4,276

Oak Bluffs, MA Homes

Section Image Section Image
  • 43 N Slope Ln, Chilmark, MA 02535
    43 N Slope Ln, Chilmark, MA 02535
    43 N Slope Ln, Chilmark, MA 02535
    /31

    $1,799,999

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    43 N Slope Ln, Chilmark, MA 02535

    Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

    Agent Photo

    Barbara O'Hara

    NorthStar Real Estate, LLC

    (508) 850-0854

    43 N Slope Ln, Chilmark, MA 02535
  • 27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    /21

    $7,000 total monthly price

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt . it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • 140 Pond Rd, Vineyard Haven, MA 02568
    140 Pond Rd, Vineyard Haven, MA 02568
    140 Pond Rd, Vineyard Haven, MA 02568
    /46

    $3,120,000 Sold Sep 16, 2025

    140 Pond Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 3,669 Sq Ft
    • Built 1993

    Last Sold Summary

    • 10% Below List Price
    • $850/SF
    • 84 Days On Market

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

    140 Pond Rd, Vineyard Haven, MA 02568
    • 22 Briarwood Ln, Vineyard Haven, MA 02568
      22 Briarwood Ln, Vineyard Haven, MA 02568
      22 Briarwood Ln, Vineyard Haven, MA 02568
      /17

      Est $1,242,091 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% Below List Price
      • $1,048/SF
      • 4 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Carol Shore Donnelly + Co

  • 124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    /34

    $3,950,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 3,413 Sq Ft

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /20

    $6,000 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    ** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • 251 State Rd, Vineyard Haven, MA 02568
    251 State Rd, Vineyard Haven, MA 02568
    251 State Rd, Vineyard Haven, MA 02568
    /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 $1,667,700

    Last Listing Agent Meg Bodnar Tea Lane Associates

    251 State Rd, Vineyard Haven, MA 02568
    • 49 Oak Ln, West Tisbury, MA 02575
      49 Oak Ln, West Tisbury, MA 02575
      /2

      Not Listed For Sale

      49 Oak Ln, West Tisbury, MA 02575

      • 4 Beds
      • 3.5 Baths
      • 2,576 Sq Ft
      • Built 1974
      49 Oak Ln, West Tisbury, MA 02575

      Last Sold Summary

      • $639/SF
      • 6 Days On Market

      Last Sold Price $1,645,000

      Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  • 122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    /36

    $3,950,000 Under Contract

    • 5 Beds
    • 4 Baths
    • 3,413 Sq Ft

    122 Old Farm Rd, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
  • 29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    /10

    $8,500 total monthly price

    • 3 Beds
    • 2 Baths
    • House for Rent

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

    Karen Overtoom Karen M. Overtoom R.E.

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
  • 420 Lamberts Cove Rd, Vineyard Haven, MA 02568
    420 Lamberts Cove Rd, Vineyard Haven, MA 02568
    420 Lamberts Cove Rd, Vineyard Haven, MA 02568
    /18

    $4,250,000 Sold Sep 09, 2025

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 3 Baths
    • 4,125 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $1,030/SF
    • 21 Days On Market

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

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • 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 $2,374,627 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

      • 8% Above List Price
      • $861/SF
      • 197 Days On Market

      Last Sold Price $2,200,000

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • 55 Old House Way, West Tisbury, MA 02575
    55 Old House Way, West Tisbury, MA 02575
    55 Old House Way, West Tisbury, MA 02575
    /65

    $2,690,000

    • 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
  • 46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    /8

    $11,800 total monthly price

    • 4 Beds
    • 4 Baths
    • 2,612 Sq Ft
    • House for Rent

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

    Karen Overtoom Karen M. Overtoom R.E.

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
  • 37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    /2

    $1,700,000 Sold Oct 20, 2025

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    • 5 Beds
    • 3 Baths
    • 1,803 Sq Ft
    • Built 1982

    Last Sold Summary

    • $943/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    • 230 Pond Rd, Vineyard Haven, MA 02568
      230 Pond Rd, Vineyard Haven, MA 02568
      /2

      Est $2,500,982 Not Listed For Sale

      230 Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,527 Sq Ft
      • Built 1999
      230 Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10% Above List Price
      • $646/SF
      • 100 Days On Market

      Last Sold Price $2,280,000

      Last Listing Agent Rose Ryley Sandpiper Realty Inc

  • 15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    /42

    $3,990,000 Pending

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

    Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
  • 5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    /8

    $16,000 total monthly price

    • 7 Beds
    • 3.5 Baths
    • 4,000 Sq Ft
    • House for Rent

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

    Karen Overtoom Karen M. Overtoom R.E.

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
  • 00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    /7

    $650,000 Sold Aug 14, 2025

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

    • Land
    • 0.2 Acre
    • $3,250,000 per Acre

    Last Sold Summary

    • 7 Days On Market

    Last Listing Agent Deb Hancock Hancock Real Estate

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    • 188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      /4

      Est $2,923,214 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

      • 7% Below List Price
      • $1,124/SF

      Last Sold Price $3,135,000

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

  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /42

    $3,299,000

    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
  • 44 Music St Wt153, West Tisbury, MA 02575
    44 Music St Wt153, West Tisbury, MA 02575
    44 Music St Wt153, West Tisbury, MA 02575
    /12

    $6,180 total monthly price

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • House for Rent

    44 Music St Wt153, West Tisbury, MA 02575

    PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

    Karen Overtoom Karen M. Overtoom R.E.

    44 Music St Wt153, West Tisbury, MA 02575
  • 140 Longview Rd, Vineyard Haven, MA 02568
    140 Longview Rd, Vineyard Haven, MA 02568
    140 Longview Rd, Vineyard Haven, MA 02568
    /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 $1,121,422

    Last Listing Agent Candy DaRosa Feiner Real Estate

    140 Longview Rd, Vineyard Haven, MA 02568
    • 248 Pond Rd, Vineyard Haven, MA 02568
      248 Pond Rd, Vineyard Haven, MA 02568
      248 Pond Rd, Vineyard Haven, MA 02568
      /34

      Est $2,441,108 Not Listed For Sale

      248 Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 3.5 Baths
      • 1 Sq Ft
      • Built 1998
      248 Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 6% Above List Price
      • $2,300,000/SF
      • 174 Days On Market

      Last Sold Price $2,300,000

      Last Listing Agent Brenda Galligan Karen M. Overtoom R E

  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /38

    $3,995,000

    • 3 Beds
    • 3.5 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    This beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • 227 S Gate Rd Wt120, West Tisbury, MA 02575
    227 S Gate Rd Wt120, West Tisbury, MA 02575
    227 S Gate Rd Wt120, West Tisbury, MA 02575
    /8

    $8,250 total monthly price

    • 7 Beds
    • 5 Baths
    • 3,528 Sq Ft
    • House for Rent

    227 S Gate Rd Wt120, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • 25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    /37

    $7,289,000 Sold Oct 15, 2025

    25 Osprey Ln, Chilmark, MA 02535

    • 4 Beds
    • 5 Baths
    • 3,777 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $1,930/SF
    • 77 Days On Market

    Current Estimated Value $6,526,503

    Last Listing Agent Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • 131 Shubael Weeks Path, Vineyard Haven, MA 02568
      131 Shubael Weeks Path, Vineyard Haven, MA 02568
      131 Shubael Weeks Path, Vineyard Haven, MA 02568
      /25

      Est $2,063,910 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

      • 3% Above List Price
      • $550/SF
      • 0 Days On Market

      Last Sold Price $2,000,000

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

  • 6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    /16

    $3,200,000

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
  • 33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    /8

    $4,500 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • 0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    /22

    $435,000 Sold Aug 26, 2025

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 18 Days On Market

    Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    • 26 Old Coach Rd, Vineyard Haven, MA 02568
      26 Old Coach Rd, Vineyard Haven, MA 02568
      /2

      Est $1,725,306 Not Listed For Sale

      26 Old Coach Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,102 Sq Ft
      • Built 1998
      26 Old Coach Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Above List Price
      • $795/SF
      • 26 Days On Market

      Last Sold Price $1,671,100

      Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  • 24 Cournoyer Rd, Vineyard Haven, MA 02568
    24 Cournoyer Rd, Vineyard Haven, MA 02568
    24 Cournoyer Rd, Vineyard Haven, MA 02568
    /19

    $2,950,000

    • 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
  • 165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    /8

    $4,800 total monthly price

    • 3 Beds
    • 3 Baths
    • 3,279 Sq Ft
    • House for Rent

    165 Christiantown Rd, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

    Karen Overtoom Karen M. Overtoom R.E.

    165 Christiantown Rd, West Tisbury, MA 02575
  • 1054 State Rd, Vineyard Haven, MA 02568
    1054 State Rd, Vineyard Haven, MA 02568
    1054 State Rd, Vineyard Haven, MA 02568
    /32

    $1,250,000 Sold Nov 12, 2025

    1054 State Rd, Vineyard Haven, MA 02568

    • 6 Beds
    • 2 Baths
    • 1,845 Sq Ft
    • Built 1881

    Last Sold Summary

    • 16% Below List Price
    • $678/SF
    • 60 Days On Market

    Current Estimated Value $1,286,394

    Last Listing Agent Stephanie Roache Donnelly + Co.

    1054 State Rd, Vineyard Haven, MA 02568
    • 260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      /79

      Not Listed For Sale

      260 South Rd, Chilmark, MA 02535

      • 6 Beds
      • 2.5 Baths
      • 2,604 Sq Ft
      • Built 1688
      260 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • $1,671/SF
      • 109 Days On Market

      Last Sold Price $4,350,000

      Last Listing Agent Jill Napior Tea Lane Associates

  • 25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /18

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,583 Sq Ft

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

    Maranda Post Compass | The O'Hanlon Group

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /8

    $8,000 total monthly price

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

    56 Chilmark Rd, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 97 Longview Rd, Vineyard Haven, MA 02568
    97 Longview Rd, Vineyard Haven, MA 02568
    97 Longview Rd, Vineyard Haven, MA 02568
    /42

    $4,150,000 Sold Feb 19, 2026

    97 Longview Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 5.5 Baths
    • 4,003 Sq Ft
    • Built 2008

    Last Sold Summary

    • 12% Below List Price
    • $1,037/SF
    • 74 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    97 Longview Rd, Vineyard Haven, MA 02568
    • 377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      /36

      Est $2,349,533 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

      • 7% Above List Price
      • $902/SF
      • 518 Days On Market

      Last Sold Price $2,197,000

      Last Listing Agent Jill Napior Tea Lane Associates

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County Oak Bluffs

Real Estate & Homes

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group