11,368

Vineyard Haven, MA Homes

Section Image
  • /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
  • /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
  • /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 $796,752

    Last Listing Agent Stacy Ickes Donnelly + Co.

    41 Trinity Park, Oak Bluffs, MA 02557
    • /25

      Est $2,103,856

      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

  • /21

    $4,695,000

    • 5 Beds
    • 4.5 Baths
    • 4,816 Sq Ft

    30 Water Gate Rd, Vineyard Haven, MA 02568

    Set privately in one of Vineyard Haven’s most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and ready access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for both gathering and quiet retreat, with an effortless indoor-outdoor flow that embraces the surrounding landscape. Bedrooms are

    Peyton Wallace Studio Realty

    30 Water Gate Rd, Vineyard Haven, 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
  • /31

    $1,325,000

    Sold Jun 30, 2025

    191 Spring Hill Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 4 Baths
    • 2,292 Sq Ft
    • Built 1992

    Last Sold Summary

    • 5% Below List Price
    • $578/SF
    • 10 Days On Market

    Current Estimated Value $1,250,478

    Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

    191 Spring Hill Rd, Vineyard Haven, MA 02568
    • /2

      Est $1,751,647

      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

  • /37

    $3,999,999

    $500K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,715 Sq Ft

    94 Weaver Ln, Vineyard Haven, MA 02568

    Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

    Emma Kennedy Sandpiper Realty, Inc.

    94 Weaver Ln, Vineyard Haven, 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

    $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 $1,777,078

      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

  • /66

    $2,775,000

    $175K PRICE DROP
    • 4 Beds
    • 8 Baths
    • 3,740 Sq Ft

    15 21st St N, Edgartown, MA 02539

    Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main

    Jennifer O'hanlon Compass LLC

    15 21st St N, Edgartown, MA 02539
  • /15

    $5,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • House for Rent

    85 Winemack St, Oak Bluffs, MA 02557

    This charming property located in East Chop is the perfect retreat for up to 6 guests, offering 3 cozy bedrooms and 2 full bathrooms. Walk into the spacious living area complete with comfortable seating and a Smart TV for your entertainment needs. The fully equipped kitchen features modern appliances and a kitchen island with seating for the kids. Enjoy your meals at the dining table with seating

    Benjamin Snow Coldwell Banker Realty - Boston

    85 Winemack St, Oak Bluffs, MA 02557
  • /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 $1,170,069

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    160 Bernard Cir, Vineyard Haven, MA 02568
    • /37

      Est $1,999,231

      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

  • /45

    $1,395,000

    • 2 Beds
    • 1.5 Baths
    • 1,126 Sq Ft

    29 Jernegan Ave, Edgartown, MA 02539

    Set on a generous .72-acre parcel just two miles from Edgartown Village and near the bike path, this thoughtfully renovated cottage offers comfortable living today with expansion potential. The property is move-in ready and provides easy access to beaches, boating, dining, and nearby conservation trails. The bright interior features an open floor plan with a spacious kitchen that flows into the

    Stephanie Roache Donnelly + Co

    29 Jernegan Ave, Edgartown, MA 02539
  • /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
  • /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 $1,801,024

    Last Listing Agent Lesley Heidt Sandpiper Realty, Inc.

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    • /2

      Est $1,370,061

      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

  • /39

    $1,575,000

    Open Sat 11:30AM - 1PM
    • 3 Beds
    • 3 Baths
    • 1,621 Sq Ft

    27 Laurel Ave, Oak Bluffs, MA 02557

    Located in exclusive East Chop, this sun-filled 3BR Cottage blends authentic Martha’s Vineyard charm with modern coastal living. Immaculate, fully furnished, and turn-key, this property presents a phenomenal island retreat or a lucrative investment with fantastic rental potential.The main home pairs classic character with upgraded 200-amp electric, featuring bright spaces, a large kitchen, and

    Lisa Sheehan Berkshire Hathaway HomeServices Robert Paul Properties

    27 Laurel Ave, Oak Bluffs, MA 02557
  • /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
  • /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 $1,027,886

    Last Listing Agent Rene Jackson Island Real Estate

    25 Windy Hill Rd, Oak Bluffs, MA 02557
    • /36

      Est $2,288,995

      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

  • /19

    $9,250,000

    $1M 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
  • /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
  • /31

    $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
    • 9 Days On Market

    Last Listing Agent Lesley Heidt Sandpiper Realty

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    • /5

      Est $2,415,474

      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

  • /46

    $2,400,000

    Pending
    • 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
  • /12

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • House for Rent

    43 Edgartown Rd, Vineyard Haven, MA 02568

    Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available

    Karen Overtoom Karen M. Overtoom R.E.

    43 Edgartown Rd, Vineyard Haven, 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

    Current Estimated Value $1,941,086

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
    • /47

      Est $1,773,263

      Not Listed For Sale

      179 Main St, Vineyard Haven, MA 02568

      • 5 Beds
      • 2.5 Baths
      • 2,134 Sq Ft
      • Built 1840
      179 Main St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

  • /16

    $565,000

    $90K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

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

    MOVE RIGHT IN! Just in time to ENJOY FOR THE SUMMER! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island.

    Rene Jackson Island Real Estate

    124 Skiff Ave Unit C-12, Vineyard Haven, 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
  • /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 $1,145,406

    Last Listing Agent Candy DaRosa Feiner Real Estate

    140 Longview Rd, Vineyard Haven, MA 02568
    • /35

      Est $1,200,512

      Not Listed For Sale

      29 Dunham Ave, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1965
      29 Dunham Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /40

    $4,300,000

    $395K 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

    $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
  • /37

    $1,175,000

    Sold Apr 22, 2026

    112 3rd St N, Edgartown, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $982/SF
    • 139 Days On Market

    Last Listing Agent Kristin Buck Donnelly + Co.

    112 3rd St N, Edgartown, MA 02568
    • /13

      Est $805,134

      Not Listed For Sale

      32 Clark Ave, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1968
      32 Clark Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home