Dukes, MA Homes

/13
$6,750,000
- Land
- 2.11 Acres
- $3,199,052 per Acre
5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

Deb Levin Studio Realty

5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
/19
$17,600 per month
- 4 Beds
- 2 Baths
- 1,584 Sq Ft
- House for Rent
50 Carls Way, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

Karen Overtoom Karen M. Overtoom R.E.

50 Carls Way, West Tisbury, MA 02575
/35
$900,000 Sold Apr 30, 2025
- 1,092 Sq Ft
- $824/SF
- 1 Day On Market
- 1 Bed
- 1.5 Baths
- Built 2008
53 Anthiers Way, Edgartown, MA 02539

This unique and beautifully handcrafted home in Edgartown is a rare find. It features 1 bedroom, 1.5 bathrooms, and a 3-bedroom septic system, offering the potential for additional bedrooms with town approval. The custom woodwork and fireplace create a warm and inviting atmosphere, while the open-concept kitchen and dining area showcase handmade wood countertops and rustic charm--making it the

Valentina Globa eXp Realty, LLC

53 Anthiers Way, Edgartown, MA 02539

/47
Est $2,411,744 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,627 Sq Ft
24 Peacegate Way, Vineyard Haven, MA 02568

24 Peacegate Way, Vineyard Haven, MA 02568

/26
$1,700,000
- 2 Beds
- 0.5 Baths
- 601 Sq Ft
108 Bay View Ave, Edgartown, MA 02539

Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

Derick Freitas Amaral & Associates Real Estate

108 Bay View Ave, Edgartown, MA 02539
/21
$8,000 per month
- 1 Bed
- 1 Bath
- 936 Sq Ft
- House for Rent
10 James Pond Way, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

Karen Overtoom Karen M. Overtoom R.E.

10 James Pond Way, West Tisbury, MA 02575
/50
$3,000,000 Sold Apr 29, 2025
- 3,311 Sq Ft
- $906/SF
- 3 Beds
- 3 Baths
- Built 2000
34 S Pond Rd, Vineyard Haven, MA 02568

Stunning Deep Bottom Pond property with an oversized 3.77-acre lot surrounded by Mother Nature’s beauty, with exclusive association access to Tisbury Great Pond and private tennis courts. This beautiful home is lovingly maintained and ready for immediate occupancy. Through the welcoming grand foyer, a cathedral-ceiling living room with a fabulous wood-burning fireplace, and slider doors leading

Stephanie Roache Donnelly + Co

34 S Pond Rd, Vineyard Haven, MA 02568

/16
Est $1,398,752 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,150 Sq Ft
31 Music St, Vineyard Haven, MA 02568

31 Music St, Vineyard Haven, MA 02568

/26
$1,700,000
- Land
- 0.96 Acre
- $1,770,833 per Acre
108 Bay View, Edgartown, MA 02539

Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

Derick Freitas Amaral & Associates RE

108 Bay View, Edgartown, MA 02539
/26
$50,000 per month
- 4 Beds
- 3 Baths
- 3,237 Sq Ft
- House for Rent
29 Naushon Rd Wt142, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

Karen Overtoom Karen M. Overtoom R.E.

29 Naushon Rd Wt142, West Tisbury, MA 02575
/56
$7,926,400 Sold Apr 28, 2025
- 4,520 Sq Ft
- $1754/SF
- 205 Days On Market
- 5 Beds
- 5 Baths
- Built 1990
32 Boldwater Rd, Edgartown, MA 02539

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

Robert Kenney Tea Lane Associates

32 Boldwater Rd, Edgartown, MA 02539

/29
Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,800 Sq Ft
30 Mill Hill Rd, Edgartown, MA 02539

30 Mill Hill Rd, Edgartown, MA 02539

/13
$1,150,000
- Land
- 2.02 Acres
- $569,307 per Acre
00 Old Field Rd, Aquinnah, MA 02535

The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

Katherine Donahue Sandpiper Realty Inc

00 Old Field Rd, Aquinnah, MA 02535
/29
$10,900 per month
- 3 Beds
- 1 Bath
- 936 Sq Ft
- House for Rent
58 Forest Rd Wt140, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

Karen Overtoom Karen M. Overtoom R.E.

58 Forest Rd Wt140, West Tisbury, MA 02575
/52
$9,525,000 Sold Apr 24, 2025
- 5,808 Sq Ft
- $1640/SF
- 297 Days On Market
- 6 Beds
- 6 Baths
- Built 2008
2 Squibnocket Rd, Chilmark, MA 02535

CHILMARK SOUTH SHORE WATER VIEWS. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a

Tina Miller Compass | Point B

2 Squibnocket Rd, Chilmark, MA 02535

/17
Est $1,415,380 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,503 Sq Ft
165 Weaver Ln, Vineyard Haven, MA 02568

165 Weaver Ln, Vineyard Haven, MA 02568

/21
$1,675,000
- 3 Beds
- 2 Baths
- 1,562 Sq Ft
111 Charles Neck Way, Vineyard Haven, MA 02568

Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

Emma Kennedy Sandpiper Realty Inc

111 Charles Neck Way, Vineyard Haven, MA 02568
/20
$12,000 per month
- 3 Beds
- 1 Bath
- 1,068 Sq Ft
- House for Rent
76 Ben Chase Rd Wt136, West Tisbury, MA 02575

Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

Karen Overtoom Karen M. Overtoom R.E.

76 Ben Chase Rd Wt136, West Tisbury, MA 02575
/42
$9,725,000 Sold Apr 24, 2025
- 5,808 Sq Ft
- $1674/SF
- 295 Days On Market
- 6 Beds
- 5.5 Baths
- Built 2008
2 Squibnocket Rd, Chilmark, MA 02535

CHILMARK SOUTH SHORE WATER VIEW. This Squibnocket gem is a Hutker Arhictect-designed family compound, main house,& guest house on 4.5 acres. Live the ultimate up-Island life with captivating water views in every direction. The home is pristine and private, with many unique features. The chef's kitchen and dining area are serene, bright, and functional. Step up to what might be the best panorama

Tina Miller Compass

2 Squibnocket Rd, Chilmark, MA 02535

/21
Est $1,621,126 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,066 Sq Ft
23 Anthiers Way, Edgartown, MA 02539

23 Anthiers Way, Edgartown, MA 02539

/35
$2,010,900
- 4 Beds
- 5 Baths
- 2,518 Sq Ft
32 Norton Orchard Rd, Edgartown, MA 02539

Discover this Edgartown gem! Enjoy a refreshed interior with new flooring, a bright updated bathroom, and modern LED lighting throughout. The kitchen boasts elegant dark green granite countertops. A solid foundation provides peace of mind. The property offers easy access to a nearby restaurant, apartments, and a clothing store, enhancing your daily convenience. **SELLER ASSISTED BY POA. DO NOT

Derek Greene The Greene Realty Group

32 Norton Orchard Rd, Edgartown, MA 02539
/22
$20,000 per month
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
709 Old County Rd Wt134, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

Karen Overtoom Karen M. Overtoom R.E.

709 Old County Rd Wt134, West Tisbury, MA 02575
/20
$675,000 Sold Apr 23, 2025
- 508 Sq Ft
- $1329/SF
- 298 Days On Market
- 2 Beds
- 2 Baths
- Built 1868
9 Forest Cir, Oak Bluffs, MA 02557

The Size will Surprise~ Cloud Nine~ Located on a quiet hidden circle with 14 enchanting cottages in the Historic Martha's Vineyard Camp Meeting Association. Steps to Circuit Avenue, beaches, shops, ferries, and restaurants. This YEAR ROUND RENOVATED Charming Cottage is FULLY INSULATED with spray foam and in 2022 Brennan and Co. installed a Daikin Multi Position Air Handler with thermostat to

Marilyn Moses Ocean Park Realty Inc

9 Forest Cir, Oak Bluffs, MA 02557

/17
Est $1,090,738 Not Listed For Sale
- 3 Beds
- 2 Baths
- 934 Sq Ft
10 Briarwood Ln, Vineyard Haven, MA 02568

10 Briarwood Ln, Vineyard Haven, MA 02568

/34
$1,590,000
- 4 Beds
- 1.5 Baths
- 1,305 Sq Ft
46 Kennebec Ave, Oak Bluffs, MA 02557

Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs' allure as a premier summer destination on Martha's Vineyard. This delightful three-season cottage has been carefully modernized over the years, offering a rare investment opportunity. Located

Michael Schweikert Ocean Park Realty, Inc.

46 Kennebec Ave, Oak Bluffs, MA 02557
/19
$30,000 per month
- 5 Beds
- 4 Baths
- 3,600 Sq Ft
- House for Rent
37 Sachem Cir, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

Karen Overtoom Karen M. Overtoom R.E.

37 Sachem Cir, West Tisbury, MA 02575
/30
$2,175,000 Sold Apr 18, 2025
- 2,779 Sq Ft
- $783/SF
- 0 Days On Market
- 5 Beds
- 4 Baths
- Built 1988
55 Old Purchase Rd, Edgartown, MA 02539

Welcome to this fabulous property in a peaceful neighborhood easily accessible to Morning Glory Farm, Edgartown Village, the bike path, and South Beach by way of Meetinghouse Way. Move right in and enjoy the Vineyard lifestyle in this spacious 5 bedroom, 3 and a half bath home, nestled on a beautifully landscaped .61-acre lot. This fabulous home has been completely renovated and thoughtfully

Stephanie Roache Donnelly + Co

55 Old Purchase Rd, Edgartown, MA 02539

/34
Est $1,214,223 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,230 Sq Ft
38 Lake St, Vineyard Haven, MA 02568

38 Lake St, Vineyard Haven, MA 02568

/8
$875,000
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568

Bright first-floor, three-bedroom, two bath condo in the popular Vineyard Haven Causeway Harborview association. Easy access to downtown shops, restaurants, harbor, ferry, and beaches. Building amenities include a shared pool, convenient storage, and on-site laundry facilities. The perfect blend of convenience and comfort for year-round living or as your ideal summer retreat.

Emma Kennedy Sandpiper Realty Inc

124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
/17
$17,600 per month
- 4 Beds
- 4 Baths
- 2,676 Sq Ft
- House for Rent
40 Summer Cir, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

Karen Overtoom Karen M. Overtoom R.E.

40 Summer Cir, West Tisbury, MA 02575
/29
$1,350,000 Sold Apr 18, 2025
- 1,119 Sq Ft
- $1206/SF
- 123 Days On Market
- 2 Beds
- 3 Baths
- Built 1983
87 Schoolhouse Rd, Edgartown, MA 02539

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

Stephanie Roache Donnelly + Co

87 Schoolhouse Rd, Edgartown, MA 02539

/32
Est $2,113,115 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,276 Sq Ft
232 Lagoon Pond Rd, Vineyard Haven, MA 02568

232 Lagoon Pond Rd, Vineyard Haven, MA 02568

/40
$1,899,000
- 4 Beds
- 3.5 Baths
- 2,061 Sq Ft
174 Middle Rd, Chilmark, MA 02535

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

Sheila Morse Island Real Estate

174 Middle Rd, Chilmark, MA 02535
/13
$15,000 per month
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
19 Lighthouse Road Aq605, Aquinnah, MA 02535

This family-friendly, three-bedroom retreat on Lighthouse Road in Aquinnah offers all the comforts of home with stunning water views of the Vineyard Sound and the Elizabeth Islands. It is beautifully decorated and nicely furnished. The home features stylish post-and-beam architecture. The main level features cathedral ceilings, wrap-around picture windows and skylights. The main level opens out

Karen Overtoom Karen M. Overtoom R.E.

19 Lighthouse Road Aq605, Aquinnah, MA 02535
/35
$1,837,500 Sold Apr 18, 2025
- 1,654 Sq Ft
- $1111/SF
- 182 Days On Market
- 4 Beds
- 3 Baths
- Built 1984
55 Charles Neck Way, Vineyard Haven, MA 02568

LONG POINT BEACH RETREAT. Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both

Wendy Harman Compass | Point B

55 Charles Neck Way, Vineyard Haven, MA 02568

/36
Est $1,636,556 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,144 Sq Ft
323 Lamberts Cove Rd, Vineyard Haven, MA 02568

323 Lamberts Cove Rd, Vineyard Haven, MA 02568

/30
$1,850,000
- 4 Beds
- 3 Baths
- 2,291 Sq Ft
63 Saddle Club Rd, Edgartown, MA 02539

Welcoming and Picturesque from outside to inside! Thru the door, into the entryway you immediately sense comfort and well-being in this beautifully cared for 4-bedroom home. Open floor plan stars a chef’s kitchen outfitted with premium luxury appliances, granite counters, and loads of cabinets along with a dining area perfect for family and friend gatherings. Family room, along with a

Martha Smith C McManus Realty Group

63 Saddle Club Rd, Edgartown, MA 02539
/2
$10,000 per month
- 6 Beds
- 3.5 Baths
- 2,100 Sq Ft
- House for Rent
15 Crowell Lane Wt119, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

Karen Overtoom Karen M. Overtoom R.E.

15 Crowell Lane Wt119, West Tisbury, MA 02575
/49
$865,000 Sold Apr 17, 2025
- 1,208 Sq Ft
- $716/SF
- 70 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
4 Quail Run Unit 17, Oak Bluffs, MA 02557

LUXURIOUS LIFESTYLE AMENITIES: RENOVATED TOWNHOUSE WITH TENNIS, PICKLEBALL + BOATING ACCESS. Welcome to this beautifully renovated 2-bedroom, 2-bathroom townhouse located in the exclusive Sengekontacket community. This nicely appointed property offers a perfect blend of comfort and convenience, making it an ideal choice for year-round living or as a rental investment opportunity.Spanning 1,208

Wendy Harman Compass | Point B

4 Quail Run Unit 17, Oak Bluffs, MA 02557

/33
Est $2,075,417 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,400 Sq Ft
119 Herring Creek Rd, Edgartown, MA 02539

119 Herring Creek Rd, Edgartown, MA 02539

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