Vineyard Haven, MA Homes

/40
$650,000 Sold Sep 10, 2025
- 759 Sq Ft
- $856/SF
- 251 Days On Market
- 2 Beds
- 0.5 Baths
- Built 1900
25 Oak Ave, Oak Bluffs, MA 02557

WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. Alternatively, you have the choice to add on to the existing building or build a new FIVE (5) BEDROOM home - Possibly more than FIVE (5) bedrooms as it’s not in a Board of Health area of concern -

Alisan Lohan-Conway Alisan Lohan-Conway Properties

25 Oak Ave, Oak Bluffs, MA 02557

/2
Est $2,217,673 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,269 Sq Ft
59 Field View Ln, Vineyard Haven, MA 02568

59 Field View Ln, Vineyard Haven, MA 02568

/63
$5,000,000
- 6 Beds
- 3.5 Baths
- 3,312 Sq Ft
31 Josiah Sachem Way, Vineyard Haven, MA 02568

An inspirational Oasis - come unwind and behold what this secluded multi-home compound has to offer. With two driveways and an open wildflower field bordered with plantings, the main house, studio barn, guesthouse and in-ground pool area at this private retreat are beautifully positioned and landscaped. Each structure is available for year-round use with abundant parking and unique charms.

Helena Kirschenbaum Studio Realty

31 Josiah Sachem Way, Vineyard Haven, MA 02568
/18
$4,250,000 Sold Sep 09, 2025
- 4,125 Sq Ft
- $1,030/SF
- 21 Days On Market
- 5 Beds
- 3 Baths
- Built 1900
420 Lamberts Cove Rd, Vineyard Haven, MA 02568

Charming West Tisbury Estate with Waterfront on Seth's Pond. This stunning property offers the perfect blend of vintage charm and modern convenience, set against the tranquil backdrop of Seth's Pond. Featuring a main house, guest house, boathouse, and barn/workshop, this property provides a rare opportunity for both relaxation and recreation. The main house, a well maintained farmhouse dating

Alyssa Halisky Wallace & Co. Sotheby's International Realty

420 Lamberts Cove Rd, Vineyard Haven, MA 02568

/31
Est $1,345,799 Not Listed For Sale
- 6 Beds
- 4 Baths
- 2,655 Sq Ft
99 Summer St, Vineyard Haven, MA 02568

99 Summer St, Vineyard Haven, MA 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
/20
$1,295,000 Sold Sep 05, 2025
- 1,584 Sq Ft
- $818/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1988
2 Upper Douglas Ln, Oak Bluffs, MA 02557

Are you still looking for a year-round, island home for your family and only finding homes that are either not in your price range or are badly in need of renovation? Look no further because all that work has been done for you with this property. Just move in and enjoy the convenient location -- close to town, schools, hospital and public transportation. This low-maintenance, 4 bedroom, 2 bath

Lynn Buder Sandpiper Realty

2 Upper Douglas Ln, Oak Bluffs, MA 02557

/15
Est $997,870 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,152 Sq Ft
20 Leonard Cir, Vineyard Haven, MA 02568

20 Leonard Cir, Vineyard Haven, MA 02568

/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
/16
$800,000 Sold Sep 04, 2025
- 1,086 Sq Ft
- $737/SF
- 16 Days On Market
- 2 Beds
- 1 Bath
- Built 1948
21 Norris Ave, Vineyard Haven, MA 02568

An Exciting Opportunity for First-Time Buyers or Island Investors.This long-time family homestead offers a rare chance to own a piece of Oak Bluffs at a price point that invites possibility. Set in a quiet, residential neighborhood, the location is just a 25–30 minute walk to the center of town, where you’ll find shopping, restaurants, grocery stores, banks, the ferry terminal, beautiful

Rene Ben David Ocean Park Realty Inc

21 Norris Ave, Vineyard Haven, MA 02568

/29
Est $1,056,183 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
129 Lagoon Ave, Vineyard Haven, MA 02568

129 Lagoon Ave, Vineyard Haven, MA 02568

/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
/29
$991,500 Sold Sep 04, 2025
- 1,624 Sq Ft
- $611/SF
- 20 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1996
11 Onondaga Ave, Vineyard Haven, MA 02568

Comfortable Island Home on a Quiet Dead-End Road in Oak Bluffs: Welcome to 11 Onondaga Avenue, the second home on the left on a short, quiet dead-end road in a well-established Oak Bluffs neighborhood enjoyed by both year-round and seasonal residents. This well-cared-for 3-bedroom, 2.5-bathroom home offers space, comfort, and a truly inviting island lifestyle--just a short walk to the Oak Bluffs

Rene Ben David Ocean Park Realty, Inc.

11 Onondaga Ave, Vineyard Haven, MA 02568

/24
Est $1,372,676 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,625 Sq Ft
92 Winyah Cir, Vineyard Haven, MA 02568

92 Winyah Cir, 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
/35
$1,295,000 Sold Sep 02, 2025
- 1,814 Sq Ft
- $714/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
35 7th St N, Edgartown, MA 02539

Welcome to this charming Cape-style home, just a short distance from the Village. Set on a spacious half-acre lot, this delightful property has been lovingly maintained. The home features an open layout that seamlessly blends comfort and functionality, making it perfect for both everyday living and entertaining. A sun-filled living room with cathedral ceilings and sliders opens to a multi-level

Stephanie Roache Donnelly + Co.

35 7th St N, Edgartown, MA 02539

/23
Est $1,270,543 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,080 Sq Ft
201 Spring St, Vineyard Haven, MA 02568

201 Spring St, Vineyard Haven, 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
/30
$1,995,000 Sold Aug 29, 2025
- 2,891 Sq Ft
- $690/SF
- 5 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
26 Box Turtle Ln, Oak Bluffs, MA 02557

This delightful home is on a scenic lot nestled within the Sengekontacket Association. Every room in the home is filled with natural light and beautiful views. It is a very short walking distance to the community boat dock and kayaking, as well as the walking trails of Sengy.Updated in 2008 by the architect owner, this home has 3 bedrooms in the main house and a lovely bedroom and bathroom in

Jayne Isford Ocean Park Realty Inc

26 Box Turtle Ln, Oak Bluffs, MA 02557

/28
Est $1,269,552 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,536 Sq Ft
175 Oak Ln, Vineyard Haven, MA 02568

175 Oak Ln, 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
/44
$1,890,000 Sold Aug 29, 2025
- 3,270 Sq Ft
- $578/SF
- 38 Days On Market
- 4 Beds
- 3 Baths
- Built 1981
1 Thames Ct, Edgartown, MA 02539

Welcome to this spacious and elegant 4- bedroom, 3-bathroom home nestled in a prime central Edgartown location. Offering over 3,200 sq ft of living space, this expansive property is perfect for a large family, accommodating guests, or serving as a lucrative income opportunity.Step inside to an inviting open-concept layout that seamlessly connects the living, dining, and kitchen

Jon Hartzband Martha's Vineyard Island-Wide Realty

1 Thames Ct, Edgartown, MA 02539

/23
Est $1,905,437 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,026 Sq Ft
171 Otis Bassett Rd, Vineyard Haven, MA 02568

171 Otis Bassett Rd, Vineyard Haven, MA 02568

/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
/28
$1,320,000 Sold Aug 29, 2025
- 1,450 Sq Ft
- $910/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
10 Eagles Nest, Edgartown, MA 02539

Nestled in the serene setting of the Dodger's Hole community, this home is brimming with natural light, soaring ceilings and clean architectural lines.The open-concept layout features a generous living area with a seamless flow to the dining, kitchen and entertaining spaces, ideal for both everyday living and hosting guests.Kitchen has brand new stainless steel appliances! The spaces are

Jennifer B. DaSilva Compass

10 Eagles Nest, Edgartown, MA 02539

/16
Est $1,211,244 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
35 Skiffs Ln, Vineyard Haven, MA 02568

35 Skiffs Ln, Vineyard Haven, MA 02568

/40
$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
/37
$2,100,000 Sold Aug 27, 2025
- 3,310 Sq Ft
- $634/SF
- 60 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2009
42 Daggett Ave, Vineyard Haven, MA 02568

This elegant farmhouse awaits your arrival! Nestled in the heart of Vineyard Haven, the desirable location is within close proximity to the Vineyard Haven Yacht Club and harbor, public beach access, ferry, downtown shops & restaurants, MV Playhouse, Owen Park Beach, new public tennis courts. Open the door to be greeted by a lovely entry way that leads into a light filled living area with

Rene Jackson Island Real Estate

42 Daggett Ave, Vineyard Haven, MA 02568

/37
Est $1,172,287 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,316 Sq Ft
43 Skiffs Ln, Vineyard Haven, MA 02568

43 Skiffs Ln, 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
/50
$4,295,000 Sold Aug 27, 2025
- 2,792 Sq Ft
- $1,538/SF
- 64 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1880
118 William St, Vineyard Haven, MA 02568

The Captain George Harding Home sits gracefully on the westerly side of iconic William Street overlooking Vineyard Haven village with distant views of the harbor. This immaculate and re-imagined Gothic Revival offers both timeless elegance and modern luxury. Completed in 2024, the comprehensive down-to-the-studs renovation includes all new systems like central air and dehumidification. Every

Alexis Holden Tea Lane Associates

118 William St, Vineyard Haven, MA 02568

/26
Est $1,484,787 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 1,968 Sq Ft
33 Hidden Village Rd, Vineyard Haven, MA 02568

33 Hidden Village Rd, Vineyard Haven, MA 02568

/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
/23
$1,800,000 Sold Aug 26, 2025
- 1,351 Sq Ft
- $1,332/SF
- 0 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1910
12 Martha's Park Rd, Oak Bluffs, MA 02557

Harthaven Cottage - This magical cottage, tucked away just 2/10's of a mile from the private association beach, is waiting for you to call it your own. A covered porch welcomes you. Once inside, you begin to take in the charming details of this classic 3-season home. There are cathedral ceilings with exposes painted beams. Home features 4 bedrooms, 1 1/2 baths and outdoor shower. Both bathrooms

Michele Moore Island Real Estate

12 Martha's Park Rd, Oak Bluffs, MA 02557

/30
Est $2,417,153 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,540 Sq Ft
41 Hidden Village Rd, Vineyard Haven, MA 02568

41 Hidden Village Rd, 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
/17
$1,450,000 Sold Aug 26, 2025
- 2,311 Sq Ft
- $627/SF
- 78 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
61 Dodgers Hole Rd, Edgartown, MA 02539

Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space.The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower

Ellen Valentgas Sotheby's International Realty

61 Dodgers Hole Rd, Edgartown, MA 02539

/30
Est $1,541,820 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,560 Sq Ft
12 Lily Farm Rd, Vineyard Haven, MA 02568

12 Lily Farm 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
/40
$2,300,000 Sold Aug 21, 2025
- 3,213 Sq Ft
- $716/SF
- 75 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2011
174 Tashmoo Ave, Vineyard Haven, MA 02568

Welcome to your dream home! The perfect blend of comfort and luxury awaits you in this custom-designed 5-bedroom, 4.5-bathroom residence. Over 3200 square feet of spacious living, upscale furnishings, finished basement with entertainment bar, and all the right touches to make every day feel like a retreat. Conveniently located under a half mile from downtown Vineyard Haven, where you will find

Lisa Lucier Anchor Realty of Martha's Vineyard

174 Tashmoo Ave, Vineyard Haven, MA 02568

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