Dukes, MA Homes

/5
$2,995,000 Pending
- Land
- 3.01 Acres
- $995,017 per Acre
9 Turkeyland Cove Rd, Edgartown, MA 02539

Turkeyland Cove: Three-Acre Estate-Sized Parcel In Katama - This beautiful and private building site is one of the last remaining 3-acre parcels in Katama. The property offers a perfect opportunity to create a signature residence, multi-generational retreat, or equestrian dream, with possibilities for a Main House, Carriage House, pool, tennis court and/or barn. The property offers easy access to

Wendy Harman

Compass

(508) 252-8527

9 Turkeyland Cove Rd, Edgartown, MA 02539
/10
$20,000 per month
- 5 Beds
- 3 Baths
- 2,352 Sq Ft
- House for Rent
55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

Karen Overtoom Karen M. Overtoom R.E.

55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
/3
$3,100,000 Sold Jul 03, 2025
- 1,500 Sq Ft
- $2067/SF
- 6 Beds
- 3 Baths
- Built 1975
10 Basin Rd, Chilmark, MA 02535

Unique compound in the heart of Menemsha - one of a kind!The cottage (520 sq.ft.), the chandlery buikding(5968 sq.ft.) and deli with an apartment(2172 sq.ft.) on just under an acre of land has tremendous potential for the right buyer!Special permits are required from the town to operate a business but they have approved a deli/restuarant, small stores and a commercial kitchen in the past.

Julianna Flanders Flanders Real Estate

10 Basin Rd, Chilmark, MA 02535

/12
Est $1,307,200 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,997 Sq Ft
3 Carole Ave, Vineyard Haven, MA 02568

3 Carole Ave, Vineyard Haven, MA 02568

/42
$1,498,000 Pending
- 3 Beds
- 4 Baths
- 2,105 Sq Ft
10 Peases Point Way N, Edgartown, MA 02539

ICONIC EDGARTOWN VILLAGE BEAUTY with elevated style just one block from Main Street! Recent renovations and upgrades give this 1840's classic a fresh and modern vibe for easy maintenance in-town living. Gracious bluestone terrace bordered with hydrangeas provides a private and serene setting for outdoor living and entertaining. Other notable features include: 3-minute walk to the heart of Main

Wendy Harman

Compass

(508) 691-7503

10 Peases Point Way N, Edgartown, MA 02539
/12
$5,500 per month
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- House for Rent
2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY VACATION RENTAL PROPERTY. The home’s timeless interior offers a sitting room with a wood-burning fireplace, a hallway opening to a large, bright, modern kitchen featuring a Viking range and large dining table. Ample counter space and a wall of built-ins are the perfect complement to family and friends that enjoy cooking together. A gas grill and outdoor seating are only

Karen Overtoom Karen M. Overtoom R.E.

2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539
/46
$6,200,000 Sold Jul 03, 2025
- 3,278 Sq Ft
- $1891/SF
- 0 Days On Market
- 4 Beds
- 4 Baths
- Built 1983
79 Rachels Way, Vineyard Haven, MA 02568

EXTRAORDINARY COASTAL RETREAT IN MINK MEADOWS — Welcome to an idyllic haven on Martha’s Vineyard, tucked within the exclusive West Chop area of Tisbury. This contemporary residence offers sweeping water views across a vibrant salt marsh and out to the sparkling expanse of Vineyard Sound, where sailboats quietly pass by across the horizon. Built in 1983 and thoughtfully maintained with numerous

Jen O'Hanlon Compass | The O'Hanlon Group

79 Rachels Way, Vineyard Haven, MA 02568

/13
Est $1,234,075 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
33 Menahan St, Vineyard Haven, MA 02568

33 Menahan St, Vineyard Haven, MA 02568

/29
$1,395,000 Pending
- 4 Beds
- 2 Baths
- 2,184 Sq Ft
42 Road To the Plains, Edgartown, MA 02539

Classic Colonial - Located between Edgartown Village and Katama, this classically styled colonial features plenty of traditional charm as well as a world of possibilities for renovations and/or expansion. The main entrance opens up to a center staircase flanked by a formal Living Room and Dining Room and there is also a kitchen with breakfast bar PLUS a first-floor bedroom and full bath. The

Wendy Harman

Compass

(508) 978-3864

42 Road To the Plains, Edgartown, MA 02539
/10
$8,500 per month
- 3 Beds
- 2 Baths
- House for Rent
29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

Karen Overtoom Karen M. Overtoom R.E.

29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
/42
$2,900,000 Sold Jul 03, 2025
- 4,476 Sq Ft
- $648/SF
- 347 Days On Market
- 7 Beds
- 5.5 Baths
- Built 1997
67 Hidden Village Rd, Vineyard Haven, MA 02568

Picturesquely sited on a spacious 4.6-acre parcel this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels providing spacious yet private surroundings. The main living

Stephanie Roache Donnelly + Co.

67 Hidden Village Rd, Vineyard Haven, MA 02568

/30
Est $2,500,413 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,555 Sq Ft
10 Crow Hollow Rd, Vineyard Haven, MA 02568

10 Crow Hollow Rd, Vineyard Haven, MA 02568

/42
$10,995,000 Pending
- 7 Beds
- 3.5 Baths
- 2,957 Sq Ft
117 N Water St, Edgartown, MA 02539

Classic Captain's Home With Deep Water Dock On Edggatown Harbor - Located on prestigious North Water Street in the heart of historic Edgartown Village, this premier harbor front home combines the best of in-town and waterfront living, with deep water dock. On the harbor front side of the home, there are 2 decks with panoramic views across the harbor. There are a total of 7 Bedrooms making the

Wendy Harman

Compass

(508) 715-6592

117 N Water St, Edgartown, MA 02539
/8
$11,800 per month
- 4 Beds
- 4 Baths
- 2,612 Sq Ft
- House for Rent
46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

Karen Overtoom Karen M. Overtoom R.E.

46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
/45
$5,250,000 Sold Jul 02, 2025
- 2,869 Sq Ft
- $1830/SF
- 37 Days On Market
- 3 Beds
- 5 Baths
- Built 1988
14 Katama Farm S, Edgartown, MA 02539

Katama Farm South - En route to this stellar location, enjoy scenic views while passing iconic Katama Farm. Less than a half-mile drive or a quarter mile walk from South Beach, this dynamic compound, which includes a spacious post and beam home and two-story barn, is privately situated on a large, beautifully landscaped, 1.6-acre parcel of land. The home is nearly 3,000sf in size and the multiple

Courtney Marek Sandpiper Realty

14 Katama Farm S, Edgartown, MA 02539

/4
Est $2,968,039 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,789 Sq Ft
188 Pond Rd, Vineyard Haven, MA 02568

188 Pond Rd, Vineyard Haven, MA 02568

/42
$16,975,000
- 6 Beds
- 4.5 Baths
- 3,606 Sq Ft
111 N Water St, Edgartown, MA 02539

Historic captain’s home circa 1850, brilliantly renovated by architect Patrick Ahearn in 2002, on coveted North Water Street. Enjoy sweeping 180 Edgartown Harbor views from bright, sunlit living spaces with heart pine floors and custom millwork. An open-concept first floor flows to an 18x29' mahogany deck, perfect for al fresco dining and entertaining. The rare double-wide lot offers a lawn

Wendy Harman

Compass

(508) 274-5363

111 N Water St, Edgartown, MA 02539
/8
$17,500 per month
- 8 Beds
- 4.5 Baths
- 3,876 Sq Ft
- House for Rent
550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and

Karen Overtoom Karen M. Overtoom R.E.

550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
/19
$850,000 Sold Jul 02, 2025
- 481 Sq Ft
- $1767/SF
- 33 Days On Market
- 1 Bed
- 1 Bath
- Built 1920
68 Winter St, Edgartown, MA 02539

Welcome to 68 Winter Street, a highly sought-after community of six, one bedroom condos located in Edgartown Village. Enjoy seasonal or year-round living at this sophisticated, garden level pied-a-terre. Elegant and well-appointed throughout, this stylish condo features open living with a nicely equipped kitchen, soaring ceilings, crown modeling, over-sized windows, and wood floors. Spacious

Michele Moore Island Real Estate

68 Winter St, Edgartown, MA 02539

/34
Est $2,551,353 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 1 Sq Ft
248 Pond Rd, Vineyard Haven, MA 02568

248 Pond Rd, Vineyard Haven, MA 02568

/22
$1,250,000
- 2 Beds
- 1 Bath
- 742 Sq Ft
47 Winemack St, Oak Bluffs, MA 02557

Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

Lisa Lucier

Anchor Realty of MV

(508) 403-9601

47 Winemack St, Oak Bluffs, MA 02557
/8
$16,000 per month
- 7 Beds
- 3.5 Baths
- 4,000 Sq Ft
- House for Rent
5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

Karen Overtoom Karen M. Overtoom R.E.

5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
/48
$5,250,000 Sold Jul 02, 2025
- 2,869 Sq Ft
- $1830/SF
- 54 Days On Market
- 3 Beds
- 4.5 Baths
- Built 1988
14 Katama Farm Rd N, Edgartown, MA 02539

Katama Farm South - En route to this stellar location, enjoy scenic pastoral views while passing iconic Katama Farm. A quarter mile from South Beach, this dynamic compound, which includes a spacious post and beam home and two-story barn, is privately situated on a large, beautifully landscaped, 1.6-acre parcel of land. The home is nearly 3,000 sf in size and the multiple outdoor living spaces

Courtney Marek Sandpiper Realty Inc

14 Katama Farm Rd N, Edgartown, MA 02539

/25
Est $2,093,611 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,636 Sq Ft
131 Shubael Weeks Path, Vineyard Haven, MA 02568

131 Shubael Weeks Path, Vineyard Haven, MA 02568

/32
$1,550,000
- 4 Beds
- 2 Baths
- 1,304 Sq Ft
11 John Wesley Ave, Oak Bluffs, MA 02568

East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm.The exterior features a wide

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 682-5574

11 John Wesley Ave, Oak Bluffs, MA 02568
/8
$3,300 per month
- 3 Beds
- 2 Baths
- 1,196 Sq Ft
- House for Rent
849 State Rd Unit 1, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

Karen Overtoom Karen M. Overtoom R.E.

849 State Rd Unit 1, Aquinnah, MA 02535
/36
$1,950,000 Sold Jul 02, 2025
- 2,691 Sq Ft
- $725/SF
- 30 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1976
51 Black Brook Crossing Rd, West Tisbury, MA 02568

This charming 4 bed/2.5 bath Cape style home is set in a perfect setting, carefully sited on 1 acre bordered by a beautiful stone wall with mature plantings. Newly renovated kitchen with plenty of cabinets and storage, quartz counters and dining room with sliders to a screened-in porch. There is a den and living room with access to a spacious deck. The Great Room features cathedral ceilings,

Brenda Galligan Karen M. Overtoom R.E.

51 Black Brook Crossing Rd, West Tisbury, MA 02568

/43
Est $4,627,484 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,932 Sq Ft
12 Norton St, Edgartown, MA 02539

12 Norton St, Edgartown, MA 02539

/21
$1,795,000
- 3 Beds
- 1 Bath
- 1,033 Sq Ft
9 Brunswick Ave, Oak Bluffs, MA 02557

PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

Alice Pierce

Coldwell Banker Realty - Hingham

(870) 917-0672

9 Brunswick Ave, Oak Bluffs, MA 02557
/8
$6,000 per month
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
- House for Rent
33 Kennebago Ave Vh414, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

Karen Overtoom Karen M. Overtoom R.E.

33 Kennebago Ave Vh414, Tisbury, MA 02568
/2
$1,595,000 Sold Jul 01, 2025
- 1,176 Sq Ft
- $1356/SF
- 2 Beds
- 2 Baths
- Built 1998
10 Red Pony Rd, West Tisbury, MA 02568

Pastoral and perfect. Room to grow or just move in.

Lisa Da silva Compass | Point B

10 Red Pony Rd, West Tisbury, MA 02568

/45
Est $1,772,609 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,576 Sq Ft
38 Edgewood Dr, Edgartown, MA 02539

38 Edgewood Dr, Edgartown, MA 02539

/41
$3,395,000
- 3 Beds
- 3.5 Baths
- 2,527 Sq Ft
5 Katama Dr, Edgartown, MA 02539

Modern Coastal Retreat In Katama: Freshly reimagined and impeccably styled, this modern coastal residence in the heart of Katama offers a rare opportunity to own a newly renovated home just one mile from South Beach. This appealing retreat has been elevated with curated finishes, high-end systems, and a designer-selected furnishing package that perfectly embodies the relaxed luxury of Vineyard

Wendy Harman

Compass

(508) 274-5363

5 Katama Dr, Edgartown, MA 02539
/4
$6,000 per month
- 3 Beds
- 2 Baths
- 1,608 Sq Ft
- House for Rent
836 State Rd, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

Karen Overtoom Karen M. Overtoom R.E.

836 State Rd, Aquinnah, MA 02535
/32
$3,925,000 Sold Jul 01, 2025
- 5,603 Sq Ft
- $701/SF
- 238 Days On Market
- 6 Beds
- 7 Baths
- Built 1995
140 Merry Farm Rd, Vineyard Haven, MA 02568

Site of the original Rainbow Farm, this 8.05-acre parcel is one of the most beautiful pieces of land in West Tisbury. The warm and convivial 5,000 sq ft home with its 4 bedrooms looks out onto a setting that is as if from a bygone era, the vast fields stretching into the distance. The spring-fed pond is a centerpiece of the pastoral view. The home itself has many surprising and charming design

Mark Jenkins Wallace & Co. Sotheby's

140 Merry Farm Rd, Vineyard Haven, MA 02568

/79
Not Listed For Sale
- 6 Beds
- 3 Baths
- 2,604 Sq Ft
260 South Rd, Chilmark, MA 02535

260 South Rd, Chilmark, MA 02535

/23
$8,995,000
- 11 Beds
- 8.5 Baths
- 6,289 Sq Ft
1 Louis Field Rd, Edgartown, MA 02539

SWEETENED WATER FARM ESTATE. Located just one mile from the heart of historic Edgartown Village, this compound in Sweetened Water Farm presents a rare opportunity to become the next steward of this extraordinary Martha’s Vineyard estate. Privately sited on 4.6 acres of exquisitely cultivated gardens, this remarkable property has been featured in several publications celebrating the island’s most

Wendy Harman

Compass

(508) 715-8610

1 Louis Field Rd, Edgartown, MA 02539
/8
$13,600 per month
- 2 Beds
- 2 Baths
- 1,967 Sq Ft
- Condo for Rent
1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy your company over meals, snacks and games

Karen Overtoom Karen M. Overtoom R.E.

1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539
/6
$430,000 Sold Jun 30, 2025
- Land
- 1.40 Acres
- $307,143 per Acre
- 0 Days On Market
0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535

Not listed in LINK.

LINK Email Cache LINK

0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535

/35
Est $7,370,865 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,207 Sq Ft
93 S Water St, Edgartown, MA 02539

93 S Water St, Edgartown, MA 02539

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