Oak Bluffs, MA Homes for Sale with Acreage

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  $9,875,000

  • 6 Beds
  • 5.5 Baths
  • 3,758 Sq Ft

  6 Wakeman Rd, Chilmark, MA 02535

  Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist’s studio, and a detached garage with an additional bedroom above — creating the ideal retreat for extended

  Jill Napior Tea Lane Associates

  6 Wakeman Rd, Chilmark, MA 02535
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  /11

  $1,250,000

  • Land
  • 1.9 Acres
  • $657,895 per Acre

  15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535

  Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit!Surrounded by ancient stone walls on three sides and mature trees, the land has stunning sunset skies, lovely pastoral

  Jill Napior Tea Lane Associates

  15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
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  /7

  $2,500,000

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

  2 Other House Rd Unit 173, 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 Unit 173, Chilmark, MA 02535
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  $5,350,000

  $300K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,402 Sq Ft

  205 South Rd, Chilmark, MA 02535

  CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a

  Tina Miller Donnelly + Co.

  205 South Rd, Chilmark, MA 02535
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  $3,600,000

  • 5 Beds
  • 3 Baths
  • 2,791 Sq Ft

  20 James Pond Way, Vineyard Haven, MA 02568

  Tucked away on 4.5 acres off Lambert’s Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert’s Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a

  Sheila Morse Island Real Estate

  20 James Pond Way, Vineyard Haven, MA 02568
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  $2,395,000

  $105K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft

  16 South Rd, Chilmark, MA 02535

  Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
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  $1,800,000

  • 4 Beds
  • 3 Baths
  • 3,158 Sq Ft

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  House & Guesthouse Near Long Point Beach! The crashing surf of the south shore, the tranquil waters of Long Cove Pond, the walking trails of the Wildlife Refuge - all minutes from this charming West Tisbury property, appropriately referred to as "Pinch Me" by the current owners. Here, the connection to nature is seamless. The main house sits high atop the trees and overlooks a sprawling lawn from

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  $1,599,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

  Emma Kennedy Sandpiper Realty, Inc.

  111 Charles Neck Way, Vineyard Haven, MA 02568
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  $16,000,000

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  0, 36, 38 Black Point Rd, Chilmark, MA 02535

  Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom home sits on one lot with two detached studios alongside. Close to nature, this seasonal home

  Abby Rabinovitz Tea Lane Associates

  0, 36, 38 Black Point Rd, Chilmark, MA 02535
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  /17

  $2,475,000

  • 4 Beds
  • 4 Baths
  • 2,250 Sq Ft

  14 Ephriam Allen Rd, West Tisbury, MA 02568

  Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevation and enjoys waterviews of Vineyard Sound and the Sanctuary. There's also a sweet detached studio

  Michelle Kelly Tea Lane Associates

  14 Ephriam Allen Rd, West Tisbury, MA 02568
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  $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
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  $2,500,000

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

  229 Oak Ln, West Tisbury, MA 02575

  A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out to a

  Doug Burke Signal House Group at Compass

  229 Oak Ln, West Tisbury, MA 02575
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  $4,650,000

  Open House 6/13

  • 6 Beds
  • 3.5 Baths
  • 3,312 Sq Ft

  31 Josiah Sachem Way, Vineyard Haven, MA 02568

  An Inspirational Oasis - Come unwind and experience a secluded multi-dwelling compound nestled along the gentle slopes of Indian Hill, where rural tranquility meets effortless island living on more than three acres of uncommon beauty. Centered around a heated saltwater pool reminiscent of a private resort, the main house, studio barn, and guesthouse with a total of 4,464 square feet of living

  Helena Kirschenbaum Studio Realty

  31 Josiah Sachem Way, Vineyard Haven, MA 02568
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  $2,300,000

  • 4 Beds
  • 3.5 Baths
  • 2,428 Sq Ft

  35 Nat's Farm Ln, West Tisbury, MA 02568

  Nestled within the prestigious Nats Farm Association, this beautifully crafted West Tisbury home offers a quintessential Martha’s Vineyard retreat. The first floor features a bright, open layout with a well-appointed kitchen, dining area, and inviting living room, ideal for gatherings. The spacious primary suite is located on the main level and includes a private office and a spa-like bath with

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  35 Nat's Farm Ln, West Tisbury, MA 02568
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  $7,950,000

  $1M PRICE DROP

  • 5 Beds
  • 7 Baths
  • 4,531 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

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  $1,575,000

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  45 Quenames Rd, Chilmark, MA 02535

  Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility

  Dawn Bellante-Holand Sandpiper Realty

  45 Quenames Rd, Chilmark, MA 02535
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  $4,450,000

  $350K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  Two homes on over 3 open acres of waterfront on the Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and guest house boast unobstructed water views, creating a

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
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  $5,450,000

  • 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
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  $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
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  /13

  $1,645,000

  • Land
  • 3.32 Acres
  • $495,482 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
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  $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
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  $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

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