Vineyard Haven, MA Homes

/38
$2,860,000 Sold Mar 10, 2025
- 3,752 Sq Ft
- $762/SF
- 290 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1836
49 William St, Vineyard Haven, MA 02568

Welcome to the timeless elegance of the Captain Swain House, nestled on the prestigious historic William Street in Vineyard Haven. This distinguished Greek Revival main residence and barn-style guest house seamlessly merges historical charm with modern luxury. Step into this meticulously updated 4-bedroom home and you will find a gourmet kitchen, a welcoming dining room, wet-bar and a screened

Alyssa Halisky Wallace & Co. Sotheby's International Realty

49 William St, Vineyard Haven, MA 02568

/26
Est $3,361,931 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 3,982 Sq Ft
156 Winyah Cir, Tisbury, MA 02568

156 Winyah Cir, Tisbury, MA 02568

/11
$619,000
- Land
- 0.61 Acre
- $1,018,930 per Acre
147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568

Vacant lot - 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

147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
/25
$917,500 Sold Mar 10, 2025
- 1,898 Sq Ft
- $483/SF
- 139 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1983
40 Hidden Cove Rd, Edgartown, MA 02539

NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

Stephanie Roache Donnelly + Co.

40 Hidden Cove Rd, Edgartown, MA 02539

/14
Not Listed For Sale
- 2 Beds
- 2.5 Baths
3 Hope's Way, Oak Bluffs, MA 02568

3 Hope's Way, Oak Bluffs, MA 02568

/37
$1,250,000
- 3 Beds
- 3 Baths
- 1,628 Sq Ft
261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

Welcome to this meticulously maintained 2+ bedroom, 3 bathroom end unit condo in Tashmoo Woods, built in 1998. The updated kitchen with granite countertops and high-end appliances opens to a dining room with a private deck overlooking lush woods. The first floor includes a den and a renovated bathroom. Upstairs, both bedrooms have ensuite bathrooms. Upgrades include propane heat, central air, a

Jennifer O'hanlon Compass

261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
/25
$917,500 Sold Mar 10, 2025
- 1,898 Sq Ft
- $483/SF
- 140 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1983
40 Hidden Cove Rd Unit 15, Oak Bluffs, MA 02557

NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

Stephanie Roache Donnelly + Co

40 Hidden Cove Rd Unit 15, Oak Bluffs, MA 02557

/26
Est $865,614 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,355 Sq Ft
4 Quail Run Unit 5, Oak Bluffs, MA 02557

4 Quail Run Unit 5, Oak Bluffs, MA 02557

/68
$4,395,000
- 3 Beds
- 5.5 Baths
- 4,046 Sq Ft
267 Barnes Rd, Oak Bluffs, MA 02557

Live the Dream on Martha's Vineyard! Whether you're seeking a year-round residence or a seasonal escape, this is a once-in-a-lifetime opportunity to own a piece of paradise. Step into a world of coastal luxury with 163 feet of pristine Lagoon frontage, complete with your own private sandy beach. Nestled on 1.25 acres of lush, landscaped paradise, this rare gem offers sweeping lawns, panoramic

Stephanie Roache Donnelly + Co.

267 Barnes Rd, Oak Bluffs, MA 02557
/24
$917,500 Sold Mar 10, 2025
- 1,898 Sq Ft
- $483/SF
- 138 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1983
40 Hidden Cove Rd Unit 15, Edgartown, MA 02539

NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

Stephanie Roache Donnelly + Co.

40 Hidden Cove Rd Unit 15, Edgartown, MA 02539

/5
Not Listed For Sale
9 Crowell Ln, Tisbury, MA 02568

9 Crowell Ln, Tisbury, MA 02568

/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
/13
$776,500 Sold Mar 05, 2025
- 768 Sq Ft
- $1,011/SF
- 17 Days On Market
- 2 Beds
- 1 Bath
- Built 1968
32 Clark Ave, Vineyard Haven, MA 02568

This two bedroom year-round home will afford you all the opportunities Vineyard Haven has to offer. This private lot is bursting with lilacs, forsythia, wisteria, raspberry canes, a mock orange bush and a peach tree. The home boasts natural light, cathedral ceilings, a comfortable kitchen and living area with two bedrooms and one full bath. There is a mudroom and a handsome, fully enclosed front

Diana Gilmore Island Real Estate

32 Clark Ave, Vineyard Haven, MA 02568

/11
Est $901,850 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
7 Richmond Ave, Oak Bluffs, MA 02568

7 Richmond Ave, Oak Bluffs, MA 02568

/67
$3,125,000
- 4 Beds
- 5 Baths
- 5,165 Sq Ft
63 Bayes Hill Rd, Oak Bluffs, MA 02557

Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

Casandra Hyland Landmarks at TODAY Real Estate

63 Bayes Hill Rd, Oak Bluffs, MA 02557
/17
$1,300,000 Sold Mar 03, 2025
- 1,241 Sq Ft
- $1,048/SF
- 4 Days On Market
- 2 Beds
- 2 Baths
- Built 2018
22 Briarwood Ln, Vineyard Haven, MA 02568

This Recently Constructed Carriage House in Vineyard Haven is the epitome of thoughtful planning with custom details and exceptional finishes throughout. The sunny second level has an open floor living and kitchen area with vaulted ceilings. Highlights include a farmer’s sink, quartz countertops, pull out kitchen cabinets and self-closing drawers. There are two bedrooms, one is ensuite and

Carol Shore Donnelly + Co

22 Briarwood Ln, Vineyard Haven, MA 02568

/16
Not Listed For Sale
- 2 Beds
- 1 Bath
- 704 Sq Ft
19 2nd Ave, Oak Bluffs, MA 02557

19 2nd Ave, Oak Bluffs, MA 02557

/4
$487,000
- Land
- 0.23 Acre
- $2,122,004 per Acre
0 California Ave Unit 76 42933, Oak Bluffs, MA 02568

Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for buildings of any size. Water and electric are nearby.

Jim Joyce Carroll & Vincent R.E.

0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
/10
$550,000 Sold Feb 28, 2025
- Land
- 0.33 Acre
- $1,656,627 per Acre
- 70 Days On Market
0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557

Secluded lot in a prime Oak Bluffs location, offering both privacy and convenience. Just moments from public access points to the sandy shores of Lagoon Pond and the vibrant downtown area, this property provides the perfect setting for your dream home. With engineering plans already in place for a 2-bedroom residence, you have the opportunity to create a custom-built home tailored to your vision.

Alyssa Halisky Wallace & Co. Sotheby's

0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557

/55
Not Listed For Sale
- 11 Beds
- 9.5 Baths
- 4,985 Sq Ft
28 & 18 Hillbrook Ln, West Tisbury, MA 02575

28 & 18 Hillbrook Ln, West Tisbury, MA 02575

/20
$3,750,000
- 4 Beds
- 2.5 Baths
- 1,800 Sq Ft
28 Beach Rd, Oak Bluffs, MA 02557

Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

Scott Lewis Lewis Real Estate Services, LLC

28 Beach Rd, Oak Bluffs, MA 02557
/10
$550,000 Sold Feb 28, 2025
- Land
- 0.33 Acre
- $1,666,667 per Acre
- 70 Days On Market
0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

Secluded lot in a prime Oak Bluffs location, offering both privacy and convenience. Just moments from public access points to the sandy shores of Lagoon Pond and the vibrant downtown area, this property provides the perfect setting for your dream home. With engineering plans already in place for a 2-bedroom residence, you have the opportunity to create a custom-built home tailored to your vision.

Alyssa Halisky Wallace & Co. Sotheby's International Realty

0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

/6
Not Listed For Sale
5 Tori Ln, Oak Bluffs, MA 02568

5 Tori Ln, Oak Bluffs, MA 02568

/11
$495,000
- Land
- 0.23 Acre
- $2,152,174 per Acre
0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557

Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the

Alyssa Halisky Wallace & Co. Sotheby's International Realty

0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557
/3
$750,000 Sold Feb 27, 2025
- 1,100 Sq Ft
- $682/SF
- 0 Days On Market
- 0.5 Baths
- Built 2021
2 Union St Unit A, Tisbury, MA 02568

Commercial Condo Not listed in LINK

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2 Union St Unit A, Tisbury, MA 02568

/6
Not Listed For Sale
00 Crowell Lane - Lot 3 4, Vineyard Haven, MA 02568

00 Crowell Lane - Lot 3 4, Vineyard Haven, MA 02568

/59
$2,250,000
- 4 Beds
- 2.5 Baths
- 2,983 Sq Ft
157 Ben Chase Rd, West Tisbury, MA 02575

You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

Madelyn Silvia Wallace & Co. Sotheby's

157 Ben Chase Rd, West Tisbury, MA 02575
/24
$1,055,000 Sold Feb 21, 2025
- 875 Sq Ft
- $1,206/SF
- 115 Days On Market
- 3 Beds
- 1 Bath
- Built 1870
18 Brunswick Ave, Vineyard Haven, MA 02568

Embrace the history and character of this delightful 1870's Oak Bluffs cottage. Formerly the Laura Thomas Smith House, it was relocated from the Vineyard Highlands area, nestled in a quaint neighborhood close to the center of town and the harbor. It was documented in a 1978 Oak Bluffs Historical Survey and has been in the same family for 98 years. This cottage features a sun-filled living room,

Cheri Mason LandVest MV

18 Brunswick Ave, Vineyard Haven, MA 02568

/28
Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,754 Sq Ft
40 Hidden Cove Rd Unit 7, Oak Bluffs, MA 02557

40 Hidden Cove Rd Unit 7, Oak Bluffs, MA 02557

/11
$495,000
- Land
- 0.23 Acre
- $2,152,174 per Acre
0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557

Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the

Alyssa Halisky Wallace & Co. Sotheby's

0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557
/45
$990,000 Sold Feb 19, 2025
- 1,618 Sq Ft
- $612/SF
- 145 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
5 Rock Pond Rd, Vineyard Haven, MA 02568

Fantastic opportunity to own a South Mountain designed and built home in the coveted Island Co-Housing community. House #5 sits back from the community road with a great side yard, patio and outdoor shower.3 Large Bedrooms include a downstairs master w/ensuite bath off the living room area with a mid-way access leading to a private patio. The entryway opens on the kitchen, with thick shaker

Kerry Quinlan-Potter Breakwater MV

5 Rock Pond Rd, Vineyard Haven, MA 02568

/3
Not Listed For Sale
- 7 Beds
- 6 Baths
- 5,186 Sq Ft
14R Temahigan Ave, Oak Bluffs, MA 02568

14R Temahigan Ave, Oak Bluffs, MA 02568

/57
$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,

June Flake Viewpoints

70 Spring St, Vineyard Haven, MA 02568
/44
$1,250,000 Sold Feb 14, 2025
- 1,781 Sq Ft
- $702/SF
- 101 Days On Market
- 5 Beds
- 3 Baths
- Built 1997
4 Lady Slipper Way, Vineyard Haven, MA 02568

This charming year round Colonial home, designed by island architect Tom Burke and stick built by Ridgewood Custom Homes, is located in the convenient Spring Hill Road Association offering close proximity to town, Tisbury's elementary school, post office, markets, Lake Tashmoo beach and town landing, Steamship ferry, and more. The main level includes eat-in kitchen with center island plus dining

June Flake Viewpoints

4 Lady Slipper Way, Vineyard Haven, MA 02568

/7
Not Listed For Sale
609 State Rd, West Tisbury, MA 02575

609 State Rd, West Tisbury, MA 02575

/24
$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

Brian Smith Portfolio Real Estate Inc.

4 High Meadow Ln, Oak Bluffs, MA 02557
/34
$950,000 Sold Feb 14, 2025
- 1,300 Sq Ft
- $731/SF
- 87 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
2 Nahomon St, Oak Bluffs, MA 02557

Welcome to 2 Nahomon St., Oak Bluffs, MA! Set on a private 1/4-acre level lot at the end of a quiet cul-de-sac, this home offers tranquility and convenience. The first floor features an ensuite bedroom for easy single-level living. Recent upgrades include a new septic system, upgraded electrical panel, new washer and dryer, and an outdoor shower. The spacious bonus room has potential to become a

Jarrod Smith Romano Real Estate

2 Nahomon St, Oak Bluffs, MA 02557

/19
Not Listed For Sale
- 2 Beds
- 1 Bath
- 797 Sq Ft
37 Circuit Ave Unit 2, Oak Bluffs, MA 02557

37 Circuit Ave Unit 2, Oak Bluffs, MA 02557

/51
$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
/27
$1,500,000 Sold Feb 13, 2025
- 2,066 Sq Ft
- $726/SF
- 154 Days On Market
- 3 Beds
- 2 Baths
- Built 1954
37 Weeks Ln, Edgartown, MA 02539

Welcome to this FULLY RENOVATED Charming Cape style home. In 2020 the home was completely gutted down to the studs and a tasteful full renovation was begun which included new electric, plumbing, walls, flooring, cabinetry, new bathrooms, a new kitchen and new exterior decking. In 2021 an oversized detached two car garage with storage above was added to the property. The home offers an attractive

Michele Casavant Vineyard Village Realty

37 Weeks Ln, Edgartown, MA 02539

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Massachusetts Dukes County Vineyard Haven

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