Vineyard Haven Homes for Sale

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  $1,399,000

  • 5 Beds
  • 2 Baths
  • 1,968 Sq Ft

  41 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568

  Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful

  Peyton Wallace Studio Realty

  41 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
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  $2,525,000

  $400K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,704 Sq Ft

  21 Davis St, Vineyard Haven, MA 02568

  Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home encompassing 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect exceptional quality

  Valene Pires The Agency

  21 Davis St, Vineyard Haven, MA 02568
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  /39

  $2,200,000

  $700K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,562 Sq Ft

  21 Woodlawn Ave, Vineyard Haven, MA 02568

  Thoughtfully designed with custom features throughout, this in-town Vineyard Haven home is the perfect blend of coastal charm and modern sophistication. The 4 bedroom 3 bath property offers a comfortable, easy flowing layout with gleaming hardwood floors and open sun-filled spaces.At the heart of the home is a chef-inspired gourmet kitchen with premium appliances, ample counter space, a

  Beth Welch Viewpoints

  21 Woodlawn Ave, Vineyard Haven, MA 02568
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  $1,995,000

  • 5 Beds
  • 3 Baths
  • 3,480 Sq Ft

  135 Mayflower Ln, Vineyard Haven, MA 02568

  Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for

  Kathleen Dawson Donnelly + Co.

  135 Mayflower Ln, Vineyard Haven, MA 02568
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  /3

  $525,000

  • Land
  • 10,454 Sq Ft
  • $2,187,500 per Acre

  Lot 1 Dolan Ave, Tisbury, MA 02568

  A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  Lot 1 Dolan Ave, Tisbury, MA 02568
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  /38

  $5,800,000

  $450K PRICE DROP

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and burgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  $2,300,000

  $900K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,274 Sq Ft

  70 Spring St, Vineyard Haven, MA 02568

  Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

  June Flake Viewpoints

  70 Spring St, Vineyard Haven, MA 02568
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  /34

  $1,250,000

  • 3 Beds
  • 3 Baths
  • 1,682 Sq Ft

  261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

  END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach

  Jennifer O'hanlon Compass LLC

  261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
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  /21

  $1,175,000

  Open House 8/17 $74K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 998 Sq Ft

  299 Daggett Ave, Vineyard Haven, MA 02568

  This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

  Alyson Parker Karen M. Overtoom R.E.

  299 Daggett Ave, Vineyard Haven, MA 02568
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  /57

  $3,295,000

  • 5 Beds
  • 4 Baths
  • 2,330 Sq Ft

  29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking.

  Madelyn Silvia Wallace & Co. Sotheby's

  29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /3

  $525,000

  • Land
  • 10,240 Sq Ft
  • $2,233,092 per Acre

  Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568

  A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

  Katherine Donahue Sandpiper Realty

  Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
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  $4,695,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  16 Frog Hollow, Vineyard Haven, MA 02568

  Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage.Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water

  Rose Ryley Wallace & Co. Sotheby's International Realty

  16 Frog Hollow, Vineyard Haven, MA 02568
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  $2,950,000

  • 5 Beds
  • 4 Baths
  • 2,374 Sq Ft

  124 Main St, Vineyard Haven, MA 02568

  Historic Elegance Meets Modern Luxury in Vineyard Haven: Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  124 Main St, Vineyard Haven, MA 02568
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  $1,895,000

  • 3 Beds
  • 2 Baths
  • 2,462 Sq Ft

  129 Beach Rd, Tisbury, MA 02568

  Rarely does such a unique, waterfront location become available. With amazing, 180+ degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the

  Michele Moore Island Real Estate

  129 Beach Rd, Tisbury, MA 02568
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  /39

  $1,488,000

  • 5 Beds
  • 4 Baths
  • 2,884 Sq Ft

  39 Ferro Way, Vineyard Haven, MA 02568

  Tucked away on a quiet cul-de-sac, this beautifully maintained multi-family property offers the perfect blend of privacy, flexibility, and convenience. Built in 2020, the home encompasses 2,884 square feet of thoughtfully designed living space, featuring a total of 5 bedrooms and 4 full bathrooms. The walkout lower level is a fully permitted Accessory Dwelling Unit (ADU), creating an ideal

  Emily Flake Viewpoints

  39 Ferro Way, Vineyard Haven, MA 02568

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