11,126

Vineyard Haven, MA Homes

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  • /9

    $1,395,000

    Open Sun 12PM - 2PM $100K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • /20

    $7,323

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,022 Sq Ft
    • Condo for Rent

    25 Simpson Ave Unit SI ID1514679P, Oak Bluffs, MA 02568

    The advertised rate of $7,323/month is the lowest available price, based on a 30 day(s) stay with a move-in date of December 4, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    25 Simpson Ave Unit SI ID1514679P, Oak Bluffs, MA 02568
  • /42

    $1,300,000

    Sold Feb 13, 2026

    169 Clover Hill Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $719/SF
    • 9 Days On Market

    Current Estimated Value $1,418,628

    Last Listing Agent Stephanie Roache Donnelly + Co

    169 Clover Hill Dr, Vineyard Haven, MA 02568
    • /3

      Est $1,660,470

      Not Listed For Sale

      18 Towanticut Ave, Oak Bluffs, MA 02557

      • 4 Beds
      • 2.5 Baths
      • 2,329 Sq Ft
      • Built 1989
      18 Towanticut Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

  • /12

    $1,200,000

    • Land
    • 10,890 Sq Ft
    • $4,800,000 per Acre

    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568

    Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs.Build Your Martha’s Vineyard Dream Home.Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha’s Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
  • /20

    $7,389

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 2,281 Sq Ft
    • Condo for Rent

    13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568

    The advertised rate of $7,390/month is the lowest available price, based on a 30 day(s) stay with a move-in date of December 2, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568
  • /32

    $487,500

    Sold Jun 30, 2026

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft
    • Built 1983

    Last Sold Summary

    • 13% Below List Price
    • $826/SF
    • 205 Days On Market

    Last Listing Agent Diana Gilmore Island Real Estate

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    • /2

      Est $2,878,297

      Not Listed For Sale

      28 Woodhaven Dr, Edgartown, MA 02539

      • 3 Beds
      • Built 2013
      28 Woodhaven Dr, Edgartown, MA 02539

      Last Sold Summary

      • 6,292 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /40

    $3,675,000

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    28 Beach Rd, Oak Bluffs, MA 02557

    Enjoy Spectacular Views From This Chic Island Retreat. Wake up to panoramic Vineyard Sound views, watch the Steamship ferries cross to Woods Hole, and enjoy sunsets stretching down the Lagoon. This turnkey 4-bedroom, 2.5-bath home is designed to embrace its remarkable waterfront setting, with covered decks on both sides capturing ocean breezes and water views from nearly every room. The first

    Agent Photo

    Wendy Harman

    Compass

    28 Beach Rd, Oak Bluffs, MA 02557
  • /29

    $64,000 Per Month

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

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557
  • /30

    $1,550,000

    Sold Oct 16, 2025

    251 State Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft
    • Built 1986

    Last Sold Summary

    • 9% Below List Price
    • $780/SF
    • 114 Days On Market

    Current Estimated Value $1,751,931

    Last Listing Agent Meg Bodnar Tea Lane Associates

    251 State Rd, Vineyard Haven, MA 02568
    • /10

      Not Listed For Sale

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • /36

    $2,325,000

    $270K PRICE DROP Pending
    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    54 Amelia's Crossing, Tisbury, MA 02568

    COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

    Agent Photo

    Wendy Harman

    Compass

    54 Amelia's Crossing, Tisbury, MA 02568
  • /12

    $15,000 Per Month

    • 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
  • /20

    $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 $1,978,938

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
    • /15

      Est $1,160,319

      Not Listed For Sale

      15 14th St N, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 2018
      15 14th St N, Edgartown, MA 02539

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Mike Sawyer Sawyer Realty Group

  • /53

    $2,295,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,015 Sq Ft

    3 Hidden Cove Rd, Oak Bluffs, MA 02557

    HIDDEN COVE GEM WITH SERENE POND VIEWS AND COVETED WATER ACCESS. Located in the desirable Hidden Cove enclave, a 65+ acre water-access community with direct access to Sengekontacket Pond and Nantucket Sound, this inviting contemporary home offers privacy, comfort, and high-end finishes throughout. Community amenities include a private boat dock, walking trails, pickleball and tennis, all

    Agent Photo

    Wendy Harman

    Compass | Point B

    3 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /20

    $20,000 Per Month

    • 3 Beds
    • 3 Baths
    • House for Rent

    40 Hidden Cove Rd, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

    Karen Overtoom Karen M. Overtoom R.E.

    40 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /28

    $1,350,000

    Sold Nov 20, 2025

    16 Majors Cove Ln, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,965 Sq Ft
    • Built 1986

    Last Sold Summary

    • 26% Below List Price
    • $687/SF
    • 156 Days On Market

    Current Estimated Value $1,526,197

    Last Listing Agent Stephanie Roache Donnelly + Co

    16 Majors Cove Ln, Edgartown, MA 02539
    • /38

      Est $1,056,884

      Not Listed For Sale

      287 County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1998
      287 County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /8

    $1,200,000

    • Land
    • 10,890 Sq Ft
    • $4,800,000 per Acre

    0 Temahigan Ave & Dover St Unit 22602202, Oak Bluffs, MA 02557

    Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs. Build Your Martha's Vineyard Dream Home. Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha's Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    0 Temahigan Ave & Dover St Unit 22602202, Oak Bluffs, MA 02557
  • /26

    $50,000 Per Month

    • 4 Beds
    • 3 Baths
    • 3,237 Sq Ft
    • House for Rent

    29 Naushon Rd Wt142, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

    Karen Overtoom Karen M. Overtoom R.E.

    29 Naushon Rd Wt142, West Tisbury, MA 02575
  • /26

    $1,500,000

    Sold Mar 30, 2026

    68 20th St S, Edgartown, MA 02539

    • 4 Beds
    • 3 Baths
    • 1,975 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $759/SF
    • 28 Days On Market

    Current Estimated Value $1,567,254

    Last Listing Agent Carol Shore Donnelly + Co

    68 20th St S, Edgartown, MA 02539
    • /26

      Est $1,558,733

      Not Listed For Sale

      19 Quantapog Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,822 Sq Ft
      • Built 1988
      19 Quantapog Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 177 Days On Market

      Last Listing Agent Frank Markwica Sandpiper Realty

  • /35

    $2,325,000

    $270K PRICE DROP Under Contract
    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    54 Amelias Crossing, Vineyard Haven, MA 02568

    COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

    Agent Photo

    Wendy Harman

    Compass | Point B

    54 Amelias Crossing, Vineyard Haven, MA 02568
  • /22

    $15,000 Per Month

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

    55 Samoset Ave, Oak Bluffs, MA 02557

    AVAILABLE SUMMER 2026: JULY 12-AUGUST 9. Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, Oak Bluffs, MA 02557
  • /2

    $525,000

    Sold May 29, 2026

    0 Lyle Ln Unit 2A, Vineyard Haven, MA 02568

    • Land
    • 31,180 Sq Ft
    • $733,445 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    0 Lyle Ln Unit 2A, Vineyard Haven, MA 02568
    • /12

      Est $1,204,550

      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

      • 209 Days On Market

      Last Listing Agent Bob Sparks American Real Estate LLC

  • /18

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one

    Lisa Lucier Anchor Realty of MV

    47 Winemack St, Oak Bluffs, MA 02557
  • /25

    $24,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft
    • House for Rent

    5 Laurel Ave, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

    Karen Overtoom Karen M. Overtoom R.E.

    5 Laurel Ave, Oak Bluffs, MA 02557
  • /26

    $1,935,000

    Sold May 06, 2026

    34 Davis St, Tisbury, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 2,453 Sq Ft
    • Built 2025

    Last Sold Summary

    • 19% Below List Price
    • $789/SF
    • 160 Days On Market

    Last Listing Agent Andrew McElhinney Compass LLC

    34 Davis St, Tisbury, MA 02568
    • /29

      Est $1,258,064

      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

      • 30 Days On Market

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /6

    $975,000

    • Land
    • 1.07 Acres
    • $911,215 per Acre

    68 Pond View Dr, Oak Bluffs, MA 02557

    Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development. Subject to the Town of Oak

    Casandra Hyland Sandpiper Realty, Inc.

    68 Pond View Dr, Oak Bluffs, MA 02557
  • /8

    $6,000 Per Month

    • 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
  • /2

    $1,850,000

    Sold Mar 31, 2026

    7 S Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $589/SF
    • 74 Days On Market

    Current Estimated Value $2,047,658

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    7 S Meadow Ln, Oak Bluffs, MA 02557
    • /14

      Est $998,385

      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

      • 22 Days On Market

      Last Listing Agent Roy Cutrer LAER Realty Partners

  • /23

    $1,800,000

    • 4 Beds
    • 3 Baths
    • 2,864 Sq Ft

    18 Wood Duck Way, Edgartown, MA 02539

    Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations. Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight

    Janna O'Loughlin Portfolio Properties

    18 Wood Duck Way, Edgartown, MA 02539
  • /27

    $21,700 Per Month

    • 5 Beds
    • 3 Baths
    • 2,168 Sq Ft
    • House for Rent

    97 3rd St N, Edgartown, MA 02539

    YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

    Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

    97 3rd St N, Edgartown, MA 02539
  • /27

    $1,560,000

    Sold Jan 15, 2026

    36 Ferro Way, Tisbury, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 4,032 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $387/SF
    • 37 Days On Market

    Current Estimated Value $1,690,530

    Last Listing Agent Hope O'Brien Compass LLC

    36 Ferro Way, Tisbury, MA 02568
    • /25

      Est $2,089,409

      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

      • 0 Days On Market

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

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