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Vineyard Haven, MA Homes for Sale

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  • 47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    /22

    $1,250,000

    • 2 Beds
    • 1 Bath
    • 742 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 403-9601

    47 Winemack St, Oak Bluffs, MA 02557
  • 9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    /21

    $1,595,000

    • 3 Beds
    • 1 Bath
    • 1,033 Sq Ft

    9 Brunswick Ave, Oak Bluffs, MA 02557

    PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATE INSIDE AND OUT. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

    Agent Photo

    Alice Pierce

    Coldwell Banker Realty - Hingham

    (508) 715-6242

    9 Brunswick Ave, Oak Bluffs, MA 02557
  • 385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    /42

    $5,995,000

    • 3 Beds
    • 6 Baths
    • 3,608 Sq Ft

    385 Barnes Rd, Vineyard Haven, MA 02568

    Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

    Agent Photo

    Wendy Harman

    Compass

    (508) 205-8817

    385 Barnes Rd, Vineyard Haven, MA 02568
  • 37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    /32

    $985,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 514-5238

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • 34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    /34

    $2,500,000

    • 6 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    34 Massasoit Ave, Oak Bluffs, MA 02568

    This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 348-7972

    34 Massasoit Ave, Oak Bluffs, MA 02568
  • 70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    /27

    $1,200,000

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    70 Carol Ln, Oak Bluffs, MA 02557

    Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 456-5742

    70 Carol Ln, Oak Bluffs, MA 02557
  • 1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
    /22

    $1,100,000

    • 2 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

    Welcome to this spacious and well-appointed home offering 2,128 square feet of comfortable living space, nestled on a generous 0.49-acre lot. Perfect for both everyday living and entertaining, this residence features beautiful hardwood floors throughout the first floor, with wall to wall carpet in the second floor bedrooms adding warmth and timeless appeal.The large open-concept kitchen

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 827-6851

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
  • 27 7th St N, Edgartown, MA 02539
    27 7th St N, Edgartown, MA 02539
    27 7th St N, Edgartown, MA 02539
    /27

    $2,400,000

    • 3 Beds
    • 3.5 Baths
    • 1,884 Sq Ft

    27 7th St N, Edgartown, MA 02539

    27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with

    Michele Casavant Vineyard Village Realty

    27 7th St N, Edgartown, MA 02539
  • 71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    /19

    $1,995,000

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft

    71 Netock Ave, Oak Bluffs, MA 02557

    On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

    Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
  • 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

    33 Lagoon Pond Rd, 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
    /46

    $2,150,000

    • 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 shower for

    Jill Napior Tea Lane Associates

    81 Leland Ave, Vineyard Haven, MA 02568
  • 14 Rebekahs Way, Vineyard Haven, MA 02568
    14 Rebekahs Way, Vineyard Haven, MA 02568
    14 Rebekahs Way, Vineyard Haven, MA 02568
    /24

    $1,950,000

    • 5 Beds
    • 3 Baths
    • 1,916 Sq Ft

    14 Rebekahs Way, Vineyard Haven, MA 02568

    Affectionately referred to as 'The Treehouse', this property encompasses all the elements of a modern, sophisticated residence while providing the warmth and comfort of a private retreat. Professionally designed by Hutker Architects, this four-bedroom home, with a den/potential fifth bedroom, is sited in a private area, conveniently located with easy access to grocery store, pharmacy, and post

    Sheila Morse Island Real Estate

    14 Rebekahs Way, Vineyard Haven, MA 02568
  • 229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    /39

    $2,650,000

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

    229 Oak Ln, West Tisbury, MA 02575

    A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out

    Doug Burke Cronigs Real Estate

    229 Oak Ln, West Tisbury, MA 02575
  • 34 Davis St, Tisbury, MA 02568
    34 Davis St, Tisbury, MA 02568
    34 Davis St, Tisbury, MA 02568
    /26

    $2,395,000

    • 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
  • 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
  • 129 Beach Rd, Tisbury, MA 02568
    129 Beach Rd, Tisbury, MA 02568
    129 Beach Rd, Tisbury, MA 02568
    /62

    $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. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private access, is

    Michele Moore Island Real Estate

    129 Beach Rd, Tisbury, MA 02568
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /26

    $2,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    /19

    $1,995,000

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft

    71 Netock Ave, Oak Bluffs, MA 02557

    On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

    Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
  • 22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    /37

    $2,240,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    22 Greenleaf Ave, Oak Bluffs, MA 02557

    Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect

    Jennifer O'hanlon Compass

    22 Greenleaf Ave, Oak Bluffs, MA 02557
  • 2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    /37

    $1,995,000

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft

    2 Farm Path, Oak Bluffs, MA 02557

    "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

    Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • 4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    /24

    $2,260,000

    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

    Brian Smith Portfolio Real Estate Inc.

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • 70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    /51

    $2,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,274 Sq Ft

    70 Spring St, Vineyard Haven, MA 02568

    Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

    June Flake Viewpoints

    70 Spring St, Vineyard Haven, MA 02568
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /24

    $2,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co.

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 46 Red Buoy Ln, Tisbury, MA 02568
    46 Red Buoy Ln, Tisbury, MA 02568
    46 Red Buoy Ln, Tisbury, MA 02568
    /24

    $2,095,000

    • 4 Beds
    • 3.5 Baths
    • 2,413 Sq Ft

    46 Red Buoy Ln, Tisbury, MA 02568

    Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space. The main level boasts a thoughtfully designed floor plan

    Andrew McElhinney Compass LLC

    46 Red Buoy Ln, Tisbury, MA 02568
  • 27 Chapde Ln, Tisbury, MA 02568
    27 Chapde Ln, Tisbury, MA 02568
    27 Chapde Ln, Tisbury, MA 02568
    /27

    $1,649,000

    • 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

    Wendy Harman Compass

    27 Chapde Ln, Tisbury, MA 02568
  • 16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    /23

    $6,500,000

    • 6 Beds
    • 5.5 Baths
    • 4,753 Sq Ft

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568

    Private West Tisbury Oasis – Modern Luxury on 4.85 AcresBuilt by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional

    Joe & Nicole Holland Vineyard Dream Realty LLC

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
  • 38 Rogers Way, Oak Bluffs, MA 02557
    38 Rogers Way, Oak Bluffs, MA 02557
    38 Rogers Way, Oak Bluffs, MA 02557
    /28

    $1,650,000

    • 3 Beds
    • 1.5 Baths
    • 2,448 Sq Ft

    38 Rogers Way, Oak Bluffs, MA 02557

    Tucked away in a private desirable Oak Bluffs neighborhood yet only minutes from the charm of downtown and the incredible OB beaches, this home is a wonderful island retreat. With four levels of finished living space, it offers room to gather, relax, entertain, and create memories in every season. Hardwood floors, open concept kitchen and living areas, crackling fireplace set the tone indoors.

    Jon Hartzband Martha's Vineyard Island-Wide Realty

    38 Rogers Way, Oak Bluffs, MA 02557
  • 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

    $655,000

    • 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
  • 28 Barling Ave, Vineyard Haven, MA 02568
    28 Barling Ave, Vineyard Haven, MA 02568
    28 Barling Ave, Vineyard Haven, MA 02568
    /30

    $1,049,000

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    28 Barling Ave, Vineyard Haven, MA 02568

    Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

    Alan Schweikert Ocean Park Realty Inc

    28 Barling Ave, Vineyard Haven, MA 02568
  • 34 Pine Ln, Vineyard Haven, MA 02568
    34 Pine Ln, Vineyard Haven, MA 02568
    34 Pine Ln, Vineyard Haven, MA 02568
    /29

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    34 Pine Ln, Vineyard Haven, MA 02568

    One level living! This ranch-style home has a great layout and some sweet, unexpected features. The living spaces are opened up to each other allowing the wall of sliders in the living room to flood the rooms with light - and these sliders give access out to the deck with serene views of the woodlands beyond; where Stoney Hill Path bounds the entire south side of the property. The primary

    Candy DaRosa Feiner Real Estate

    34 Pine Ln, Vineyard Haven, MA 02568
  • 31 Josiah Sachem Way, Vineyard Haven, MA 02568
    31 Josiah Sachem Way, Vineyard Haven, MA 02568
    31 Josiah Sachem Way, Vineyard Haven, MA 02568
    /63

    $5,000,000

    • 6 Beds
    • 3.5 Baths
    • 3,312 Sq Ft

    31 Josiah Sachem Way, Vineyard Haven, MA 02568

    An inspirational Oasis - come unwind and behold what this secluded multi-home compound has to offer. With two driveways and an open wildflower field bordered with plantings, the main house, studio barn, guesthouse and in-ground pool area at this private retreat are beautifully positioned and landscaped. Each structure is available for year-round use with abundant parking and unique charms.

    Helena Kirschenbaum Studio Realty

    31 Josiah Sachem Way, Vineyard Haven, MA 02568
  • 50 Canonicus Ave, Oak Bluffs, MA 02557
    50 Canonicus Ave, Oak Bluffs, MA 02557
    50 Canonicus Ave, Oak Bluffs, MA 02557
    /22

    $970,000

    • 2 Beds
    • 0.5 Baths
    • 953 Sq Ft

    50 Canonicus Ave, Oak Bluffs, MA 02557

    Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

    Michele Moore Island Real Estate

    50 Canonicus Ave, Oak Bluffs, MA 02557
  • 9 Fowler Ave, Edgartown, MA 02539
    9 Fowler Ave, Edgartown, MA 02539
    9 Fowler Ave, Edgartown, MA 02539
    /27

    $5,250,000

    • 4 Beds
    • 3.5 Baths
    • 3,018 Sq Ft

    9 Fowler Ave, Edgartown, MA 02539

    Edgartown Waterfront - Classic New England architecture meets the timeless allure of Martha’s Vineyard. This exceptional waterfront estate is set on the edge of Sengekontacket Pond, offering a sandy shoreline, panoramic water views, and a private mooring — the perfect setting for boating, paddle boarding, fishing, and clamming.A gated entrance opens to a beautifully landscaped property

    Andrew McElhinney Compass LLC

    9 Fowler Ave, Edgartown, MA 02539
  • 26 Hampson Ave, Oak Bluffs, MA 02557
    26 Hampson Ave, Oak Bluffs, MA 02557
    26 Hampson Ave, Oak Bluffs, MA 02557
    /31

    $999,999

    • 2 Beds
    • 2 Baths
    • 1,078 Sq Ft

    26 Hampson Ave, Oak Bluffs, MA 02557

    Location, Location, Location! This unique property on the beautiful island of Martha's Vineyard presents an incredible opportunity for the buyer with vision to complete and personalize a home full of potential. The original residence, built in 1920, offers 2 bedrooms and 1 bath and has been expanded with a substantial newer addition, creating increased living space and a finished garage area

    Rene Ben David Ocean Park Realty, Inc.

    26 Hampson Ave, Oak Bluffs, MA 02557
  • 112 3rd St N, Edgartown, MA 02568
    112 3rd St N, Edgartown, MA 02568
    112 3rd St N, Edgartown, MA 02568
    /36

    $1,275,000

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft

    112 3rd St N, Edgartown, MA 02568

    Nestled on a lush and private parcel close to The Boulevard, this contemporary three-bedroom, two-bath residence offers the perfect blend of style and comfortable living. Highlights include a gas fireplace, wood floors, an expansive deck to relax on, and established gardens. There’s even a shed to store all your summer gear. Enjoy this oasis as is or use as a foundation for future

    Kristin Buck Donnelly + Co

    112 3rd St N, Edgartown, MA 02568
  • 9 Bayview Ave, Oak Bluffs, MA 02568
    9 Bayview Ave, Oak Bluffs, MA 02568
    9 Bayview Ave, Oak Bluffs, MA 02568
    /21

    $1,249,999

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft

    9 Bayview Ave, Oak Bluffs, MA 02568

    Oak Bluffs Charmer – Welcome to 9 Bayview Avenue, a 3-bedroom, 2-bath home tucked away on a quiet road in Oak Bluffs. Sited on a level 10,050 sq. ft. lot, this property offers 1,428 sq. ft. of light-filled living space.The main level features a spacious living room, kitchen, and dining area, along with a first-floor bedroom and full bath. Upstairs, two comfortable bedrooms share a full

    Andrew McElhinney Compass LLC

    9 Bayview Ave, Oak Bluffs, MA 02568
  • 39 Iron Hill Rd, Oak Bluffs, MA 02557
    39 Iron Hill Rd, Oak Bluffs, MA 02557
    39 Iron Hill Rd, Oak Bluffs, MA 02557
    /49

    $2,000,000

    • 5 Beds
    • 5.5 Baths
    • 4,334 Sq Ft

    39 Iron Hill Rd, Oak Bluffs, MA 02557

    Welcome to 39 Iron Hill Rd, Oak Bluffs (Martha’s Vineyard)—a private multifamily colonial within Iron Hill Farm, near Island Alpaca, Island Grown Initiative, miles of trails, and access to Duarte’s Pond, with convenient proximity to Vineyard Haven and Oak Bluffs beaches and amenities. The 4,334± sq. ft. property offers 5 BR / 5.5 BA in total. Main residence (4BR/4.5BA) features two ensuite

    Lisa Da Silva Compass | Point B

    39 Iron Hill Rd, Oak Bluffs, MA 02557
  • 9 Beach Pebble Rd, Vineyard Haven, MA 02568
    9 Beach Pebble Rd, Vineyard Haven, MA 02568
    9 Beach Pebble Rd, Vineyard Haven, MA 02568
    /6

    $1,595,000

    • Land
    • 3.2 Acres
    • $498,438 per Acre

    9 Beach Pebble Rd, Vineyard Haven, MA 02568

    Vacant land in West Tisbury's Makonikey Community with access to the beautiful Lower Makonikey Association beach. This rare offering spans over 3 acres, with a 1.4-acre area providing the ideal location for a substantial residence in keeping with the distinguished homes that define this exclusive neighborhood. This property presents a unique opportunity to create an exceptional island retreat.

    Cassie Bradley Wallace & Co. Sotheby's International Realty

    9 Beach Pebble Rd, Vineyard Haven, MA 02568

Showing Results 1 - 40, Page 1 of 5

Massachusetts Dukes County Vineyard Haven

Real Estate & Homes for Sale in Vineyard Haven, MA

Frequently Asked Questions

What are the most popular zip codes in Vineyard Haven, MA?
The most popular zip codes in Vineyard Haven, MA include 02568, 02539, 02536, 02575 and 02535.
What are the most popular neighborhoods near Vineyard Haven, MA?
The most popular neighborhoods near Vineyard Haven, MA are Vineyard Haven, Oak Bluffs, West Tisbury, Edgartown and Falmouth Village.
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