssen Way and Eel Pond Lane provide exceptional flexibility for site planning, privacy, and design. With utilities already in place, it's the perfect canvas to bring your Vineyard vision to life. A truly rare chance to secure a significant parcel in one of Edgartown’s most desirable locations.  

Other notes: This classic Vineyard property has been owned by the same family for almost a century.
Easy walk to Sheriff’s Meadow nature reserve.

5 Lenssen Way & 63 Eel Pond Lane

Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its best. Set on 2.25 secluded acres, spectacular panoramic views stretch across the shimmering waters of Lagoon Pond, a private haven for kayaking, sailing, and peaceful exploration. The thoughtfully designed interior features four bedrooms and three full bathrooms, with generous windows framing breathtaking water views from nearly every room. A large family room/library, additional formal living room, and a private guest suite set apart on the far side of the residence offer ample space for homeowners and guests. Outside, the lawn sweeps to the water's edge, where a sandy shoreline invites you to launch a kayak, cast a line, or linger over a sunset picnic. Direct water access puts boating and paddling within easy reach. A detached three-car garage with a finished room above provides generous storage for watercraft, paddleboards, and all the trappings of Island adventure.
Just minutes from the shops, restaurants, and harbor are worlds away in feeling, yet close to the best of the Island. Note: Septic Passed Title V inspection, but buyer will need an enhanced de-nitrification septic system Per town of Tisbury regulations. Expansion to six bedrooms possible.

94 Weaver Lane

Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands.  The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by Heikki Soikkeli, the house is light filled with 140 windows so every room has windows on 3 of the 4 sides.  The house has 3 self contained bedroom wings and a stunning Lew French fireplace and chimney.  The property sits on a private 48 ft elevated 425 ft setback site in the highly desirable Spring Point community --  48 homeowners on 330 acres with 90 acres of common land, 2 tennis courts and 5 miles of quiet paths and pretty well maintained country dirt roads -- with the finest north shore bluff path along a 1 mile stunning private sandy beach abutting the dreamy Great Rock Bight Beach Cove next to the 200 acre Menemsha Hills Reservation. The house is a short walk on a grassy canopied path to the beach.  The living room, primary bedroom and kitchen have grand water views.

78 Hammett Road

Nestled within the serene landscape of Aquinnah, this 3.8-acre parcel offers a unique blend of natural beauty and historical significance. Bordered by ancient stone walls and mature vegetation, the elevated terrain provides a bucolic setting for a private residence. Already in place is a private well, 3-bedroom septic, and full engineering.

0 Jeffers Way

In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it!

37 Circuit Avenue 4

In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view of Downtown Oak Bluffs. Sit back and watch the boats come into the harbor at one of the many seating areas or enjoy diner al fresco under the stars. This spacious unit has many custom wooden features including a staircase leading to the rooftop deck creating a storage area and sleep nook with daybed. Take a step down to the comfortable living area. With hardwood floors throughout, the kitchen and dining area are divided with custom cabinetry. The spacious bedroom has an additional alcove area with pull down skylight, ideal for an exercise area or office. A tiled bathroom with full tub and shower can be entered off the hall or bedroom. A separate Laundry room is shared by 2 other units.

37 Circuit Avenue 5

Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The detached studio complete with loft, full bath, AC and 2 additional garage spaces is a private retreat for work, art, music, yoga or even for spill-over accommodations. The Chef’s kitchen boasts handcrafted cabinetry, naturally beautiful soapstone countertops, a professional Viking gas range and Miele dishwasher. The bathrooms feature custom built vanities with luxurious marble countertops and wainscoting surrounds each wall. Outside, a Zen-inspired garden, flowering hydrangea plants and a newly rebuilt oversized deck are perfect for small or large gatherings. Additional features include 2 wood-burning fireplaces, new mini-split units, 2 outdoor showers, optional base-board heating and hardwood floors throughout. Enjoy Association amenities like tennis, pickleball, kayak racks, community dock and moorings for larger boats. To truly make this a seamless transition to “Vineyard Life” the seller is open to including a Boston Whaler, a small sailboat, and an inflatable zodiac in the sale.

50 Hidden Cove Road

Set in the heart of Edgartown Village, this pristine Cape offers an exceptional combination of charm, comfort, and in-town convenience. Just moments from boutique shopping, acclaimed galleries, fine dining, and the scenic harbor, this four-bedroom, three-bath home captures the quintessential Vineyard lifestyle. Two entrances enhance the home’s functionality: a formal front entry leads directly to the inviting living room, while a casual back entrance opens to the bright, cheerful kitchen, complete with a built-in banquette dining area. The outstanding primary wing at the rear of the house features a separate entrance with French doors opening to a pergola patio. The suite boasts a cathedral-ceiling bedroom, a private sitting area, a full bath, and a kitchenette—perfect for extended guests or private retreats. The first floor also includes an additional full bath, a second bedroom, and a convenient laundry room. Upstairs offers a spacious primary bedroom, an additional bedroom, and a full bath. 
The beautifully landscaped backyard offers two patios, ideal for alfresco dining and entertaining. Completing this exceptional offering are a full basement, a storage shed, and a one-car garage with additional side-by-side parking. With effortless access to the Village, Sheriff’s Meadow scenic trails, and Fuller Street Beach, this home is a quintessential Edgartown charmer, combining location, elegance, and comfort in one exceptional package.

13 Plantingfield Way

Nestled on a private 1.7-acre parcel in the peaceful Bold Meadow neighborhood, this classic expanded Cape offers a perfect blend of comfort, space, and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from all that Edgartown has to offer.

The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a wood-burning fireplace and a separate TV/family room. The well-appointed kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar for casual dining. An eat-in area opens through sliding glass doors to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens.

The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level.

Upstairs, two guest bedrooms share a full bath, while a loft above the two-car garage provides flexible bonus space, currently used as an artist’s studio.

The home is served by a four-bedroom septic system, with the potential to expand to six bedrooms subject to Board of Health approval and installation of an enhanced system.

With easy access to nearby bike paths, pristine beaches, and the shops and restaurants of downtown Edgartown, this property offers an exceptional combination of location, privacy, and lifestyle.

2 Bold Meadow Road

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family.  Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area.  The first floor features Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet.  The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis.  The lower level consists of a finished bonus room, laundry, and a full bathroom with tub and storage area. This home and its established gardens have been lovingly maintained, and its location in a delightful neighborhood of highly sought-after East Chop, gives you all that Martha's Vineyard living can offer.  Passed Title V Inspection.

17 John Wesley Avenue

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