Homes in ZIP Code 02568

/39
$3,250,000
- 5 Beds
- 3.5 Baths
- 4,068 Sq Ft
241 Daggett Ave, Vineyard Haven, MA 02568

Built in 2016 by Squash Meadow Builders, this exceptional five bedroom Colonial sits moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Spanning four levels, it blends timeless architecture with modern comfort. The main floor offers open living with gas fireplace, a gourmet kitchen with custom built-ins and bench seating, and a sunlit sunroom for relaxed coastal living. A private

Alyssa Halisky Wallace & Co. Sotheby's International Realty

241 Daggett Ave, Vineyard Haven, MA 02568
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/8
$6,000 total monthly price
- 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
/25
$949,000 Sold Jun 23, 2025

345 Franklin St, Vineyard Haven, MA 02568
- 3 Beds
- 1.5 Baths
- 1,012 Sq Ft
- Built 1986
Last Sold Summary
- $938/SF
- 49 Days On Market
Current Estimated Value $963,496

Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

345 Franklin St, Vineyard Haven, MA 02568

/13
Est $1,188,703 Not Listed For Sale

33 Menahan St, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
- Built 1993
33 Menahan St, Vineyard Haven, MA 02568

Last Sold Summary
- $830/SF
- 48 Days On Market
Last Sold Price $1,185,000

Last Listing Agent Katherine Donahue Sandpiper Realty Inc

/24
$2,195,000 Pending
- 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
/12
$6,180 total monthly price
- 3 Beds
- 3.5 Baths
- 1,872 Sq Ft
- House for Rent
44 Music St Wt153, West Tisbury, MA 02575

PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

Karen Overtoom Karen M. Overtoom R.E.

44 Music St Wt153, West Tisbury, MA 02575
/34
$1,050,000 Sold Jun 30, 2025

160 Bernard Cir, Vineyard Haven, MA 02568
- 4 Beds
- 2 Baths
- 1,606 Sq Ft
- Built 1977
Last Sold Summary
- 12% Below List Price
- $654/SF
- 45 Days On Market
Current Estimated Value $1,116,442

Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

160 Bernard Cir, Vineyard Haven, MA 02568

/14
Est $984,867 Not Listed For Sale

51 Manchester Ave, Vineyard Haven, MA 02568
- 2 Beds
- 1 Bath
- 1,024 Sq Ft
- Built 1978
51 Manchester Ave, Vineyard Haven, MA 02568

Last Sold Summary
- 3% Above List Price
- $933/SF
- 22 Days On Market
Last Sold Price $955,000

Last Listing Agent Roy Cutrer LAER Realty Partners

/26
$1,999,000
- 3 Beds
- 3.5 Baths
- 2,453 Sq Ft
34 Davis St, Tisbury, MA 02568

NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island's harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

Andrew McElhinney Compass Massachusetts, LLC

34 Davis St, Tisbury, MA 02568
/12
$15,000 total monthly price
- 5 Beds
- 6.5 Baths
- 4,137 Sq Ft
- House for Rent
41 Naushon Rd Wt116, Aquinnah, MA 02575

Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

Karen Overtoom Karen M. Overtoom R.E.

41 Naushon Rd Wt116, Aquinnah, MA 02575
/21
$982,000 Sold Dec 19, 2025

25 Windy Hill Rd, Oak Bluffs, MA 02557
- 3 Beds
- 1 Bath
- 980 Sq Ft
- Built 1971
Last Sold Summary
- 1% Below List Price
- $1,002/SF
- 10 Days On Market
Current Estimated Value $969,547

Last Listing Agent Rene Jackson Island Real Estate

25 Windy Hill Rd, Oak Bluffs, MA 02557

/30
Est $2,374,627 Not Listed For Sale

10 Crow Hollow Rd, Vineyard Haven, MA 02568
- 3 Beds
- 2.5 Baths
- 2,555 Sq Ft
- Built 1983
10 Crow Hollow Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 8% Above List Price
- $861/SF
- 197 Days On Market
Last Sold Price $2,200,000

Last Listing Agent Julianna Flanders Flanders Real Estate

/37
$1,825,000 Pending
- 4 Beds
- 3 Baths
- 3,142 Sq Ft
7 S Meadow Ln, Oak Bluffs, MA 02557

Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs’ most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the

Katie Donahue Sandpiper Realty

7 S Meadow Ln, Oak Bluffs, MA 02557
/8
$8,250 total monthly price
- 7 Beds
- 5 Baths
- 3,528 Sq Ft
- House for Rent
227 S Gate Rd Wt120, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

Karen Overtoom Karen M. Overtoom R.E.

227 S Gate Rd Wt120, West Tisbury, MA 02575
/4
$1,350,000 Sold Aug 15, 2025

35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
- 3 Beds
- 2 Baths
- 1,864 Sq Ft
- Built 1970
Last Sold Summary
- 7% Below List Price
- $724/SF
- 12 Days On Market
Last Listing Agent Lesley Heidt Sandpiper Realty Inc

35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

/2
Est $2,500,982 Not Listed For Sale

230 Pond Rd, Vineyard Haven, MA 02568
- 4 Beds
- 4 Baths
- 3,527 Sq Ft
- Built 1999
230 Pond Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 10% Above List Price
- $646/SF
- 100 Days On Market
Last Sold Price $2,280,000

Last Listing Agent Rose Ryley Sandpiper Realty Inc

/24
$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 into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom

Alyssa Halisky Wallace & Co. Sotheby's International Realty

5 Pine Tree Ln, Vineyard Haven, MA 02568
/8
$18,500 total monthly price
- 4 Beds
- 3.5 Baths
- 1,714 Sq Ft
- House for Rent
4 Windy Way Wt143, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

Karen Overtoom Karen M. Overtoom R.E.

4 Windy Way Wt143, West Tisbury, MA 02575
/2
$1,067,000 Sold Sep 26, 2025

112 W Spring St, Vineyard Haven, MA 02568
- 3 Beds
- 2.5 Baths
- 1,503 Sq Ft
- Built 2000
Last Sold Summary
- 7% Below List Price
- $710/SF
- 95 Days On Market
Current Estimated Value $1,151,848

Last Listing Agent Katherine Donahue Sandpiper Realty Inc

112 W Spring St, Vineyard Haven, MA 02568

/4
Est $2,923,214 Not Listed For Sale

188 Pond Rd, Vineyard Haven, MA 02568
- 4 Beds
- 3 Baths
- 2,789 Sq Ft
- Built 1996
188 Pond Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 7% Below List Price
- $1,124/SF
Last Sold Price $3,135,000

Last Listing Agent Rose Ryley Wallace & Co. Sotheby's

/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
/8
$4,800 total monthly price
- 3 Beds
- 3 Baths
- 3,279 Sq Ft
- House for Rent
165 Christiantown Rd, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

Karen Overtoom Karen M. Overtoom R.E.

165 Christiantown Rd, West Tisbury, MA 02575
/19
$1,865,000 Sold Dec 04, 2025

71 Netock Ave, Oak Bluffs, MA 02557
- 4 Beds
- 5 Baths
- 2,820 Sq Ft
- Built 1982
Last Sold Summary
- 7% Below List Price
- $661/SF
- 11 Days On Market
Current Estimated Value $1,891,636

Last Listing Agent Ellen Valentgas Sotheby's International Realty

71 Netock Ave, Oak Bluffs, MA 02557

/34
Est $2,441,108 Not Listed For Sale

248 Pond Rd, Vineyard Haven, MA 02568
- 5 Beds
- 3.5 Baths
- 1 Sq Ft
- Built 1998
248 Pond Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 6% Above List Price
- $2,300,000/SF
- 174 Days On Market
Last Sold Price $2,300,000

Last Listing Agent Brenda Galligan Karen M. Overtoom R E

/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
/42
$19,000 total monthly price
- 6 Beds
- 6.5 Baths
- 6,950 Sq Ft
- House for Rent
40 Sweet William Way, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

Karen Overtoom Karen M. Overtoom R.E.

40 Sweet William Way, West Tisbury, MA 02575
/25
$1,125,000 Sold Oct 28, 2025

140 Longview Rd, Vineyard Haven, MA 02568
- 3 Beds
- 1.5 Baths
- 1,432 Sq Ft
- Built 1964
Last Sold Summary
- 13% Below List Price
- $786/SF
- 97 Days On Market
Current Estimated Value $1,121,422

Last Listing Agent Candy DaRosa Feiner Real Estate

140 Longview Rd, Vineyard Haven, MA 02568

/25
Est $2,063,910 Not Listed For Sale

131 Shubael Weeks Path, Vineyard Haven, MA 02568
- 5 Beds
- 3 Baths
- 3,636 Sq Ft
- Built 1985
131 Shubael Weeks Path, Vineyard Haven, MA 02568

Last Sold Summary
- 3% Above List Price
- $550/SF
- 0 Days On Market
Last Sold Price $2,000,000

Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

/23
$1,795,000 Pending
- 4 Beds
- 3 Baths
- 2,038 Sq Ft
25 Hampson Ave, Oak Bluffs, MA 02568

Location is everything. Fantastic Cape in a quiet neighborhood, just a 10-minute walk to harbor and downtown. The first-floor plan includes a spacious living-room that opens to an eat-in kitchen, large Master with full bath, and a second bedroom with a full bath. The second floor has a beautiful large open space area for a media room, study or playroom and 2 more large bedrooms with another full

Lenny Altieri Premier Properties

25 Hampson Ave, Oak Bluffs, MA 02568
/27
$18,840 total monthly price
- 3 Beds
- 2.5 Baths
- House for Rent
21 William St Vh430, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

Karen Overtoom Karen M. Overtoom R.E.

21 William St Vh430, Tisbury, MA 02568
/32
$1,100,000 Sold Jun 27, 2025

10 Kims Way, Oak Bluffs, MA 02568
- 4 Beds
- 2.5 Baths
- 1,976 Sq Ft
- Built 1985
Last Sold Summary
- 12% Below List Price
- $557/SF
- 156 Days On Market
Last Listing Agent Michael Schweikert Ocean Park Realty, Inc.

10 Kims Way, Oak Bluffs, MA 02568

/2
Est $1,725,306 Not Listed For Sale

26 Old Coach Rd, Vineyard Haven, MA 02568
- 3 Beds
- 2.5 Baths
- 2,102 Sq Ft
- Built 1998
26 Old Coach Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 3% Above List Price
- $795/SF
- 26 Days On Market
Last Sold Price $1,671,100

Last Listing Agent Dawn Bellante Sandpiper Realty Inc

/32
$560,000
- 1 Bed
- 1.5 Baths
- 590 Sq Ft
21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

Diana Gilmore Island Real Estate

21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
/28
$32,000 total monthly price
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
- House for Rent
37 Mempremagog Ave Vh410, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

Karen Overtoom Karen M. Overtoom R.E.

37 Mempremagog Ave Vh410, Tisbury, MA 02568
/19
$1,095,000 Sold May 02, 2025

31 Davis St, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,945 Sq Ft
- Built 1966
Last Sold Summary
- 2% Above List Price
- $563/SF
- 5 Days On Market
Current Estimated Value $1,212,803

Last Listing Agent Sheila Morse Island Real Estate

31 Davis St, Vineyard Haven, MA 02568

/2
Est $1,357,971 Not Listed For Sale

45 Pine Tree Ln, Vineyard Haven, MA 02568
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
- Built 1961
45 Pine Tree Ln, Vineyard Haven, MA 02568

Last Sold Summary
- 10% Below List Price
- $884/SF
Last Sold Price $1,237,500

Last Listing Agent Sheila Morse Island Real Estate

/18
$1,100,000
- 2 Beds
- 2 Baths
- 1,583 Sq Ft
25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

Maranda Post Compass | The O'Hanlon Group

25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
/18
$10,000 total monthly price
- 3 Beds
- 1.5 Baths
- 1,144 Sq Ft
- House for Rent
100 Franklin Terrace Vh411, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

Karen Overtoom Karen M. Overtoom R.E.

100 Franklin Terrace Vh411, Tisbury, MA 02568
/2
$505,000 Sold Sep 26, 2025

02 John Hoft Rd Unit 2, Tisbury, MA 02568
- Land
- 1.3 Acres
- $388,462 per Acre
Last Sold Summary
- 5% Below List Price
- 120 Days On Market
Last Listing Agent Tony Tobia Tobia Real Estate, LTD

02 John Hoft Rd Unit 2, Tisbury, MA 02568

/36
Est $2,349,533 Not Listed For Sale

377 State Rd, Vineyard Haven, MA 02568
- 4 Beds
- 2.5 Baths
- 2,436 Sq Ft
- Built 1970
377 State Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 7% Above List Price
- $902/SF
- 518 Days On Market
Last Sold Price $2,197,000

Last Listing Agent Jill Napior Tea Lane Associates

Showing Results 41 - 80, Page 2 of 18

Massachusetts Dukes County Vineyard Haven 02568

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