Vineyard Haven, MA Homes

/2
$799,000
- Land
- 0.92 Acre
- $870,181 per Acre
22 Bramble Path Unit 214, West Tisbury, MA 02568

Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

Michele Casavant Vineyard Village Realty

22 Bramble Path Unit 214, West Tisbury, MA 02568
/17
$929,000 Sold Aug 18, 2025

299 Franklin St, Vineyard Haven, MA 02568
- 3 Beds
- 1.5 Baths
- 1,286 Sq Ft
- Built 1950
Last Sold Summary
- $722/SF
- 6 Days On Market
Current Estimated Value $973,665

Last Listing Agent Lisa Lucier Anchor Realty of MV

299 Franklin St, Vineyard Haven, MA 02568

/32
Est $1,152,101 Not Listed For Sale

10 Elm St, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,429 Sq Ft
- Built 1970
10 Elm St, Vineyard Haven, MA 02568

Last Sold Summary
- 3% Above List Price
- $784/SF
- 35 Days On Market
Last Sold Price $1,120,000

Last Listing Agent Christine Rose Martha's Vineyard Island-Wide Realty

/4
$2,995,000
- 4 Beds
- 4.5 Baths
- 3,024 Sq Ft
9 Hagerty Dr, Tisbury, MA 02568

West Chop Dream Home in the Making!Experience the charm of this brand-new Shingle Style Colonial, currently under construction—where modern luxury meets timeless elegance. Featuring 4 spacious bedrooms, 4 full baths, and a half bath, this inviting home offers ample space for relaxing, entertaining, and everything in between. You will be wired for sound with speakers inside and poolside so

Lisa Gilberto C McManus Realty Group

9 Hagerty Dr, Tisbury, MA 02568
/22
$1,299,000 Sold Jun 25, 2025

2 Boylston Dr, Edgartown, MA 02539
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
- Built 1984
Last Sold Summary
- 13% Below List Price
- $859/SF
- 77 Days On Market
Current Estimated Value $1,362,530

Last Listing Agent Martha Smith C McManus Realty Group

2 Boylston Dr, Edgartown, MA 02539

/30
Est $1,403,928 Not Listed For Sale

88 Hopps Farm Rd, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
- Built 1992
88 Hopps Farm Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 6% Above List Price
- $908/SF
- 80 Days On Market
Last Sold Price $1,330,000

Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

/14
$1,295,000
- 4 Beds
- 2 Baths
- 1,764 Sq Ft
54 Columbian Ave, Oak Bluffs, MA 02557

Nestled in a quiet Oak Bluffs neighborhood, this charming, sun-filled four-bedroom, two-bath home sits on a spacious corner lot and offers an ideal opportunity for both seasonal and year-round living. The home features a functional layout with a cozy wood burning stove and abundant natural light throughout. The main level offers a spacious living area open to a kitchen, both with wide plank

Katrina Lima Donnelly + Co

54 Columbian Ave, Oak Bluffs, MA 02557
/28
$1,320,000 Sold Aug 29, 2025

10 Eagles Nest, Edgartown, MA 02539
- 3 Beds
- 2 Baths
- 1,450 Sq Ft
- Built 1987
Last Sold Summary
- 5% Below List Price
- $910/SF
- 6 Days On Market
Current Estimated Value $1,374,510

Last Listing Agent Jennifer B. DaSilva Compass

10 Eagles Nest, Edgartown, MA 02539

/22
Not Listed For Sale

33 Summer St, Vineyard Haven, MA 02568
- 4 Beds
- 3 Baths
- 1,250 Sq Ft
- Built 1924
33 Summer St, Vineyard Haven, MA 02568

Last Sold Summary
- $898/SF
- 19 Days On Market
Last Sold Price $1,122,000

Last Listing Agent Emma Kennedy Sandpiper Realty Inc

/24
$3,500,000 Pending
- 7 Beds
- 5 Baths
- 3,880 Sq Ft
35 New York Ave, Oak Bluffs, MA 02568

An exceptional chance to own one of the few five-unit apartment buildings available on Martha’s Vineyard. Ideally located within a short walk to Oak Bluffs Center, the Harbor, ferry service, and public beaches, this property offers both convenience and strong income potential. The building includes five well-maintained apartments with a total of 7 bedrooms and has been thoughtfully renovated and

Emma Kennedy Sandpiper Realty, Inc.

35 New York Ave, Oak Bluffs, MA 02568
/37
$2,100,000 Sold Aug 27, 2025

42 Daggett Ave, Vineyard Haven, MA 02568
- 3 Beds
- 3.5 Baths
- 3,310 Sq Ft
- Built 2009
Last Sold Summary
- 4% Below List Price
- $634/SF
- 60 Days On Market
Current Estimated Value $2,319,809

Last Listing Agent Rene Jackson Island Real Estate

42 Daggett Ave, Vineyard Haven, MA 02568

/44
Est $4,726,843 Not Listed For Sale

59 Hagerty Dr, Vineyard Haven, MA 02568
- 6 Beds
- 7 Baths
- 5,034 Sq Ft
- Built 2003
59 Hagerty Dr, Vineyard Haven, MA 02568

Last Sold Summary
- 6% Above List Price
- $884/SF
- 11 Days On Market
Last Sold Price $4,450,000

Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's International Realty

/2
$595,000 Pending
- Land
- 0.27 Acre
- $2,228,464 per Acre
5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568

Serious Seller.......Price will be discounted for cash sale................A perfect Vineyard location that is convenient to beaches, a bike path and both downtown Oak Bluffs and Vineyard Haven. This is a unique location in an area of very substantial homes. Per an island engineer, your future house can possibly have up to seven bedrooms and have up to three floors. Include on the property

Ed Charter Arrowhead Homes

5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568
/12
$686,000 Sold Jul 23, 2025

124 Skiff Ave Unit A-10, Vineyard Haven, MA 02568
- 2 Beds
- 1 Bath
- 725 Sq Ft
- Built 1953
Last Sold Summary
- $946/SF
- 31 Days On Market
Current Estimated Value $707,611

Last Listing Agent Carleen Cordwell Anchor Realty of Martha's Vineyard

124 Skiff Ave Unit A-10, Vineyard Haven, MA 02568

/15
Est $1,048,710 Not Listed For Sale

73 Leonard Cir, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 966 Sq Ft
- Built 1980
73 Leonard Cir, Vineyard Haven, MA 02568

Last Sold Summary
- $1,087/SF
- 25 Days On Market
Last Sold Price $1,050,000

Last Listing Agent Leslie Floyd Portfolio Real Estate Inc.

/16
$1,193,000
- 3 Beds
- 1.5 Baths
- 1,040 Sq Ft
50 Lantern Ln, Vineyard Haven, MA 02568

In a peaceful Vineyard Haven setting just moments from town, 50 Lantern Lane offers a refined take on classic island living. Privately sited in a quiet enclave yet only one mile from Main Street, Owen Park Beach, and dining and just 1.2 miles from the ferry—this property blends convenience with serenity. The three bedroom, two bath residence spans 1,040 square feet and features a thoughtfully

Madelyn Silvia Wallace & Co. Sotheby's International Realty

50 Lantern Ln, Vineyard Haven, MA 02568
/29
$1,075,000 Sold Feb 26, 2026

34 Pine Ln, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 1984
Last Sold Summary
- 14% Below List Price
- $960/SF
- 93 Days On Market
Current Estimated Value $1,176,508

Last Listing Agent Candy DaRosa Feiner Real Estate

34 Pine Ln, Vineyard Haven, MA 02568

/20
Est $1,315,457 Not Listed For Sale

225 Longview Rd, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,730 Sq Ft
- Built 1977
225 Longview Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 3% Below List Price
- $780/SF
- 18 Days On Market
Last Sold Price $1,350,000

Last Listing Agent Michele Casavant Vineyard Village Realty

/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
/27
$1,475,000 Sold Oct 10, 2025

11 John Wesley Ave, Oak Bluffs, MA 02568
- 4 Beds
- 1.5 Baths
- 1,304 Sq Ft
- Built 1905
Last Sold Summary
- 5% Below List Price
- $1,131/SF
- 103 Days On Market
Last Listing Agent Lisa Lucier Anchor Realty of MV

11 John Wesley Ave, Oak Bluffs, MA 02568

/2
Est $2,200,128 Not Listed For Sale

59 Field View Ln, Vineyard Haven, MA 02568
- 4 Beds
- 4 Baths
- 3,269 Sq Ft
- Built 1975
59 Field View Ln, Vineyard Haven, MA 02568

Last Sold Summary
- $673/SF
- 76 Days On Market
Last Sold Price $2,200,000

Last Listing Agent Emma Kennedy Sandpiper Realty Inc

/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
/41
$1,850,000 Sold Aug 04, 2025

26 Tia Anna Ln, Oak Bluffs, MA 02557
- 3 Beds
- 3 Baths
- 2,210 Sq Ft
- Built 1980
Last Sold Summary
- 7% Below List Price
- $837/SF
- 22 Days On Market
Current Estimated Value $1,924,011

Last Listing Agent Marilyn Moses Ocean Park Realty Inc

26 Tia Anna Ln, Oak Bluffs, MA 02557

/31
Est $1,491,638 Not Listed For Sale

99 Summer St, Vineyard Haven, MA 02568
- 6 Beds
- 4 Baths
- 2,655 Sq Ft
- Built 1985
99 Summer St, Vineyard Haven, MA 02568

Last Sold Summary
- 49% Above List Price
- $377/SF
- 0 Days On Market
Last Sold Price $1,000,000

Last Listing Agent LINK Email Cache LINK

/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
/2
$3,500,000 Sold Oct 07, 2025

339 Lake St, Vineyard Haven, MA 02568
- 3 Beds
- 3.5 Baths
- 2,448 Sq Ft
- Built 2001
Last Sold Summary
- $1,430/SF
- 0 Days On Market
Last Listing Agent LINK Email Cache LINK

339 Lake St, Vineyard Haven, MA 02568

/15
Est $1,040,038 Not Listed For Sale

20 Leonard Cir, Vineyard Haven, MA 02568
- 4 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1984
20 Leonard Cir, Vineyard Haven, MA 02568

Last Sold Summary
- 12% Above List Price
- $803/SF
- 30 Days On Market
Last Sold Price $925,000

Last Listing Agent Roy Cutrer LAER Realty Partners

/37
$1,499,000 Pending
- 3 Beds
- 2.5 Baths
- 2,232 Sq Ft
25 Boylston Dr, Edgartown, MA 02539

CUSTOM BUILT EXPANDED CAPE IN A QUIET EDGARTOWN NEIGHBORHOOD. Set on 1⁄2 acre, this pristine and meticulously maintained home has quality features throughout, including beautiful wide pine floors and top-quality appliances. Enter into this charming home to the first-floor open living space that includes a living room, dining area both with custom built-ins and a large kitchen with premium quartz

Patricia Lyman Compass

25 Boylston Dr, Edgartown, MA 02539
/22
$1,150,000 Sold Apr 11, 2025

41 Old County Rd, Vineyard Haven, MA 02568
- 3 Beds
- 1.5 Baths
- 1,264 Sq Ft
- Built 1983
Last Sold Summary
- 11% Below List Price
- $910/SF
- 216 Days On Market
Current Estimated Value $1,202,252

Last Listing Agent Jared Bicknell Compass | The O'Hanlon Group

41 Old County Rd, Vineyard Haven, MA 02568

/29
Est $1,124,161 Not Listed For Sale

129 Lagoon Ave, Vineyard Haven, MA 02568
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
- Built 1983
129 Lagoon Ave, Vineyard Haven, MA 02568

Last Sold Summary
- 13% Above List Price
- $864/SF
- 12 Days On Market
Last Sold Price $995,000

Last Listing Agent Hope O'Brien Compass Massachusetts, LLC

/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
/13
$2,237,500 Sold Nov 19, 2025

26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
- 4 Beds
- 3 Baths
- 2,299 Sq Ft
- Built 1974
Last Sold Summary
- 16% Below List Price
- $973/SF
- 120 Days On Market
Last Listing Agent Jill Napior Tea Lane Associates

26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

/24
Est $1,441,478 Not Listed For Sale

92 Winyah Cir, Vineyard Haven, MA 02568
- 4 Beds
- 2 Baths
- 2,625 Sq Ft
- Built 1983
92 Winyah Cir, Vineyard Haven, MA 02568

Last Sold Summary
- 26% Above List Price
- $434/SF
- 78 Days On Market
Last Sold Price $1,140,000

Last Listing Agent Doug Burke Cronigs Real Estate

/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
/19
$1,265,000 Sold Mar 11, 2025

62 Lagoon Pond Rd Unit B, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,682 Sq Ft
- Built 2010
Last Sold Summary
- 14% Below List Price
- $752/SF
- 357 Days On Market
Last Listing Agent Allison Fisher Snowden Donnelly + Co

62 Lagoon Pond Rd Unit B, Vineyard Haven, MA 02568

/23
Est $1,341,483 Not Listed For Sale

201 Spring St, Vineyard Haven, MA 02568
- 4 Beds
- 2 Baths
- 2,080 Sq Ft
- Built 1976
201 Spring St, Vineyard Haven, MA 02568

Last Sold Summary
- 25% Above List Price
- $517/SF
- 225 Days On Market
Last Sold Price $1,075,000

Last Listing Agent Kristin Buck Donnelly + Co.

/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
$2,495,000 Sold Nov 20, 2025

16 Mockingbird Dr, Edgartown, MA 02539
- 4 Beds
- 6 Baths
- 2,694 Sq Ft
- Built 2016
Last Sold Summary
- 6% Below List Price
- $926/SF
- 161 Days On Market
Current Estimated Value $2,464,348

Last Listing Agent Emma Kennedy Sandpiper Realty Inc

16 Mockingbird Dr, Edgartown, MA 02539

/28
Est $1,272,772 Not Listed For Sale

175 Oak Ln, Vineyard Haven, MA 02568
- 4 Beds
- 2 Baths
- 1,536 Sq Ft
- Built 1986
175 Oak Ln, Vineyard Haven, MA 02568

Last Sold Summary
- 13% Above List Price
- $732/SF
- 19 Days On Market
Last Sold Price $1,125,000

Last Listing Agent Joanna Fairchild eXp Realty

/49
$1,750,000 Under Contract
- 5 Beds
- 5.5 Baths
- 4,334 Sq Ft
39 Iron Hill Rd, Oak Bluffs, MA 02557

Welcome to 39 Iron Hill Rd, Oak Bluffs (Martha’s Vineyard)—a private multifamily colonial within Iron Hill Farm, near Island Alpaca, Island Grown Initiative, miles of trails, and access to Duarte’s Pond, with convenient proximity to Vineyard Haven and Oak Bluffs beaches and amenities. The 4,334± sq. ft. property offers 5 BR / 5.5 BA in total. Main residence (4BR/4.5BA) features two ensuite

Lisa Da Silva Compass | Point B

39 Iron Hill Rd, Oak Bluffs, MA 02557

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