4,092

Oak Bluffs, MA Homes

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  • /33

    $1,550,000

    Sold Jun 15, 2026

    1 Red Arrow Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2013

    Last Sold Summary

    • 3% Below List Price
    • $775/SF
    • 17 Days On Market

    Current Estimated Value $1,586,383

    Last Listing Agent Candy DaRosa Feiner Real Estate

    1 Red Arrow Rd, Vineyard Haven, MA 02568
    • /24

      Est $1,282,032

      Not Listed For Sale

      110 Otis Bassett Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1972
      110 Otis Bassett Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Jennifer O'hanlon Compass LLC

  • /4

    $1,449,000

    $251K PRICE DROP Pending
    • Land
    • 3.9 Acres
    • $371,538 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

    Thomas Wallace Wallace & Co. Sotheby's

    34 Ebens Ln, Chilmark, MA 02535
  • /39

    $2,225,000

    Sold Oct 24, 2025

    9 Beetlebung Grove Way, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,968 Sq Ft
    • Built 1994

    Last Sold Summary

    • 11% Below List Price
    • $750/SF
    • 98 Days On Market

    Current Estimated Value $2,510,212

    Last Listing Agent Stephanie Roache Donnelly + Co.

    9 Beetlebung Grove Way, Chilmark, MA 02535
    • /37

      Est $1,261,884

      Not Listed For Sale

      43 Skiffs Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1991
      43 Skiffs Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Chelsea Brennan Lamacchia Realty, Inc.

  • /2

    $749,000

    $50K PRICE DROP
    • Land
    • 39,996 Sq Ft
    • $815,726 per Acre

    22 Bramble Path Unit 214, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path Unit 214, West Tisbury, MA 02568
  • /45

    $1,700,000

    Sold Oct 08, 2025

    51 Skiffs Ln, Vineyard Haven, MA 02568

    • 7 Beds
    • 4.5 Baths
    • 3,213 Sq Ft
    • Built 1979

    Last Sold Summary

    • 5% Below List Price
    • $529/SF
    • 52 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    51 Skiffs Ln, Vineyard Haven, MA 02568
    • /49

      Est $1,884,103

      Not Listed For Sale

      75 Skiffs Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,548 Sq Ft
      • Built 1984
      75 Skiffs Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 186 Days On Market

      Last Listing Agent Kelly Mercier The Agency

  • /30

    $2,995,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    300 N Rd 18 Belhaven Way, Chilmark, MA 02535

    Tucked away on 4.4 spectacular acres just off North Road, this one-of-a-kind Chilmark retreat blends timeless Vineyard charm with exceptional privacy. A shaded driveway leads to classic stone walls and cedar gates opening into a beautifully landscaped courtyard. The inviting porch overlooks lush gardens, creating a peaceful outdoor sanctuary. Inside, warm, light-filled living spaces and the

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    300 N Rd 18 Belhaven Way, Chilmark, MA 02535
  • /2

    $440,000

    Sold Sep 22, 2025

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    • /15

      Est $1,216,663

      Not Listed For Sale

      14 Galway Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 1.5 Baths
      • 1,338 Sq Ft
      • Built 1966
      14 Galway Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /55

    $5,100,000

    $350K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,513 Sq Ft

    61 Stonewall Rd, Chilmark, MA 02535

    Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    61 Stonewall Rd, Chilmark, MA 02535
  • /30

    $1,416,500

    Sold Nov 25, 2025

    11 Ephriam Allen Rd, West Tisbury, MA 02568

    • 1 Bed
    • 1 Bath
    • 780 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Below List Price
    • $1,816/SF
    • 34 Days On Market

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    11 Ephriam Allen Rd, West Tisbury, MA 02568
    • /3

      Est $1,466,692

      Not Listed For Sale

      362 State Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • Built 1953
      362 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Nora Jardin Island Real Estate

  • /78

    $35,000,000

    • 8 Beds
    • 8 Baths
    • 6,841 Sq Ft

    146 Quenames Rd, Chilmark, MA 02535

    Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

    Grace Hagerty Grace Hagerty Real Estate Inc

    146 Quenames Rd, Chilmark, MA 02535
  • /34

    $2,175,000

    Sold Oct 10, 2025

    24 Alex Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 2,879 Sq Ft
    • Built 1985

    Last Sold Summary

    • 13% Below List Price
    • $755/SF
    • 89 Days On Market

    Current Estimated Value $2,498,946

    Last Listing Agent Elissa Lash Tea Lane Associates

    24 Alex Way, Vineyard Haven, MA 02568
    • /22

      Est $1,244,290

      Not Listed For Sale

      496 Lamberts Cove Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 1,286 Sq Ft
      • Built 1955
      496 Lamberts Cove Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 212 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /34

    $2,095,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,363 Sq Ft

    139 Tea Ln, Chilmark, MA 02535

    Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow seamlessly together. A wall of glass doors opens to the outdoors, creating an effortless

    Meg Bodnar Tea Lane Associates

    139 Tea Ln, Chilmark, MA 02535
  • /16

    $475,000

    Sold Oct 20, 2025

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 7% Above List Price
    • 11 Days On Market

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    • /26

      Est $1,506,198

      Not Listed For Sale

      33 Hidden Village Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 2.5 Baths
      • 1,968 Sq Ft
      • Built 1980
      33 Hidden Village Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /36

    $1,349,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,436 Sq Ft

    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    This coastal contemporary residence is located on a private 1.60-acre lot in West Tisbury, with convenient access to Long Point Wildlife Refuge and access to "Coveted" Lambert's Cove Beach. The home features four bedrooms and two full bathrooms. On the first floor, you'll find two bright bedrooms, a modernized bathroom, and sliders from the living area that lead to a new AZEK deck and enclosed

    Marilyn Moses Ocean Park Realty Inc

    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • /27

    $1,875,000

    Sold Aug 27, 2025

    212 Charles Neck Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $1,085/SF
    • 71 Days On Market

    Current Estimated Value $1,829,798

    Last Listing Agent Perry Patterson MV Luxury Homes LLC

    212 Charles Neck Way, Vineyard Haven, MA 02568
    • /30

      Est $2,535,298

      Not Listed For Sale

      41 Hidden Village Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 2,540 Sq Ft
      • Built 1981
      41 Hidden Village Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 335 Days On Market

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

  • /31

    $2,250,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    25 Fulling Mill Rd, Chilmark, MA 02535

    Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

    Thomas Wallace Wallace & Co. Sotheby's

    25 Fulling Mill Rd, Chilmark, MA 02535
  • /12

    $1,075,000

    Sold Dec 18, 2025

    1 Crowberry Ln Unit 19, Chilmark, MA 02535

    • Land
    • 4.32 Acres
    • $248,843 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 22 Days On Market

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    1 Crowberry Ln Unit 19, Chilmark, MA 02535
    • /45

      Est $1,165,622

      Not Listed For Sale

      5 Rock Pond Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,618 Sq Ft
      • Built 1999
      5 Rock Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 145 Days On Market

      Last Listing Agent Kerry Quinlan-Potter Breakwater MV

  • /55

    $2,950,000

    • 3 Beds
    • 3 Baths
    • 1,469 Sq Ft

    28 Black Point Rd, Chilmark, MA 02535

    Bright & Airy Black Point Retreat with Private Access to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a constant backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach.

    Michele Moore Island Real Estate

    28 Black Point Rd, Chilmark, MA 02535
  • /28

    $1,400,000

    Sold Dec 18, 2025

    42 Hidden Village Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,702 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $823/SF
    • 60 Days On Market

    Current Estimated Value $1,555,359

    Last Listing Agent Diana Gilmore Island Real Estate

    42 Hidden Village Rd, Vineyard Haven, MA 02568
    • /29

      Est $1,820,997

      Not Listed For Sale

      49 Oak Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 2,576 Sq Ft
      • Built 1974
      49 Oak Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Wendy Harman Compass Massachusetts, LLC

  • /65

    $2,550,000

    $649K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,618 Sq Ft

    55 Old House Way, West Tisbury, MA 02575

    Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

    Leslie Graham Anchor Realty of Martha's Vineyard

    55 Old House Way, West Tisbury, MA 02575
  • /30

    $3,375,000

    Sold Sep 26, 2025

    179 Tisbury Ln E, West Tisbury, MA 02575

    • 4 Beds
    • 2 Baths
    • 2,813 Sq Ft
    • Built 1982

    Last Sold Summary

    • 13% Below List Price
    • $1,200/SF
    • 73 Days On Market

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    179 Tisbury Ln E, West Tisbury, MA 02575
    • /22

      Est $1,219,176

      Not Listed For Sale

      41 Old County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,264 Sq Ft
      • Built 1983
      41 Old County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 216 Days On Market

      Last Listing Agent Jared Bicknell Compass LLC

  • /13

    $1,400,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,345 Sq Ft

    318 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Walk to the splendid sands of Lamberts Cove Beach for an afternoon dip followed by a romantic dinner at the nearby Inn. Fabulous location. The enchanting path to the white-rimmed cove is a mere 4-minute walk away. Main house with three bedrooms,large living room, many-windowed kitchen, artist's studio and upstairs sun room. The newer two story Guest House is bright and inviting nestled in the

    Holly Alaimo Tashmoo Realty

    318 Lamberts Cove Rd, Vineyard Haven, MA 02568
  • /59

    $2,225,000

    Sold Jun 10, 2026

    157 Ben Chase Rd, West Tisbury, MA 02575

    • 4 Beds
    • 2.5 Baths
    • 2,983 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $746/SF
    • 465 Days On Market

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

    157 Ben Chase Rd, West Tisbury, MA 02575
    • /17

      Est $1,263,773

      Not Listed For Sale

      22 Briarwood Ln, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,241 Sq Ft
      • Built 2018
      22 Briarwood Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Carol Shore Donnelly + Co

  • /36

    $2,250,000

    Pending
    • 4 Beds
    • 4 Baths
    • 2,340 Sq Ft

    11 Oak Ln, Vineyard Haven, MA 02568

    Welcome to 11 Oak Lane, a rare West Tisbury offering that lives as a true Martha's Vineyard family compound, an income-producing investment, or both. Set on 2.7 private acres, the property has been meticulously maintained and recently updated from the systems up, giving you the flexibility to gather generations under one address, live in one home and rent the other, or simply enjoy an exceptional

    Patrick McCarthy Grace Hagerty Real Estate Inc

    11 Oak Ln, Vineyard Haven, MA 02568
    • /32

      Not Listed For Sale

      140 Merry Farm Rd, Vineyard Haven, MA 02568

      • 6 Beds
      • 7 Baths
      • 5,603 Sq Ft
      • Built 1995
      140 Merry Farm Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 238 Days On Market

      Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

  • /9

    $1,600,000

    • Land
    • 5.15 Acres
    • $310,680 per Acre

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575

    Over five acres of privacy in one of the Island's most sought-after settings. This 5.15-acre parcel offers a rare opportunity to build a primary residence and accessory structure on old farmland surrounded by large, mature trees. Idyllic stonewalls run along some of the property lines.Large parcel size and building envelope ensures that the character of the neighborhood endures. Adjacent Land

    Julianna Flanders Flanders Real Estate

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    • /44

      Est $1,707,246

      Not Listed For Sale

      26 Manaquayak Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 2,320 Sq Ft
      • Built 1960
      26 Manaquayak Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /31

    $15,400,000

    • 6 Beds
    • 9 Baths
    • 6,967 Sq Ft

    8 Snail Rd, Chilmark, MA 02535

    Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects

    Brian Dougherty Corcoran Property Advisors

    8 Snail Rd, Chilmark, MA 02535

Showing Results 161 - 200, Page 5 of 18

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