179

Newest Homes for Sale in Vineyard Haven, MA

Section Image Section Image
  • 24 Harrison Ave, Oak Bluffs, MA 02557
    24 Harrison Ave, Oak Bluffs, MA 02557
    24 Harrison Ave, Oak Bluffs, MA 02557
    /20

    $2,595,000

    • 2 Beds
    • 3 Baths
    • 1,586 Sq Ft

    24 Harrison Ave, Oak Bluffs, MA 02557

    East Chop with Water View! The perfect size vacation house or year round living, with all the bells and whistles, water views and located in the most desired neighborhood on East Chop! Designed by Hutker Architects, built with high quality craftsmanship by J.G. Early and landscape design by Dan Gordon Landscape Architects. This recently completed cozy 2BR/2.5 BA with solar panels providing

    Perry Patterson MV Luxury Homes

    24 Harrison Ave, Oak Bluffs, MA 02557
  • 53 Circuit Ave, Oak Bluffs, MA 02557
    53 Circuit Ave, Oak Bluffs, MA 02557
    53 Circuit Ave, Oak Bluffs, MA 02557
    /75

    $5,500,000

    • 6 Beds
    • 6 Baths
    • 5,706 Sq Ft

    53 Circuit Ave, Oak Bluffs, MA 02557

    This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the

    Stephanie Roache Donnelly + Co

    53 Circuit Ave, Oak Bluffs, MA 02557
  • 49 The Blvd, Edgartown, MA 02539
    49 The Blvd, Edgartown, MA 02539
    49 The Blvd, Edgartown, MA 02539
    /28

    $2,850,000

    • 6 Beds
    • 1 Bath
    • 1,957 Sq Ft

    49 The Blvd, Edgartown, MA 02539

    Two side by side cottages built in 1945 Directly Pondfront on Sengekontacket with 180 degree views over the pond out to the Causeway, State Beach, Nantucket Sound and beyond. A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    49 The Blvd, Edgartown, MA 02539
  • 60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    /9

    $1,600,000

    • Land
    • 5.15 Acres
    • $310,680 per Acre

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575

    Over five acres of privacy in one of the Island's most sought-after settings. This 5.15-acre parcel offers a rare opportunity to build a primary residence and accessory structure on old farmland surrounded by large, mature trees. Idyllic stonewalls run along some of the property lines.Large parcel size and building envelope ensures that the character of the neighborhood endures. Adjacent Land

    Julianna Flanders Flanders Real Estate

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
  • 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
  • 27 Beach Rd, Oak Bluffs, MA 02557
    27 Beach Rd, Oak Bluffs, MA 02557
    27 Beach Rd, Oak Bluffs, MA 02557
    /31

    $2,995,000

    • 4 Beds
    • 1.5 Baths
    • 3,462 Sq Ft

    27 Beach Rd, Oak Bluffs, MA 02557

    WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    27 Beach Rd, Oak Bluffs, MA 02557
  • 99 Oak Ln, Vineyard Haven, MA 02568
    99 Oak Ln, Vineyard Haven, MA 02568
    99 Oak Ln, Vineyard Haven, MA 02568
    /30

    $2,200,000

    • 4 Beds
    • 3 Baths
    • 3,771 Sq Ft

    99 Oak Ln, Vineyard Haven, MA 02568

    This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet

    Rose Ryley Wallace & Co. Sotheby's

    99 Oak Ln, Vineyard Haven, MA 02568
  • 33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
    /27

    $260,000

    • 1 Bed
    • 1 Bath
    • 319 Sq Ft

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 27F, a comfortable studio offering the perfect combination of a Martha’s Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
  • 21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
    /43

    $527,500

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568

    Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
  • 27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
    /41

    $287,500

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 9C, an inviting Martha’s Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
  • 27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
    /32

    $310,000

    • 1 Bed
    • 1 Bath
    • 419 Sq Ft

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha’s Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 10C, Oak Bluffs, 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
    /43

    $945,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    74 Chase Ln, Vineyard Haven, MA 02568

    Great Location! Cape Cod style year round home well maintained 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 clean basement adds additional 768 SF, with egress walkout door and large windows letting in sunshine. Includes two lots. The house has two propane monitors, one on the first floor and one in the

    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
  • 27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
    /18

    $250,000

    • 1 Bed
    • 1 Bath
    • 331 Sq Ft

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568

    Island Inn ....tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to State Beach and then further on into Edgartown ...OR a short distance north to Oak Bluffs center, ferry

    Patti Dean Wiggy's Pond Real Estate

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
  • 11 Stanley St, Oak Bluffs, MA 02557
    11 Stanley St, Oak Bluffs, MA 02557
    11 Stanley St, Oak Bluffs, MA 02557
    /17

    $1,255,000

    • 3 Beds
    • 1.5 Baths
    • 912 Sq Ft

    11 Stanley St, Oak Bluffs, MA 02557

    Nestled on a cul-de-sac is this sweet 3 bedroom ranch. Located on a .34 acre lot with plenty of room to expand this solid home and still have enough space for an ADU on this spacious lot. Well maintained over the years with recent upgrades including, roof, siding, new insulation, flooring and paint. Natural light floods the house from the bank of windows in the living room to the sliding glass

    Lisa Lucier Anchor Realty of Martha's Vineyard

    11 Stanley St, Oak Bluffs, MA 02557
  • 3 Dukes County Ave, Oak Bluffs, MA 02557
    3 Dukes County Ave, Oak Bluffs, MA 02557
    3 Dukes County Ave, Oak Bluffs, MA 02557
    /24

    $935,000

    • 2 Beds
    • 1 Bath
    • 763 Sq Ft

    3 Dukes County Ave, Oak Bluffs, MA 02557

    A Gem of a Marthas Vineyard Camp Meeting House Association Home, 3 Dukes County Ave. Located down from the Oak Bluffs Harbor. A couple house from Sunset Pond.Convenient to Beaches,Harbor, Resturants, Shopping, Dancing Music and walk to and from the Steamship Authority.2 bedroom,1 queen bedroom 1 full bed and twin bunk room with built in wardrobe and desk bathroom. Bathroom shower bath

    Karen Trotier Laer Realty Partners

    3 Dukes County Ave, Oak Bluffs, MA 02557
  • 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
  • 2 Winemack St, Oak Bluffs, MA 02557
    2 Winemack St, Oak Bluffs, MA 02557
    2 Winemack St, Oak Bluffs, MA 02557
    /28

    $1,195,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2 Winemack St, Oak Bluffs, MA 02557

    Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you’ll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping,

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    2 Winemack St, Oak Bluffs, MA 02557
  • 150 Field View Ln, Vineyard Haven, MA 02568
    150 Field View Ln, Vineyard Haven, MA 02568
    150 Field View Ln, Vineyard Haven, MA 02568
    /20

    $1,600,000

    • 4 Beds
    • 2.5 Baths
    • 2,334 Sq Ft

    150 Field View Ln, Vineyard Haven, MA 02568

    A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you

    Sheila Morse Island Real Estate

    150 Field View Ln, Vineyard Haven, MA 02568
  • 20 Hidden Cove Rd, Oak Bluffs, MA 02557
    20 Hidden Cove Rd, Oak Bluffs, MA 02557
    20 Hidden Cove Rd, Oak Bluffs, MA 02557
    /45

    $1,625,000

    • 4 Beds
    • 3 Baths
    • 1,898 Sq Ft

    20 Hidden Cove Rd, Oak Bluffs, MA 02557

    Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded

    Jennifer DaSilva Compass | Point B

    20 Hidden Cove Rd, Oak Bluffs, MA 02557
  • 14 High Meadow Ln, Oak Bluffs, MA 02557
    14 High Meadow Ln, Oak Bluffs, MA 02557
    14 High Meadow Ln, Oak Bluffs, MA 02557
    /37

    $1,750,000

    • 3 Beds
    • 4 Baths
    • 1,932 Sq Ft

    14 High Meadow Ln, Oak Bluffs, MA 02557

    Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double

    Jennifer DaSilva Compass | Point B

    14 High Meadow Ln, Oak Bluffs, MA 02557
  • 61 Winemack St, Oak Bluffs, MA 02557
    61 Winemack St, Oak Bluffs, MA 02557
    61 Winemack St, Oak Bluffs, MA 02557
    /7

    $850,000

    • 2 Beds
    • 1 Bath
    • 992 Sq Ft

    61 Winemack St, Oak Bluffs, MA 02557

    Located in Oak Bluffs' desirable East Chop neighborhood, this 10,000± sq. ft. R2-zoned property offers an exceptional opportunity to renovate or build new (subject to applicable approvals). The existing two-bedroom, one-bath home is being sold as is. The level lot features a spacious yard and is ideally located just 0.9 miles from the East Chop Lighthouse, 1.3 miles from the East Chop Beach Club,

    Andrew McElhinney Compass LLC

    61 Winemack St, Oak Bluffs, MA 02557
  • 8 Woodhaven Dr, Edgartown, MA 02539
    8 Woodhaven Dr, Edgartown, MA 02539
    8 Woodhaven Dr, Edgartown, MA 02539
    /42

    $3,225,000

    • 3 Beds
    • 4.5 Baths
    • 3,219 Sq Ft

    8 Woodhaven Dr, Edgartown, MA 02539

    Hidden behind a veil of privacy on a generous coastal sanctuary, an extraordinary property waits to be discovered. This custom masterpiece blends timeless architecture with a modern, elusive sophistication, offering comfortable finished living space within an impressive total structure. Cross the threshold onto rich hardwood floors where light dances beneath a dramatic cathedral ceiling, drawing

    Jennifer B. DaSilva Compass

    8 Woodhaven Dr, Edgartown, MA 02539
  • 77 Sixth St N, Edgartown, MA 02539
    77 Sixth St N, Edgartown, MA 02539
    77 Sixth St N, Edgartown, MA 02539
    /18

    $2,500,000

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

    77 Sixth St N, Edgartown, MA 02539

    WATERVIEWS of Sengenotacket when you pull out of the driveway at 77 SIXTH STREET NORTH, EDGARTOWN. NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2027; just in time to bring in the 2027 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

    Michele Casavant Vineyard Village Realty

    77 Sixth St N, Edgartown, MA 02539
  • 54 Towanticut Ave, Oak Bluffs, MA 02568
    54 Towanticut Ave, Oak Bluffs, MA 02568
    54 Towanticut Ave, Oak Bluffs, MA 02568
    /23

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    54 Towanticut Ave, Oak Bluffs, MA 02568

    Living is easy in this beautifully maintained 3-bedroom, 2-bath air-conditioned Ranch located just one mile from the center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace, an updated kitchen with granite countertops and stainless-steel appliances, and a dining area with sliders leading to a spacious deck and outdoor shower overlooking the yard. The generous

    JoJo Lambert Island Home Realty Inc.

    54 Towanticut Ave, Oak Bluffs, 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
  • 0 Heather Ln Unit 56, Oak Bluffs, MA 02568
    0 Heather Ln Unit 56, Oak Bluffs, MA 02568
    /2

    $425,000

    • Land
    • 7,840 Sq Ft
    • $2,361,111 per Acre

    0 Heather Ln Unit 56, Oak Bluffs, MA 02568

    Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

    Jennifer DaSilva Compass | Point B

    0 Heather Ln Unit 56, Oak Bluffs, MA 02568
  • 0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
    0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
    /2

    $425,000

    • Land
    • 7,840 Sq Ft
    • $2,361,111 per Acre

    0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568

    Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

    Jennifer B. DaSilva Compass

    0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
  • 323 County Rd, Oak Bluffs, MA 02557
    323 County Rd, Oak Bluffs, MA 02557
    323 County Rd, Oak Bluffs, MA 02557
    /33

    $1,225,000

    • 1 Bed
    • 2 Baths
    • 1,428 Sq Ft

    323 County Rd, Oak Bluffs, MA 02557

    This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and

    Nancy Beckwith Anchor Realty of Martha's Vineyard

    323 County Rd, Oak Bluffs, MA 02557
  • 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
  • 170 Barnes Rd, Oak Bluffs, MA 02557
    170 Barnes Rd, Oak Bluffs, MA 02557
    170 Barnes Rd, Oak Bluffs, MA 02557
    /19

    $1,095,000

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft

    170 Barnes Rd, Oak Bluffs, MA 02557

    Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back

    Christine Rose Martha's Vineyard Island-Wide Realty

    170 Barnes Rd, Oak Bluffs, MA 02557
  • 99 Ocean Ave, Oak Bluffs, MA 02557
    99 Ocean Ave, Oak Bluffs, MA 02557
    99 Ocean Ave, Oak Bluffs, MA 02557
    /36

    $3,975,000

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

    99 Ocean Ave, Oak Bluffs, MA 02557

    A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home to family and

    Perry Patterson MV Luxury Homes

    99 Ocean Ave, Oak Bluffs, MA 02557
  • 33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
    /18

    $239,000

    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568

    Want to own a slice of Martha's Vineyard? As an owner of this studio style "Condo-tel", you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm

    Rene Jackson Island Real Estate

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
  • 22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    /6

    $1,895,000

    • Land
    • 1.87 Acres
    • $1,014,997 per Acre

    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568

    An exceptional offering—the final homesite available within The Preserve at The Woodlands, one of Oak Bluffs’ most coveted residential enclaves. Create a custom coastal retreat in an extraordinary setting where architecturally designed residences, protected conservation land, and the timeless beauty of Martha’s Vineyard converge.This 1.87-acre homesite represents the final opportunity to

    Marilyn Moses Ocean Park Realty Inc

    22 Paddock Rd Unit 85, Oak Bluffs, 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
  • 43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    /25

    $5,495,000

    $500K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,234 Sq Ft

    43 Sengekontacket Rd, Oak Bluffs, MA 02557

    Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

    Peyton Wallace Studio Realty LLC

    43 Sengekontacket Rd, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 5

Massachusetts Dukes County

Newest Listings 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, 02575, 02536, 02539 and 02543.
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 Woods Hole.
How to Buy a Home How to Finance a Home How to Sell a Home

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

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group