Dukes, MA Homes

/28
$1,950,000
- 4 Beds
- 2.5 Baths
- 3,268 Sq Ft
7 Upper Meadow Ln, Oak Bluffs, MA 02557

Tucked at the end of a quiet cul-de-sac in the desirable Meadow View Farms neighborhood, this spacious Colonial offers over 3,200 square feet of comfortable and inviting living space. This home is ideal for those who love to host lively gatherings while providing comfortable accommodations for all. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary

Lesley Heidt Sandpiper Realty Inc

7 Upper Meadow Ln, Oak Bluffs, MA 02557
/29
$34,000 per month
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
- House for Rent
15 Loon Lane Ch203, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

Karen Overtoom Karen M. Overtoom R.E.

15 Loon Lane Ch203, Chilmark, MA 02535
/37
$1,835,000 Sold May 23, 2025
- 2,391 Sq Ft
- $767/SF
- 59 Days On Market
- 4 Beds
- 4 Baths
- Built 2001
41 Smith Hollow Dr, Edgartown, MA 02539

Discover this exquisite, contemporary home nestled in the heart of Edgartown's Smith Hollow, conveniently located just off the bike path and mere minutes from the lively Edgartown Village. Situated in a welcoming, family-oriented neighborhood, this stylish residence boasts a bright and airy open floor plan.The Great Room captivates with its soaring cathedral wood ceiling and robust timber accent

Marilyn Moses Ocean Park Realty Inc

41 Smith Hollow Dr, Edgartown, MA 02539

/34
Est $1,390,350 Not Listed For Sale
- 4 Beds
- 1 Bath
- 1,640 Sq Ft
125 Skiff Ave, Vineyard Haven, MA 02568

125 Skiff Ave, Vineyard Haven, MA 02568

/6
$1,149,000
- 3 Beds
- 2 Baths
- 960 Sq Ft
67 12th St S, Edgartown, MA 02539

This ranch style 3 bedroom home centrally located in a quiet neighborhood is close to the bike path with easy access to town and beaches. Sited on a 12,000 square foot parcel with a spacious privately enclosed yard and mature gardens. First floor includes an efficient galley kitchen with a quaint dining area. The living room leads out to a cozy front porch. There is also a spacious side deck that

Brenda Galligan Karen M. Overtoom R.E.

67 12th St S, Edgartown, MA 02539
/20
$20,000 per month
- 3 Beds
- 3 Baths
- House for Rent
40 Hidden Cove Rd, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

Karen Overtoom Karen M. Overtoom R.E.

40 Hidden Cove Rd, Oak Bluffs, MA 02557
/33
$1,790,000 Sold May 23, 2025
- 1,674 Sq Ft
- $1069/SF
- 36 Days On Market
- 2 Beds
- 2 Baths
- Built 1977
8 Massasoit Rd, Edgartown, MA 02539

This incredibly charming Katama Cape Cod-style home that has been completely refreshed top to bottom! An updated kitchen with high-end appliances, including a wine fridge, two brand new bathrooms, central AC, new heating system, and a new second floor deck are just some of the improvements. There are two bedrooms, one on each floor. The second floor has a comfortable lounge area, and a cozy loft

Cheri Mason Landvest MV

8 Massasoit Rd, Edgartown, MA 02539

/10
Est $2,470,681 Not Listed For Sale
- 5 Beds
- 4 Baths
- 2,398 Sq Ft
87 Bellevue Ave, Vineyard Haven, MA 02568

87 Bellevue Ave, Vineyard Haven, MA 02568

/8
$695,000
- Land
- 0.29 Acre
- $2,396,552 per Acre
37 Double Ox Rd, Oak Bluffs, MA 02557

This is your opportunity to get in on the ground floor of Lagoon Ridge, a stunning, new development. Several homes are already in place. This beautiful, wooded Lot is located down meandering, newly paved roads, just .4 mile from Barnes Road and the Lagoon. For the outdoor enthusiast, walk and ride the numerous hiking and biking trails that traverse the abutting conservation lands. All utility

Lynn Buder Sandpiper Realty Inc

37 Double Ox Rd, Oak Bluffs, MA 02557
/29
$64,000 per month
- 4 Beds
- 7 Baths
- 3,600 Sq Ft
- House for Rent
385 Barnes Rd Ob534, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

Karen Overtoom Karen M. Overtoom R.E.

385 Barnes Rd Ob534, Oak Bluffs, MA 02557
/28
$1,270,000 Sold May 23, 2025
- 2,192 Sq Ft
- $579/SF
- 57 Days On Market
- 3 Beds
- 2 Baths
- Built 1940
60 Prospect Ave, Oak Bluffs, MA 02557

OAK BLUFFS ~ APPROVED 4 BEDROOM SEPTIC IN PLACE - This home LIVES LARGE and offers 3 Distinct Structures situated on a BEAUTIFUL landscaped .34 Acre private lot ~EASY WALK or BIKE RIDE to OAK BLUFFS HARBOR, Town, Sandy Beaches, Ferry Ports and Town Parks! Tastefully renovated SPACIOUS Split-Level Home featuring a lovely and functional open floor plan. The main level displays beautiful hardwood

Marilyn Moses Ocean Park Realty Inc

60 Prospect Ave, Oak Bluffs, MA 02557

/36
Est $2,520,452 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
225 Great Plains Rd, Vineyard Haven, MA 02568

225 Great Plains Rd, Vineyard Haven, MA 02568

/9
$695,000
- Land
- 0.29 Acre
- $2,396,552 per Acre
37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557

This is your opportunity to get in on the ground floor of what will be a stunning, new development --- Lagoon Ridge. Several homes are already in place. This beautiful, wooded parcel is located down meandering, newly paved roads, just .4 mile from Barnes Road and the Lagoon. For the outdoor enthusiast, walk and ride the numerous hiking and biking trails that traverse the abutting conservation

Lynn Buder Sandpiper Realty

37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557
/25
$24,000 per month
- 3 Beds
- 2 Baths
- 1,257 Sq Ft
- House for Rent
5 Laurel Ave, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage decor and beautiful bamboo floors. Entertainment options include

Karen Overtoom Karen M. Overtoom R.E.

5 Laurel Ave, Oak Bluffs, MA 02557
/24
$665,000 Sold May 23, 2025
- 806 Sq Ft
- $825/SF
- 171 Days On Market
- 3 Beds
- 2 Baths
- Built 1876
51 Rural Cir, Oak Bluffs, MA 02557

The Spirit of '76 is a lovely Campground cottage nestled into the landscape for privacy and shade. Just a couple of blocks to the beach, town center, shops, and restaurants. A fabulous wrap around porch with various seating areas. Built in 1876 this wonderful throwback of yesteryear features some original furnishings included in the sale. With a classic front parlor, dining room, and kitchen, a

Lisa Lucier Anchor Realty of Martha's Vineyard

51 Rural Cir, Oak Bluffs, MA 02557

/39
Est $6,712,733 Not Listed For Sale
- 5 Beds
- 6 Baths
- 6,546 Sq Ft
103 Main St, Vineyard Haven, MA 02568

103 Main St, Vineyard Haven, MA 02568

/32
$2,250,000
- 4 Beds
- 3 Baths
- 2,522 Sq Ft
29 Old Nursery Ln, Chilmark, MA 02535

Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

Julianna Flanders Flanders Real Estate

29 Old Nursery Ln, Chilmark, MA 02535
/30
$20,000 per month
- 4 Beds
- 2 Baths
- 1,920 Sq Ft
- House for Rent
291 Barnes Rd Ob516, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

Karen Overtoom Karen M. Overtoom R.E.

291 Barnes Rd Ob516, Oak Bluffs, MA 02557
/27
$1,600,000 Sold May 22, 2025
- 1,594 Sq Ft
- $1004/SF
- 532 Days On Market
- 3 Beds
- 2 Baths
- Built 1933
2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the

Carol Shore Donnelly + Co

2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

/34
Est $1,628,990 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
84 Christiantown Rd, Vineyard Haven, MA 02568

84 Christiantown Rd, Vineyard Haven, MA 02568

/6
$950,000
- 1 Bed
- 1 Bath
- 534 Sq Ft
136 W Spring St, Vineyard Haven, MA 02568

136 Spring Street - Sited on 0.32 acres and just moments from the Tisbury School and downtown Vineyard Haven, this one bedroom, one bathroom home is serviced by a 4-bedroom septic system, allowing for immediate expansion.Note: This property is also being marketed as a compound with the abutting 4BR/2.5BA home at 128 Spring Street.

David Dickinson Compass | Point B

136 W Spring St, Vineyard Haven, MA 02568
/14
$14,200 per month
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- House for Rent
59 Prospect Ave Ob502, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

Karen Overtoom Karen M. Overtoom R.E.

59 Prospect Ave Ob502, Oak Bluffs, MA 02557
/13
$1,195,000 Sold May 22, 2025
- 1,110 Sq Ft
- $1077/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
34 10th St S, Edgartown, MA 02539

This charming 3 bedroom, 2 bathroom ranch-style Edgartown home offers comfortable single-level living with classic Vineyard appeal. The layout includes a dedicated living room, and an open kitchen and dining area. The primary suite features a private bath, while two additional bedrooms share a full bathroom. Outside, the property provides deck overlooking the yard for enjoying the outdoors.

Rose Ryley Sandpiper Realty Inc

34 10th St S, Edgartown, MA 02539

/30
Est $1,840,649 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,046 Sq Ft
8 Harpoon Hollow, Aquinnah, MA 02535

8 Harpoon Hollow, Aquinnah, MA 02535

/32
$1,750,000
- 5 Beds
- 4 Baths
- 2,436 Sq Ft
128 W Spring St, Vineyard Haven, MA 02568

128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

David Dickinson Compass | Point B

128 W Spring St, Vineyard Haven, MA 02568
/40
$16,400 per month
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- House for Rent
20 Katama Bay Rd Ed350, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.

Karen Overtoom Karen M. Overtoom R.E.

20 Katama Bay Rd Ed350, Edgartown, MA 02539
/36
$5,500,000 Sold May 20, 2025
- 3,262 Sq Ft
- $1686/SF
- 295 Days On Market
- 4 Beds
- 5 Baths
- Built 1984
12 Tamarack Ln, Oak Bluffs, MA 02536

This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges.

Betsy Kessler Rutledge Properties

12 Tamarack Ln, Oak Bluffs, MA 02536

/30
Est $2,453,061 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,404 Sq Ft
10 Gerts Way, Edgartown, MA 02539

10 Gerts Way, Edgartown, MA 02539

/11
$575,000
- Land
- 0.29 Acre
- $1,982,759 per Acre
112 County Rd, Oak Bluffs, MA 02557

Discover the perfect opportunity to build your dream home on this desirable parcel located at 112 County Road, Oak Bluffs. This spacious lot offers convenient access to local amenities, beaches, ferry terminals, and town attractions. With its central location and natural surroundings, this property is ideal for those seeking both privacy and convenience. Bring your vision to life on Martha’s

Kiet Bordley Fort Hill Brokerage Group

112 County Rd, Oak Bluffs, MA 02557
/30
$20,000 per month
- 4 Beds
- 3 Baths
- 2,226 Sq Ft
- House for Rent
54 Schoolhouse Road Ed330, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny

Karen Overtoom Karen M. Overtoom R.E.

54 Schoolhouse Road Ed330, Edgartown, MA 02539
/45
$1,225,000 Sold May 19, 2025
- 1,725 Sq Ft
- $710/SF
- 338 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
51 Head of the Pond Rd, Vineyard Haven, MA 02568

Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby. Association covenants allow up to two

Bruce Stuart Bruce Stuart and Associates

51 Head of the Pond Rd, Vineyard Haven, MA 02568

/29
Est $2,140,407 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
165 W Tisbury Rd, Edgartown, MA 02539

165 W Tisbury Rd, Edgartown, MA 02539

/48
$5,495,000 Open Sat 10AM - 12PM
- 3 Beds
- 3.5 Baths
- 4,131 Sq Ft
36 Crocker Dr, Edgartown, MA 02539

Stunning Katama Retreat ~ Welcome to this newly constructed architectural gem, nestled on half an acre abutting serene common land in the heart of Katama. Perfectly positioned just blocks from the Field Club, close to South Beach, the bike path, and Edgartown Village, this home offers the ultimate indoor-outdoor Martha's Vineyard lifestyle. The elegant entryway sets the tone, leading into a

Stephanie Roache Donnelly + Co.

36 Crocker Dr, Edgartown, MA 02539
/31
$50,000 per month
- 5 Beds
- 5 Baths
- 2,975 Sq Ft
- House for Rent
17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

Karen Overtoom Karen M. Overtoom R.E.

17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
/18
$1,850,000 Sold May 19, 2025
- 1,428 Sq Ft
- $1296/SF
- 158 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1982
18 Katama Dr, Edgartown, MA 02539

Ocean views - Nestled on a quiet corner lot, this classic beach house offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain . The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus

Bonnie Pierce Wallace & Co. Sotheby's International Realty

18 Katama Dr, Edgartown, MA 02539

/36
Est $2,245,934 Not Listed For Sale
- 6 Beds
- 4 Baths
- 2,705 Sq Ft
9 Heather Trail, Vineyard Haven, MA 02568

9 Heather Trail, Vineyard Haven, MA 02568

/30
$6,595,000
- 4 Beds
- 4 Baths
- 3,052 Sq Ft
20 Eliot Ave, Chilmark, MA 02535

Waterfront home on Stonewall Pond. Nestled along the serene shores of Stonewall Pond, this waterfront home is located in one is Chilmark’s most idyllic locations. This remarkable property offers an unparalleled living experience with breathtaking Atlantic Ocean views and exclusive access to Stonewall Beach. Step inside and be greeted by a seamless fusion of elegance and comfort. The interior

Alyssa Halisky Wallace & Co. Sotheby's

20 Eliot Ave, Chilmark, MA 02535
/29
$18,000 per month
- 4 Beds
- 2.5 Baths
- 2,027 Sq Ft
- House for Rent
12 Cottle Lane Ed341, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

Karen Overtoom Karen M. Overtoom R.E.

12 Cottle Lane Ed341, Edgartown, MA 02539
/18
$1,200,000 Sold May 19, 2025
- 2,080 Sq Ft
- $577/SF
- 590 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
193 Franklin Terrace, Vineyard Haven, MA 02568

Perched on a sunny sloping lot, this 3-bedroom, 2-bath year-round home in a quiet established neighborhood is walking distance to the heart of town and close to everything. Septic can accommodate 4 bedrooms. Deck with grilling area and outdoor shower looking over the landscaped side yard. On the main level, open kitchen with a large island. On the lower level, 3 bedrooms, 2 have walkout access. A

Claire Callagy Compass

193 Franklin Terrace, Vineyard Haven, MA 02568

/19
Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,714 Sq Ft
43 Look St, Vineyard Haven, MA 02568

43 Look St, Vineyard Haven, MA 02568

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