46

Oak Bluffs, MA Homes for Sale

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  • 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
  • 20 Edson Forrest Rd, West Tisbury, MA 02575
    20 Edson Forrest Rd, West Tisbury, MA 02575
    20 Edson Forrest Rd, West Tisbury, MA 02575
    /48

    $3,950,000

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

    20 Edson Forrest Rd, West Tisbury, MA 02575

    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. A full restoration of this this three-bedroom house (with six-bedroom septic) in 2022 created a luxury home with a thoughtful layout, 2 story expansion, and exceptional

    Meg Bodnar Tea Lane Associates

    20 Edson Forrest Rd, West Tisbury, MA 02575
  • 25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    /31

    $2,395,000

    • 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

    25 Fulling Mill Rd, Chilmark, MA 02535
  • 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
  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /41

    $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
  • 229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    /39

    $2,550,000

    • 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 Cronigs Real Estate

    229 Oak Ln, West Tisbury, MA 02575
  • 27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    /39

    $3,395,000

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

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 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

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • 16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    /30

    $2,475,000

    • 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
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /39

    $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
  • 104 Pond View Farm Rd, Vineyard Haven, MA 02568
    104 Pond View Farm Rd, Vineyard Haven, MA 02568
    104 Pond View Farm Rd, Vineyard Haven, MA 02568
    /55

    $4,450,000

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

    104 Pond View Farm Rd, Vineyard Haven, MA 02568

    Two homes on over 3 flat 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
  • 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
  • 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
    /30

    $950,000

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

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    NEW PRICE - 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 LLC

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • 29 Old Nursery Ln, Chilmark, MA 02535
    29 Old Nursery Ln, Chilmark, MA 02535
    29 Old Nursery Ln, Chilmark, MA 02535
    /32

    $2,250,000

    • 4 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    29 Old Nursery Ln, Chilmark, MA 02535

    Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

    Julianna Flanders Flanders Real Estate

    29 Old Nursery Ln, Chilmark, MA 02535
  • 78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    /53

    $6,750,000

    • 5 Beds
    • 3.5 Baths
    • 4,050 Sq Ft

    78 Hammett Rd, Chilmark, MA 02535

    Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

    Robert Kenney Tea Lane Associates

    78 Hammett Rd, Chilmark, MA 02535
  • 47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    /8

    $1,575,000

    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    47 Quenames Rd, Chilmark, MA 02535

    On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

    Dawn Bellante Sandpiper Realty, Inc.

    47 Quenames Rd, Chilmark, MA 02535
  • 40 Scotchmans Ln, Vineyard Haven, MA 02568
    40 Scotchmans Ln, Vineyard Haven, MA 02568
    40 Scotchmans Ln, Vineyard Haven, MA 02568
    /36

    $1,390,000

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft

    40 Scotchmans Ln, Vineyard Haven, MA 02568

    A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

    Jim Osmundsen Donnelly + Co.

    40 Scotchmans Ln, Vineyard Haven, MA 02568
  • 10 Trotters Ln, West Tisbury, MA 02575
    10 Trotters Ln, West Tisbury, MA 02575
    10 Trotters Ln, West Tisbury, MA 02575
    /27

    $1,800,000

    • 3 Beds
    • 3 Baths
    • 2,293 Sq Ft

    10 Trotters Ln, West Tisbury, MA 02575

    Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

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

    10 Trotters Ln, West Tisbury, MA 02575
  • 26 Flint Hill Rd, West Tisbury, MA 02575
    26 Flint Hill Rd, West Tisbury, MA 02575
    26 Flint Hill Rd, West Tisbury, MA 02575
    /13

    $1,645,000

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

    26 Flint Hill Rd, 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 no

    Dawn Bellante Sandpiper Realty, Inc.

    26 Flint Hill Rd, West Tisbury, MA 02575
  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    /40

    $1,895,000

    • 4 Beds
    • 3.5 Baths
    • 2,061 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • 0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    /7

    $2,000,000

    • Land
    • 21,801 Sq Ft
    • $3,996,004 per Acre

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568

    1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

    Peter Cronig Cronigs Real Estate

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
  • 25 Coffins Field Rd, Edgartown, MA 02539
    25 Coffins Field Rd, Edgartown, MA 02539
    25 Coffins Field Rd, Edgartown, MA 02539
    /4

    $1,025,000

    • Land
    • 1 Acre
    • $1,025,000 per Acre

    25 Coffins Field Rd, Edgartown, MA 02539

    Per the BOH, this property can accommodate a 6-bedroom home and with appropriate permitting may allow for an additional/separate structure such as a garage or studio. Property is not serviced by a well or septic system. Buyer is responsible for obtaining permits and installation. Association Dues $650.00

    Casandra Hyland Sandpiper Realty, Inc.

    25 Coffins Field Rd, Edgartown, MA 02539
  • 32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
    /25

    $3,200,000

    • Land
    • 19.3 Acres
    • $165,803 per Acre

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

    A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

    Jill Napior Tea Lane Associates

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
  • 345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    /23

    $1,550,000

    • 5 Beds
    • 5 Baths
    • 2,266 Sq Ft

    345 North Rd, Chilmark, MA 02535

    This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

    Jessica Campbell Flanders Real Estate

    345 North Rd, Chilmark, MA 02535
  • 31 North Rd, Chilmark, MA 02535
    31 North Rd, Chilmark, MA 02535
    31 North Rd, Chilmark, MA 02535
    /22

    $1,200,000

    • 2 Beds
    • 1 Bath
    • 576 Sq Ft

    31 North Rd, Chilmark, MA 02535

    Surrounded by three-season perennial gardens, this sun-filled two bedroom cottage offers an airy open floor plan with high ceilings that create an impressive sense of space. Natural light pours in through four skylights and classic 8 over 8 windows, while a deck off the side and rear of the home provides seamless indoor outdoor living.This home underwent a major renovation in Spring of 2024

    Russell Maloney Russell Maloney Real Estate

    31 North Rd, Chilmark, MA 02535
  • 34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    /21

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

    Peyton Wallace Studio Realty

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
  • 20 Brook Hollow Rd, Vineyard Haven, MA 02568
    20 Brook Hollow Rd, Vineyard Haven, MA 02568
    20 Brook Hollow Rd, Vineyard Haven, MA 02568
    /33

    $1,650,000

    • 4 Beds
    • 3 Baths
    • 2,056 Sq Ft

    20 Brook Hollow Rd, Vineyard Haven, MA 02568

    This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

    Jim Feiner Feiner Real Estate

    20 Brook Hollow Rd, Vineyard Haven, MA 02568
  • 25 Coffins Field Rd Unit 18, Edgartown, MA 02539
    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
    /5

    $1,025,000

    • Land
    • 43,472 Sq Ft
    • $1,027,054 per Acre

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539

    This one-acre lot is nestled in a peaceful, centrally located neighborhood, offering the perfect balance of privacy and convenience. Abutting conservation land, the property provides a serene natural setting while supporting a spacious six-bedroom home. Enjoy easy access to town, nearby beaches, bike paths, a public gym, veterinarian services, shopping, the airport, and a variety of dining

    Casandra Hyland Sandpiper Realty

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
  • 22 Bramble Path Unit 214, West Tisbury, MA 02568
    22 Bramble Path Unit 214, West Tisbury, MA 02568
    /2

    $799,000

    • Land
    • 39,996 Sq Ft
    • $870,181 per Acre

    22 Bramble Path Unit 214, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path Unit 214, West Tisbury, MA 02568
  • 146 Quenames Rd, Chilmark, MA 02535
    146 Quenames Rd, Chilmark, MA 02535
    146 Quenames Rd, Chilmark, MA 02535
    /155

    $35,000,000

    • 8 Beds
    • 8 Baths
    • 6,841 Sq Ft

    146 Quenames Rd, Chilmark, MA 02535

    Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

    Grace Hagerty Grace Hagerty Real Estate Inc

    146 Quenames Rd, Chilmark, MA 02535
  • 46 Tiercel Ln, Chilmark, MA 02535
    46 Tiercel Ln, Chilmark, MA 02535
    46 Tiercel Ln, Chilmark, MA 02535
    /20

    $1,650,000

    • 2 Beds
    • 1 Bath
    • 716 Sq Ft

    46 Tiercel Ln, Chilmark, MA 02535

    Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort and

    Stacy Ickes Donnelly + Co

    46 Tiercel Ln, Chilmark, MA 02535
  • 85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    /37

    $7,950,000

    • 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 features a beautifully renovated farmhouse blending modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property also includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    85 Reservoir Rd, Vineyard Haven, MA 02568
  • 37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
    37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
    37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
    /8

    $1,295,000

    • Land
    • 4.4 Acres
    • $294,318 per Acre

    37 Bijah's Way Unit 96, 101, 102, 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, NHESP has been completed and there are no restrictions on the lot, there's a septic design and the

    Elissa Lash Tea Lane Associates

    37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
  • 60 Bartimus Luce Rd, Vineyard Haven, MA 02568
    60 Bartimus Luce Rd, Vineyard Haven, MA 02568
    60 Bartimus Luce Rd, Vineyard Haven, MA 02568
    /32

    $22,950,000

    • 7 Beds
    • 8.5 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
  • 2 Other House Rd Unit 173, Chilmark, MA 02535
    2 Other House Rd Unit 173, Chilmark, MA 02535
    2 Other House Rd Unit 173, Chilmark, MA 02535
    /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
  • 45 Quenames Rd, Chilmark, MA 02535
    45 Quenames Rd, Chilmark, MA 02535
    45 Quenames Rd, Chilmark, MA 02535
    /9

    $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 spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with

    Dawn Bellante Sandpiper Realty, Inc.

    45 Quenames Rd, Chilmark, MA 02535
  • 205 South Rd, Chilmark, MA 02535
    205 South Rd, Chilmark, MA 02535
    205 South Rd, Chilmark, MA 02535
    /42

    $5,650,000

    • 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
  • 188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    /52

    $1,800,000

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

    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    Long Point Beach - House plus ADU! 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 two

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
  • 111 Charles Neck Way, Vineyard Haven, MA 02568
    111 Charles Neck Way, Vineyard Haven, MA 02568
    111 Charles Neck Way, Vineyard Haven, MA 02568
    /21

    $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
  • 308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    /40

    $7,350,000

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

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535
  • 22 Bramble Path, West Tisbury, MA 02568
    22 Bramble Path, West Tisbury, MA 02568
    /2

    $799,000

    • Land
    • 39,639 Sq Ft
    • $878,022 per Acre

    22 Bramble Path, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path, West Tisbury, MA 02568

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County Oak Bluffs

Real Estate & Homes for Sale in Oak Bluffs, MA

Frequently Asked Questions

What are the most popular zip codes in Oak Bluffs, MA?
The most popular zip codes in Oak Bluffs, MA include 02535, 02568, 02575, 02539 and 02540.
What are the most popular neighborhoods near Oak Bluffs, MA?
The most popular neighborhoods near Oak Bluffs, MA are Chilmark, West Tisbury, Edgartown, Vineyard Haven and Oak Bluffs.
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