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Vineyard Haven Homes for Sale

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  • 398 Main St, Vineyard Haven, MA 02568
    398 Main St, Vineyard Haven, MA 02568
    398 Main St, Vineyard Haven, MA 02568
    /109

    $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 living

    Peter Cronig Cronigs Real Estate

    398 Main St, Vineyard Haven, MA 02568
  • 41 & 0 Cook St, Tisbury, MA 02568
    41 & 0 Cook St, Tisbury, MA 02568
    41 & 0 Cook St, Tisbury, MA 02568
    /28

    $1,790,000

    • 3 Beds
    • 2.5 Baths
    • 2,347 Sq Ft

    41 & 0 Cook St, Tisbury, MA 02568

    Enjoy the rare opportunity to own a beautifully maintained Vineyard Haven home together with an adjacent 16,000 sq. ft. buildable lot, totaling approximately .69 acres. Just moments from downtown, the ferry, shops, restaurants, and harbor, this offering combines convenience, privacy, and future potential.The updated home features 3 bedrooms, 2.5 bathrooms, wood floors throughout, central air, and

    Jennifer O'hanlon Compass

    41 & 0 Cook St, Tisbury, MA 02568
  • 96 Dunham Ave, Vineyard Haven, MA 02568
    96 Dunham Ave, Vineyard Haven, MA 02568
    96 Dunham Ave, Vineyard Haven, MA 02568
    /26

    $949,000

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    96 Dunham Ave, Vineyard Haven, MA 02568

    NESTLED ON AN OVERSIZED LOT in a highly convenient Vineyard Haven location, this classic 1972 center-entrance Colonial offers timeless charm and exceptional potential. Inside, an inviting open-concept living space is anchored by a wood-burning fireplace, while soaring vaulted ceilings over the dining area and kitchen create an airy, light-filled atmosphere ideal for gathering with family and

    Leslie C. Floyd Portfolio Properties

    96 Dunham 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

    $4,695,000

    • 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
  • 41 & 0 Cook Rd, Vineyard Haven, MA 02568
    41 & 0 Cook Rd, Vineyard Haven, MA 02568
    41 & 0 Cook Rd, Vineyard Haven, MA 02568
    /33

    $1,790,000

    • 3 Beds
    • 2.5 Baths
    • 2,347 Sq Ft

    41 & 0 Cook Rd, Vineyard Haven, MA 02568

    Experience the perfect blend of character, modern comfort, and future potential with this beautifully maintained Vineyard Haven property, offered together with an adjacent 16,000 square foot buildable lot. Encompassing approximately .69 acres in total, this unique offering provides immediate enjoyment along with the flexibility to create a family compound, construct a second home, or potentially

    Jennifer O'hanlon Compass LLC

    41 & 0 Cook Rd, Vineyard Haven, MA 02568
  • 41 Hagerty Dr, Vineyard Haven, MA 02568
    41 Hagerty Dr, Vineyard Haven, MA 02568
    41 Hagerty Dr, Vineyard Haven, MA 02568
    /79

    $5,950,000

    Open Sun 11AM - 12PM
    • 6 Beds
    • 6.5 Baths
    • 5,424 Sq Ft

    41 Hagerty Dr, Vineyard Haven, MA 02568

    Welcome to your Vineyard dream home in the highly sought-after West Chop neighborhood. This exceptional brand-new construction offers 6 bedrooms, 6 full baths, and 1 half bath, thoughtfully designed with timeless coastal elegance and modern luxury. Filled with natural light, the home’s bright and airy interior showcases impeccable craftsmanship, spacious living areas, and a gourmet chef’s kitchen

    Joe & Nicole Holland Vineyard Dream Realty LLC

    41 Hagerty Dr, 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 off

    Tina Miller Donnelly + Co

    52 Heath Hen Ln Unit 5, 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
  • 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

    $1,175,000

    $74K 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
  • 54 Amelias Crossing, Vineyard Haven, MA 02568
    54 Amelias Crossing, Vineyard Haven, MA 02568
    54 Amelias Crossing, Vineyard Haven, MA 02568
    /35

    $2,595,000

    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    54 Amelias Crossing, Vineyard Haven, MA 02568

    COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

    Agent Photo

    Wendy Harman

    Compass | Point B

    54 Amelias Crossing, 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

    $1,195,000

    • 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
  • 299 Daggett Ave, Vineyard Haven, MA 02568
    299 Daggett Ave, Vineyard Haven, MA 02568
    299 Daggett Ave, Vineyard Haven, MA 02568
    /21

    $1,175,000

    $74K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave, 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.

    Alyson Parker Karen M. Overtoom R.E.

    299 Daggett Ave, 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
  • 139 Main St, Vineyard Haven, MA 02568
    139 Main St, Vineyard Haven, MA 02568
    139 Main St, Vineyard Haven, MA 02568
    /75

    $3,750,000

    • 5 Beds
    • 6.5 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 Properties

    139 Main St, Vineyard Haven, MA 02568
  • 124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
    /28

    $550,000

    $49K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

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

    JUST COMPLETED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants. The beautifully maintained common grounds feature colorful landscaping, picnic

    Stephanie Roache Donnelly + Co.

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
  • 39 Ferro Way, Vineyard Haven, MA 02568
    39 Ferro Way, Vineyard Haven, MA 02568
    39 Ferro Way, Vineyard Haven, MA 02568
    /29

    $1,488,000

    • 5 Beds
    • 4 Baths
    • 2,884 Sq Ft

    39 Ferro Way, Vineyard Haven, MA 02568

    Tucked away on a quiet cul-de-sac, this beautifully maintained single-family home offers the perfect blend of privacy and convenience. Built in 2020, the property features 5 spacious bedrooms and 4 full bathrooms across 2,884 square feet of thoughtfully designed living space.Set on a generous 15,593 sq ft lot, the home provides ample outdoor space with exciting potential for a guest house,

    Emily Flake Viewpoints

    39 Ferro Way, Vineyard Haven, MA 02568
  • 159 Lake St, Vineyard Haven, MA 02568
    159 Lake St, Vineyard Haven, MA 02568
    159 Lake St, Vineyard Haven, MA 02568
    /36

    $2,400,000

    • 5 Beds
    • 4 Baths
    • 3,328 Sq Ft

    159 Lake St, Vineyard Haven, MA 02568

    Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a

    Alyssa Halisky Wallace & Co. Sotheby's

    159 Lake St, Vineyard Haven, MA 02568
  • Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
    /3

    $525,000

    • Land
    • 10,240 Sq Ft
    • $2,233,092 per Acre

    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568

    A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

    Katherine Donahue Sandpiper Realty

    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
  • Lot 1 Dolan Ave, Tisbury, MA 02568
    Lot 1 Dolan Ave, Tisbury, MA 02568
    Lot 1 Dolan Ave, Tisbury, MA 02568
    /3

    $525,000

    • Land
    • 10,454 Sq Ft
    • $2,187,500 per Acre

    Lot 1 Dolan Ave, Tisbury, MA 02568

    A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    Lot 1 Dolan Ave, Tisbury, MA 02568
  • 51 Summer St, Vineyard Haven, MA 02568
    51 Summer St, Vineyard Haven, MA 02568
    51 Summer St, Vineyard Haven, MA 02568
    /35

    $1,369,000

    $26K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,783 Sq Ft

    51 Summer St, Vineyard Haven, MA 02568

    Rare under-$1.4M value story in Vineyard Haven. In a Martha’s Vineyard price range where buyers are often choosing between smaller homes, dated interiors, limited bath count, or properties needing immediate improvements, 51 Summer Street offers a cleaner path. This updated 4-bedroom, 2.5-bath home features 1,783 square feet of well-planned living space in a convenient Vineyard Haven setting near

    Janet Scott eXp Realty

    51 Summer 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
  • 237 Lagoon Pond Rd, Vineyard Haven, MA 02568
    237 Lagoon Pond Rd, Vineyard Haven, MA 02568
    237 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /21

    $2,150,000

    $100K 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
  • 261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    /34

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 1,682 Sq Ft

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach

    Jennifer O'hanlon Compass LLC

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
  • 119 N William St, Vineyard Haven, MA 02568
    119 N William St, Vineyard Haven, MA 02568
    119 N William St, Vineyard Haven, MA 02568
    /28

    $950,000

    • 3 Beds
    • 1.5 Baths
    • 1,395 Sq Ft

    119 N William St, Vineyard Haven, MA 02568

    A rare opportunity to own a historic Martha’s Vineyard home just moments from town. Originally built in 1900, this charming 3-bedroom, 1.5 bath home in Vineyard Haven offers 1,395 sq ft of living space on a 0.20-acre lot, blending classic island character with an unbeatable location! Enjoy the ease of walk-to-town living in Vineyard Haven, with nearby access to shops, restaurants, the harbor and

    Kelly Mercier The Agency

    119 N William St, 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
    /32

    $1,625,000

    • 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, perfect

    Alyssa Halisky Wallace & Co. Sotheby's

    26 Union St Unit 7, Tisbury, MA 02568
  • 94 Weaver Ln, Vineyard Haven, MA 02568
    94 Weaver Ln, Vineyard Haven, MA 02568
    94 Weaver Ln, Vineyard Haven, MA 02568
    /37

    $3,999,999

    $500K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,715 Sq Ft

    94 Weaver Ln, Vineyard Haven, MA 02568

    Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

    Emma Kennedy Sandpiper Realty, Inc.

    94 Weaver Ln, 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
    /36

    $4,300,000

    $395K 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
  • 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

    $1,575,000

    • 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
  • 21 Davis St, Vineyard Haven, MA 02568
    21 Davis St, Vineyard Haven, MA 02568
    21 Davis St, Vineyard Haven, MA 02568
    /35

    $2,825,000

    $100K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,704 Sq Ft

    21 Davis St, Vineyard Haven, MA 02568

    Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the

    Valene Pires The Agency

    21 Davis St, Vineyard Haven, MA 02568
  • 81 Leland Ave, Vineyard Haven, MA 02568
    81 Leland Ave, Vineyard Haven, MA 02568
    81 Leland Ave, Vineyard Haven, MA 02568
    /47

    $1,975,000

    • 3 Beds
    • 2.5 Baths
    • 1,902 Sq Ft

    81 Leland Ave, Vineyard Haven, MA 02568

    Close to town with exceptional indoor / outdoor flow & privacy.Consider this beautifully designed home just minutes from town. The first floor features a bright, open kitchen + dining area flowing into a welcoming living room with a fireplace. From there, step onto a spacious deck—ideal for al fresco dining and lounging—complete with direct access to a hot tub and nearby outdoor

    Jill Napior Tea Lane Associates

    81 Leland Ave, Vineyard Haven, MA 02568
  • 5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    /24

    $1,999,000

    • 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 into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • 15 Goah Way, Vineyard Haven, MA 02568
    15 Goah Way, Vineyard Haven, MA 02568
    15 Goah Way, Vineyard Haven, MA 02568
    /10

    $1,100,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,581 Sq Ft

    15 Goah Way, Vineyard Haven, MA 02568

    2 bedroom 2 bath cottage with 1 bedroom 1 bath ADU. Large 15,950 square foot lot, short distance to school and town. Second floor bedroom space is large and possibly convertable to 2 bedrooms. New windows and 2 mini split systems, ADU also has a mini split unit. ADU is beleived to have been built in 2017. Property is loacted in Tashmoo watershed district and will require an upgrade to an nitrogen

    Roy Cutrer Jr Laer Realty Partners

    15 Goah Way, Vineyard Haven, MA 02568
  • 16 Frog Hollow, Vineyard Haven, MA 02568
    16 Frog Hollow, Vineyard Haven, MA 02568
    16 Frog Hollow, Vineyard Haven, MA 02568
    /25

    $4,695,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    16 Frog Hollow, Vineyard Haven, MA 02568

    Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage.Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water

    Rose Ryley Wallace & Co. Sotheby's International Realty

    16 Frog Hollow, Vineyard Haven, 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 Williams Realty

    116 Franklin Terrace, 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

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 1,738 Sq Ft

    22 Oklahoma Ave, Vineyard Haven, MA 02568

    3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 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 your mortgage. The main house features a stunning solarium or sunroom, a cheerful

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

    22 Oklahoma Ave, 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
    /9

    $1,495,000

    • 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
    /12

    $1,495,000

    • 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

    Stephanie Burke Portfolio Properties

    33 Alyssa Ln, 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
    /26

    $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
  • 124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    /16

    $565,000

    $90K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

    MOVE RIGHT IN! Just in time to ENJOY FOR THE SUMMER! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island.

    Rene Jackson Island Real Estate

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
  • 187 Lagoon Pond Rd, Vineyard Haven, MA 02568
    187 Lagoon Pond Rd, Vineyard Haven, MA 02568
    187 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /27

    $2,695,000

    $130K PRICE DROP
    • 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

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County Marthas Vineyard Vineyard Haven

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

Learn more about living in Vineyard Haven

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

Vineyard Haven Oak Bluffs West Tisbury Jamestown Village
Median Home Price
$1,750,000
$1,587,000
$1,912,500
$1,750,000
Median Sale Price
$1,390,000
+10% YoY
$1,350,000
+17% YoY
$1,737,500
+6% YoY
$1,400,000
+1% YoY
Median Single Family Price
$1,735,000
$1,530,000
$1,825,000
$1,775,000
Median Condo Price
$1,150,000
$912,000
--
$1,000,000
Total Active Listings
64
73
30
9
Market Conditions
7 Months of Supply
Buyer's Market
5 Months of Supply
Balanced Market
6 Months of Supply
Buyer's Market
4 Months of Supply
Balanced 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 is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. 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.
Is Vineyard Haven, MA a safe neighborhood?
Vineyard Haven, MA is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
How much do you need to make to afford a house in Vineyard Haven?
The median home price in Vineyard Haven is $1,750,000. If you put a 20% down payment of $350,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $8,820 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $378K 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 02543.
What are the most popular neighborhoods near Vineyard Haven, Marthas Vineyard, MA?
The most popular neighborhoods near Vineyard Haven, Marthas Vineyard, MA are Oak Bluffs, West Tisbury, Edgartown, Woods Hole and Chilmark.
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