10,865

Vineyard Haven, MA Homes

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  • /4

    $809,000

    • Land
    • 16,988 Sq Ft
    • $2,074,359 per Acre

    7 Highland Ave, Oak Bluffs, MA 02557

    Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

    Shera Toledo eXp Realty, LLC

    7 Highland Ave, Oak Bluffs, MA 02557
  • /41

    $13,500 Per Month

    • 5 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    14 Bernard Cir, Vineyard Haven, MA 02568

    ** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    14 Bernard Cir, Vineyard Haven, MA 02568
  • /2

    $699,000

    Sold Aug 31, 2026

    61 Third St N Unit 47, Edgartown, MA 02539

    • Land
    • 21,780 Sq Ft
    • $1,398,000 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    61 Third St N Unit 47, Edgartown, MA 02539
    • /38

      Est $2,017,870

      Not Listed For Sale

      83 Dolan Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 3,841 Sq Ft
      • Built 1994
      83 Dolan Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Courtney Marek Sandpiper Realty

  • /12

    $3,400,000

    New Construction
    • 3 Beds
    • 4.5 Baths
    • 3,260 Sq Ft

    27 Double Ox Rd, Oak Bluffs, MA 02557

    Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living

    Lesley Heidt Sandpiper Realty, Inc.

    27 Double Ox Rd, Oak Bluffs, MA 02557
  • /16

    $3,000 Per Month

    • 1 Bath
    • 400 Sq Ft
    • House for Rent

    90 Edgartown Rd, Vineyard Haven, MA 02568

    Winter Rental: September to May 30, 2027. Renovated Studio Cottage on Martha's Vineyard w/private feel. Within walking distance of shops, dining, and the ferry. Lots of trees for year-round enjoyment. Open floor plan with Murphy bed for additional space and a large, comfortable sofa, galley kitchen with granite countertops, stainless steel appliances, amazing tiled bathroom with laundry, plenty

    Kim Seawright Generations Realty Group

    90 Edgartown Rd, Vineyard Haven, MA 02568
  • /23

    $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
    • 9 Days On Market

    Current Estimated Value $1,181,877

    Last Listing Agent Katherine Donahue Sandpiper Realty

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

      Est $2,840,676

      Not Listed For Sale

      89 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,728 Sq Ft
      • Built 1830
      89 Main St, Vineyard Haven, MA 02568

  • /19

    $7,950,000

    $3M PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    33 Goethals Way, Vineyard Haven, MA 02568

    A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

    Buder Team Sandpiper Realty, Inc.

    33 Goethals Way, Vineyard Haven, MA 02568
  • /19

    $30,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,600 Sq Ft
    • House for Rent

    37 Sachem Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

    Karen Overtoom Karen M. Overtoom R.E.

    37 Sachem Cir, West Tisbury, MA 02575
  • /29

    $2,450,000

    Sold Jun 02, 2026

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,336 Sq Ft
    • Built 1953

    Last Sold Summary

    • 6% Below List Price
    • $1,834/SF
    • 67 Days On Market

    Last Listing Agent Rene Ben David Ocean Park Realty Inc

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    • /31

      Est $1,476,638

      Not Listed For Sale

      48 Puritan Dr, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,999 Sq Ft
      • Built 1985
      48 Puritan Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Jennifer B. DaSilva Compass

  • /2

    $450,000

    • Land
    • 20,538 Sq Ft
    • $954,401 per Acre

    0 Old Country Ln Unit 4, Vineyard Haven, MA 02568

    Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.

    Brenda Galligan Karen M. Overtoom R.E.

    0 Old Country Ln Unit 4, Vineyard Haven, MA 02568
  • /34

    $12,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • House for Rent

    267 Great Plains Road Wt117, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

    Karen Overtoom Karen M. Overtoom R.E.

    267 Great Plains Road Wt117, West Tisbury, MA 02575
  • /42

    $4,150,000

    Sold Feb 19, 2026

    97 Longview Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 5.5 Baths
    • 4,003 Sq Ft
    • Built 2008

    Last Sold Summary

    • 12% Below List Price
    • $1,037/SF
    • 74 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    97 Longview Rd, Vineyard Haven, MA 02568
    • /27

      Est $1,623,466

      Not Listed For Sale

      13 Saddle Club Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,729 Sq Ft
      • Built 1988
      13 Saddle Club Rd, Edgartown, MA 02539

      Last Sold Summary

      • 227 Days On Market

      Last Listing Agent Elaine Miller & Partners Realty, EMPR Sandpiper Realty

  • /46

    $2,400,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 3,873 Sq Ft

    50 Hidden Cove Rd, Edgartown, MA 02539

    Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering

    Sean Federowicz Landmarks at TODAY Real Estate

    50 Hidden Cove Rd, Edgartown, MA 02539
  • /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
  • /3

    $665,000

    Sold Mar 06, 2026

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557

    • Land
    • 11,133 Sq Ft
    • $2,601,721 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 37 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557
    • /42

      Not Listed For Sale

      67 Hidden Village Rd, Vineyard Haven, MA 02568

      • 7 Beds
      • 5.5 Baths
      • 4,476 Sq Ft
      • Built 1997
      67 Hidden Village Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 347 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co.

  • /33

    $1,095,000

    $130K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 1,428 Sq Ft

    323 County Rd, Oak Bluffs, MA 02557

    This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment.The home features a bright, open-concept kitchen, dining,

    Nancy Beckwith Anchor Realty of Martha's Vineyard

    323 County Rd, Oak Bluffs, MA 02557
  • /28

    $38,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    17 Otis Bassett Rd, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

    Karen Overtoom Karen M. Overtoom R.E.

    17 Otis Bassett Rd, West Tisbury, MA 02575
  • /2

    $880,000

    Sold Oct 17, 2025

    5 Johns Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1987

    Last Sold Summary

    • $645/SF
    • 0 Days On Market

    Current Estimated Value $1,066,290

    Last Listing Agent LINK Email Cache LINK

    5 Johns Way, Oak Bluffs, MA 02557
    • /46

      Est $6,600,732

      Not Listed For Sale

      79 Rachels Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,278 Sq Ft
      • Built 1983
      79 Rachels Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Jennifer O'hanlon Compass LLC

  • /59

    $2,650,000

    • 3 Beds
    • 2.5 Baths
    • 2,874 Sq Ft

    10 Woodhaven Dr, Edgartown, MA 02539

    Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortable year-round

    Leslie C. Floyd Portfolio Properties

    10 Woodhaven Dr, 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
  • /30

    $1,050,000

    Sold Oct 06, 2025

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • 11% Below List Price
    • $794/SF
    • 62 Days On Market

    Current Estimated Value $1,066,886

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, Oak Bluffs, MA 02557
    • /2

      Est $1,522,729

      Not Listed For Sale

      23 Anthiers Way, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 2,066 Sq Ft
      • Built 1950
      23 Anthiers Way, Edgartown, MA 02539

  • /39

    $4,050,000

    $645K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,606 Sq Ft

    95 Hines Point Rd, Vineyard Haven, MA 02568

    A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor

    Elissa Lash Tea Lane Associates

    95 Hines Point Rd, Vineyard Haven, MA 02568
  • /8

    $4,800 Per Month

    • 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
  • /36

    $2,900,000

    Sold Mar 30, 2026

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft
    • Built 1988

    Last Sold Summary

    • $561/SF
    • 35 Days On Market

    Current Estimated Value $2,968,781

    Last Listing Agent Casandra Hyland Sandpiper Realty, Inc.

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    • /32

      Est $2,368,903

      Not Listed For Sale

      232 Lagoon Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 2,276 Sq Ft
      • Built 1970
      232 Lagoon Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 220 Days On Market

      Last Listing Agent Kerry Bourne Grade A Realty

  • /21

    $1,475,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    7 Boylston Dr, Edgartown, MA 02539

    Well-maintained three-bedroom, two-bath home set on a quiet road in a convenient Edgartown location. The property is bordered by more than 100 acres of conservation land, offering a peaceful setting and added privacy while remaining close to Edgartown Village, beaches, bike paths, and everyday amenities.The home features comfortable living and dining spaces along with a beautifully

    Patrick McCarthy Grace Hagerty Real Estate Inc

    7 Boylston Dr, Edgartown, MA 02539
  • /40

    $32,500 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,222 Sq Ft
    • House for Rent

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. 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 &83 Ashtonw Vh408, Tisbury, MA 02568
  • /36

    $1,275,000

    Sold Jul 31, 2026

    9 Brunswick Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,033 Sq Ft
    • Built 1862

    Last Sold Summary

    • $1,234/SF
    • 1 Day On Market

    Current Estimated Value $1,252,940

    Last Listing Agent Alice Pierce Coldwell Banker Realty - Hingham

    9 Brunswick Ave, Oak Bluffs, MA 02557
    • /44

      Est $1,790,815

      Not Listed For Sale

      30 Hillside Path, Vineyard Haven, MA 02568

      • 3 Beds
      • 4 Baths
      • 3,114 Sq Ft
      • Built 1999
      30 Hillside Path, Vineyard Haven, MA 02568

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /15

    $1,925,000

    • 5 Beds
    • 1 Bath
    • 2,232 Sq Ft

    8 Pequot Ave, Oak Bluffs, MA 02557

    Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time. Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends. The front porch has been a gathering place for 50+ years, and the views have not been expanded. So much

    Kerry Quinlan-Potter Breakwater MV

    8 Pequot Ave, Oak Bluffs, MA 02557
  • /12

    $860,000

    Sold Feb 09, 2026

    8 Hitchings Cir, Oak Bluffs, MA 02557

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $698/SF
    • 22 Days On Market

    Last Listing Agent Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
    • /2

      Est $1,914,015

      Not Listed For Sale

      54 Bold Meadow Rd, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,026 Sq Ft
      • Built 1993
      54 Bold Meadow Rd, Edgartown, MA 02539

  • /41

    $1,975,000

    $175K PRICE DROP
    • 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

Showing Results 121 - 160, Page 4 of 18

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