Homes for Sale in 02568

/22
$970,000
- 2 Beds
- 0.5 Baths
- 953 Sq Ft
50 Canonicus Ave, Oak Bluffs, MA 02557

Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

Michele Moore Island Real Estate

50 Canonicus Ave, Oak Bluffs, MA 02557
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/28
$2,825,000
- 5 Beds
- 2 Baths
- 2,386 Sq Ft
187 Lagoon Pond Rd, Vineyard Haven, MA 02568

For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal.Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly

Erin Leighton Compass

187 Lagoon Pond Rd, Vineyard Haven, MA 02568
/36
$2,595,000
- 5 Beds
- 4 Baths
- 3,328 Sq Ft
159 Lake St, Vineyard Haven, MA 02568

Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a

Alyssa Halisky Wallace & Co. Sotheby's

159 Lake St, Vineyard Haven, MA 02568
/21
$1,159,999
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
9 Bayview Ave, Oak Bluffs, MA 02568

Oak Bluffs Charmer – Welcome to 9 Bayview Avenue, a 3-bedroom, 2-bath home tucked away on a quiet road in Oak Bluffs. Sited on a level 10,050 sq. ft. lot, this property offers 1,428 sq. ft. of light-filled living space. The main level features a spacious living room, kitchen, and dining area, along with a first-floor bedroom and full bath. Upstairs, two comfortable bedrooms share a full bathroom,

Andrew McElhinney Compass LLC

9 Bayview Ave, Oak Bluffs, MA 02568
/6
$1,595,000
- Land
- 3.2 Acres
- $498,438 per Acre
9 Beach Pebble Rd, Vineyard Haven, MA 02568

Vacant land in West Tisbury's Makonikey Community with access to the beautiful Lower Makonikey Association beach. This rare offering spans over 3 acres, with a 1.4-acre area providing the ideal location for a substantial residence in keeping with the distinguished homes that define this exclusive neighborhood. This property presents a unique opportunity to create an exceptional island retreat.

Cassie Bradley Wallace & Co. Sotheby's International Realty

9 Beach Pebble Rd, Vineyard Haven, MA 02568
/42
$2,150,000
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
33 Lagoon Pond Rd, Vineyard Haven, MA 02568

Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

Madelyn Silvia Wallace & Co. Sotheby's International Realty

33 Lagoon Pond Rd, Vineyard Haven, MA 02568
/39
$2,600,000
- 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
/31
$1,150,000
- 2 Beds
- 1 Bath
- 1,040 Sq Ft
73 & 0 Old Country Ln, Vineyard Haven, MA 02568

Charming 2-bedroom, 1-bath ranch house in Vineyard Haven, in town—just minutes from shops, restaurants, and schools. This well-maintained property offers a functional layout with a bright living area, a cozy kitchen overlooking the backyard, two comfortable bedrooms, and a full bathroom. The house has a full basement with ample room for storage and projects. This home is situated on two lots,

Julianna Flanders Flanders Real Estate

73 & 0 Old Country Ln, Vineyard Haven, MA 02568
/39
$2,650,000
- 6 Beds
- 3.5 Baths
- 3,000 Sq Ft
63 Crowell Ln, Vineyard Haven, MA 02568

Extraordinary West Chop Opportunity - Two Homes on 1.80 Acres in Vineyard Haven Nestled next to the desirable West Chop/Mink Meadows neighborhoods, this unique property features two dwellings, making it a perfect opportunity for multi-generational living, guest accommodations, or rental potential.The welcoming, farm-style front porch on the main house looks out onto a large yard. Inside, the

Heather Dyas-Fried Tea Lane Associates

63 Crowell Ln, Vineyard Haven, MA 02568
/48
$1,595,000
- 5 Beds
- 4 Baths
- 2,516 Sq Ft
651 State Rd, Vineyard Haven, MA 02568

Fabulous multi-building compound offered in West Tisbury. Well maintained main house dating to 1880 has many features common to classic older homes but has been updated to provide comfort and year-round livability. Bright and cozy there are lots of rooms and spaces to provide for a larger group of individuals with a total of 4 bedrooms in the main house and a partially finished walk-out

Jim Feiner Feiner Real Estate

651 State Rd, Vineyard Haven, MA 02568
/26
$2,195,000
- 3 Beds
- 3.5 Baths
- 2,453 Sq Ft
34 Davis St, Tisbury, MA 02568

NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island's harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

Andrew McElhinney Compass Massachusetts, LLC

34 Davis St, Tisbury, MA 02568
/34
$3,250,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
6 Brewster Ave, Oak Bluffs, MA 02557

Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

Katherine Donahue Sandpiper Realty Inc

6 Brewster Ave, Oak Bluffs, MA 02557
/74
$14,500,000
- 6 Beds
- 5 Baths
- 4,964 Sq Ft
825 Main St, Vineyard Haven, MA 02568

Set on 1.75 acres this waterfront home features 200+/- feet of sandy beach on the outer harbor in the community of West Chop. Upon entering the home, the stunning view of the outer harbor and Nantucket Sound is breathtakingly beautiful. Perfect for hosting large parties or intimate family gatherings the spacious living room spills onto the large deck through two sets of French doors. Gleaming

Judy Federowicz Landmarks at TODAY Real Estate

825 Main St, Vineyard Haven, MA 02568
/10
$619,000
- Land
- 0.61 Acre
- $1,014,754 per Acre
0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568

Vacant Land - NO LIMIT on bedroom count! You just have to meet setbacks. Once you build your dream home, you will able to explore nature just steps away. Nearby there are two Lagoon access points for kayaking and swimming, as well as walking trails within the Martha's Vineyard Land Bank and Sheriff's Meadow properties. Enjoy the peace of a rural setting, yet remain conveniently close to the ferry

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

0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
/28
$2,495,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
268 Tashmoo Ave, Vineyard Haven, MA 02568

Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

Michele Casavant Vineyard Village Realty

268 Tashmoo Ave, Vineyard Haven, MA 02568
/47
$5,450,000
- 4 Beds
- 5.5 Baths
- 3,300 Sq Ft
8 Paddock Rd, Oak Bluffs, MA 02557

Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

Lesley Heidt Sandpiper Realty Inc

8 Paddock Rd, Oak Bluffs, MA 02557
/14
$799,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Nora Jardin Island Real Estate

60R Carol Ln, Oak Bluffs, MA 02557
/15
$799,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60 -R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Sheila Morse Island Real Estate

60 -R Carol Ln, Oak Bluffs, MA 02557
/26
$1,850,000
- 4 Beds
- 2.5 Baths
- 3,268 Sq Ft
7 Upper Meadow Ln, Oak Bluffs, MA 02557

Meadowview Farms - Tucked at the end of a quiet cul-de-sac, this spacious Colonial offers more than 3,200 square feet of comfortable living space. This home is ideal for those who love to host lively gatherings while providing ample accommodations. Inside, you’ll find four well-sized bedrooms and two and a half baths, including a generous primary suite with double walk-in closets and a private

Lesley Heidt Sandpiper Realty

7 Upper Meadow Ln, Oak Bluffs, MA 02557
/4
$600,000
- Land
- 0.23 Acre
- $2,614,379 per Acre
00 Bernard Cir Unit 10, Tisbury, MA 02568

Rare opportunity to build your dream home in a quiet, well-established Vineyard Haven neighborhood. This level parcel offers excellent potential with flexible zoning that allows for as many bedrooms as will fit within the allowable footprint, governed by 20-foot front and rear setbacks and 10-foot sides. Not located in the watershed district, the property does not require an enhanced septic

Patrick McCarthy Grace Hagerty Real Estate Inc

00 Bernard Cir Unit 10, Tisbury, MA 02568
/8
$599,000
- Land
- 0.29 Acre
- $2,065,517 per Acre
37 Double Ox Rd, Oak Bluffs, MA 02557

This is your opportunity to get in on the ground floor of Lagoon Ridge, a stunning, new development. Several homes are already in place. This beautiful, wooded Lot is located down meandering, newly paved roads, just .4 mile from Barnes Road and the Lagoon. For the outdoor enthusiast, walk and ride the numerous hiking and biking trails that traverse the abutting conservation lands. All utility

Lynn Buder Sandpiper Realty Inc

37 Double Ox Rd, Oak Bluffs, MA 02557
/21
$1,999,999
- 4 Beds
- 3 Baths
- 2,730 Sq Ft
5 Pine Tree Ln, Vineyard Haven, MA 02568

Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for

Kristin Francoeur Gibson Sotheby's International Realty

5 Pine Tree Ln, Vineyard Haven, MA 02568
/38
$1,575,000
- 5 Beds
- 3.5 Baths
- 2,436 Sq Ft
128 W Spring St, Vineyard Haven, MA 02568

128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

David Dickinson Compass

128 W Spring St, Vineyard Haven, MA 02568
/54
$1,830,000
- 4 Beds
- 4 Baths
- 1,600 Sq Ft
12 & 14 Maple Ave, Oak Bluffs, MA 02557

Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

Leslie Floyd Portfolio Properties

12 & 14 Maple Ave, Oak Bluffs, MA 02557
/45
$6,395,000
- 6 Beds
- 5.5 Baths
- 7,000 Sq Ft
400 Barnes Rd, Vineyard Haven, MA 02568

Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

Jennifer DaSilva Compass | Point B

400 Barnes Rd, Vineyard Haven, MA 02568
/39
$3,500,000
- 3 Beds
- 4 Baths
- 2,500 Sq Ft
27 Clambelly Rd, Chilmark, MA 02535

A place of serenity tucked in the woods of Chilmark. Complete renovation 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 flooring. LED lighting throughout house, Media

Julianna Flanders Flanders Real Estate

27 Clambelly Rd, Chilmark, MA 02535
/53
$3,750,000
- 5 Beds
- 6.5 Baths
- 4,372 Sq Ft
139 Main St, Vineyard Haven, MA 02568

Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming

Leslie Floyd Portfolio Properties

139 Main St, Vineyard Haven, MA 02568
/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
/43
$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

111 Charles Neck Way, Vineyard Haven, MA 02568
/42
$2,375,000
- 6 Beds
- 4.5 Baths
- 2,970 Sq Ft
128 W Spring St, Vineyard Haven, MA 02568

A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

David Dickinson Compass

128 W Spring St, Vineyard Haven, MA 02568
/47
$2,375,000
- 6 Beds
- 4.5 Baths
- 2,970 Sq Ft
128 & 136 Spring St, Vineyard Haven, MA 02568

A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

David Dickinson Compass | Point B

128 & 136 Spring St, Vineyard Haven, MA 02568
/43
$4,999,000
- 6 Beds
- 5.5 Baths
- 3,214 Sq Ft
15 Tamarack Ln, Oak Bluffs, MA 02557

FARM NECK: The original 1780 Farm House was tastefully restored in 1985 to honor the land and legacy of Farm Neck. This serene 3.7 acre oasis of rolling greenery with a variety of mature trees and lots of natural privacy has an up Island feel with the down Island convenience to fine dining, shopping, ferry, airport, bike paths and includes Stockholder Membership in the popular Farm Neck Golf

Michael Schweikert Ocean Park Realty, Inc.

15 Tamarack Ln, Oak Bluffs, MA 02557
/8
$725,000
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568

Enjoy effortless year-round living with easy access to Vineyard Haven's downtown shops, restaurants, the harbor, ferry, and nearby beaches. Bright and inviting first-floor three-bedroom, two-bath condo in the sought-after Causeway Harborview association. The association offers practical amenities--including a shared pool, ample storage, and on-site laundry--that support a comfortable lifestyle in

Emma Kennedy Sandpiper Realty Inc

124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
/29
$4,500,000
- 5 Beds
- 6 Baths
- 5,598 Sq Ft
71 Stoney Hill Rd, Vineyard Haven, MA 02568

A combination of luxury, comfort, and natural beauty, this expansive custom, 6,000+ square foot, five bedroom, post and beam home is sited on more than seven acres of land, surrounded by more than 200 acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow

Sheila Morse Island Real Estate

71 Stoney Hill Rd, Vineyard Haven, MA 02568
/39
$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
/73
$6,495,000
- 7 Beds
- 5.5 Baths
- 4,730 Sq Ft
180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568

A storybook sanctuary in Pilot Hill. For the first time in 37 years, one of the rarest and most beautiful properties within Pilot Hill Farm is being offered for sale.Set on nearly eight acres, this unique estate includes a thoughtfully renovated antique farmhouse and several distinctive outbuildings: a pool, guest house, an art studio, and a carriage house with room for three cars, plus a

Alexis Holden Tea Lane Associates

180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
/4
$625,000
- Land
- 0.34 Acre
- $1,815,277 per Acre
0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

Andrew McElhinney Compass LLC

0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/22
$1,199,000
- 2 Beds
- 1 Bath
- 742 Sq Ft
47 Winemack St, Oak Bluffs, MA 02557

Oak Bluffs -East Chop-Close to the ocean. Two 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 bath, and a

Lisa Lucier

Anchor Realty of MV

(508) 403-9601

47 Winemack St, Oak Bluffs, MA 02557
/4
$675,000
- Land
- 0.23 Acre
- $2,941,176 per Acre
0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime LocationThis flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to

Andrew McElhinney Compass LLC

0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/36
$2,500,000
- 4 Beds
- 3 Baths
- 2,350 Sq Ft
16 South Rd, Chilmark, MA 02535

Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated

Michele Casavant Vineyard Village Realty

16 South Rd, Chilmark, MA 02535

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Massachusetts Dukes County Vineyard Haven 02568

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