Homes for Sale in 02568

/20
$1,149,000
- 3 Beds
- 2 Baths
- 1,373 Sq Ft
72 Moonstone Way, Vineyard Haven, MA 02568

Nestled in a quiet neighborhood just a short stroll from Lake Tashmoo and less than a mile from Main Street, Owen Park Beach, and the Steamship Authority, this lovingly maintained Colonial Saltbox offers the perfect blend of comfort, convenience, and island charm. With a strong rental history, the home is ideally suited as a vacation getaway, year-round residence, or investment property. The

Carol Shore Donnelly + Co

72 Moonstone Way, Vineyard Haven, MA 02568
/28
$1,350,000

$49K PRICE DROP
- 2 Beds
- 1 Bath
- 1,996 Sq Ft
29 Scotchmans Ln, Vineyard Haven, MA 02568

Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings offer exciting possibilities for artists,

Diana Gilmore Island Real Estate

29 Scotchmans Ln, Vineyard Haven, MA 02568
/2
$794,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60R Carol Ln, Oak Bluffs, MA 02557

Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete

Michele Moore Island Real Estate

60R Carol Ln, Oak Bluffs, MA 02557
/29
$1,995,000

Open Sat 9:30AM - 11:30AM
- 3 Beds
- 2.5 Baths
- 1,439 Sq Ft
33 Vineyard Ave, Oak Bluffs, MA 02557

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property 3B/2Ba in total features a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined

Allison Cameron Parry Douglas Elliman of MA, LLC

33 Vineyard Ave, Oak Bluffs, MA 02557
/12
$3,400,000

New Construction
- 3 Beds
- 4.5 Baths
- 3,260 Sq Ft
27 Double Ox Rd, Oak Bluffs, MA 02557

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living

Lesley Heidt Sandpiper Realty, Inc.

27 Double Ox Rd, Oak Bluffs, MA 02557
/39
$1,575,000
- 3 Beds
- 3 Baths
- 1,621 Sq Ft
27 Laurel Ave, Oak Bluffs, MA 02557

Located in exclusive East Chop, this sun-filled 3BR Cottage blends authentic Martha’s Vineyard charm with modern coastal living. Immaculate, fully furnished, and turn-key, this property presents a phenomenal island retreat or a lucrative investment with fantastic rental potential.The main home pairs classic character with upgraded 200-amp electric, featuring bright spaces, a large kitchen, and

Lisa Sheehan Berkshire Hathaway HomeServices Robert Paul Properties

27 Laurel Ave, Oak Bluffs, MA 02557
/9
$1,200,000
- Land
- 3.42 Acres
- $350,877 per Acre
23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557

Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted

Katherine Donahue Sandpiper Realty

23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557
/37
$3,750,000
- 4 Beds
- 3 Baths
- 2,204 Sq Ft
9 Weston Ave, Oak Bluffs, MA 02568

This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor

Gerrett Conover Landvest MV

9 Weston Ave, Oak Bluffs, MA 02568
/40
$1,750,000
- 3 Beds
- 3.5 Baths
- 2,376 Sq Ft
28 Grovedale Rd, Oak Bluffs, MA 02557

GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate

David White OwnerEntry.com

28 Grovedale Rd, Oak Bluffs, MA 02557
/36
$2,575,000
- 4 Beds
- 1.5 Baths
- 1,606 Sq Ft
12 Samoset Ave, Oak Bluffs, MA 02557

Classic Oak Bluffs Victorian Steps from Beach, Harbor & Town.. Built in 1875 by famed architect Samuel Pratt, this Classic Oak Bluffs Victorian offers a rare opportunity to own a piece of Vineyard history just one block from the sandy beach. Located moments from the harbor, ferries, shops, restaurants, and all the attractions of downtown Oak Bluffs, this warm and welcoming four-bedroom home

Marilyn Moses Ocean Park Realty Inc

12 Samoset Ave, Oak Bluffs, MA 02557
/9
$1,200,000
- Land
- 3.42 Acres
- $350,877 per Acre
23 Onkokemmy Rd, West Tisbury, MA 02557

Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

23 Onkokemmy Rd, West Tisbury, MA 02557
/35
$1,075,000
- 3 Beds
- 2 Baths
- 1,135 Sq Ft
21 Butler Ave, Oak Bluffs, MA 02557

Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with the comfort, privacy, and functionality of a thoughtfully modernized home. Two-car off-street parking—an exceptional Campground amenity—adds everyday convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away.

Jennifer O'hanlon Compass LLC

21 Butler Ave, Oak Bluffs, MA 02557
/110
$2,000,000
- 4 Beds
- 6 Baths
- 2,972 Sq Ft
398 Main St, Vineyard Haven, MA 02568

Ideally situated on Main Street in Vineyard Haven, just moments from the Yacht Club and West Chop, this charming four-bedroom, six-bathroom home offers the perfect blend of convenience, comfort, and Island living. Set on a quarter-acre lot, the property features a private and inviting backyard—ideal for entertaining, gardening, or simply enjoying warm summer evenings. Inside, generous living

Peter Cronig Cronigs Real Estate

398 Main St, Vineyard Haven, MA 02568
/31
$15,400,000
- 6 Beds
- 9 Baths
- 6,967 Sq Ft
8 Snail Rd, Chilmark, MA 02535

Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects

Brian Dougherty Corcoran Property Advisors

8 Snail Rd, Chilmark, MA 02535
/38
$3,099,000

$100K PRICE DROP
- 3 Beds
- 3.5 Baths
- 3,082 Sq Ft
53 Stoney Hill Rd, Vineyard Haven, MA 02568

This custom-built Martha’s Vineyard residence blends timeless elegance with contemporary luxury, offering exclusive access to Lambert’s Cove Beach.At its heart is a chef’s kitchen with bespoke cabinetry, honed Carrara marble, Wolf and Sub-Zero appliances, Miele dishwasher, and Hudson Valley lighting. An adjacent custom bar features Dolomite Italian granite, ideal for entertaining.The home boasts

Jennifer B. DaSilva Compass

53 Stoney Hill Rd, Vineyard Haven, MA 02568
/31
$1,790,000
- 3 Beds
- 2.5 Baths
- 2,347 Sq Ft
41 & 0 Cook St, Tisbury, MA 02568

Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready to build on immediately or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or investment. An easement is being established along the existing driveway to

Jennifer O'hanlon Compass

41 & 0 Cook St, Tisbury, MA 02568
/26
$949,000
- 3 Beds
- 2 Baths
- 1,328 Sq Ft
96 Dunham Ave, Vineyard Haven, MA 02568

NESTLED ON AN OVERSIZED LOT in a highly convenient Vineyard Haven location, this classic 1972 center-entrance Colonial offers timeless charm and exceptional potential. Inside, an inviting open-concept living space is anchored by a wood-burning fireplace, while soaring vaulted ceilings over the dining area and kitchen create an airy, light-filled atmosphere ideal for gathering with family and

Leslie C. Floyd Portfolio Properties

96 Dunham Ave, Vineyard Haven, MA 02568
/36
$1,399,000

Open Sat 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
/33
$1,790,000
- 3 Beds
- 2.5 Baths
- 2,347 Sq Ft
41 & 0 Cook Rd, Vineyard Haven, MA 02568

Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready for your plans or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or future investment. An easement is being established along the existing driveway to

Jennifer O'hanlon Compass LLC

41 & 0 Cook Rd, Vineyard Haven, MA 02568
/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
/50
$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 Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard perfect for kids and dogs. The yard also encompasses a sweet vegetable garden, a storage shed, and outdoor shower. Inside is open with

Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
/18
$1,199,000
- 3 Beds
- 2 Baths
- 1,302 Sq Ft
47 Winemack St, Oak Bluffs, MA 02557

Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one

Lisa Lucier Anchor Realty of MV

47 Winemack St, Oak Bluffs, MA 02557
/5
$639,000
- Land
- 12,998 Sq Ft
- $2,141,421 per Acre
52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568

GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process. Conveniently located just off

Tina Miller Donnelly + Co

52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
/3
$639,000
- Land
- 13,068 Sq Ft
- $2,130,000 per Acre
52 Heath Hen Ln, Vineyard Haven, MA 02568

GOOD TO GO! This sunny 13,000-square-foot sunny lot is ready for your Vineyard home. The property comes with a complete six bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process.Conveniently located just

Tina Miller Donnelly + Co.

52 Heath Hen Ln, Vineyard Haven, MA 02568
/14
$825,000
- 2 Beds
- 1 Bath
- 985 Sq Ft
19 Perkins Ave, Oak Bluffs, MA 02557

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

Katherine Donahue Sandpiper Realty

19 Perkins Ave, Oak Bluffs, MA 02557
/36
$2,295,000
- 3 Beds
- 2 Baths
- 1,425 Sq Ft
312 E Chop Dr, Oak Bluffs, MA 02557

“The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts

Alyssa Halisky Wallace & Co. Sotheby's

312 E Chop Dr, Oak Bluffs, MA 02557
/36
$2,295,000
- 3 Beds
- 2 Baths
- 1,425 Sq Ft
312 E Chop Dr, Vineyard Haven, MA 02568

''The Doll House'' is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of

Alyssa Halisky Wallace & Co. Sotheby's International Realty

312 E Chop Dr, Vineyard Haven, MA 02568
/33
$1,599,000
- 3 Beds
- 2.5 Baths
- 1,645 Sq Ft
7 Ploughshare Ln, Oak Bluffs, MA 02557

Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

Emma Kennedy Sandpiper Realty, Inc.

7 Ploughshare Ln, Oak Bluffs, MA 02557
/26
$1,349,000
- 3 Beds
- 2 Baths
- 1,863 Sq Ft
3 Troy St, Oak Bluffs, MA 02557

Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a

Alyssa Halisky Wallace & Co. Sotheby's International Realty

3 Troy St, Oak Bluffs, MA 02557
/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
/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
/53
$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
/73
$4,125,000

Open House 8/08 $525K PRICE DROP
- 7 Beds
- 4.5 Baths
- 3,312 Sq Ft
31 Josiah Sachem Way, Vineyard Haven, MA 02568

OPEN HOUSE Saturday, August 8th 10:30am-12:30pm. 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

Helena Kirschenbaum Studio Realty

31 Josiah Sachem Way, Vineyard Haven, MA 02568
/16
$1,175,000

$74K PRICE DROP
- 3 Beds
- 1 Bath
- 998 Sq Ft
299 Daggett Ave Unit A, Vineyard Haven, MA 02568

This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

Karen Overtoom Karen M. Overtoom R.E.

299 Daggett Ave Unit A, Vineyard Haven, MA 02568
/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
/12
$1,195,000
- 1 Bed
- 1 Bath
- 768 Sq Ft
61 Wood Chips Cir, Vineyard Haven, MA 02568

Set on a private, wooded lot in Vineyard Haven, this recently built home offers a rare combination of immediate enjoyment and exceptional future potential. Built in 2021, the thoughtfully designed 1-bedroom residence features a bright, modern interior, energy-efficient solar panels, and a peaceful setting surrounded by nature. The true value lies in the property’s remarkable expansion

Andrew McElhinney Compass LLC

61 Wood Chips Cir, Vineyard Haven, MA 02568
/21
$1,175,000

$74K PRICE DROP
- 3 Beds
- 1 Bath
- 998 Sq Ft
299 Daggett Ave, Vineyard Haven, MA 02568

This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

Alyson Parker Karen M. Overtoom R.E.

299 Daggett Ave, Vineyard Haven, MA 02568
/42
$4,600,000

$350K PRICE DROP
- 6 Beds
- 5.5 Baths
- 3,998 Sq Ft
15 Tamarack Ln, Oak Bluffs, MA 02557

Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic

Stephanie Roache Donnelly + Co.

15 Tamarack Ln, Oak Bluffs, MA 02557
/4
$809,000
- Land
- 16,901 Sq Ft
- $2,085,052 per Acre
7 Highland Ave Unit 119, Vineyard Haven, MA 02568

Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

Shera Toledo eXp Realty

7 Highland Ave Unit 119, Vineyard Haven, MA 02568
/58
$2,895,000
- 5 Beds
- 4 Baths
- 2,300 Sq Ft
27 Spring St, Vineyard Haven, MA 02568

Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five

Alexis Holden Tea Lane Associates

27 Spring St, Vineyard Haven, MA 02568

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