Vineyard Haven, MA Homes for Sale

/41
$1,200,000
- 3 Beds
- 1.5 Baths
- 1,304 Sq Ft
14 21st St N, Edgartown, MA 02539

Move-in ready 3-bedroom, 1.5-bathroom house with a warm and welcoming interior. The main level includes an efficient kitchen, living room, dining room with sliders to the mahogany deck and outdoor shower, 1 bedroom, laundry, and convenient half-bath. A one car garage is attached to the main level. The 2 large bedrooms and a full bath are located upstairs. Enjoy the private backyard with its well

Fran Agnoli The Agency

14 21st St N, Edgartown, MA 02539
/43
$1,985,000
- 6 Beds
- 2.5 Baths
- 2,836 Sq Ft
36 Smith Hollow Dr, Edgartown, MA 02539

Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate two-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and

Katherine Donahue Sandpiper Realty Inc

36 Smith Hollow Dr, Edgartown, MA 02539
/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
/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
/4
$474,000
- Land
- 0.55 Acre
- $861,818 per Acre
11 Boylston Dr Unit 1.314, Edgartown, MA 02539

A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island’s top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

Alyssa Halisky Wallace & Co. Sotheby's

11 Boylston Dr Unit 1.314, Edgartown, MA 02539
/42
$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
/23
$2,260,000
- 4 Beds
- 3.5 Baths
- 2,810 Sq Ft
4 High Meadow Ln, Oak Bluffs, MA 02557

Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

Kate Burnside Portfolio Properties

4 High Meadow Ln, 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
/26
$875,000
- 2 Beds
- 1 Bath
- 861 Sq Ft
24 School St, Oak Bluffs, MA 02557

An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining

Stephanie Roache Donnelly + Co.

24 School St, Oak Bluffs, MA 02557
/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
/38
$1,350,000
- 4 Beds
- 3 Baths
- 1,714 Sq Ft
116 Franklin Terrace, Vineyard Haven, MA 02568

Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full

Pricila Ray Keller Williams Realty

116 Franklin Terrace, 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
/20
$1,300,000
- 4 Beds
- 2 Baths
- 1,566 Sq Ft
344 Greenwood Ave, Vineyard Haven, MA 02568

This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles

Katie Donahue Sandpiper Realty

344 Greenwood Ave, Vineyard Haven, MA 02568
/41
$8,900,000 Pre-Foreclosure
- 8 Beds
- 9 Baths
- 8,560 Sq Ft
150 E Chop Dr, Oak Bluffs, MA 02557

Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

Moira Lown Coldwell Banker Realty - Wellesley

150 E Chop Dr, Oak Bluffs, MA 02557
/26
$1,595,000
- 5 Beds
- 3 Baths
- 1,810 Sq Ft
22 Old Lighthouse Rd, Vineyard Haven, MA 02568

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for

Jessie Holtham Wallace & Co. Sotheby's

22 Old Lighthouse Rd, Vineyard Haven, MA 02568
/61
$4,695,000
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
16 Frog Hollow, Vineyard Haven, MA 02568

Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage.Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water

Rose Ryley Wallace & Co. Sotheby's

16 Frog Hollow, Vineyard Haven, MA 02568
/77
$1,295,000 Open Tue 11AM - 2PM
- 3 Beds
- 1 Bath
- 1,033 Sq Ft
9 Brunswick Ave, Oak Bluffs, MA 02557

PRIME LOCATION! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED inside and out. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts NEW flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new

Alice Pierce Coldwell Banker Realty - Martha's Vineyard

9 Brunswick Ave, Oak Bluffs, MA 02557
/30
$985,000
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
22 Clark Ave, Vineyard Haven, MA 02568

A Sweet Spot to call Home. West Chop charms are many in this delightful setting. Acres upon acres of nearby conservation trails make walks, hikes and bike rides an easy daily appeal. Equal distance to Owen Little Way town beach and Vineyard Haven Main Street shops and amenities as well as harbor and ferry port. This move-in ready Clark Avenue abode offers the magic formula of single level living

Helena Kirschenbaum Studio Realty

22 Clark Ave, Vineyard Haven, MA 02568
/46
$1,299,000
- 3 Beds
- 3 Baths
- 1,750 Sq Ft
185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

Experience sun-drenched living in one of Tashmoo Woods’ most desirable floor plans. This beautifully maintained 3-bedroom, 3-bath home offers full access to the coveted Tashmoo Woods amenities, including a pristine pool and pool house, multiple tennis courts, a children’s play area, a private launch on Lake Tashmoo, and a beautiful Association beach on the Sound. Inside, soaring ceilings and

Candy DaRosa Feiner Real Estate

185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
/134
$3,200,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
70 Spring St, Vineyard Haven, MA 02568

NOW INCLUDING RARE 12,527 S.F. TOWN APPROVED BUILDING LOT ON WILLIAM STREET! Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House*, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District, just two blocks to all the shops, restaurants, galleries, town beach, tennis,

June Flake Viewpoints

70 Spring St, Vineyard Haven, MA 02568
/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
/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
/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
/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
/4
$445,000
- Land
- 0.56 Acre
- $794,643 per Acre
5 Candle Maker Cir Unit 1.331, Edgartown, MA 02539

Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows

Alyssa Halisky Wallace & Co. Sotheby's

5 Candle Maker Cir Unit 1.331, Edgartown, MA 02539
/44
$2,700,000
- 4 Beds
- 3 Baths
- 1,399 Sq Ft
34 Windemere Rd, Oak Bluffs, MA 02557

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to

JoJo Lambert Island Home Realty Inc.

34 Windemere Rd, Oak Bluffs, MA 02557
/8
$925,000
- 2 Beds
- 1 Bath
- 806 Sq Ft
260 The Blvd, Edgartown, MA 02539

Two-bedroom, one bath, renovated cottage in Ocean Heights, Edgartown, offering a classic island “camp” charm with a thoroughly modern interior. Over three phases of work (2001, 2021, 2025), the owners have rebuilt key exterior elements, upgraded major systems, and fully refreshed the living space to create a cozy move-in-ready home. The central living area features a cathedral ceiling and large

Sean Federowicz Landmarks at TODAY Real Estate

260 The Blvd, Edgartown, MA 02539
/2
$674,000
- Land
- 0.49 Acre
- $1,375,510 per Acre
56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568

Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either

Marilyn Moses Ocean Park Realty Inc

56 Holmes Hole Rd Unit 10, 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
/4
$474,000
- Land
- 0.55 Acre
- $861,818 per Acre
11 Boylston Dr, Edgartown, MA 02539

A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island's top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

Alyssa Halisky Wallace & Co. Sotheby's International Realty

11 Boylston Dr, Edgartown, MA 02539
/27
$5,250,000
- 4 Beds
- 3.5 Baths
- 3,018 Sq Ft
9 Fowler Ave, Edgartown, MA 02539

Edgartown Waterfront - Classic New England architecture meets the timeless allure of Martha’s Vineyard. This exceptional waterfront estate is set on the edge of Sengekontacket Pond, offering a sandy shoreline, panoramic water views, and a private mooring — the perfect setting for boating, paddle boarding, fishing, and clamming.A gated entrance opens to a beautifully landscaped property

Andrew McElhinney Compass LLC

9 Fowler Ave, Edgartown, MA 02539
/2
$1,250,000
- 1 Bed
- 1 Bath
- 855 Sq Ft
0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

Peyton Wallace Studio Realty

0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
/27
$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
/9
$2,250,000
- 3 Beds
- 3.5 Baths
- 2,475 Sq Ft
35 Double Ox Rd, Oak Bluffs, MA 02557

Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

Marilyn Moses Ocean Park Realty Inc

35 Double Ox Rd, Oak Bluffs, MA 02557
/58
$2,495,000
- 3 Beds
- 3.5 Baths
- 3,530 Sq Ft
61 Causeway Rd, Vineyard Haven, MA 02568

Welcome to this fabulous property nestled just a short stroll from all the best of Vineyard Haven. Easily accessible and within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse, the location is ideal. This beautifully designed home has been lovingly maintained and offers a wonderful balance of Vineyard charm and modern convenience.

Stephanie Roache Donnelly + Co

61 Causeway Rd, Vineyard Haven, MA 02568
/42
$2,150,000 Open Tue 12PM - 2PM
- 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
/3
$2,100,000
- 3 Beds
- 3.5 Baths
- 2,019 Sq Ft
2 Hope's Way, Oak Bluffs, MA 02557

ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Purchase lot ($700,000)& Execute a BUILDING CONTRACT ($1,400,000 )or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty

Marilyn Moses Ocean Park Realty Inc

2 Hope's Way, Oak Bluffs, MA 02557
/22
$925,000
- 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
/67
$2,300,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
70 Spring St, Vineyard Haven, MA 02568

Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

June Flake Viewpoints

70 Spring St, Vineyard Haven, MA 02568
/23
$2,400,000
- 3 Beds
- 3.5 Baths
- 1,883 Sq Ft
27 7th St N, Edgartown, MA 02539

27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with

Michele Casavant Vineyard Village Realty

27 7th St N, Edgartown, MA 02539

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