Dukes County MA Houses for Sale

/28
$1,250,000
- 4 Beds
- 2 Baths
- 1,820 Sq Ft
11 Flamingo Dr, Edgartown, MA 02539

Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living

Skip Dostal, Jr Martha's Vineyard Real Estate

11 Flamingo Dr, Edgartown, MA 02539
/99
$1,325,000
- 3 Beds
- 3 Baths
- 1,682 Sq Ft
261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

ASSOCIATION POOL, TENNIS, LAKE TASHMOO BEACH, PLUS GOLF NEARBY! This meticulously maintained 2+ bedroom, 3 bathroom end unit condo in the prestigious Tashmoo Woods Association has it ALL! The updated kitchen, with granite countertops and high-end appliances, opens to a dining room with access to a private deck overlooking lush woods. The living room, featuring a wood-burning fireplace,

Jen O'Hanlon Compass | The O'Hanlon Group

261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
/20
$3,750,000
- 4 Beds
- 2.5 Baths
- 1,800 Sq Ft
28 Beach Rd, Oak Bluffs, MA 02557

Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

Scott Lewis Lewis Real Estate Services, LLC

28 Beach Rd, Oak Bluffs, MA 02557
/35
$1,870,000
- 5 Beds
- 3 Baths
- 2,432 Sq Ft
32 Flamingo Dr, Edgartown, MA 02539

This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

Skip Dostal Martha's Vineyard R.E.

32 Flamingo Dr, Edgartown, MA 02539
/41
$7,950,000
- 5 Beds
- 7 Baths
- 3,762 Sq Ft
85 Reservoir Rd, Vineyard Haven, MA 02568

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

Alyssa Halisky Wallace & Co. Sotheby's International Realty

85 Reservoir Rd, Vineyard Haven, MA 02568
/17
$995,000
- 2 Beds
- 0.5 Baths
- 952 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
/31
$1,750,000
- 2 Beds
- 2 Baths
- 2,042 Sq Ft
15 Jernegan Pond Rd, Edgartown, MA 02539

Nestled at the end of a quiet drive, 15 Jernegan Pond Road offers the opportunity to create your Vineyard retreat. The existing home and small barn sit on a private and serene lot overlooking a small, picturesque pond -- an ideal setting for those seeking privacy, natural beauty, and potential. The current structures require significant renovation or rebuild, and with a sewer tie-in, can be

Lesley Heidt Sandpiper Realty Inc

15 Jernegan Pond Rd, Edgartown, MA 02539
/37
$1,995,000
- 4 Beds
- 3 Baths
- 3,058 Sq Ft
2 Farm Path, Oak Bluffs, MA 02557

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

Sean Federowicz Landmarks at TODAY Real Estate

2 Farm Path, Oak Bluffs, MA 02557
/32
$2,999,000
- 8 Beds
- 7.5 Baths
- 3,770 Sq Ft
72 Chappaquiddick Ave, Edgartown, MA 02539

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 COURT that doubles into TWO PICKLE BALL COURTS, and a BASKETBALL

Michele Casavant Vineyard Village Realty

72 Chappaquiddick Ave, Edgartown, MA 02539
/73
$13,995,000
- 7 Beds
- 9 Baths
- 6,343 Sq Ft
5 Briggs Rd, Edgartown, MA 02539

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/16ft x 42ft 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/376ft of frontage on Wintucket Cove. An expansive property, merging

Alisan Lohan-Conway Alisan Lohan-Conway Properties

5 Briggs Rd, Edgartown, MA 02539
/42
$19,900,000
- 8 Beds
- 7.5 Baths
- 6,041 Sq Ft
114 N Water St, Edgartown, MA 02539

The property is currently rented; showings require a minimum of 48 hours’ notice. Move-In Ready – CONSTRUCTION COMPLETE - This stunning 8-bedroom, 7.5-bath generational home, completed in 2025, is fully furnished and move-in ready. The property features a 6-bedroom, 5.5-bath main residence, a 1-bedroom, 1-bath guest house with its own kitchen, and a 2-car carriage house with 1-bedroom living

Erin Hegarty Compass

114 N Water St, Edgartown, MA 02539
/29
$2,500,000 Open Tue 11AM - 2PM
- 6 Beds
- 3.5 Baths
- 1,616 Sq Ft
34 Massasoit Ave, Oak Bluffs, MA 02568

Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to

Carleen Cordwell Anchor Realty of Martha's Vineyard

34 Massasoit Ave, Oak Bluffs, MA 02568
/27
$3,100,000
- 1 Bed
- 1 Bath
- 1,028 Sq Ft
114 Meeting House Way, Edgartown, MA 02539

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

Rose Ryley Sandpiper Realty

114 Meeting House Way, Edgartown, MA 02539
/28
$3,100,000
- 1 Bed
- 1 Bath
- 1,028 Sq Ft
114 Meeting House Way, Edgartown, MA 02539

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

Rose Ryley Sandpiper Realty Inc

114 Meeting House Way, Edgartown, MA 02539
/24
$2,195,000
- 4 Beds
- 3 Baths
- 2,262 Sq Ft
30 Sengekontacket Rd, Oak Bluffs, MA 02557

Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

Cassie Bradley Wallace & Co. Sotheby's International Realty

30 Sengekontacket Rd, Oak Bluffs, MA 02557
/59
$2,550,000
- 4 Beds
- 2.5 Baths
- 2,983 Sq Ft
157 Ben Chase Rd, West Tisbury, MA 02575

You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

Madelyn Silvia Wallace & Co. Sotheby's

157 Ben Chase Rd, West Tisbury, MA 02575
/32
$2,995,000
- 4 Beds
- 3 Baths
- 2,770 Sq Ft
36 Tashmoo Ave, Vineyard Haven, MA 02568

This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven's most quiet and quaint neighborhoods. With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also

Alyssa Halisky Wallace & Co. Sotheby's International Realty

36 Tashmoo Ave, Vineyard Haven, MA 02568
/39
$3,750,000
- 4 Beds
- 3 Baths
- 2,204 Sq Ft
9 Weston Ave, Oak Bluffs, MA 02557

This 4-bedroom / 3-bath home lies in the middle of East Chop at the highest point on the bluff offering expansive views of Vineyard Sound. The home features a large clear story living room with fireplace, a family room/kitchen also with fireplace, a huge screened porch opening up to a large deck area and a first floor bedroom with private bath. The 2nd floor offers two guest bedrooms and a master

Gerrett Conover Landvest MV

9 Weston Ave, Oak Bluffs, MA 02557
/12
$2,950,000
- 3 Beds
- 1 Bath
- 936 Sq Ft
9 N Neck Rd, Edgartown, MA 02539

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,

Leslie C. Floyd Portfolio Real Estate, Inc.

9 N Neck Rd, Edgartown, MA 02539
/46
$4,590,000
- 3 Beds
- 2.5 Baths
- 1,870 Sq Ft
4 Down Harbor Rd, Edgartown, MA 02539

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

Cheri Mason Landvest MV

4 Down Harbor Rd, Edgartown, MA 02539
/16
$6,700,000
- 8 Beds
- 9.5 Baths
- 6,229 Sq Ft
26 Curtis Ln, Edgartown, MA 02539

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.

Thomas Melone Thomas Melone

26 Curtis Ln, Edgartown, MA 02539
/38
$6,500,000
- 4 Beds
- 5.5 Baths
- 4,136 Sq Ft
10 Tilton Way, Edgartown, MA 02539

This newly built traditionally styled Greek Revival 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

Gerrett Conover Landvest MV

10 Tilton Way, Edgartown, MA 02539
/57
$3,200,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
70 Spring St, Vineyard Haven, MA 02568

NOW INCLUDING RARE 12,527 S.F. TOWN APPROVED BUILDING LOT ON WILLIAM STREET! 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, just two blocks to all the shops, restaurants, galleries, town beach,

June Flake Viewpoints

70 Spring St, Vineyard Haven, MA 02568
/23
$1,625,000
- 5 Beds
- 5 Baths
- 2,316 Sq Ft
345 North Rd, Chilmark, MA 02535

Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

Mark Jenkins Wallace & Co. Sotheby's International Realty

345 North Rd, Chilmark, MA 02535
/18
$15,950,000
- 6 Beds
- 9 Baths
- 1,320 Sq Ft
68 N Water St, Edgartown, MA 02539

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 SternMcCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details.Upon entering,

Thomas Wallace Wallace & Co. Sotheby's International Realty

68 N Water St, Edgartown, MA 02539
/27
$9,750,000
- 5 Beds
- 7 Baths
- 4,078 Sq Ft
1 Field Club Dr, Edgartown, MA 02539

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

Thomas Wallace Wallace & Co. Sotheby's

1 Field Club Dr, Edgartown, MA 02539
/24
$2,445,000
- 4 Beds
- 3.5 Baths
- 2,810 Sq Ft
4 High Meadow Ln, Oak Bluffs, MA 02557

Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

Brian Smith Portfolio Real Estate Inc.

4 High Meadow Ln, Oak Bluffs, MA 02557
/42
$4,150,000
- 4 Beds
- 3.5 Baths
- 3,552 Sq Ft
4 Boldwater Rd, Edgartown, MA 02539

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

Thomas Wallace Wallace & Co. Sotheby's International Realty

4 Boldwater Rd, Edgartown, MA 02539
/30
$1,999,000
- 4 Beds
- 3 Baths
- 2,730 Sq Ft
5 Pine Tree Ln, Vineyard Haven, MA 02568

Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

Alyssa Halisky Wallace & Co. Sotheby's International Realty

5 Pine Tree Ln, Vineyard Haven, MA 02568
/43
$16,500,000
- 4 Beds
- 4.5 Baths
- 3,705 Sq Ft
64 Squibnocket Farm Rd, Chilmark, MA 02535

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore.Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

Thomas Wallace Wallace & Co. Sotheby's

64 Squibnocket Farm Rd, Chilmark, MA 02535
/51
$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
/49
$849,000
- 1 Bed
- 1 Bath
- 803 Sq Ft
26 Winthrop Ave, Oak Bluffs, MA 02557

Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

Alisan Lohan-Conway Alisan Lohan-Conway Properties

26 Winthrop Ave, Oak Bluffs, MA 02557
/47
$5,750,000
- 4 Beds
- 4.5 Baths
- 3,643 Sq Ft
4 Somerset Ln, Edgartown, MA 02539

MOVE-IN READY: LUXURY ISLAND LIVING AT SOMERSETConstruction is now complete at Four Somerset Lane—a brand-new residence in an exclusive enclave of just five luxury homes, perfectly situated between Edgartown Village and South Beach. Developed by Stanmar, owners of the renowned Winnetu Oceanside Resort, Somerset blends modern coastal design with timeless island charm.Designed by

Wendy Harman Compass | Point B

4 Somerset Ln, Edgartown, MA 02539
/24
$2,150,000
- 2 Beds
- 2.5 Baths
- 2,137 Sq Ft
30 Franklin Ave, Oak Bluffs, MA 02568

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

Stacy Ickes Donnelly + Co.

30 Franklin Ave, Oak Bluffs, MA 02568
/9
$1,445,000
- 0.5 Baths
- 1,283 Sq Ft
4 Lagoon Pond Rd, Vineyard Haven, MA 02568

Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

Jarrett Hurwitz Keller Williams Realty

4 Lagoon Pond Rd, Vineyard Haven, MA 02568
/24
$2,095,000
- 4 Beds
- 3.5 Baths
- 2,413 Sq Ft
46 Red Buoy Ln, Tisbury, MA 02568

Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space. The main level boasts a thoughtfully designed floor plan

Andrew McElhinney Compass LLC

46 Red Buoy Ln, Tisbury, MA 02568
/83
$5,905,000
- 4 Beds
- 4.5 Baths
- 3,809 Sq Ft
62 N Summer St, Edgartown, MA 02539

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

Martha Smith C McManus Realty Group

62 N Summer St, Edgartown, MA 02539
/27
$3,350,000
- 3 Beds
- 2 Baths
- 1,562 Sq Ft
11 Greenhouse Ln, Chilmark, MA 02535

11 Greenhouse Lane...an incredible opportunity to own in this sought after private enclave with deeded private south shore beach and pond access close by...this charming vintage cape enjoys views over wetlands out to the Atlantic beyond! Three bedrooms, two baths, living room with fireplace, dining area, updated kitchen, screened porch and outside shower. The owners have taken full advantage of

Deb Hancock Hancock Real Estate

11 Greenhouse Ln, Chilmark, MA 02535
/46
$3,500,000
- 4 Beds
- 2.5 Baths
- 2,383 Sq Ft
100 Gosnolds Way, Chilmark, MA 02535

Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where

Julianna Flanders Flanders Real Estate

100 Gosnolds Way, Chilmark, MA 02535
/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

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