4,288

Oak Bluffs, MA Homes

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  • 97 Longview Rd, Vineyard Haven, MA 02568
    97 Longview Rd, Vineyard Haven, MA 02568
    97 Longview Rd, Vineyard Haven, MA 02568
    /42

    $4,695,000

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

    97 Longview Rd, Vineyard Haven, MA 02568

    This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls, sited on 2.2 acres, this serene property offers luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels with generous decks ideal for outdoor living and entertaining. The upper

    Stephanie Roache Donnelly + Co.

    97 Longview Rd, Vineyard Haven, MA 02568
  • 27 Abel's Neck Rd Unit ID1301705P, Chilmark, MA 02535
    27 Abel's Neck Rd Unit ID1301705P, Chilmark, MA 02535
    27 Abel's Neck Rd Unit ID1301705P, Chilmark, MA 02535
    /32

    $20,817 total monthly price

    • 3 Beds
    • 2 Baths
    • Condo for Rent

    27 Abel's Neck Rd Unit ID1301705P, Chilmark, MA 02535

    Experience the essence of Chilmark with this exquisite property set on over 2 acres of pastoral land, offering water views and charming stone walls. Ideally located less than 1.25 miles from all Chilmark beaches, including St. Lucy Vincent, Squibnocket, and Menemsha, and just half a mile from the Chilmark General Store, this home is a perfect retreat.The main house features two formal

    27 Abel's Neck Rd Unit ID1301705P, Chilmark, MA 02535
  • 32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    /17

    $1,900,000 Pending

    • Land
    • 3.3 Acres
    • $575,758 per Acre

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

    South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark

    Jill Napior Tea Lane Associates

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    • 1005 State Rd, West Tisbury, MA 02575
      1005 State Rd, West Tisbury, MA 02575
      1005 State Rd, West Tisbury, MA 02575
      /40

      Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,500 Sq Ft

      1005 State Rd, West Tisbury, MA 02575

      1005 State Rd, West Tisbury, MA 02575
  • 15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    /42

    $4,250,000

    • 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
  • 27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    /21

    $7,000 per month plus fees

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

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt not to long ago 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 chefs Kitchen, living room ,dining area and fireplace area. Walk out the

    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

    • 3,669 Sq Ft
    • $850/SF
    • 84 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1993

    140 Pond Rd, Vineyard Haven, MA 02568

    Welcome to this beautifully updated and privately situated home in one of West Tisbury’s most desirable associations. Residents enjoy exclusive access to tennis courts, walking trails, horse pastures and Tisbury Great Pond. Designed for both comfort and luxury, this spacious 4+ bedroom, 3 bathroom property is ideal as a year-round residence or upscale vacation retreat.The first floor

    Jon Hartzband Martha's Vineyard Island-Wide Realty

    140 Pond 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 $2,439,395 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,555 Sq Ft

      10 Crow Hollow Rd, Vineyard Haven, MA 02568

      10 Crow Hollow Rd, Vineyard Haven, MA 02568
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /42

    $3,995,000

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

    96 Hammett Ln, Chilmark, MA 02535

    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
  • 39 Old Coach Rd, West Tisbury, MA 02568
    39 Old Coach Rd, West Tisbury, MA 02568
    39 Old Coach Rd, West Tisbury, MA 02568
    /14

    $8,400 per month plus fees

    • 4 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • House for Rent

    39 Old Coach Rd, West Tisbury, MA 02568

    Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

    Joseph D'Amico Dee Development Company

    39 Old Coach Rd, West Tisbury, MA 02568
  • 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

    • 4,125 Sq Ft
    • $1,030/SF
    • 21 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1900

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Charming West Tisbury Estate with Waterfront on Seth's Pond. This stunning property offers the perfect blend of vintage charm and modern convenience, set against the tranquil backdrop of Seth's Pond. Featuring a main house, guest house, boathouse, and barn/workshop, this property provides a rare opportunity for both relaxation and recreation. The main house, a well maintained farmhouse dating

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • 230 Pond Rd, Vineyard Haven, MA 02568
      230 Pond Rd, Vineyard Haven, MA 02568
      /2

      Est $2,592,481 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,527 Sq Ft

      230 Pond Rd, Vineyard Haven, MA 02568

      230 Pond Rd, Vineyard Haven, MA 02568
  • 27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    /41

    $3,500,000

    • 3 Beds
    • 4 Baths
    • 2,500 Sq Ft

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /20

    $4,250 per month plus fees

    • 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.

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • 234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    /38

    $1,850,000 Sold Sep 09, 2025

    • 1,918 Sq Ft
    • $965/SF
    • 60 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1988

    234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    LONG POINT BEACH RETREAT. Privately set on a spacious 1.4-acre parcel in the highly coveted Long Point area of West Tisbury, this beautifully renovated beach house offers the ultimate Vineyard escape. Move-in ready and being sold turnkey, it combines style, comfort, and convenience in an unbeatable location. The sun-filled living room with a cathedral ceiling and gas fireplace, and dining area

    Stephanie Roache Donnelly + Co.

    234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    • 188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      /4

      Est $2,911,900 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,789 Sq Ft

      188 Pond Rd, Vineyard Haven, MA 02568

      188 Pond Rd, Vineyard Haven, MA 02568
  • 300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    /36

    $3,250,000

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

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

    Rebecca V Conroy Conroy & Company R.E., Inc.

    300 North 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 per month plus fees

    • 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
  • 31 N Slope Ln, Chilmark, MA 02535
    31 N Slope Ln, Chilmark, MA 02535
    31 N Slope Ln, Chilmark, MA 02535
    /34

    $2,475,000 Sold Sep 05, 2025

    • 2,300 Sq Ft
    • $1,076/SF
    • 117 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1983

    31 N Slope Ln, Chilmark, MA 02535

    Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working

    Bill Rossi Studio Realty

    31 N Slope Ln, Chilmark, MA 02535
    • 248 Pond Rd, Vineyard Haven, MA 02568
      248 Pond Rd, Vineyard Haven, MA 02568
      248 Pond Rd, Vineyard Haven, MA 02568
      /34

      Est $2,469,174 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 1 Sq Ft

      248 Pond Rd, Vineyard Haven, MA 02568

      248 Pond Rd, Vineyard Haven, MA 02568
  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /39

    $3,299,000

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

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    Nestled in one of the island’s most sought-after locations, this exceptional property offers refined coastal living with access to the famed Lambert’s Cove Beach yet a short drive to VH.Thoughtfully designed, it features 3 spacious bedrooms each with an en suite bath, providing comfort and privacy for all. Primary suite is a true retreat with a brand new luxurious bathroom. At the heart of the

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
  • 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 per month plus fees

    • 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
  • 19 S Vine Ln, Vineyard Haven, MA 02568
    19 S Vine Ln, Vineyard Haven, MA 02568
    19 S Vine Ln, Vineyard Haven, MA 02568
    /21

    $1,325,000 Sold Aug 29, 2025

    • 1,982 Sq Ft
    • $669/SF
    • 89 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1992

    19 S Vine Ln, Vineyard Haven, MA 02568

    This charming Cape-style home, built in 1992, is tucked away in a quiet, subdivision on South Vine Lane. With three bedrooms and two bathrooms, it blends classic Island character with modern comforts. The inviting living room features vaulted ceilings and a double-sided fireplace, creating a bright and spacious atmosphere perfect for both relaxing and entertaining. The kitchen, filled with

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    19 S Vine Ln, Vineyard Haven, MA 02568
    • 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 $2,091,937 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,636 Sq Ft

      131 Shubael Weeks Path, Vineyard Haven, MA 02568

      131 Shubael Weeks Path, Vineyard Haven, MA 02568
  • 122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    /36

    $4,950,000

    • 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
  • 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 per month plus fees

    • 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
  • 50 Bradley Martin Rd, Vineyard Haven, MA 02568
    50 Bradley Martin Rd, Vineyard Haven, MA 02568
    50 Bradley Martin Rd, Vineyard Haven, MA 02568
    /37

    $1,925,000 Sold Aug 28, 2025

    • 1,736 Sq Ft
    • $1,109/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    50 Bradley Martin Rd, Vineyard Haven, MA 02568

    Two level contemporary residence located in West Tisbury off Tiah's Cove Road, close to the 174 Acre Land Bank Sepiessa Point Reserve on Tisbury Great Pond. Light filled rooms with high ceilings, solarium, large screened in porch & fireplace in this completely renovated home. Private 3 acre site is laden with specimen trees, walking trails and meditation gardens. Close proximity to West Tisbury

    Rebecca V Conroy Conroy & Company R.E., Inc.

    50 Bradley Martin 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

      • 6 Beds
      • 2.5 Baths
      • 2,604 Sq Ft

      260 South Rd, Chilmark, MA 02535

      260 South Rd, Chilmark, MA 02535
  • 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

    $4,950,000

    • 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
  • 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 per month plus fees

    • 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
  • 212 Charles Neck Way, Vineyard Haven, MA 02568
    212 Charles Neck Way, Vineyard Haven, MA 02568
    212 Charles Neck Way, Vineyard Haven, MA 02568
    /27

    $1,875,000 Sold Aug 27, 2025

    • 1,728 Sq Ft
    • $1,085/SF
    • 71 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    212 Charles Neck Way, Vineyard Haven, MA 02568

    This beautifully renovated South Shore retreat, located in a tranquil setting, features 3 bedrooms, 2 1/2 bathrooms, central air, all new Bosch appliances, in ground pool and mature perennial gardens galore! Sitting on 1.5 acres, this location provides easy access to Long Point Beach and the Red Pony Farm equestrian center and, includes access to the coveted Lamberts Cove Beach. The first floor

    Perry Patterson MV Luxury Homes LLC

    212 Charles Neck Way, Vineyard Haven, MA 02568
    • 68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      /31

      Est $3,105,492 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,300 Sq Ft

      68 Meeting House Rd, Chilmark, MA 02535

      68 Meeting House Rd, Chilmark, MA 02535
  • 88 & 90 Quenames Rd, Chilmark, MA 02535
    88 & 90 Quenames Rd, Chilmark, MA 02535
    88 & 90 Quenames Rd, Chilmark, MA 02535
    /25

    $3,600,000

    • 3 Beds
    • 3 Baths
    • 4,382 Sq Ft

    88 & 90 Quenames Rd, Chilmark, MA 02535

    Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

    Julianna Flanders Flanders Real Estate

    88 & 90 Quenames Rd, 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 per month plus fees

    • 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

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • 0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    /21

    $435,000 Sold Aug 26, 2025

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre
    • 20 Days On Market

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

    Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

    Emma Bryant Landmarks at TODAY Real Estate

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    • 377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      /36

      Est $2,327,183 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,436 Sq Ft

      377 State Rd, Vineyard Haven, MA 02568

      377 State Rd, Vineyard Haven, MA 02568
  • 11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    /35

    $2,850,000

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    11 By the Woods, Chilmark, MA 02535

    Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main House,

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • 165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    /8

    $4,800 per month plus fees

    • 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
  • 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

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre
    • 18 Days On Market

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

    Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

    Emma Kiley Bryant Landmarks at TODAY Real Estate

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    • 30 Pond Ln, Vineyard Haven, MA 02568
      30 Pond Ln, Vineyard Haven, MA 02568
      30 Pond Ln, Vineyard Haven, MA 02568
      /14

      Est $2,709,570 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,926 Sq Ft

      30 Pond Ln, Vineyard Haven, MA 02568

      30 Pond Ln, Vineyard Haven, MA 02568

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