52

Vineyard Haven Homes for Sale

Section Image Section Image
  • 22 Oklahoma Ave, Vineyard Haven, MA 02568
    22 Oklahoma Ave, Vineyard Haven, MA 02568
    22 Oklahoma Ave, Vineyard Haven, MA 02568
    /26

    $1,445,000

    • 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

    22 Oklahoma Ave, Vineyard Haven, MA 02568
  • 169 Clover Hill Dr, Vineyard Haven, MA 02568
    169 Clover Hill Dr, Vineyard Haven, MA 02568
    169 Clover Hill Dr, Vineyard Haven, MA 02568
    /42

    $1,350,000

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft

    169 Clover Hill Dr, Vineyard Haven, MA 02568

    Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home sits on a generous 0.86-acre lot less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal--close to restaurants, shopping, and the ferry, yet with enough land to accommodate the existing detached two-car garage and the potential for an Accessory Dwelling Unit. The three-bedroom home offers a

    Stephanie Roache Donnelly + Co.

    169 Clover Hill Dr, Vineyard Haven, MA 02568
  • 185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    /46

    $1,299,000

    • 3 Beds
    • 3 Baths
    • 1,750 Sq Ft

    185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    Experience sun-drenched living in one of Tashmoo Woods’ most desirable floor plans. This beautifully maintained 3-bedroom, 3-bath home offers full access to the coveted Tashmoo Woods amenities, including a pristine pool and pool house, multiple tennis courts, a children’s play area, a private launch on Lake Tashmoo, and a beautiful Association beach on the Sound. Inside, soaring ceilings and

    Candy DaRosa Feiner Real Estate

    185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
  • 344 Greenwood Ave, Vineyard Haven, MA 02568
    344 Greenwood Ave, Vineyard Haven, MA 02568
    344 Greenwood Ave, Vineyard Haven, MA 02568
    /20

    $1,300,000

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft

    344 Greenwood Ave, Vineyard Haven, MA 02568

    This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles

    Katie Donahue Sandpiper Realty

    344 Greenwood Ave, Vineyard Haven, MA 02568
  • 22 Clark Ave, Vineyard Haven, MA 02568
    22 Clark Ave, Vineyard Haven, MA 02568
    22 Clark Ave, Vineyard Haven, MA 02568
    /30

    $985,000

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    22 Clark Ave, Vineyard Haven, MA 02568

    A Sweet Spot to call Home. West Chop charms are many in this delightful setting. Acres upon acres of nearby conservation trails make walks, hikes and bike rides an easy daily appeal. Equal distance to Owen Little Way town beach and Vineyard Haven Main Street shops and amenities as well as harbor and ferry port. This move-in ready Clark Avenue abode offers the magic formula of single level living

    Helena Kirschenbaum Studio Realty

    22 Clark 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
    /12

    $1,495,000

    • 3 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 3/4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space. with half bath. Open kitchen, dining & entertainment area. Large side deck. 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 bedroom with cathedral

    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

    • 3 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 3/4 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 Real Estate, Inc.

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • 51 Lantern Ln, Vineyard Haven, MA 02568
    51 Lantern Ln, Vineyard Haven, MA 02568
    51 Lantern Ln, Vineyard Haven, MA 02568
    /14

    $835,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    51 Lantern Ln, Vineyard Haven, MA 02568

    Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

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

    51 Lantern Ln, Vineyard Haven, MA 02568
  • 151 Tashmoo Ave, Vineyard Haven, MA 02568
    151 Tashmoo Ave, Vineyard Haven, MA 02568
    151 Tashmoo Ave, Vineyard Haven, MA 02568
    /28

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 2,690 Sq Ft

    151 Tashmoo Ave, Vineyard Haven, MA 02568

    The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to

    Brenda Galligan Karen M. Overtoom R.E.

    151 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
    /26

    $1,595,000

    • 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

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
  • 28 Pine Tree Ln, Vineyard Haven, MA 02568
    28 Pine Tree Ln, Vineyard Haven, MA 02568
    28 Pine Tree Ln, Vineyard Haven, MA 02568
    /61

    $2,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    28 Pine Tree Ln, Vineyard Haven, MA 02568

    Enjoy beach-close living—just 0.2 miles to the shore—in sought-after West Chop. This welcoming 5BR/3.5BA colonial blends classic Vineyard character with modern comforts, including central air, an updated kitchen, and three fireplaces. Approximately 3,152± sq ft (expanded from 2,632± with a 520± sq ft finished space over the garage) offers flexible, easy flow to a large fenced backyard with a

    Lisa Da Silva Compass | Point B

    28 Pine Tree Ln, Vineyard Haven, MA 02568
  • 27 Chapde Ln, Tisbury, MA 02568
    27 Chapde Ln, Tisbury, MA 02568
    27 Chapde Ln, Tisbury, MA 02568
    /27

    $1,615,000

    • 3 Beds
    • 2.5 Baths
    • 1,740 Sq Ft

    27 Chapde Ln, Tisbury, MA 02568

    Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that

    Agent Photo

    Wendy Harman

    Compass

    (774) 515-4591

    27 Chapde Ln, Tisbury, 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
    /15

    $625,000

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

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

    MOVE RIGHT IN! 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. At the bottom of the hill you will find

    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
    /28

    $2,825,000

    • 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
  • 159 Lake St, Vineyard Haven, MA 02568
    159 Lake St, Vineyard Haven, MA 02568
    159 Lake St, Vineyard Haven, MA 02568
    /36

    $2,595,000

    • 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
  • 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /42

    $2,150,000

    • 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
  • 63 Crowell Ln, Vineyard Haven, MA 02568
    63 Crowell Ln, Vineyard Haven, MA 02568
    63 Crowell Ln, Vineyard Haven, MA 02568
    /39

    $2,650,000

    • 6 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    63 Crowell Ln, Vineyard Haven, MA 02568

    Extraordinary West Chop Opportunity - Two Homes on 1.80 Acres in Vineyard Haven Nestled next to the desirable West Chop/Mink Meadows neighborhoods, this unique property features two dwellings, making it a perfect opportunity for multi-generational living, guest accommodations, or rental potential.The welcoming, farm-style front porch on the main house looks out onto a large yard. Inside, the

    Heather Dyas-Fried Tea Lane Associates

    63 Crowell Ln, Vineyard Haven, MA 02568
  • 34 Davis St, Tisbury, MA 02568
    34 Davis St, Tisbury, MA 02568
    34 Davis St, Tisbury, MA 02568
    /26

    $2,195,000

    • 3 Beds
    • 3.5 Baths
    • 2,453 Sq Ft

    34 Davis St, Tisbury, MA 02568

    NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island's harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

    Andrew McElhinney Compass Massachusetts, LLC

    34 Davis St, Tisbury, MA 02568
  • 825 Main St, Vineyard Haven, MA 02568
    825 Main St, Vineyard Haven, MA 02568
    825 Main St, Vineyard Haven, MA 02568
    /74

    $14,500,000

    • 6 Beds
    • 5 Baths
    • 4,964 Sq Ft

    825 Main St, Vineyard Haven, MA 02568

    Set on 1.75 acres this waterfront home features 200+/- feet of sandy beach on the outer harbor in the community of West Chop. Upon entering the home, the stunning view of the outer harbor and Nantucket Sound is breathtakingly beautiful. Perfect for hosting large parties or intimate family gatherings the spacious living room spills onto the large deck through two sets of French doors. Gleaming

    Judy Federowicz Landmarks at TODAY Real Estate

    825 Main St, Vineyard Haven, MA 02568
  • 0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
    /10

    $619,000

    • Land
    • 0.61 Acre
    • $1,014,754 per Acre

    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568

    Vacant Land - NO LIMIT on bedroom count! You just have to meet setbacks. Once you build your dream home, you will able to explore nature just steps away. Nearby there are two Lagoon access points for kayaking and swimming, as well as walking trails within the Martha's Vineyard Land Bank and Sheriff's Meadow properties. Enjoy the peace of a rural setting, yet remain conveniently close to the ferry

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

    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
  • 268 Tashmoo Ave, Vineyard Haven, MA 02568
    268 Tashmoo Ave, Vineyard Haven, MA 02568
    268 Tashmoo Ave, Vineyard Haven, MA 02568
    /28

    $2,495,000

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    268 Tashmoo Ave, Vineyard Haven, MA 02568

    Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

    Michele Casavant Vineyard Village Realty

    268 Tashmoo Ave, Vineyard Haven, MA 02568
  • 00 Bernard Cir Unit 10, Tisbury, MA 02568
    00 Bernard Cir Unit 10, Tisbury, MA 02568
    00 Bernard Cir Unit 10, Tisbury, MA 02568
    /4

    $600,000

    • Land
    • 0.23 Acre
    • $2,614,379 per Acre

    00 Bernard Cir Unit 10, Tisbury, MA 02568

    Rare opportunity to build your dream home in a quiet, well-established Vineyard Haven neighborhood. This level parcel offers excellent potential with flexible zoning that allows for as many bedrooms as will fit within the allowable footprint, governed by 20-foot front and rear setbacks and 10-foot sides. Not located in the watershed district, the property does not require an enhanced septic

    Patrick McCarthy Grace Hagerty Real Estate Inc

    00 Bernard Cir Unit 10, Tisbury, 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

    $1,999,999

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

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for

    Kristin Francoeur Gibson Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • 128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    /38

    $1,575,000

    • 5 Beds
    • 3.5 Baths
    • 2,436 Sq Ft

    128 W Spring St, Vineyard Haven, MA 02568

    128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

    David Dickinson Compass

    128 W 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
    /53

    $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 Floyd Portfolio Properties

    139 Main St, Vineyard Haven, MA 02568
  • 128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    /42

    $2,375,000

    • 6 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    128 W Spring St, Vineyard Haven, MA 02568

    A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

    David Dickinson Compass

    128 W Spring St, Vineyard Haven, MA 02568
  • 128 & 136 Spring St, Vineyard Haven, MA 02568
    128 & 136 Spring St, Vineyard Haven, MA 02568
    128 & 136 Spring St, Vineyard Haven, MA 02568
    /47

    $2,375,000

    • 6 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    128 & 136 Spring St, Vineyard Haven, MA 02568

    A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

    David Dickinson Compass | Point B

    128 & 136 Spring St, Vineyard Haven, MA 02568
  • 124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    /8

    $725,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

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

    Enjoy effortless year-round living with easy access to Vineyard Haven's downtown shops, restaurants, the harbor, ferry, and nearby beaches. Bright and inviting first-floor three-bedroom, two-bath condo in the sought-after Causeway Harborview association. The association offers practical amenities--including a shared pool, ample storage, and on-site laundry--that support a comfortable lifestyle in

    Emma Kennedy Sandpiper Realty Inc

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
  • 71 Stoney Hill Rd, Vineyard Haven, MA 02568
    71 Stoney Hill Rd, Vineyard Haven, MA 02568
    71 Stoney Hill Rd, Vineyard Haven, MA 02568
    /29

    $4,500,000

    • 5 Beds
    • 6 Baths
    • 5,598 Sq Ft

    71 Stoney Hill Rd, Vineyard Haven, MA 02568

    A combination of luxury, comfort, and natural beauty, this expansive custom, 6,000+ square foot, five bedroom, post and beam home is sited on more than seven acres of land, surrounded by more than 200 acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow

    Sheila Morse Island Real Estate

    71 Stoney Hill Rd, Vineyard Haven, MA 02568
  • 180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
    180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
    180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
    /73

    $6,495,000

    • 7 Beds
    • 5.5 Baths
    • 4,730 Sq Ft

    180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568

    A storybook sanctuary in Pilot Hill. For the first time in 37 years, one of the rarest and most beautiful properties within Pilot Hill Farm is being offered for sale.Set on nearly eight acres, this unique estate includes a thoughtfully renovated antique farmhouse and several distinctive outbuildings: a pool, guest house, an art studio, and a carriage house with room for three cars, plus a

    Alexis Holden Tea Lane Associates

    180 Pilot Hill Farm Rd, 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
    /35

    $12,500,000

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

    33 Goethals Way, Vineyard Haven, MA 02568

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

    Lynn Buder Sandpiper Realty Inc

    33 Goethals Way, Vineyard Haven, MA 02568
  • 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
    /21

    $599,000

    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

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

    Newly priced ~ fully renovated building and move-in ready! Outstanding, year-round, two-bedroom condo on the ground level with dedicated parking, and conveniently located close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. This building (Building A) is undergoing a complete renovation including a new roof, siding, windows and doors, trim, decks and steps. Enjoy this freshly

    Stephanie Roache Donnelly + Co.

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
  • 735 Franklin St, Vineyard Haven, MA 02568
    735 Franklin St, Vineyard Haven, MA 02568
    735 Franklin St, Vineyard Haven, MA 02568
    /41

    $2,950,000

    • 5 Beds
    • 4 Baths
    • 3,361 Sq Ft

    735 Franklin St, Vineyard Haven, MA 02568

    Welcome to this stunning 4-bedroom, 3-bathroom primary residence along with a 1-bedroom studio apartment over the one-car garage, ideally located in West Chop! Together, they include approximately 3,871 square feet of beautifully renovated living space (an additional 510 sqft of living space on the 3rd floor in the main house is not included on the town assessment). Situated on a .99-acre lot,

    Emily Flake Viewpoints

    735 Franklin St, Vineyard Haven, MA 02568
  • 21 Woodlawn Ave, Vineyard Haven, MA 02568
    21 Woodlawn Ave, Vineyard Haven, MA 02568
    21 Woodlawn Ave, Vineyard Haven, MA 02568
    /39

    $2,495,000

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

    21 Woodlawn Ave, Vineyard Haven, MA 02568

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

    Beth Welch Viewpoints

    21 Woodlawn Ave, Vineyard Haven, MA 02568
  • 129 Beach Rd, Tisbury, MA 02568
    129 Beach Rd, Tisbury, MA 02568
    129 Beach Rd, Tisbury, MA 02568
    /135

    $1,895,000

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

    129 Beach Rd, Tisbury, MA 02568

    Unique, waterfront property with amazing, 180 degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Sellers have been actively making improvements to increase the commercial usage. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2

    Michele Moore Island Real Estate

    129 Beach Rd, Tisbury, MA 02568
  • 41 Crowell Ln, Tisbury, MA 02568
    41 Crowell Ln, Tisbury, MA 02568
    41 Crowell Ln, Tisbury, MA 02568
    /58

    $4,900,000

    • 5 Beds
    • 5 Baths
    • 4,185 Sq Ft

    41 Crowell Ln, Tisbury, MA 02568

    The wait is over, move right into your West Chop dream home! Located in the picturesque landscape of West Chop, this luxurious new development by Novo Builds offers an exquisite blend of modern design and coastal charm. Known for their innovative designs and high-quality craftsmanship, Novo Builds is transforming this iconic island with their latest project, providing an ideal sanctuary for

    Joe & Nicole Holland Vineyard Dream Realty LLC

    41 Crowell Ln, Tisbury, MA 02568
  • 12 Park Ave, Vineyard Haven, MA 02568
    12 Park Ave, Vineyard Haven, MA 02568
    12 Park Ave, Vineyard Haven, MA 02568
    /18

    $1,045,000

    • 3 Beds
    • 2 Baths
    • 1,469 Sq Ft

    12 Park Ave, Vineyard Haven, MA 02568

    Welcome to this delightful Cape-style home offering easy access to Vineyard Haven shopping and the Island's bike paths. Nestled on just under an acre of land, this inviting residence features three spacious bedrooms and two full bathrooms, providing ample space for year-round living or weekend getaways. Inside, you'll find a warm and welcoming open concept, perfect for both relaxing and

    Sheila Morse Island Real Estate

    12 Park Ave, Vineyard Haven, MA 02568
  • 113 Leonard Cir, Vineyard Haven, MA 02568
    113 Leonard Cir, Vineyard Haven, MA 02568
    113 Leonard Cir, Vineyard Haven, MA 02568
    /23

    $1,099,000

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

    113 Leonard Cir, Vineyard Haven, MA 02568

    This charming four-bedroom Cape features an updated, open-concept design seamlessly connecting the living, kitchen, and dining areas. The first floor includes a bright, well-lit bedroom and an updated shared bathroom. Upstairs, the three additional bedrooms boast soaring cathedral ceilings that maximize natural light, creating a bright and cheerful atmosphere. A shared bath with a shower and

    Alyson Parker Karen M. Overtoom R.E.

    113 Leonard Cir, Vineyard Haven, MA 02568
  • 50 Lantern Ln, Vineyard Haven, MA 02568
    50 Lantern Ln, Vineyard Haven, MA 02568
    50 Lantern Ln, Vineyard Haven, MA 02568
    /16

    $1,193,000

    • 3 Beds
    • 1.5 Baths
    • 1,040 Sq Ft

    50 Lantern Ln, Vineyard Haven, MA 02568

    *NOTE: The seller is offering a $25,000 credit towards the required septic upgrade. Nestled in a quiet enclave on Lantern Lane, this charming 3-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and island charm. Located just moments from the heart of Vineyard Haven, you'll enjoy easy access to shops, restaurants, and the ferry. The interior of the home features a bright and

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    50 Lantern Ln, Vineyard Haven, MA 02568
  • 9 Hagerty Dr, Tisbury, MA 02568
    9 Hagerty Dr, Tisbury, MA 02568
    9 Hagerty Dr, Tisbury, MA 02568
    /4

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,024 Sq Ft

    9 Hagerty Dr, Tisbury, MA 02568

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

    Lisa Gilberto C McManus Realty Group

    9 Hagerty Dr, Tisbury, 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

Frequently Asked Questions

Is Vineyard Haven a good place to live?
Vineyard Haven is a good place to live. Vineyard Haven is considered somewhat walkable and somewhat bikeable. 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 4.4 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 6.21%, your estimated principal and interest payment would be $8,580 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $368K 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, 02535 and 02539.
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.

Home Trends in Vineyard Haven, MA

On average, homes in Vineyard Haven, Marthas Vineyard sell after 118 days on the market compared to the national average of 53 days. The median sale price for homes in Vineyard Haven, Marthas Vineyard over the last 12 months is $1,325,000, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,325,000
Median Single Family Sale Price
$1,735,000
Median Townhouse Sale Price
$1,445,000
Median 2 Bedroom Sale Price
$686,000
Median 1 Bedroom Sale Price
$160,000
Average Price Per Sq Ft
$946
Number of Homes for Sale
44
Last 12 months Home Sales
78
Months of Supply
6.80
Median List Price
$1,750,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
8%
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 © 2025 CoStar Group