Oak Bluffs, MA Homes for Sale with Acreage

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  $2,950,000

  • 1 Bed
  • 1 Bath
  • 726 Sq Ft

  18 Allen Farm Rd, Chilmark, MA 02535

  Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1 + bedroom cottage with screened porch, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished,

  Patty Kendall Kendall & Kendall

  18 Allen Farm Rd, Chilmark, MA 02535
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  /51

  $7,950,000

  • 4 Beds
  • 5 Baths
  • 3,490 Sq Ft

  308 South Rd, Chilmark, MA 02535

  Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets.

  Rose Ryley Sandpiper Realty Inc

  308 South Rd, Chilmark, MA 02535
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  /22

  $1,449,000

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

  Brenda Galligan Karen M. Overtoom R.E.

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  $4,950,000

  • 5 Beds
  • 4 Baths
  • 4,044 Sq Ft

  49 Gosnold's Way, Chilmark, MA 02535

  Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

  Meg Bodnar Tea Lane Associates

  49 Gosnold's Way, Chilmark, MA 02535
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  $1,695,000

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft

  251 State Rd, Vineyard Haven, MA 02568

  This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

  Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  $7,450,000

  • 5 Beds
  • 3 Baths
  • 2,269 Sq Ft

  34 Edys Island Way, Chilmark, MA 02535

  Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the

  Jill Napior Tea Lane Associates

  34 Edys Island Way, Chilmark, MA 02535
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  $4,850,000

  • 5 Beds
  • 3 Baths
  • 3,440 Sq Ft

  146 Quansoo Rd, Chilmark, MA 02535

  Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

  Meg Bodnar Tea Lane Associates

  146 Quansoo Rd, Chilmark, MA 02535
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  $1,325,000

  • Land
  • 4.40 Acres
  • $301,136 per Acre

  37 Bijah's Way, Chilmark, MA 02535

  This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this

  Elissa Lash Tea Lane Associates

  37 Bijah's Way, Chilmark, MA 02535
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  $14,000,000

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

  8 Snail Rd, Chilmark, MA 02535

  This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

  Alyssa Halisky Wallace & Co. Sotheby's

  8 Snail Rd, Chilmark, MA 02535
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  $2,895,000

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

  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
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  /31

  $2,450,000

  • 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 International Realty

  25 Fulling Mill Rd, Chilmark, MA 02535
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  $1,485,000 Open Sun 11AM - 1PM

  • 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 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 fenced

  Marilyn Moses Ocean Park Realty Inc

  145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  $4,395,000

  • 3 Beds
  • 5 Baths
  • 3,314 Sq Ft

  20 Edson Forest Rd, Vineyard Haven, MA 02568

  Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. This three bedroom home (with six-bedroom septic system) was fully renovated down to the studs and finished in 2022, resulting in a truly beautiful luxury home with a

  Meg Bodnar Tea Lane Associates

  20 Edson Forest Rd, Vineyard Haven, MA 02568
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  $2,495,000

  • 5 Beds
  • 3.5 Baths
  • 2,685 Sq Ft

  35 Woody Bottom Rd, West Tisbury, MA 02575

  This Cape style 5 bed/ 3.5 bath home is located in a nice area privately sited on 3 acres. This home features a nice floor plan thatincludes a fully equipped kitchen with center island, custom cabinetry and granite counters. Just off the kitchen is a sunny breakfastroom, a separate dining room, a spacious living room with fireplace and 2 sets of sliders to a backyard deck. There is a cozy

  Brenda Galligan Karen M. Overtoom R.E.

  35 Woody Bottom Rd, West Tisbury, MA 02575
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  $8,995,000

  • 5 Beds
  • 7 Baths
  • 3,762 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  $2,550,000

  • 4 Beds
  • 3 Baths
  • 2,983 Sq Ft

  157 Ben Chase Rd, West Tisbury, MA 02575

  You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

  Madelyn Silvia Wallace & Co. Sotheby's

  157 Ben Chase Rd, West Tisbury, MA 02575
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  $2,500,000

  • Land
  • 1.40 Acres
  • $1,785,714 per Acre

  2 Other House Rd, Chilmark, MA 02535

  Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

  Russell Maloney Russell Maloney Real Estate

  2 Other House Rd, Chilmark, MA 02535
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  /13

  $975,000

  • Land
  • 3.73 Acres
  • $261,394 per Acre

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568

  Exceptional opportunity in West Tisbury! This 3.73-acre parcel offers peace and privacy on a quiet dead-end road, moments from Sepiessa, Tiah’s Cove, and Long Point beaches. With potential for up to 10+ bedrooms (1 per 10,000 SF), the property is a blank canvas for your dream Vineyard compound—main house, guest house, barn, garage, and more with proper permits. Pool/pool house possible by special

  Janna O'Loughlin Portfolio Real Estate, Inc.

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
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  $975,000

  • Land
  • 3.83 Acres
  • $254,569 per Acre

  25 N Vine Ln, West Tisbury, MA 02568

  Exceptional opportunity in West Tisbury! This 3.73-acre parcel offers peace and privacy on a quiet dead-end road, moments from Sepiessa, Tiah's Cove, and Long Point beaches. With potential for up to 16 bedrooms (1 per 10,000 SF), the property is a blank canvas for your dream Vineyard compound--main house, guest house, barn, garage, and more with proper permits. Pool/pool house possible by special

  Janna O'Loughlin Portfolio Properties

  25 N Vine Ln, West Tisbury, MA 02568
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  $1,425,000

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

  38 Fire Tower Rd, 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, West Tisbury, MA 02568
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  $1,345,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  9 Galway Rd, Vineyard Haven, MA 02568

  Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

  Julianna Flanders Flanders Real Estate

  9 Galway Rd, Vineyard Haven, MA 02568
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  $2,799,000

  • 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 house & 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

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
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  /2

  $995,000

  • Land
  • 3.05 Acres
  • $326,230 per Acre

  00 Quenames Rd, Chilmark, MA 02535

  Handsome, large level parcel of land in Chilmark! Bounds are in, lot lines are flagged and brush cut, as well as a bit of the lot interior so that you can appreciate the size and orientation of the parcel. 6-Bedroom septic design has been approved and well will be installed soon. Quenames Road is off South Road, a short hop to West Tisbury village center with Alley's General Store, the Town's

  Candy DaRosa Feiner Real Estate

  00 Quenames Rd, Chilmark, MA 02535
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  $22,950,000 New Construction

  • 7 Beds
  • 9 Baths
  • 8,200 Sq Ft

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568

  This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design,

  Gerrett Conover Landvest MV

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568

Showing Results 41 - 64, Page 2 of 2