62

Vineyard Haven Homes for Sale

Section Image Section Image
  • 33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    /9

    $1,325,000

    $170K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • 33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    /13

    $1,325,000

    $170K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • 22 Oklahoma Ave, Vineyard Haven, MA 02568
    22 Oklahoma Ave, Vineyard Haven, MA 02568
    22 Oklahoma Ave, Vineyard Haven, MA 02568
    /19

    $1,250,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,738 Sq Ft

    22 Oklahoma Ave, Vineyard Haven, MA 02568

    HOUSE + APARTMENT NEAR LAGOON! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This clean and bright, move-in ready property features a 3 BR, 1 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset the mortgage. The main house, featuring a wonderful sun-room, a cheerful

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    22 Oklahoma Ave, Vineyard Haven, MA 02568
  • 30 Water Gate Rd, Vineyard Haven, MA 02568
    30 Water Gate Rd, Vineyard Haven, MA 02568
    30 Water Gate Rd, Vineyard Haven, MA 02568
    /21

    $3,495,000

    $1M PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,816 Sq Ft

    30 Water Gate Rd, Vineyard Haven, MA 02568

    Set privately in one of Vineyard Haven’s most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and ready access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for both gathering and quiet retreat, with an effortless indoor-outdoor flow that embraces the surrounding landscape. Bedrooms are

    Peyton Wallace Studio Realty

    30 Water Gate Rd, Vineyard Haven, MA 02568
  • 29 and 33 Lagoon Pond Rd, Tisbury, MA 02568
    29 and 33 Lagoon Pond Rd, Tisbury, MA 02568
    29 and 33 Lagoon Pond Rd, Tisbury, MA 02568
    /39

    $3,295,000

    • 5 Beds
    • 4 Baths
    • 2,330 Sq Ft

    29 and 33 Lagoon Pond Rd, Tisbury, MA 02568

    Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking.

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    29 and 33 Lagoon Pond Rd, Tisbury, MA 02568
  • 116 Franklin Terrace, Vineyard Haven, MA 02568
    116 Franklin Terrace, Vineyard Haven, MA 02568
    116 Franklin Terrace, Vineyard Haven, MA 02568
    /38

    $1,325,000

    $25K PRICE DROP
    • 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 Wiliams Realty Cape Cod & Colonial Partners

    116 Franklin Terrace, Vineyard Haven, MA 02568
  • 33 Goethals Way, Vineyard Haven, MA 02568
    33 Goethals Way, Vineyard Haven, MA 02568
    33 Goethals Way, Vineyard Haven, MA 02568
    /19

    $7,950,000

    $3M PRICE DROP
    • 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

    Buder Team Sandpiper Realty, Inc.

    33 Goethals Way, Vineyard Haven, MA 02568
  • 0 Old Country Ln Unit 4, Vineyard Haven, MA 02568
    0 Old Country Ln Unit 4, Vineyard Haven, MA 02568
    /2

    $450,000

    • Land
    • 20,538 Sq Ft
    • $954,401 per Acre

    0 Old Country Ln Unit 4, Vineyard Haven, MA 02568

    Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.

    Brenda Galligan Karen M. Overtoom R.E.

    0 Old Country Ln Unit 4, Vineyard Haven, MA 02568
  • 95 Hines Point Rd, Vineyard Haven, MA 02568
    95 Hines Point Rd, Vineyard Haven, MA 02568
    95 Hines Point Rd, Vineyard Haven, MA 02568
    /39

    $4,050,000

    $645K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,606 Sq Ft

    95 Hines Point Rd, Vineyard Haven, MA 02568

    A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor

    Elissa Lash Tea Lane Associates

    95 Hines Point Rd, Vineyard Haven, MA 02568
  • 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /41

    $1,975,000

    $175K PRICE DROP
    • 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
  • 26 Union St Unit 7, Tisbury, MA 02568
    26 Union St Unit 7, Tisbury, MA 02568
    26 Union St Unit 7, Tisbury, MA 02568
    /25

    $1,599,000

    $26K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,532 Sq Ft

    26 Union St Unit 7, Tisbury, MA 02568

    Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower. Also on

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    26 Union St Unit 7, Tisbury, MA 02568
  • 41 Edgartown Rd, Vineyard Haven, MA 02568
    41 Edgartown Rd, Vineyard Haven, MA 02568
    41 Edgartown Rd, Vineyard Haven, MA 02568
    /26

    $1,299,000

    $100K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,968 Sq Ft

    41 Edgartown Rd, Vineyard Haven, MA 02568

    Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful

    Peyton Wallace Studio Realty LLC

    41 Edgartown Rd, Vineyard Haven, MA 02568
  • 124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568
    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568
    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568
    /15

    $725,000

    • 2 Beds
    • 1 Bath
    • 703 Sq Ft

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

    Vineyard Haven- Walk to the Ferry from this 2 bedroom condo with pool. Located near the downtown area a desirable place for a rental property or live there year-round. The property features common grounds, picnic tables, and seating by the pool to relax and enjoy the outdoors.

    Lisa Lucier Anchor Realty of MV

    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568
  • 41 Cook Rd, Vineyard Haven, MA 02568
    41 Cook Rd, Vineyard Haven, MA 02568
    41 Cook Rd, Vineyard Haven, MA 02568
    /26

    $1,285,000

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,347 Sq Ft

    41 Cook Rd, Vineyard Haven, MA 02568

    Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An

    Jennifer O'hanlon Compass

    41 Cook Rd, Vineyard Haven, MA 02568
  • 5 Paula Ave, Vineyard Haven, MA 02568
    5 Paula Ave, Vineyard Haven, MA 02568
    5 Paula Ave, Vineyard Haven, MA 02568
    /33

    $1,400,000

    • 5 Beds
    • 2.5 Baths
    • 2,083 Sq Ft

    5 Paula Ave, Vineyard Haven, MA 02568

    Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert's Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert's Cove Beach, this well-positioned property offers the perfect blend of convenience, privacy, and potential. Spanning three levels, this five-bedroom,

    Emma Bryant Studio Realty

    5 Paula Ave, Vineyard Haven, MA 02568
  • 74 Chase Ln, Vineyard Haven, MA 02568
    74 Chase Ln, Vineyard Haven, MA 02568
    74 Chase Ln, Vineyard Haven, MA 02568
    /42

    $905,000

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    74 Chase Ln, Vineyard Haven, MA 02568

    Great Location Cape Cod style year round furnished home well maintained on a private dead end road close to Tashmoo Landing. New roof 2025, new windows, basement insulation replaced. A solid well built home ready for new owners to enjoy! Open concept kitchen to dining room. Three bedrooms and one full one half bath. Additional living area with full clean dry basement adds 768 SF with egress

    Janna O'Loughlin Portfolio Properties

    74 Chase Ln, Vineyard Haven, MA 02568
  • 4 Lagoon Pond Rd, Vineyard Haven, MA 02568
    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /9

    $1,395,000

    $600K PRICE DROP
    • 0.5 Baths
    • 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
  • 27 Spring St, Vineyard Haven, MA 02568
    27 Spring St, Vineyard Haven, MA 02568
    27 Spring St, Vineyard Haven, MA 02568
    /58

    $2,895,000

    • 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 a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five

    Alexis Holden Tea Lane Associates

    27 Spring St, Vineyard Haven, MA 02568
  • 125 Mayflower Ln, Vineyard Haven, MA 02568
    125 Mayflower Ln, Vineyard Haven, MA 02568
    125 Mayflower Ln, Vineyard Haven, MA 02568
    /42

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,056 Sq Ft

    125 Mayflower Ln, Vineyard Haven, MA 02568

    Nestled on an acre of beautifully landscaped grounds in a tranquil, park-like setting, this home is tucked away on a quiet lane within an established neighborhood. Located just a quarter mile from miles of Land Bank walking trails and less than two miles from Main Street, it offers the perfect opportunity to embrace the Vineyard lifestyle, just minutes from the vibrant center of Vineyard Haven.

    Courtney Marek Sandpiper Realty, Inc.

    125 Mayflower Ln, Vineyard Haven, MA 02568
  • 52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
    /5

    $639,000

    • Land
    • 12,998 Sq Ft
    • $2,141,421 per Acre

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process.Conveniently located just

    Tina Miller Donnelly + Co

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
  • 20 Sunnyside Ave, Vineyard Haven, MA 02568
    20 Sunnyside Ave, Vineyard Haven, MA 02568
    20 Sunnyside Ave, Vineyard Haven, MA 02568
    /38

    $5,995,000

    • 3 Beds
    • 3 Baths
    • 2,280 Sq Ft

    20 Sunnyside Ave, Vineyard Haven, MA 02568

    Waterfront Estate with Deep-Water Dock & Private Beach.Experience an exceptional Martha’s Vineyard waterfront lifestyle at this rare Lagoon Pond offering, ideally located just minutes from Vineyard Haven’s vibrant harbor, restaurants and shops. The property features a private deep-water dock—ideal for the avid boater—along with its own sandy beach for effortless access to the

    Peyton Wallace Studio Realty

    20 Sunnyside Ave, Vineyard Haven, MA 02568
  • 7 Fawndale Rd, Vineyard Haven, MA 02568
    7 Fawndale Rd, Vineyard Haven, MA 02568
    7 Fawndale Rd, Vineyard Haven, MA 02568
    /37

    $1,150,000

    • 4 Beds
    • 3 Baths
    • 1,924 Sq Ft

    7 Fawndale Rd, Vineyard Haven, MA 02568

    Welcome to 7 Fawndale Road in Vineyard Haven. Located just 1 mile from Main St., this delightful property offers comfortable living and flexible spaces. The main level features offers single-story living featuring an open living and dining area with wood beams, a bay window, partial cathedral ceiling, skylight, and wood floors. The galley-style kitchen offers plenty of cabinetry and counter

    Michele Moore Island Real Estate

    7 Fawndale Rd, Vineyard Haven, MA 02568
  • 528 Main St, Vineyard Haven, MA 02568
    528 Main St, Vineyard Haven, MA 02568
    528 Main St, Vineyard Haven, MA 02568
    /31

    $1,600,000

    $200K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,670 Sq Ft

    528 Main St, Vineyard Haven, MA 02568

    Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    528 Main St, Vineyard Haven, MA 02568
  • 0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    /7

    $2,000,000

    • Land
    • 21,801 Sq Ft
    • $3,996,004 per Acre

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568

    1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business.Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

    Peter Cronig Cronigs Real Estate

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
  • 0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568
    0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568
    0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568
    /4

    $1,800,000

    • Land
    • 1.1 Acres
    • $1,635,026 per Acre

    0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568

    This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and heavily wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful

    Gerrett Conover Landvest MV

    0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568
  • 398 Main St, Vineyard Haven, MA 02568
    398 Main St, Vineyard Haven, MA 02568
    398 Main St, Vineyard Haven, MA 02568
    /48

    $2,000,000

    • 4 Beds
    • 6 Baths
    • 2,972 Sq Ft

    398 Main St, Vineyard Haven, MA 02568

    Ideally situated on Main Street in Vineyard Haven, just moments from the Yacht Club and West Chop, this charming four-bedroom, six-bathroom home offers the perfect blend of convenience, comfort, and Island living.Set on a quarter-acre lot, the property features a private and inviting backyard—ideal for entertaining, gardening, or simply enjoying warm summer evenings. Inside, generous

    Peter Cronig Cronigs Real Estate

    398 Main St, Vineyard Haven, MA 02568
  • 52 Heath Hen Ln, Vineyard Haven, MA 02568
    52 Heath Hen Ln, Vineyard Haven, MA 02568
    52 Heath Hen Ln, Vineyard Haven, MA 02568
    /3

    $639,000

    • Land
    • 13,068 Sq Ft
    • $2,130,000 per Acre

    52 Heath Hen Ln, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot sunny lot is ready for your Vineyard home. The property comes with a complete six bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process.Conveniently located just

    Tina Miller Donnelly + Co.

    52 Heath Hen Ln, Vineyard Haven, MA 02568
  • 18 Sylvan Ave, Vineyard Haven, MA 02568
    18 Sylvan Ave, Vineyard Haven, MA 02568
    18 Sylvan Ave, Vineyard Haven, MA 02568
    /30

    $2,095,000

    • 4 Beds
    • 4 Baths
    • 2,876 Sq Ft

    18 Sylvan Ave, Vineyard Haven, MA 02568

    COMING SOON! Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound deck overlooking the natural landscape. It truly feels like its own private enclave, both inside and

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    18 Sylvan Ave, Vineyard Haven, MA 02568
  • 41 Renear St, Vineyard Haven, MA 02568
    41 Renear St, Vineyard Haven, MA 02568
    41 Renear St, Vineyard Haven, MA 02568
    /54

    $1,150,000

    • 3 Beds
    • 1.5 Baths
    • 1,284 Sq Ft

    41 Renear St, Vineyard Haven, MA 02568

    Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure — a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together.Set on a generous .26-acre R10 parcel, this three-bedroom home offers the warmth and craftsmanship of an

    Leslie C. Floyd Portfolio Properties

    41 Renear St, Vineyard Haven, MA 02568
  • 299 Daggett Ave Unit A, Vineyard Haven, MA 02568
    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
    /16

    $1,095,000

    $154K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568

    This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

    Karen Overtoom Karen M. Overtoom R.E.

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
  • 268 Tashmoo Ave, Vineyard Haven, MA 02568
    268 Tashmoo Ave, Vineyard Haven, MA 02568
    268 Tashmoo Ave, Vineyard Haven, MA 02568
    /28

    $2,290,000

    $205K PRICE DROP
    • 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
  • 22 Old Lighthouse Rd, Vineyard Haven, MA 02568
    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
    /25

    $1,595,000

    $55K PRICE DROP
    • 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 International Realty

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
  • 110 Clover Hill Dr, Vineyard Haven, MA 02568
    110 Clover Hill Dr, Vineyard Haven, MA 02568
    110 Clover Hill Dr, Vineyard Haven, MA 02568
    /31

    $1,495,000

    $80K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 3,072 Sq Ft

    110 Clover Hill Dr, Vineyard Haven, MA 02568

    Minutes to downtown and the ferry, this updated year-round home checks every box buyers are asking for right now: space, flexibility, and a move-in ready setup in a highly convenient location. 3 bedrooms, 4 bathrooms, and over 3,000 sq ft of living space, including a private lower-level apartment ideal for guests, extended family, or income potential. The main level offers hardwood floors, a

    Jim Feiner Feiner Real Estate

    110 Clover Hill Dr, Vineyard Haven, MA 02568
  • 70 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
    70 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
    70 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
    /22

    $1,429,900

    • 4 Beds
    • 4 Baths
    • 2,552 Sq Ft

    70 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568

    Classic Vineyard Charm Meets Effortless Island Living! Brimming w/original character and timeless appeal, this delightful 3-bedroom, 3-bath home w/1BR, 1BA ADU offers a perfect blend of historic charm + thoughtful updates in one of Martha’s Vineyard’s most sought-after communities. Original hardwood floors flow throughout, setting a warm + inviting tone, while lovingly preserved original details

    Liz Carlson CB Realty

    70 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
  • 237 Lagoon Pond Rd, Vineyard Haven, MA 02568
    237 Lagoon Pond Rd, Vineyard Haven, MA 02568
    237 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /22

    $1,999,500

    $251K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,867 Sq Ft

    237 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area.Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water

    Alison Rich Carroll & Vincent R.E.

    237 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • 36 Circuit Ave, Vineyard Haven, MA 02568
    36 Circuit Ave, Vineyard Haven, MA 02568
    36 Circuit Ave, Vineyard Haven, MA 02568
    /17

    $899,000

    $96K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,264 Sq Ft

    36 Circuit Ave, Vineyard Haven, MA 02568

    This cared for contemporary is located in a mature neighborhood abutting Sheriff's Meadow. It has a three bedroom, one bath reverse floor-plan design that captures ample natural light from a serene park-like setting. Hardwoods and ceramic tile flooring, A/C mini-split heat-pumps, a rear balcony deck, outdoor shower, and a delightful terraced patio compliment this new opportunity. *Seller is

    Sean Federowicz Landmarks at TODAY Real Estate

    36 Circuit Ave, Vineyard Haven, MA 02568
  • 70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    /75

    $3,200,000

    $600K PRICE DROP
    • 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
  • 61 Wood Chips Cir, Vineyard Haven, MA 02568
    61 Wood Chips Cir, Vineyard Haven, MA 02568
    61 Wood Chips Cir, Vineyard Haven, MA 02568
    /12

    $1,095,000

    $100K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 768 Sq Ft

    61 Wood Chips Cir, Vineyard Haven, MA 02568

    Set on a private, wooded lot in Vineyard Haven, this recently built home offers a rare combination of immediate enjoyment and exceptional future potential. Built in 2021, the thoughtfully designed 1-bedroom residence features a bright, modern interior, energy-efficient solar panels, and a peaceful setting surrounded by nature.The true value lies in the property’s remarkable expansion

    Andrew McElhinney Compass LLC

    61 Wood Chips Cir, Vineyard Haven, MA 02568
  • 0 Old Country Ln Unit 73571746, Vineyard Haven, MA 02568
    0 Old Country Ln Unit 73571746, Vineyard Haven, MA 02568
    0 Old Country Ln Unit 73571746, Vineyard Haven, MA 02568
    /4

    $450,000

    • Land
    • 20,473 Sq Ft
    • $957,447 per Acre

    0 Old Country Ln Unit 73571746, Vineyard Haven, MA 02568

    Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.

    Brenda Galligan Karen M. Overtoom R.E.

    0 Old Country Ln Unit 73571746, Vineyard Haven, MA 02568
  • 21 W Spring St, Vineyard Haven, MA 02568
    21 W Spring St, Vineyard Haven, MA 02568
    21 W Spring St, Vineyard Haven, MA 02568
    /34

    $1,450,000

    • 4 Beds
    • 3 Baths
    • 1,270 Sq Ft

    21 W Spring St, Vineyard Haven, MA 02568

    Charming Property in the Heart of Vineyard Haven. A rare opportunity to own a beautifully maintained main house and guest house nestled on a generous 25,100 square foot lot in Tisbury. This special offering combines charm, privacy and versatility, surrounded by a stunningly landscaped yard. The main house has three full bedrooms and two full bathrooms. The one-bedroom and one-bathroom guest house

    Casandra Hyland Sandpiper Realty, Inc.

    21 W Spring St, Vineyard Haven, MA 02568

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County

Real Estate & Homes for Sale in Vineyard Haven, Marthas Vineyard

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.
Learn more about living in Vineyard Haven

Vineyard Haven, Marthas Vineyard, MA Home Prices vs. Nearby Neighborhoods

Vineyard Haven Oak Bluffs West Tisbury
Median Home Price
$1,780,000
$1,539,000
$1,950,000
Median Sale Price
$1,400,000
+11% YoY
$1,275,000
-1% YoY
$1,500,000
-17% YoY
Avg. Price per Square Foot
$938
$985
$1,299
Median Single Family Price
$1,735,000
$1,600,000
$1,875,000
Median Condo Price
$1,175,000
$849,000
--
Total Active Listings
62 listings
93 listings
30 listings
Market Conditions
8 Months of Supply
Buyer's Market
6 Months of Supply
Buyer's Market
8 Months of Supply
Buyer's Market

Frequently Asked Questions

Is Vineyard Haven a good place to live?
Vineyard Haven is a good place to live. Vineyard Haven is considered car-dependent and somewhat bikeable with minimal transit options. Vineyard Haven has 2 parks for recreational activities.It is fairly sparse in population with 5.0 people per acre and a median age of 48. The average household income is $124,840 which is above the national average. College graduates make up 41.1% of residents. A majority of residents in Vineyard Haven are home owners, with 34% of residents renting and 66% of residents owning their home. A local real estate agent serving Vineyard Haven can help you decide if this neighborhood is the right one for you. Learn more on our Vineyard Haven neighborhood guide.
How much do you need to make to afford a house in Vineyard Haven?
The median home price in Vineyard Haven is $1,780,000. If you put a 20% down payment of $356,000 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $9,430 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $404K a year to afford the median home price in Vineyard Haven. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Vineyard Haven is $125K.
What are the best public schools in Vineyard Haven?
The best public schools that serve Vineyard Haven are:
What are the best private schools in Vineyard Haven?
The best private schools that serve Vineyard Haven are:
What are the most popular zip codes in Vineyard Haven, Marthas Vineyard, MA?
The most popular zip codes in Vineyard Haven, Marthas Vineyard, MA include 02568, 02575, 02536, 02539 and 02535.
What are the most popular neighborhoods near Vineyard Haven, Marthas Vineyard, MA?
The most popular neighborhoods near Vineyard Haven, Marthas Vineyard, MA are West Tisbury, Oak Bluffs, Edgartown, Woods Hole and Chilmark.
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group