Vineyard Haven, MA Homes

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  $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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  $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
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  $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
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  Est $1,235,062 Not Listed For Sale

  3 Carole Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,997 Sq Ft
  • Built 1985

  3 Carole Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 7% Above List Price
  • $576/SF
  • 209 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Bob Sparks American Real Estate LLC
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  $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
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  $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
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  $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
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  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
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  $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
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  $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
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  $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
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  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
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  $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
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  $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
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  $700,500 Sold May 07, 2025

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539

  • Land
  • 0.55 Acre
  • $1,273,636 per Acre

  Last Sold Summary

  • 3% Above List Price
  • 0 Days On Market

  Last Listing Agent Jim Joyce Carroll & Vincent R.E.

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539
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  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
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  $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
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  $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
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  $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
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  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
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  $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
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  $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
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  $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
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  Est $1,718,736 Not Listed For Sale

  38 Edgewood Dr, Edgartown, MA 02539

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft
  • Built 1987

  38 Edgewood Dr, Edgartown, MA 02539

  Last Sold Summary

  • 1% Above List Price
  • $660/SF
  • 48 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty
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  $1,985,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,836 Sq Ft

  36 Smith Hollow Dr, Edgartown, MA 02539

  Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate two-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  36 Smith Hollow Dr, Edgartown, MA 02539
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  $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
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  $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
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  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
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  $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
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  $10,800 total monthly price

  • 2 Beds
  • 4 Baths
  • 1,800 Sq Ft
  • House for Rent

  256 Sandpiper Lane Vh417, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

  Karen Overtoom Karen M. Overtoom R.E.

  256 Sandpiper Lane Vh417, Tisbury, MA 02568
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  $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
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  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
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  $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
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  $7,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  83 Ashtons Way, Vineyard Haven, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

  Karen Overtoom Karen M. Overtoom R.E.

  83 Ashtons Way, Vineyard Haven, MA 02568
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  $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
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  Est $2,376,001 Not Listed For Sale

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft
  • Built 1948

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Below List Price
  • $1,447/SF
  • 0 Days On Market

  Last Sold Price $2,398,500

  Last Listing Agent LINK Email Cache LINK
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  $1,600,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,975 Sq Ft

  68 20th St S, Edgartown, MA 02539

  This well-maintained custom Cape Cod–style home is ideally suited for year-round living, vacation getaway, or employee housing. Located at the end of a quiet street next to Pennywise Preserve conservation land, it enjoys extra privacy. The main level features an open layout with vaulted ceilings. There is a spacious den above an oversized two-car garage and an expansive deck for entertaining

  Carol Shore Donnelly + Co

  68 20th St S, Edgartown, MA 02539
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  $25,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,334 Sq Ft
  • House for Rent

  100 Connie's Way Vh401, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way Vh401, Tisbury, MA 02568
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  $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
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  Est $1,291,533 Not Listed For Sale

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1999

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $722/SF
  • 141 Days On Market

  Last Sold Price $1,285,000

  Last Listing Agent Kerry Quinlan-Potter Breakwater MV

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