83

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
    /27

    $1,699,999

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    43 N Slope Ln, Chilmark, MA 02535

    Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully

    Agent Photo

    Barbara O'Hara

    NorthStar Real Estate LLC

    43 N Slope Ln, Chilmark, MA 02535
  • 63 Putnam Rd, Chilmark, MA 02535
    63 Putnam Rd, Chilmark, MA 02535
    63 Putnam Rd, Chilmark, MA 02535
    /42

    $4,995,000

    • 3 Beds
    • 2.5 Baths
    • 2,095 Sq Ft

    63 Putnam Rd, Chilmark, MA 02535

    Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a

    Agent Photo

    Wendy Harman

    Compass

    63 Putnam Rd, Chilmark, MA 02535
  • 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
  • 49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    /35

    $5,200,000

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

    49 Gosnold's Way, Chilmark, MA 02535

    Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper

    Bonnie Pierce Wallace & Co. Sotheby's

    49 Gosnold's Way, Chilmark, MA 02535
  • 0 High Mark Rd Unit 66, Chilmark, MA 02535
    0 High Mark Rd Unit 66, Chilmark, MA 02535
    0 High Mark Rd Unit 66, Chilmark, MA 02535
    /9

    $1,900,000

    • Land
    • 15.05 Acres
    • $126,246 per Acre

    0 High Mark Rd Unit 66, Chilmark, MA 02535

    A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on the island today.The parcel directly abuts the nearly 80 acres of conservation land at the

    Russell Maloney Russell Maloney Real Estate

    0 High Mark Rd Unit 66, Chilmark, MA 02535
  • 20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    /33

    $3,600,000

    • 5 Beds
    • 3 Baths
    • 2,701 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
  • 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

    This magnificent Spring Point waterfront property, perched 50 ft above sea level and 425 ft back from the North Shore bluff, boasts beautiful views of the Vineyard Sound, Aquinnah coastline and the Elizabeth Islands -- and year dramatic year round sunsets. The property at the end of a well maintained wide dirt road 1 mile from North Rd is SECLUDED and TRANQUIL. It's a SHORT WALK TO THE BEACH,

    Robert Kenney Tea Lane Associates

    78 Hammett Rd, Chilmark, MA 02535
  • 52 Oak Knoll Rd, Vineyard Haven, MA 02568
    52 Oak Knoll Rd, Vineyard Haven, MA 02568
    52 Oak Knoll Rd, Vineyard Haven, MA 02568
    /35

    $1,225,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    52 Oak Knoll Rd, Vineyard Haven, MA 02568

    Year-round living in the desirable Island Farms Road neighborhood of West Tisbury. This well-built three-bedroom, two-bath home offers a comfortable layout with a first-floor primary bedroom. While ready for your personal updates, it provides a solid foundation to create your forever home. The open kitchen and living area offer a welcoming space for everyday living while the screened porch

    Tina Miller Donnelly + Co.

    52 Oak Knoll Rd, Vineyard Haven, MA 02568
  • 63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /66

    $1,899,000

    $101K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,075 Sq Ft

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

    Valene Pires The Agency

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • 47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    /8

    $1,325,000

    $250K PRICE DROP
    • 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
  • 34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    /46

    $6,250,000

    • 5 Beds
    • 2.5 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 an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a

    Jill Napior Tea Lane Associates

    34 Edys Island Way, Chilmark, MA 02535
  • 21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    /42

    $2,250,000

    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535

    Jessie Holtham Wallace & Co. Sotheby's International Realty

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
  • 44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    /52

    $5,295,000

    • 4 Beds
    • 3 Baths
    • 3,432 Sq Ft

    44 Cencelle St, Chilmark, MA 02535

    This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

    Meg Bodnar Tea Lane Associates

    44 Cencelle St, Chilmark, MA 02535
  • 34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    /8

    $2,725,000

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

    34 Ebens Ln, 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 LLC

    34 Ebens Ln, Chilmark, MA 02535
  • 131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
    /6

    $3,750,000

    • Land
    • 3.6 Acres
    • $1,041,667 per Acre

    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575

    Set on a picturesque peninsula along Tisbury Great Pond, this exceptional pondfront parcel offers a rare opportunity to own a piece of Martha's Vineyard's rural landscape. Currently used for equestrian activities, the expansive open acreage is nestled in one of the Island's most beautiful and unspoiled settings, evoking West Tisbury's rich agricultural heritage. This property is a blank slate,

    Meg Bodnar Tea Lane Associates

    131 Pond View Farm Rd Unit 1-7, 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
  • 10 Danls Way, West Tisbury, MA 02575
    10 Danls Way, West Tisbury, MA 02575
    10 Danls Way, West Tisbury, MA 02575
    /53

    $1,795,000

    $50K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,552 Sq Ft

    10 Danls Way, West Tisbury, MA 02575

    Historic West Tisbury farmhouse with detached guest cottage on 1.27 acres in the heart of West Tisbury. Just moments from Alley's General Store, 7a Foods, North Tisbury Village, and a short drive to beaches and both up- and downd Island destinations. This property presents a rare opportunity for a family compound, multi-generational living, or investment with rental income potential. The

    Emma Bryant Studio Realty

    10 Danls Way, West Tisbury, MA 02575
  • 0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    /38

    $16,000,000

    • Land
    • 46 Acres
    • $347,826 per Acre

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, 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 seasonal home sits on one lot with two detached studios alongside. Close to nature, this home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
  • 30 & 40 Elias Ln, West Tisbury, MA 02575
    30 & 40 Elias Ln, West Tisbury, MA 02575
    30 & 40 Elias Ln, West Tisbury, MA 02575
    /30

    $3,995,000

    • 6 Beds
    • 3.5 Baths
    • 3,070 Sq Ft

    30 & 40 Elias Ln, West Tisbury, MA 02575

    A beautiful pastoral, private family compound in West Tisbury, on 7.5 glorious acres of meadow comprised of two parcels, offers a rare opportunity. Elias Lane is a quiet country road tucked behind Misty Meadows and just minutes from West Tisbury village. The property features a lovingly maintained 4 BDR main house with a well appointed kitchen, recent sun porch addition an elegant Lew French

    Elissa Lash Tea Lane Associates

    30 & 40 Elias Ln, West Tisbury, MA 02575
  • 4 Rock Pond, West Tisbury, MA 02575
    4 Rock Pond, West Tisbury, MA 02575
    4 Rock Pond, West Tisbury, MA 02575
    /32

    $1,150,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,059 Sq Ft

    4 Rock Pond, West Tisbury, MA 02575

    4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the

    Trish Lyman Compass | Point B

    4 Rock Pond, West Tisbury, MA 02575
  • 64 Christiantown Rd, Vineyard Haven, MA 02568
    64 Christiantown Rd, Vineyard Haven, MA 02568
    64 Christiantown Rd, Vineyard Haven, MA 02568
    /42

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft

    64 Christiantown Rd, Vineyard Haven, MA 02568

    This stunning 3,000 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home

    Karen Overtoom Karen M. Overtoom R.E.

    64 Christiantown Rd, Vineyard Haven, MA 02568
  • 4 Rock Pond Rd, Vineyard Haven, MA 02568
    4 Rock Pond Rd, Vineyard Haven, MA 02568
    4 Rock Pond Rd, Vineyard Haven, MA 02568
    /31

    $1,150,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,059 Sq Ft

    4 Rock Pond Rd, Vineyard Haven, MA 02568

    4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the home

    Patricia Lyman Compass

    4 Rock Pond Rd, Vineyard Haven, MA 02568
  • 65 Carl's Way, West Tisbury, MA 02568
    65 Carl's Way, West Tisbury, MA 02568
    65 Carl's Way, West Tisbury, MA 02568
    /25

    $7,300,000

    • 5 Beds
    • 5.5 Baths
    • 3,539 Sq Ft

    65 Carl's Way, West Tisbury, MA 02568

    Stylized Private Waterfront Retreat close to townperched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes

    Jill Napior Tea Lane Associates

    65 Carl's Way, West Tisbury, MA 02568
  • 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

    $995,000

    $105K PRICE DROP
    • Land
    • 1 Acre
    • $995,000 per Acre

    25 Coffins Field Rd, Edgartown, MA 02539

    This 1.0-acre parcel is approved by the West Tisbury Board of Health for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist with costs associated with the design, permitting, and installation of the septic system.The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently

    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
    /17

    $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 Opportunity An 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 pristine

    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
    /25

    $1,450,000

    $100K PRICE DROP
    • 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
  • 35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    /42

    $5,400,000

    • 3 Beds
    • 2 Baths
    • 2,710 Sq Ft

    35 S Bowl Rd, Chilmark, MA 02535

    Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking

    Tina Miller Donnelly + Co.

    35 S Bowl 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
    /14

    $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
  • 10 Abels Neck Rd, Chilmark, MA 02535
    10 Abels Neck Rd, Chilmark, MA 02535
    10 Abels Neck Rd, Chilmark, MA 02535
    /20

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft

    10 Abels Neck Rd, Chilmark, MA 02535

    Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway

    Julianna Flanders Flanders Real Estate

    10 Abels Neck Rd, 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

    $1,425,000

    $475K PRICE DROP
    • 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
    /6

    $995,000

    $105K PRICE DROP
    • Land
    • 43,472 Sq Ft
    • $996,994 per Acre

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539

    Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist the buyer with costs associated with the design, permitting, and installation of the septic system. The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently

    Casandra Hyland Sandpiper Realty

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
  • 18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    /13

    $2,250,000

    $250K PRICE DROP
    • 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. 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 full furnished with exception of some art and a few

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd, Chilmark, MA 02535
  • 22 Bramble Path Unit 214, West Tisbury, MA 02568
    22 Bramble Path Unit 214, West Tisbury, MA 02568
    /2

    $749,000

    $50K PRICE DROP
    • Land
    • 39,996 Sq Ft
    • $815,726 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
  • 61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    /55

    $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
  • 146 Quenames Rd, Chilmark, MA 02535
    146 Quenames Rd, Chilmark, MA 02535
    146 Quenames Rd, Chilmark, MA 02535
    /78

    $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
  • 139 Tea Ln, Chilmark, MA 02535
    139 Tea Ln, Chilmark, MA 02535
    139 Tea Ln, Chilmark, MA 02535
    /34

    $2,195,000

    • 3 Beds
    • 3 Baths
    • 2,363 Sq Ft

    139 Tea Ln, Chilmark, MA 02535

    Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow seamlessly together. A wall of glass doors opens to the outdoors, creating an effortless

    Meg Bodnar Tea Lane Associates

    139 Tea Ln, Chilmark, MA 02535
  • 145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /36

    $1,399,000

    Open Wed 10AM - 12PM
    • 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 "Coveted" 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

    Marilyn Moses Ocean Park Realty Inc

    145 Vineyard Meadow Farms 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

    $2,250,000

    $200K PRICE DROP
    • 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
  • 28 Black Point Rd, Chilmark, MA 02535
    28 Black Point Rd, Chilmark, MA 02535
    28 Black Point Rd, Chilmark, MA 02535
    /55

    $2,950,000

    • 3 Beds
    • 3 Baths
    • 1,469 Sq Ft

    28 Black Point Rd, Chilmark, MA 02535

    Bright & Airy Black Point Retreat with Private Access to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a constant backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach.

    Michele Moore Island Real Estate

    28 Black Point Rd, Chilmark, MA 02535

Showing Results 1 - 40, Page 1 of 3

Massachusetts Dukes County

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 02536.
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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