Tisbury, MA Homes

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  $3,500,000

  • 7 Beds
  • 5 Baths
  • 3,880 Sq Ft

  35 New York Ave, Oak Bluffs, MA 02568

  An exceptional chance to own one of the few five-unit apartment buildings available on Martha’s Vineyard. Ideally located within a short walk to Oak Bluffs Center, the Harbor, ferry service, and public beaches, this property offers both convenience and strong income potential. The building includes five well-maintained apartments with a total of 7 bedrooms and has been thoughtfully renovated and

  Emma Kennedy Sandpiper Realty, Inc.

  35 New York Ave, Oak Bluffs, MA 02568
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• 

  

  

  /8

  $11,800 total monthly price

  • 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
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  /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 $938,316

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

  345 Franklin St, Vineyard Haven, MA 02568
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  /14

  Est $1,013,552 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  51 Manchester Ave, Vineyard Haven, MA 02568

  51 Manchester Ave, Vineyard Haven, MA 02568
• 

  

  

  /23

  $2,260,000

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

  Kate Burnside Portfolio Properties

  4 High Meadow Ln, Oak Bluffs, MA 02557
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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
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  /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 $1,091,009

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  160 Bernard Cir, Vineyard Haven, MA 02568
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  /2

  Est $2,548,131 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,527 Sq Ft

  230 Pond Rd, Vineyard Haven, MA 02568

  230 Pond Rd, Vineyard Haven, MA 02568
• 

  

  /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
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  /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
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  /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

  Last Listing Agent Rene Jackson Island Real Estate

  25 Windy Hill Rd, Oak Bluffs, MA 02557
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  /34

  Est $2,473,034 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
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  /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
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  /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
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  /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
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  /25

  Est $2,104,866 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
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  /3

  $2,100,000

  • 3 Beds
  • 3.5 Baths
  • 2,019 Sq Ft

  2 Hope's Way, Oak Bluffs, MA 02557

  ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Purchase lot ($700,000)& Execute a BUILDING CONTRACT ($1,400,000 )or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty

  Marilyn Moses Ocean Park Realty Inc

  2 Hope's Way, Oak Bluffs, MA 02557
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  /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
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  /13

  $776,500 Sold Mar 05, 2025

  32 Clark Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $1,011/SF
  • 17 Days On Market

  Current Estimated Value $789,751

  Last Listing Agent Diana Gilmore Island Real Estate

  32 Clark Ave, Vineyard Haven, MA 02568
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  /2

  Est $1,809,681 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,102 Sq Ft

  26 Old Coach Rd, Vineyard Haven, MA 02568

  26 Old Coach Rd, Vineyard Haven, MA 02568
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  /30

  $2,950,000

  • 3 Beds
  • 2.5 Baths
  • 1,845 Sq Ft

  33 Ocean Ave, Oak Bluffs, MA 02557

  A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and

  Marcia Sullivan Garvey Donnelly + Co.

  33 Ocean Ave, Oak Bluffs, MA 02557
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  /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
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  /6

  $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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  /45

  Est $1,789,848 Not Listed For Sale

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

  38 Edgewood Dr, Edgartown, MA 02539

  38 Edgewood Dr, Edgartown, MA 02539
• 

  

  /34

  $3,250,000

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  6 Brewster Ave, Oak Bluffs, MA 02557

  Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  6 Brewster Ave, Oak Bluffs, MA 02557
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  /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
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  /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 $1,101,318

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  112 W Spring St, Vineyard Haven, MA 02568
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  /2

  Est $1,388,663 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  45 Pine Tree Ln, Vineyard Haven, MA 02568
• 

  

  /40

  $1,985,000

  • 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
• 

  

  /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
• 

  

  /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
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  /36

  Est $2,360,766 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  377 State Rd, Vineyard Haven, MA 02568

  377 State Rd, Vineyard Haven, MA 02568
• 

  

  /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
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  /25

  $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
• 

  

  /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

  Last Listing Agent Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
• 

  

  /5

  Est $2,512,811 Not Listed For Sale

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

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568
• 

  

  /42

  $1,350,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  169 Clover Hill Dr, Vineyard Haven, MA 02568

  Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home sits on a generous 0.86-acre lot less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal—close to restaurants, shopping, and the ferry, yet with enough land to accommodate the existing detached two-car garage and the potential for an Accessory Dwelling Unit. The three-bedroom home offers a

  Stephanie Roache Donnelly + Co

  169 Clover Hill Dr, Vineyard Haven, MA 02568
• 

  

  /15

  $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
• 

  

  /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
• 

  

  /14

  Est $2,771,008 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,926 Sq Ft

  30 Pond Ln, Vineyard Haven, MA 02568

  30 Pond Ln, Vineyard Haven, MA 02568

Showing Results 41 - 80, Page 2 of 18