20

Vineyard Haven Houses for Sale

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  • /52

    $3,950,000

    • 5 Beds
    • 7 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 C. Floyd Portfolio Real Estate, Inc.

    139 Main St, Vineyard Haven, MA 02568
  • /47

    $2,675,000

    • 6 Beds
    • 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
  • /39

    $2,900,000

    • 4 Beds
    • 3 Baths
    • 2,562 Sq Ft

    21 Woodlawn Ave, Vineyard Haven, MA 02568

    Experience the perfect blend of coastal charm and modern sophistication in this beautifully designed Vineyard Haven home. Ideally situated in-town, this 4-bedroom, 3-bath home offers a comfortable, easy flowing layout, complemented by gleaming hardwood floors and a warm, inviting atmosphere. Located just a short stroll from the ferry, vibrant shops, restaurants and the Vineyard Haven Yacht Club,

    Beth Welch Viewpoints; Bobbi Flake Reed, Inc.

    21 Woodlawn Ave, Vineyard Haven, MA 02568
  • /42

    $3,195,000

    • 5 Beds
    • 4 Baths
    • 2,300 Sq Ft

    27 Spring St, Vineyard Haven, MA 02568

    Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features five fireplaces, (one currently hidden behind a plastered wall), a gracious living room, dining room,

    Alexis Holden Tea Lane Associates

    27 Spring St, Vineyard Haven, MA 02568
  • /32

    $3,145,000

    • 4 Beds
    • 3 Baths
    • 2,770 Sq Ft

    36 Tashmoo Ave, Vineyard Haven, MA 02568

    This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven's most quiet and quaint neighborhoods. With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    36 Tashmoo Ave, Vineyard Haven, MA 02568
  • /30

    $2,195,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • /51

    $2,300,000

    • 4 Beds
    • 4 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
  • /37

    $2,150,000 New Construction

    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Discover this stunning newly contructed single-family home in the heart of downtown Vineyard Haven. This beautifully crafted 3-bedroom, 3-bathroom residence offers high-end finishes and thoughtful design throughout.The modern kitchen and bathrooms feature elegant quartz countertops, while tile showers with custom glass enclosures add a touch of luxury. Each bedroom includes spacious

    Mike Sawyer Sawyer Realty Group

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /35

    $12,500,000

    • 5 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    33 Goethals Way, Vineyard Haven, MA 02568

    A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

    Lynn Buder Sandpiper Realty Inc

    33 Goethals Way, Vineyard Haven, MA 02568
  • /29

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,398 Sq Ft

    324 Greenwood Ave, Vineyard Haven, MA 02568

    Charming Cape-style home offering 3 bedrooms and 2 full bathrooms on a .28-acre lot. This inviting property features a renovated kitchen and renovated bathrooms, new appliances, energy-efficient splits for heating and cooling, and a thoughtful layout that blends comfort and functionality. The first floor includes an open kitchen and dining area, creating a perfect space for both everyday

    Emily Flake Viewpoints

    324 Greenwood Ave, Vineyard Haven, MA 02568
  • /21

    $650,000

    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

    Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been delightfully renovated, featuring new hardwood floors, an updated bathroom, updated

    Stephanie Roache Donnelly + Co.

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
  • /62

    $1,995,000

    • 4 Beds
    • 2 Baths
    • 2,462 Sq Ft

    129 Beach Rd, Tisbury, MA 02568

    Unique, waterfront property with amazing, 180 degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private access,

    Michele Moore Island Real Estate

    129 Beach Rd, Tisbury, MA 02568
  • /50

    $4,495,000

    • 4 Beds
    • 5 Baths
    • 2,792 Sq Ft

    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
  • /52

    $1,460,000

    • 4 Beds
    • 3 Baths
    • 2,961 Sq Ft

    208 Irenes Way, Tisbury, MA 02568

    Welcome to this 4 bedroom 3 bathroom 2,961 square foot home! Enjoy the open, first floor layout, finished walk out basement, beautiful hardwood flooring and a quality kitchen with new granite countertops. Just off of the kitchen there is a convenient first floor bedroom, bathroom and laundry room, as well as a lovely bonus space currently enjoyed as a sunroom with a sliding door to the large

    Emma Bryant Landmarks at TODAY Real Estate

    208 Irenes Way, Tisbury, MA 02568
  • /29

    $6,795,000

    • 3 Beds
    • 3 Baths
    • 2,589 Sq Ft

    57 Hines Point Rd, Vineyard Haven, MA 02568

    Lily Hill - a rare Hines Point offering that includes a waterfront home with exquisite views, a deep water mooring and dock, and 130 feet of private fine-sand beach. Poised on a knoll on the western shore of the Lagoon, Lily Hill evokes a more peaceful time with sweeping views of the sky and water. Enjoy a swim at your private beach morning, noon or night. Watch the play of light across the water

    Elissa Lash Tea Lane Associates

    57 Hines Point Rd, Vineyard Haven, MA 02568
  • /20

    $1,295,000

    • 4 Beds
    • 2 Baths
    • 1,306 Sq Ft

    113 Leonard Cir, Vineyard Haven, MA 02568

    Adorable four bedroom cape features an updated open concept living, kitchen and dining area with a cozy screened in porch accessed via French doors. Wood floors, high ceilings and an abundance of windows throughout the home create a unified and pleasing aesthetic as well as a sense of light and spaciousness. Also included on the first floor are a bedroom with lots of natural light and a nicely

    Alyson Parker Karen M. Overtoom R.E.

    113 Leonard Cir, Vineyard Haven, MA 02568
  • /41

    $1,650,000

    • 5 Beds
    • 3.5 Baths
    • 4,032 Sq Ft

    36 Ferro Way, Tisbury, MA 02568

    36 Ferro Way, Vineyard Haven – A Stunning Colonial on Martha’s VineyardWelcome to 36 Ferro Way, a beautifully crafted Colonial-style home nestled in the heart of world-famous Martha’s Vineyard. This exceptional five-bedroom, three-and-a-half-bathroom residence boasts an expansive floor plan, abundant natural light, and a charming farmer’s porch that warmly invites you inside.Step into the heart

    Michael Harney Sotheby's International Realty

    36 Ferro Way, Tisbury, MA 02568
  • /57

    $3,200,000

    • 4 Beds
    • 4 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
  • /9

    $1,445,000

    • 1 Bath
    • 1,283 Sq Ft

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

    Jarrett Hurwitz Keller Williams Realty

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /46

    $1,495,000

    • 3 Beds
    • 2 Baths
    • 1,862 Sq Ft

    249 State Rd, Vineyard Haven, MA 02568

    You haven't missed the boat. And if you live here, you will never miss the boat.This fully furnished, classic Vineyard-style home can be your home in time for spring. This beautifully restored 3-bedroom, 2-bath home has touches from the old Vineyard—a sun porch for napping or reading, a large yard with magnificant magnolia tree, and a detached garage for your Island car. You will never

    Barbara Twiss Laer Realty Partners

    249 State Rd, Vineyard Haven, MA 02568

Why Live in Vineyard Haven

Vineyard Haven in Martha’s Vineyard is a lively year-round neighborhood with a bohemian atmosphere. The area features ivy-covered fences, stone driveways, and gray-shingled buildings along Main Street, which runs parallel to the waterfront. Artisan cheese stores, clothing retailers, and sandwich shops contribute to the local charm. The Vineyard Haven ferry offers year-round transport to New Bedford, facilitating daily commutes for construction workers. Housing is relatively affordable by island standards, though property taxes are high to support the ferry. Home styles vary from 19th-century colonials to modern condos near the waterfront. The neighborhood contrasts with more formal Edgartown and down-home Oak Bluffs, offering unique things to do. Highlights include the Bunch of Grapes bookstore, second-hand stores like Act Two, and dining spots such as Mocha Mott’s and Bobby B’s. Beaches like Owen Park Beach and Tisbury Town Beach provide scenic harbor views, while Lake Tashmoo Town Beach features large shoreline rocks. The Beach Road Weekend music festival and sports leagues at Veterans Memorial Park add to the community's vibrancy. Educationally, Vineyard Haven is served by the highly rated Tisbury School for K-8 and Martha’s Vineyard Regional High School, a National Blue Ribbon Schools award winner. The Vineyard Haven Public Library offers community programs, and the nearby Mass General Brigham Martha’s Vineyard Hospital provides comprehensive healthcare. Vineyard Haven is well-connected, with State Road linking it to other island towns and Martha’s Vineyard Airport 15 minutes away by car.

Home Trends in Vineyard Haven, MA

Housing Trends

Median Sale Price
$397,263
Median Single Family Sale Price
$289,990
Median Townhouse Sale Price
$320,903
Average Price Per Sq Ft
$213
Number of Homes for Sale
6
Last 12 months Home Sales
45
Months of Supply
1.60
Median List Price
$324,903
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-35%
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