4,092

Oak Bluffs, MA Homes

Section Image
    • 35 Plum Bush Point Rd, West Tisbury, MA 02568
      35 Plum Bush Point Rd, West Tisbury, MA 02568
      35 Plum Bush Point Rd, West Tisbury, MA 02568
      /7

      Est $1,186,501

      Not Listed For Sale

      35 Plum Bush Point Rd, West Tisbury, MA 02568

      35 Plum Bush Point Rd, West Tisbury, MA 02568

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Tina Miller Donnelly + Co.

  • 38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
    /10

    $1,425,000

    • Land
    • 3.01 Acres
    • $473,422 per Acre

    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

    The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

    Elissa Lash Tea Lane Associates

    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
    • 23 Indian Hollow Rd, West Tisbury, MA 02575
      23 Indian Hollow Rd, West Tisbury, MA 02575
      23 Indian Hollow Rd, West Tisbury, MA 02575
      /42

      Not Listed For Sale

      23 Indian Hollow Rd, West Tisbury, MA 02575

      • 4 Beds
      • 2.5 Baths
      • 2,928 Sq Ft
      • Built 1993
      23 Indian Hollow Rd, West Tisbury, MA 02575

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Wendy Harman Compass

  • 26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    /13

    $1,575,000

    $70K PRICE DROP
    • Land
    • 3.32 Acres
    • $474,398 per Acre

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

    Dawn Bellante-Holand Sandpiper Realty

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    • 57 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
      57 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
      /2

      Est $1,105,471

      Not Listed For Sale

      57 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,450 Sq Ft
      • Built 1973
      57 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  • 23 Flanders Ln, Chilmark, MA 02535
    23 Flanders Ln, Chilmark, MA 02535
    23 Flanders Ln, Chilmark, MA 02535
    /49

    $9,750,000

    • 7 Beds
    • 5 Baths
    • 3,617 Sq Ft

    23 Flanders Ln, Chilmark, MA 02535

    A rare offering of land, history, and sweeping water views — this exceptional 8.7+/- acre estate commands panoramic views of Menemsha Pond and Vineyard Sound from its rolling lawns and open meadows. Property includes parking and access to Menemsha Pond.Whether you're drawn by the storied architecture, the expansive land, or the irreplaceable Vineyard Sound vistas, this is a compound that

    Julianna Flanders Flanders Real Estate

    23 Flanders Ln, Chilmark, MA 02535
    • 46 Crow Hollow Rd, Vineyard Haven, MA 02568
      46 Crow Hollow Rd, Vineyard Haven, MA 02568
      46 Crow Hollow Rd, Vineyard Haven, MA 02568
      /28

      Est $1,558,955

      Not Listed For Sale

      46 Crow Hollow Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,497 Sq Ft
      • Built 1985
      46 Crow Hollow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 284 Days On Market

      Last Listing Agent Jennifer B. DaSilva Compass

  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /38

    $3,099,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built Martha’s Vineyard residence blends timeless elegance with contemporary luxury, offering exclusive access to Lambert’s Cove Beach.At its heart is a chef’s kitchen with bespoke cabinetry, honed Carrara marble, Wolf and Sub-Zero appliances, Miele dishwasher, and Hudson Valley lighting. An adjacent custom bar features Dolomite Italian granite, ideal for entertaining.The home boasts

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    • 36 Music St, West Tisbury, MA 02575
      36 Music St, West Tisbury, MA 02575
      36 Music St, West Tisbury, MA 02575
      /20

      Not Listed For Sale

      36 Music St, West Tisbury, MA 02575

      • 3 Beds
      • 2.5 Baths
      • 1,688 Sq Ft
      • Built 1840
      36 Music St, West Tisbury, MA 02575

      Last Sold Summary

      • 15 Days On Market

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

  • 100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    /46

    $3,400,000

    • 4 Beds
    • 2.5 Baths
    • 2,383 Sq Ft

    100 Gosnolds Way, Chilmark, MA 02535

    Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you

    Julianna Flanders Flanders Real Estate

    100 Gosnolds Way, Chilmark, MA 02535
    • 1081 State Rd, West Tisbury, MA 02575
      1081 State Rd, West Tisbury, MA 02575
      1081 State Rd, West Tisbury, MA 02575
      /21

      Not Listed For Sale

      1081 State Rd, West Tisbury, MA 02575

      • 3 Beds
      • 1 Bath
      • 1,182 Sq Ft
      • Built 1935
      1081 State Rd, West Tisbury, MA 02575

      Last Sold Summary

      • 258 Days On Market

      Last Listing Agent Susan Anson Anson Realty

  • 6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    /23

    $2,900,000

    $300K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Enjoy the carefree ease of Mid Century Modern architecture in this pristine classic, filled with sunshine and treetop views. Located on a quiet hilltop in Chilmark and offered turn-key furnished, this simple but elegant summer home features four bedrooms, three baths, with original details and design. Its open all-on-one-floor layout with large glass panel doors and windows throughout lead to a

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
    • 5 Stillpoint Meadows Rd, West Tisbury, MA 02575
      5 Stillpoint Meadows Rd, West Tisbury, MA 02575
      5 Stillpoint Meadows Rd, West Tisbury, MA 02575
      /47

      Not Listed For Sale

      5 Stillpoint Meadows Rd, West Tisbury, MA 02575

      • 5 Beds
      • 4 Baths
      • 3,283 Sq Ft
      • Built 1714
      5 Stillpoint Meadows Rd, West Tisbury, MA 02575

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Katherine Donahue Sandpiper Realty

  • 24 Cournoyer Rd, Vineyard Haven, MA 02568
    24 Cournoyer Rd, Vineyard Haven, MA 02568
    24 Cournoyer Rd, Vineyard Haven, MA 02568
    /11

    $2,495,000

    $455K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,506 Sq Ft

    24 Cournoyer Rd, Vineyard Haven, MA 02568

    This mixed use building is zoned for residential and commercial use. It is extremely well built with an emphasis on non-toxic materials throughout. High ceilings on all three levels. There are radiant floors mixed with forced hot air/AC. The building offers a variety of uses for a new owner. The existing spaces are very versatile and would be ideal for any service oriented business given the

    Jill Napior Tea Lane Associates

    24 Cournoyer Rd, Vineyard Haven, MA 02568
    • 87 Longview Rd, West Tisbury, MA 02575
      87 Longview Rd, West Tisbury, MA 02575
      87 Longview Rd, West Tisbury, MA 02575
      /8

      Not Listed For Sale

      87 Longview Rd, West Tisbury, MA 02575

      87 Longview Rd, West Tisbury, MA 02575

      Last Sold Summary

      • 175 Days On Market

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

  • 3 Bens Way, Chilmark, MA 02535
    3 Bens Way, Chilmark, MA 02535
    3 Bens Way, Chilmark, MA 02535
    /46

    $3,900,000

    • 3 Beds
    • 4 Baths
    • 2,960 Sq Ft

    3 Bens Way, Chilmark, MA 02535

    Sited on 3.94 acres in the North Tabor Farm subdivision, this 3 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and the heated,

    Russell Maloney Russell Maloney Real Estate

    3 Bens Way, Chilmark, MA 02535
    • 32 S Pond Rd, West Tisbury, MA 02575
      32 S Pond Rd, West Tisbury, MA 02575
      /2

      Not Listed For Sale

      32 S Pond Rd, West Tisbury, MA 02575

      • 3 Beds
      • 3 Baths
      • 2,670 Sq Ft
      • Built 2012
      32 S Pond Rd, West Tisbury, MA 02575

    • 43 Pin Oak Cir, West Tisbury, MA 02575
      43 Pin Oak Cir, West Tisbury, MA 02575
      43 Pin Oak Cir, West Tisbury, MA 02575
      /31

      Not Listed For Sale

      43 Pin Oak Cir, West Tisbury, MA 02575

      • 3 Beds
      • 3 Baths
      • 2,356 Sq Ft
      • Built 1974
      43 Pin Oak Cir, West Tisbury, MA 02575

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Grace Bishop Compass

    • 99 Cygnet Way, Chilmark, MA 02535
      99 Cygnet Way, Chilmark, MA 02535
      99 Cygnet Way, Chilmark, MA 02535
      /12

      Not Listed For Sale

      99 Cygnet Way, Chilmark, MA 02535

      99 Cygnet Way, Chilmark, MA 02535

      Last Sold Summary

      • 792 Days On Market

      Last Listing Agent Russell Maloney Russell Maloney Real Estate

    • 31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      /20

      Est $1,444,630

      Not Listed For Sale

      31 Cross Rip Ln, Chilmark, MA 02535

      • 1 Bed
      • 1 Bath
      • 512 Sq Ft
      • Built 1999
      31 Cross Rip Ln, Chilmark, MA 02535

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Elissa Lash Tea Lane Associates

    • 47 Willow Tree Hollow Rd, West Tisbury, MA 02568
      47 Willow Tree Hollow Rd, West Tisbury, MA 02568
      47 Willow Tree Hollow Rd, West Tisbury, MA 02568
      /18

      Not Listed For Sale

      47 Willow Tree Hollow Rd, West Tisbury, MA 02568

      • 4 Beds
      • 2 Baths
      • 2,179 Sq Ft
      • Built 1987
      47 Willow Tree Hollow Rd, West Tisbury, MA 02568

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Suzanne Lanzone Suzanne Lanzone & Associates LLC

    • 10 Crow Hollow Rd, Vineyard Haven, MA 02568
      10 Crow Hollow Rd, Vineyard Haven, MA 02568
      10 Crow Hollow Rd, Vineyard Haven, MA 02568
      /30

      Est $2,496,394

      Not Listed For Sale

      10 Crow Hollow Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,555 Sq Ft
      • Built 1983
      10 Crow Hollow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 197 Days On Market

      Last Listing Agent Julianna Flanders Flanders Real Estate

    • 188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      /4

      Est $3,146,527

      Not Listed For Sale

      188 Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 2,789 Sq Ft
      • Built 1996
      188 Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      Last Listing Agent Rose Ryley Wallace & Co. Sotheby's

    • 68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      /31

      Est $3,561,464

      Not Listed For Sale

      68 Meeting House Rd, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,300 Sq Ft
      • Built 1990
      68 Meeting House Rd, Chilmark, MA 02535

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Peyton Wallace Compass

    • 16 Rock Pond Rd, Vineyard Haven, MA 02568
      16 Rock Pond Rd, Vineyard Haven, MA 02568
      16 Rock Pond Rd, Vineyard Haven, MA 02568
      /36

      Est $1,363,349

      Not Listed For Sale

      16 Rock Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,780 Sq Ft
      • Built 1999
      16 Rock Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 141 Days On Market

      Last Listing Agent Kerry Quinlan-Potter Breakwater MV

    • 8 Coffins Field Rd, Edgartown, MA 02539
      8 Coffins Field Rd, Edgartown, MA 02539
      /2

      Est $2,920,961

      Not Listed For Sale

      8 Coffins Field Rd, Edgartown, MA 02539

      • 6 Beds
      • 4 Baths
      • 3,440 Sq Ft
      • Built 2000
      8 Coffins Field Rd, Edgartown, MA 02539

    • 4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      /75

      Est $4,153,162

      Not Listed For Sale

      4 Tilton Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 1,362 Sq Ft
      • Built 1975
      4 Tilton Rd, Chilmark, MA 02535

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

    • 243 Pond Rd, Vineyard Haven, MA 02568
      243 Pond Rd, Vineyard Haven, MA 02568
      243 Pond Rd, Vineyard Haven, MA 02568
      /20

      Est $3,949,899

      Not Listed For Sale

      243 Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 3.5 Baths
      • 3,836 Sq Ft
      • Built 2003
      243 Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Doug Herr Priestley Smadbeck & Mone

    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,261,919

      Not Listed For Sale

      7 the Aerie, Chilmark, MA 02535

      • 3 Beds
      • 1.5 Baths
      • 1,386 Sq Ft
      • Built 1989
      7 the Aerie, Chilmark, MA 02535

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Julianna Flanders Flanders Real Estate

    • 22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      /17

      Est $2,951,228

      Not Listed For Sale

      22 Tabor Hills, Chilmark, MA 02535

      • 3 Beds
      • 2.5 Baths
      • 2,375 Sq Ft
      • Built 1997
      22 Tabor Hills, Chilmark, MA 02535

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Julianna Flanders Flanders Real Estate

    • 225 Great Plains Rd, Vineyard Haven, MA 02568
      225 Great Plains Rd, Vineyard Haven, MA 02568
      225 Great Plains Rd, Vineyard Haven, MA 02568
      /93

      Est $2,571,842

      Not Listed For Sale

      225 Great Plains Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 3,000 Sq Ft
      • Built 2004
      225 Great Plains Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

    • 9 Heather Trail, Vineyard Haven, MA 02568
      9 Heather Trail, Vineyard Haven, MA 02568
      9 Heather Trail, Vineyard Haven, MA 02568
      /36

      Est $1,894,516

      Not Listed For Sale

      9 Heather Trail, Vineyard Haven, MA 02568

      • 6 Beds
      • 3.5 Baths
      • 2,705 Sq Ft
      • Built 1998
      9 Heather Trail, Vineyard Haven, MA 02568

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Julianna Flanders Flanders Real Estate

    • 25 Carls Way, Vineyard Haven, MA 02568
      25 Carls Way, Vineyard Haven, MA 02568
      25 Carls Way, Vineyard Haven, MA 02568
      /23

      Est $1,987,061

      Not Listed For Sale

      25 Carls Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,040 Sq Ft
      • Built 2006
      25 Carls Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Brenda Codding Up Island Realty

    • 29 S Pond Rd, Vineyard Haven, MA 02568
      29 S Pond Rd, Vineyard Haven, MA 02568
      29 S Pond Rd, Vineyard Haven, MA 02568
      /58

      Not Listed For Sale

      29 S Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 5.5 Baths
      • 4,190 Sq Ft
      • Built 1998
      29 S Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Sheila Morse Island Real Estate

    • 10 Briarwood Ln, Vineyard Haven, MA 02568
      10 Briarwood Ln, Vineyard Haven, MA 02568
      10 Briarwood Ln, Vineyard Haven, MA 02568
      /17

      Est $1,132,029

      Not Listed For Sale

      10 Briarwood Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 934 Sq Ft
      • Built 1984
      10 Briarwood Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

    • 187 Oak Ln, Vineyard Haven, MA 02568
      187 Oak Ln, Vineyard Haven, MA 02568
      /2

      Not Listed For Sale

      187 Oak Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,894 Sq Ft
      • Built 1983
      187 Oak Ln, Vineyard Haven, MA 02568

    • 1 Coffins Field Rd, Edgartown, MA 02539
      1 Coffins Field Rd, Edgartown, MA 02539
      1 Coffins Field Rd, Edgartown, MA 02539
      /30

      Est $1,800,186

      Not Listed For Sale

      1 Coffins Field Rd, Edgartown, MA 02539

      • 6 Beds
      • 3 Baths
      • 3,120 Sq Ft
      • Built 1997
      1 Coffins Field Rd, Edgartown, MA 02539

      Last Sold Summary

      • 504 Days On Market

      Last Listing Agent Fred Mascolo Jane Brown Assoc.

    • 26 Pinkletink Rd, Chilmark, MA 02535
      26 Pinkletink Rd, Chilmark, MA 02535
      26 Pinkletink Rd, Chilmark, MA 02535
      /30

      Est $3,841,742

      Not Listed For Sale

      26 Pinkletink Rd, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,748 Sq Ft
      • Built 1979
      26 Pinkletink Rd, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Wendy Harman Compass

    • 299 Oak Ln, Vineyard Haven, MA 02568
      299 Oak Ln, Vineyard Haven, MA 02568
      299 Oak Ln, Vineyard Haven, MA 02568
      /37

      Est $1,355,562

      Not Listed For Sale

      299 Oak Ln, Vineyard Haven, MA 02568

      • 5 Beds
      • 3 Baths
      • 2,124 Sq Ft
      • Built 1986
      299 Oak Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Amy Kurth Vineyard Real Estate

    • 127 Old County Rd, Vineyard Haven, MA 02568
      127 Old County Rd, Vineyard Haven, MA 02568
      127 Old County Rd, Vineyard Haven, MA 02568
      /13

      Est $1,841,620

      Not Listed For Sale

      127 Old County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 2,073 Sq Ft
      • Built 1991
      127 Old County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Deb Hancock Hancock Real Estate

Showing Results 281 - 320, Page 8 of 18

Massachusetts Dukes County

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