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Vineyard Haven Homes for Sale

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  • 59 Hagerty Dr, Vineyard Haven, MA 02568
    59 Hagerty Dr, Vineyard Haven, MA 02568
    59 Hagerty Dr, Vineyard Haven, MA 02568
    /38

    $6,150,000

    • 6 Beds
    • 7 Baths
    • 5,034 Sq Ft

    59 Hagerty Dr, Vineyard Haven, MA 02568

    Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and

    Carol Shore Donnelly + Co

    59 Hagerty Dr, Vineyard Haven, MA 02568
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /21

    $1,895,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft

    Unlisted Address

    Rarely does such a unique, waterfront location become available. 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. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the

    Michele Moore Island Real Estate

    Unlisted Address
  • 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
  • 74 Chase Ln, Vineyard Haven, MA 02568
    74 Chase Ln, Vineyard Haven, MA 02568
    74 Chase Ln, Vineyard Haven, MA 02568
    /42

    $945,000

    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    74 Chase Ln, Vineyard Haven, MA 02568

    Great Location! Cape Cod style home on a private dead end road close to Tashmoo Landing.Open concept kitchen to dining room. Three bedrooms and one full, one half bath. Full basement adds additional 768 SF, with egress walkout door. Includes two lots. The house has two electric fired heat pumps for heating and cooling. Additional backup heat is forced hot water baseboard, and propane

    Janna O'Loughlin Portfolio Properties

    74 Chase Ln, 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
    /17

    $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 Martha's Vineyard

    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568
  • 36 Hines Point Rd, Vineyard Haven, MA 02568
    36 Hines Point Rd, Vineyard Haven, MA 02568
    36 Hines Point Rd, Vineyard Haven, MA 02568
    /40

    $3,100,000

    • 3 Beds
    • 1 Bath
    • 973 Sq Ft

    36 Hines Point Rd, Vineyard Haven, MA 02568

    HINES POINT WATERFRONT GEM with 85 feet of frontage on the Lagoon, offering ever-changing water views and the perfect vantage point to watch the Steamship Authority ferries arrive in Vineyard Haven Harbor. Enjoy the charming, timeless cottage with a one-car garage as an idyllic summer retreat, or bring your Vineyard vision to life with beautiful architectural plans by Sullivan +Associates

    Tina Miller Donnelly + Co.

    36 Hines Point 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
    /30

    $1,800,000

    • 4 Beds
    • 4 Baths
    • 2,334 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
  • 124 Main St, Vineyard Haven, MA 02568
    124 Main St, Vineyard Haven, MA 02568
    124 Main St, Vineyard Haven, MA 02568
    /46

    $2,695,000

    $255K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,374 Sq Ft

    124 Main St, Vineyard Haven, MA 02568

    Historic Water View Elegance Meets Modern Luxury in Vineyard Haven: Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    124 Main St, 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
  • 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 earlier

    Leslie C. Floyd Portfolio Properties

    41 Renear St, 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
    /16

    $995,000

    • 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
  • 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
  • 124 Skiff Ave Unit B-12, Vineyard Haven, MA 02568
    124 Skiff Ave Unit B-12, Vineyard Haven, MA 02568
    124 Skiff Ave Unit B-12, Vineyard Haven, MA 02568
    /24

    $429,000

    • 1 Bed
    • 1 Bath
    • 305 Sq Ft

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

    Welcome to Unit B-12 at the Causeway Condominiums, a turnkey studio offering comfortable, low-maintenance island living just a short walk to the charming village of Vineyard Haven. Thoughtfully designed to maximize space and functionality, this inviting residence features warm bamboo flooring throughout, a custom Murphy bed, and a beautifully crafted custom mahogany closet and storage system,

    Marilyn Moses Ocean Park Realty Inc

    124 Skiff Ave Unit B-12, 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
    /22

    $3,995,000

    $700K 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 access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for gathering and quiet retreat, with an effortless indoor-outdoor flow. Bedrooms are thoughtfully arranged in separate wings, with a

    Peyton Wallace Studio Realty LLC

    30 Water Gate Rd, Vineyard Haven, MA 02568
  • 29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /57

    $3,295,000

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

    29 & 33 Lagoon Pond Rd, Vineyard Haven, 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

    29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • 41 Edgartown Rd, Vineyard Haven, MA 02568
    41 Edgartown Rd, Vineyard Haven, MA 02568
    41 Edgartown Rd, Vineyard Haven, MA 02568
    /26

    $1,399,000

    • 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
  • 5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    /21

    $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 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
  • 41 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
    41 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
    41 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
    /27

    $1,399,000

    • 5 Beds
    • 2 Baths
    • 1,968 Sq Ft

    41 Edgartown Vineyard Haven 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

    41 Edgartown Vineyard Haven Rd, 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
  • 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
  • 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
  • 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
  • 135 Mayflower Ln, Vineyard Haven, MA 02568
    135 Mayflower Ln, Vineyard Haven, MA 02568
    135 Mayflower Ln, Vineyard Haven, MA 02568
    /34

    $1,995,000

    • 5 Beds
    • 3 Baths
    • 3,480 Sq Ft

    135 Mayflower Ln, Vineyard Haven, MA 02568

    Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for

    Kathleen Dawson Donnelly + Co.

    135 Mayflower Ln, 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
    /31

    $1,790,000

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

    41 & 0 Cook Rd, Vineyard Haven, MA 02568

    Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready to build on immediately or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or investment. An easement is being established along the existing driveway to

    Jennifer O'hanlon Compass

    41 & 0 Cook Rd, Vineyard Haven, 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
  • 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
  • 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
  • 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
    /39

    $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 multi-family property offers the perfect blend of privacy, flexibility, and convenience. Built in 2020, the home encompasses 2,884 square feet of thoughtfully designed living space, featuring a total of 5 bedrooms and 4 full bathrooms. The walkout lower level is a fully permitted Accessory Dwelling Unit (ADU), creating an ideal

    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
    /31

    $2,195,000

    $205K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,328 Sq Ft

    159 Lake St, Vineyard Haven, MA 02568

    Tucked back from scenic Lake Street, this distinctive home offers privacy and charm on a landscaped 0.7 acre lot with mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm, inviting feel. The four-level design provides flexibility and character. The main level features a spacious kitchen with a center island open to the dining area, and

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    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
  • 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
    /22

    $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
  • 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

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County

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
Median Home Price
$1,800,000
$1,605,000
$1,897,500
Median Sale Price
$1,470,000
+15% YoY
$1,297,500
+8% YoY
$1,550,000
-6% YoY
Median Single Family Price
$1,895,000
$1,745,000
$1,825,000
Median Condo Price
$1,100,000
$869,000
--
Total Active Listings
85 listings
89 listings
35 listings
Market Conditions
9 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 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 $1,800,000. If you put a 20% down payment of $360,000 and had a 30-year fixed mortgage with an interest rate of 6.67%, your estimated principal and interest payment would be $9,260 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $397K 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.
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