10,865

Vineyard Haven, MA Homes

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  • /41

    $287,500

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 9C, an inviting Martha’s Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
  • /28

    $32,000 Per Month

    • 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
  • /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
    • /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

  • /24

    $310,000

    • 1 Bed
    • 1 Bath
    • 419 Sq Ft

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha’s Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
  • /27

    $18,840 Per Month

    • 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
  • /26

    $800,000

    Sold Jun 04, 2026

    17 Mariner Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1983

    Last Sold Summary

    • 11% Below List Price
    • $694/SF
    • 32 Days On Market

    Current Estimated Value $867,058

    Last Listing Agent Karl Olsen Carlson & Company, LLC

    17 Mariner Rd, Vineyard Haven, MA 02568
    • /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

  • /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
  • /9

    $19,000 Per Month

    • 6 Beds
    • 2.5 Baths
    • 2,155 Sq Ft
    • House for Rent

    17 Umbagog Ave Wt109, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Umbagog Ave Wt109, West Tisbury, MA 02575
  • /26

    $1,800,000

    Sold Oct 15, 2025

    82 Skiff Ave, Tisbury, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 1,913 Sq Ft
    • Built 2020

    Last Sold Summary

    • 10% Below List Price
    • $941/SF
    • 128 Days On Market

    Current Estimated Value $1,669,529

    Last Listing Agent Lenny Altieri Premier Properties

    82 Skiff Ave, 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

  • /52

    $2,850,000

    • 5 Beds
    • 3 Baths
    • 1,957 Sq Ft

    49 The Blvd, Edgartown, MA 02539

    A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond.Set along the Boulevard, behind a traditional white picket fence, this .66 acre property features two side-by-side cottages dating back to the 1940s and captures

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    49 The Blvd, Edgartown, MA 02539
  • /34

    $25,000 Per Month

    • 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
  • /19

    $750,000

    Sold Nov 07, 2025

    41 Trinity Park, Oak Bluffs, MA 02557

    • 4 Beds
    • 1 Bath
    • 1,154 Sq Ft
    • Built 1867

    Last Sold Summary

    • 6% Below List Price
    • $650/SF
    • 14 Days On Market

    Current Estimated Value $827,958

    Last Listing Agent Stacy Ickes Donnelly + Co.

    41 Trinity Park, Oak Bluffs, MA 02557
    • /2

      Est $1,793,582

      Not Listed For Sale

      26 Old Coach Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,923 Sq Ft
      • Built 1998
      26 Old Coach Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /16

    $287,500

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 9C, an inviting Martha's Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
  • /30

    $20,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • House for Rent

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

    Karen Overtoom Karen M. Overtoom R.E.

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557
  • /26

    $1,600,000

    Sold Nov 07, 2025

    96 Pondview Dr, Oak Bluffs, MA 02536

    • 4 Beds
    • 2.5 Baths
    • 2,115 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $757/SF
    • 35 Days On Market

    Last Listing Agent Doug Burke Signal House Group at Compass

    96 Pondview Dr, Oak Bluffs, MA 02536
    • /45

      Est $1,786,952

      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

      • 48 Days On Market

      Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  • /27

    $260,000

    • 1 Bed
    • 1 Bath
    • 319 Sq Ft

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha’s Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
  • /25

    $13,600 Per Month

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • House for Rent

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

    Karen Overtoom Karen M. Overtoom R.E.

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
  • /6

    $1,200,000

    Sold Aug 14, 2026

    66 Munroe Avenue and 17 Madison Ave Unit 180 &182, Oak Bluffs, MA 02557

    • Land
    • 22,498 Sq Ft
    • $2,323,330 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    66 Munroe Avenue and 17 Madison Ave Unit 180 &182, Oak Bluffs, MA 02557
    • /37

      Est $2,082,905

      Not Listed For Sale

      41 Smith Hollow Dr, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,391 Sq Ft
      • Built 2001
      41 Smith Hollow Dr, Edgartown, MA 02539

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /22

    $260,000

    • 1 Bed
    • 1 Bath
    • 319 Sq Ft

    33 Island Inn Rd Unit 25 F, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha's Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    33 Island Inn Rd Unit 25 F, Oak Bluffs, MA 02568
  • /8

    $18,500 Per Month

    • 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
  • /39

    $1,375,000

    Sold Sep 08, 2026

    27 Laurel Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 3 Baths
    • 1,621 Sq Ft
    • Built 1908

    Last Sold Summary

    • 13% Below List Price
    • $848/SF
    • 43 Days On Market

    Current Estimated Value $1,461,607

    Last Listing Agent Lisa Sheehan Berkshire Hathaway HomeServices Robert Paul Properties

    27 Laurel Ave, Oak Bluffs, MA 02557
    • /2

      Est $1,389,002

      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

  • /18

    $1,100,000

    $99K PRICE DROP
    • 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
  • /8

    $17,500 Per Month

    • 8 Beds
    • 4.5 Baths
    • 3,876 Sq Ft
    • House for Rent

    550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing

    Karen Overtoom Karen M. Overtoom R.E.

    550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
  • /27

    $1,625,000

    Sold May 12, 2026

    7 Upper Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $497/SF
    • 74 Days On Market

    Current Estimated Value $1,766,366

    Last Listing Agent Lesley Heidt Sandpiper Realty, Inc.

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    • /36

      Est $2,379,823

      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

      • 518 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /21

    $849,000

    $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In-Town Oak Bluffs Condo with Panoramic Water ViewsExperience the best of island living in this charming in-town Oak Bluffs condo, offering just under 800 square feet of comfortable and versatile living space.The condo features one generously sized bedroom plus a separate sleep nook, offering flexibility for guests, a home office, or additional sleeping accommodations. The nook could

    Lisa Lucier Anchor Realty of Martha's Vineyard

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • /8

    $18,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

    Karen Overtoom Karen M. Overtoom R.E.

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
  • /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

    Current Estimated Value $1,061,116

    Last Listing Agent Rene Jackson Island Real Estate

    25 Windy Hill Rd, Oak Bluffs, MA 02557
    • /5

      Est $2,552,473

      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

      • 0 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /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
  • /30

    $28,500 Per Month

    • 9 Beds
    • 6.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    9 Tuckernuck Ave, Oak Bluffs, MA 02557

    **SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    9 Tuckernuck Ave, Oak Bluffs, MA 02557
  • /16

    $530,000

    Sold Aug 07, 2026

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft
    • Built 1953

    Last Sold Summary

    • 19% Below List Price
    • $753/SF
    • 270 Days On Market

    Current Estimated Value $612,029

    Last Listing Agent Rene Jackson Island Real Estate

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    • /50

      Est $3,242,095

      Not Listed For Sale

      118 William St, Vineyard Haven, MA 02568

      • 4 Beds
      • 4.5 Baths
      • 2,792 Sq Ft
      • Built 1880
      118 William St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Alexis Holden Tea Lane Associates

Showing Results 41 - 80, Page 2 of 18

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