Dukes County MA Homes for Sale

/44
$2,599,000
- 6 Beds
- 4 Baths
- 2,400 Sq Ft
111 Eastville Ave, Oak Bluffs, MA 02557

PRICE REDUCTION! Just steps from the beach and minutes to downtown Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal home offers an unbeatable location and a proven rental history. Set on an oversized lot just two parcels from the beach, the residence features six bedrooms and four bathrooms, providing generous space for family, friends, or guests. Enjoy sweeping 180 water

Ed Charter Arrowhead Homes

111 Eastville Ave, Oak Bluffs, MA 02557
/74
$14,500,000
- 6 Beds
- 5 Baths
- 4,964 Sq Ft
825 Main St, Vineyard Haven, MA 02568

Set on 1.75 acres this waterfront home features 200+/- feet of sandy beach on the outer harbor in the community of West Chop. Upon entering the home, the stunning view of the outer harbor and Nantucket Sound is breathtakingly beautiful. Perfect for hosting large parties or intimate family gatherings the spacious living room spills onto the large deck through two sets of French doors. Gleaming

Judy Federowicz Landmarks at TODAY Real Estate

825 Main St, Vineyard Haven, MA 02568
/51
$3,995,000
- 4 Beds
- 4 Baths
- 4,920 Sq Ft
56 N Neck Rd, Edgartown, MA 02539

A RARE CHAPPAQUIDDICK LEGACY ESTATE w/BEACH ACCESS -- Privacy & Island Living at its finest. Step into a world where time slows, ocean breezes carry the scent of salt and cedar, and each day begins and ends with the relaxing sounds of the local fauna and the Vineyard Sound. This 18.4-ac. multi-residence estate, with 4 conforming size parcels, on Martha's Vineyard's treasured Chappaquiddick Island

Leslie Floyd Portfolio Properties

56 N Neck Rd, Edgartown, MA 02539
/27
$1,900,000
- 4 Beds
- 4 Baths
- 2,202 Sq Ft
2 Farmers Rd, Edgartown, MA 02539

This house and guesthouse combination are situated in a very special location. Located equidistant between town and South Beach. The neighboring properties are quite impressive. Across the lane is over 28 acres of Edgartown Conservation Commission land. The property currently has two dwellings, a three bedroom main house and a one bedroom guesthouse. A separate toolshed has an additional finished

Neal Stiller Cronigs Real Estate

2 Farmers Rd, Edgartown, MA 02539
/2
$674,000
- Land
- 0.49 Acre
- $1,375,510 per Acre
56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568

Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either

Marilyn Moses Ocean Park Realty Inc

56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568
/6
$1,595,000
- Land
- 3.2 Acres
- $498,438 per Acre
9 Beach Pebble Rd, Vineyard Haven, MA 02568

Vacant land in West Tisbury's Makonikey Community with access to the beautiful Lower Makonikey Association beach. This rare offering spans over 3 acres, with a 1.4-acre area providing the ideal location for a substantial residence in keeping with the distinguished homes that define this exclusive neighborhood. This property presents a unique opportunity to create an exceptional island retreat.

Cassie Bradley Wallace & Co. Sotheby's International Realty

9 Beach Pebble Rd, Vineyard Haven, MA 02568
/4
$474,000
- Land
- 0.55 Acre
- $861,818 per Acre
11 Boylston Dr, Edgartown, MA 02539

A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island's top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

Alyssa Halisky Wallace & Co. Sotheby's International Realty

11 Boylston Dr, Edgartown, MA 02539
/73
$6,495,000
- 7 Beds
- 5.5 Baths
- 4,730 Sq Ft
180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568

A storybook sanctuary in Pilot Hill. For the first time in 37 years, one of the rarest and most beautiful properties within Pilot Hill Farm is being offered for sale.Set on nearly eight acres, this unique estate includes a thoughtfully renovated antique farmhouse and several distinctive outbuildings: a pool, guest house, an art studio, and a carriage house with room for three cars, plus a

Alexis Holden Tea Lane Associates

180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
/47
$5,500,000
- 4 Beds
- 2 Baths
- 2,808 Sq Ft
31 Butlers Cove Rd, Edgartown, MA 02539

This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft of private Atlantic

Gerrett Conover Landvest MV

31 Butlers Cove Rd, Edgartown, MA 02539
/33
$8,900,000
- 4 Beds
- 8 Baths
- 7,767 Sq Ft
4 Jacobs Neck Rd, Edgartown, MA 02539

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

Deb Hancock Hancock Real Estate

4 Jacobs Neck Rd, Edgartown, MA 02539
/39
$10,500,000
- 8 Beds
- 6 Baths
- 3,888 Sq Ft
47 E Chop Dr, Oak Bluffs, MA 02568

East Chop waterfront - Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its

Perry Patterson MV Luxury Homes, LLC

47 E Chop Dr, Oak Bluffs, MA 02568
/26
$1,900,000
- 3 Beds
- 2.5 Baths
- 1,784 Sq Ft
12 Lobsterville Rd, Aquinnah, MA 02535

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

Tina Palmer Conroy & Company R.E., Inc.

12 Lobsterville Rd, Aquinnah, MA 02535
/27
$5,250,000
- 4 Beds
- 3.5 Baths
- 3,018 Sq Ft
9 Fowler Ave, Edgartown, MA 02539

Edgartown Waterfront - Classic New England architecture meets the timeless allure of Martha’s Vineyard. This exceptional waterfront estate is set on the edge of Sengekontacket Pond, offering a sandy shoreline, panoramic water views, and a private mooring — the perfect setting for boating, paddle boarding, fishing, and clamming.A gated entrance opens to a beautifully landscaped property

Andrew McElhinney Compass LLC

9 Fowler Ave, Edgartown, MA 02539
/68
$4,395,000
- 3 Beds
- 5.5 Baths
- 4,046 Sq Ft
267 Barnes Rd, Oak Bluffs, MA 02557

Live the Dream on Martha’s Vineyard! Whether you're seeking a year-round residence or a seasonal escape, this is a once-in-a-lifetime opportunity to own a piece of paradise. Step into a world of coastal luxury with 163 feet of pristine Lagoon frontage, complete with your own private sandy beach. Nestled on 1.25 acres of lush, landscaped paradise, this rare gem offers sweeping lawns, panoramic

Stephanie Roache Donnelly + Co

267 Barnes Rd, Oak Bluffs, MA 02557
/33
$3,895,000
- 4 Beds
- 2.5 Baths
- 2,243 Sq Ft
44 Plantingfield Way, Edgartown, MA 02539

Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round property offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. The property is currently configured as a three-bedroom, 1-1/2 bathroom main house with a 1BR/1BA accessory apartment over a one-car, detached garage on a

David Dickinson Compass

44 Plantingfield Way, Edgartown, MA 02539
/4
$1,950,000
- Land
- 1.1 Acres
- $1,771,278 per Acre
5 Weaver Ln, Tisbury, MA 02568

This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful

Gerrett Conover Landvest MV

5 Weaver Ln, Tisbury, MA 02568
/2
$1,250,000
- 1 Bed
- 1 Bath
- 855 Sq Ft
0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

Peyton Wallace Studio Realty

0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
/28
$2,825,000
- 5 Beds
- 2 Baths
- 2,386 Sq Ft
187 Lagoon Pond Rd, Vineyard Haven, MA 02568

For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal.Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly

Erin Leighton Compass

187 Lagoon Pond Rd, Vineyard Haven, MA 02568
/16
$1,149,000
- 3 Beds
- 2 Baths
- 1,596 Sq Ft
96 Manchester Ave, Oak Bluffs, MA 02557

Nestled in a quiet neighborhood less than two miles from the heart of Circuit Avenue, this contemporary cape-style home is ready to welcome you. A charming farmer's porch invites you into a spacious living area with cathedral ceilings and an open-concept design that seamlessly connects the kitchen, dining, and living spaces--perfect for gathering with family and friends. The main level features a

Michele Moore Island Real Estate

96 Manchester Ave, Oak Bluffs, MA 02557
/26
$8,500,000
- 4 Beds
- 6 Baths
- 5,884 Sq Ft
24 Katama Bay View Rd, Edgartown, MA 02539

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

Thomas Wallace Wallace & Co. Sotheby's

24 Katama Bay View Rd, Edgartown, MA 02539
/39
$2,495,000
- 4 Beds
- 3 Baths
- 2,562 Sq Ft
21 Woodlawn Ave, Vineyard Haven, MA 02568

Experience the perfect blend of coastal charm and modern sophistication in this beautifully designed Vineyard Haven home. Ideally situated in-town, this 4-bedroom, 3-bath home offers a comfortable, easy flowing layout, complemented by gleaming hardwood floors and a warm, inviting atmosphere. Located just a short stroll from the ferry, vibrant shops, restaurants and the Vineyard Haven Yacht Club,

Beth Welch Viewpoints

21 Woodlawn Ave, Vineyard Haven, MA 02568
/9
$2,250,000
- 3 Beds
- 3.5 Baths
- 2,475 Sq Ft
35 Double Ox Rd, Oak Bluffs, MA 02557

Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

Marilyn Moses Ocean Park Realty Inc

35 Double Ox Rd, Oak Bluffs, MA 02557
/31
$7,250,000
- 5 Beds
- 6.5 Baths
- 5,454 Sq Ft
54 Fuller St, Edgartown, MA 02539

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

Gerrett Conover Landvest MV

54 Fuller St, Edgartown, MA 02539
/9
$2,000,000
- Land
- 1.28 Acres
- $1,562,500 per Acre
5 Louis Field Rd Unit 121.3, Edgartown, MA 02539

CREATE YOUR LEGACY ISLAND RETREAT IN THIS IDYLLIC LOCATION. Nestled within the entrance to Sweetened Water Farm, this 1.28-acre parcel represents a rare opportunity to create your own vision within one of Edgartown’s most sought-after settings. Located just one mile from the heart of historic Edgartown Village, this beautifully sited lot offers the ideal balance of privacy and proximity,

Wendy Harman Compass | Point B

5 Louis Field Rd Unit 121.3, Edgartown, MA 02539
/15
$5,100,000
- Land
- 2.34 Acres
- $2,182,285 per Acre
7 Overview Ln Unit 47, Oak Bluffs, MA 02557

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy

Alyssa Halisky Wallace & Co. Sotheby's

7 Overview Ln Unit 47, Oak Bluffs, MA 02557
/8
$725,000
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568

Enjoy effortless year-round living with easy access to Vineyard Haven's downtown shops, restaurants, the harbor, ferry, and nearby beaches. Bright and inviting first-floor three-bedroom, two-bath condo in the sought-after Causeway Harborview association. The association offers practical amenities--including a shared pool, ample storage, and on-site laundry--that support a comfortable lifestyle in

Emma Kennedy Sandpiper Realty Inc

124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
/27
$2,400,000
- 3 Beds
- 3.5 Baths
- 1,884 Sq Ft
27 7th St N, Edgartown, MA 02539

27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with

Michele Casavant Vineyard Village Realty

27 7th St N, Edgartown, MA 02539
/15
$5,100,000
- Land
- 2.34 Acres
- $2,179,487 per Acre
7 Overview Ln, Oak Bluffs, MA 02557

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

Alyssa Halisky Wallace & Co. Sotheby's International Realty

7 Overview Ln, Oak Bluffs, MA 02557
/42
$2,150,000
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
33 Lagoon Pond Rd, Vineyard Haven, MA 02568

Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

Madelyn Silvia Wallace & Co. Sotheby's International Realty

33 Lagoon Pond Rd, Vineyard Haven, MA 02568
/3
$2,100,000
- 3 Beds
- 3.5 Baths
- 2,019 Sq Ft
2 Hope's Way, Oak Bluffs, MA 02557

ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Purchase lot ($700,000)& Execute a BUILDING CONTRACT ($1,400,000 )or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty

Marilyn Moses Ocean Park Realty Inc

2 Hope's Way, Oak Bluffs, MA 02557
/22
$970,000
- 2 Beds
- 0.5 Baths
- 953 Sq Ft
50 Canonicus Ave, Oak Bluffs, MA 02557

Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

Michele Moore Island Real Estate

50 Canonicus Ave, Oak Bluffs, MA 02557
/20
$850,000
- 2 Beds
- 1 Bath
- 834 Sq Ft
21 Clay Pit Rd, Edgartown, MA 02539

EDGARTOWN COTTAGE ON A COUNTRY LANE - Nestled on a spacious .56-acre lot in the Lily Pond District, this charming 2-bedroom, 1-bath cottage offers a rare opportunity to create your own Island haven. Renovate or build to suit just a short distance from all that Edgartown village has to offer — shops, restaurants, harbor, and beaches — you’ll enjoy both privacy and convenience in one of the

Leslie C. Floyd Portfolio Real Estate, Inc.

21 Clay Pit Rd, Edgartown, MA 02539
/67
$2,300,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
70 Spring St, Vineyard Haven, MA 02568

Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

June Flake Viewpoints

70 Spring St, Vineyard Haven, MA 02568
/51
$9,499,000
- 4 Beds
- 7 Baths
- 5,458 Sq Ft
43 Peases Point Way S, Edgartown, MA 02539

Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

Katherine Donahue Sandpiper Realty Inc

43 Peases Point Way S, Edgartown, MA 02539
/14
$4,950,000
- Land
- 14.4 Acres
- $343,750 per Acre
3 Jacob's Neck Rd Unit 2, Edgartown, MA 02539

Build your dream home or homes on a special two lot 14+ acre private wooded property surrounding a beautiful 4.5 acre meadow in the grand Boldwater Association (BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

Robert Kenney Tea Lane Associates

3 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
/26
$1,345,000
- 3 Beds
- 1 Bath
- 1,150 Sq Ft
9 Galway Rd, Vineyard Haven, MA 02568

Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

Julianna Flanders Flanders Real Estate

9 Galway Rd, Vineyard Haven, MA 02568
/39
$3,500,000
- 3 Beds
- 4 Baths
- 2,500 Sq Ft
27 Clambelly Rd, Chilmark, MA 02535

A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

Julianna Flanders Flanders Real Estate

27 Clambelly Rd, Chilmark, MA 02535
/34
$1,625,000
- 2 Beds
- 2.5 Baths
- 1,532 Sq Ft
26 Union St Unit 7, Tisbury, MA 02568

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower. Also on

Alyssa Halisky Wallace & Co. Sotheby's International Realty

26 Union St Unit 7, Tisbury, MA 02568
/45
$1,600,000
- 4 Beds
- 3 Baths
- 1,738 Sq Ft
10 Dory Cir, Edgartown, MA 02539

Edgartown Village Opportunity – Main House & New Guest CottageTucked just off Upper Main Street, this unique Edgartown property offers exceptional flexibility with two dwellings—perfect for personal use, rental income, or a combination of both. The main house has been thoughtfully updated with numerous improvements, including a new kitchen, renovated bath, upgraded electrical, and HVAC

Stacy Ickes Donnelly + Co

10 Dory Cir, Edgartown, MA 02539
/28
$10,500,000
- 7 Beds
- 6 Baths
- 3,888 Sq Ft
47 E Chop Dr, Oak Bluffs, MA 02568

East Chop direct waterfront – Enjoy the ultimate. in waterfront living experiences. Features 6 bedrooms, spectacular water views, dock with 9 slips, and just steps from beaches, tennis club, downtown and ferries to mainland! Property has been extensively renovated recently. Uses include -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion,2.) Currently

Perry Patterson MV Luxury Homes LLC

47 E Chop Dr, Oak Bluffs, MA 02568

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