Vineyard Haven, MA Homes for Sale

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  $700,000

  • Land
  • 0.26 Acre
  • $2,670,736 per Acre

  35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

  Welcome to Lagoon Ridge.....Oak Bluffs’ newest and most sought-after neighborhood! Build your 3 bedroom dream home on this lofty setting, 95 feet above Lagoon Pond, featuring sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This exceptional building lot is among the last of the remaining opportunities in this thriving new community. Utilities are already at the site,

  Marilyn Moses Ocean Park Realty Inc

  35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
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  $3,125,000 Open Fri 12PM - 2PM

  • 4 Beds
  • 5 Baths
  • 5,165 Sq Ft

  63 Bayes Hill Rd, Oak Bluffs, MA 02557

  Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

  Casandra Hyland Landmarks at TODAY Real Estate

  63 Bayes Hill Rd, Oak Bluffs, MA 02557
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  /2

  $799,000

  • Land
  • 0.91 Acre
  • $878,022 per Acre

  22 Bramble Path, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path, West Tisbury, MA 02568
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  $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
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  /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
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  $2,995,000

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

  27 Spring St, Vineyard Haven, MA 02568

  Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features five fireplaces, (one currently hidden behind a plastered wall), a gracious living room, dining

  Alexis Holden Tea Lane Associates

  27 Spring St, Vineyard Haven, MA 02568
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  /42

  $2,289,000

  • 4 Beds
  • 3.5 Baths
  • 1,900 Sq Ft

  113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557

  UNIQUE IN-TOWN INVESTMENT opportunity in the heart of Oak Bluffs. This COMMERCIALLY ZONED B1 property offers flexibility and a strong existing rental history. Built in 2017, the MULTI-FAMILY building combines modern efficiency with an unbeatable location — just a short stroll to Oak Bluffs harbor, the Inkwell Beach, art galleries, shopping on Circuit Avenue, restaurants, the Historic Flying

  Grace Hagerty Grace Hagerty Real Estate Inc

  113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557
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  $5,450,000

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

  8 Paddock Rd, Oak Bluffs, MA 02557

  Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

  Lesley Heidt Sandpiper Realty Inc

  8 Paddock Rd, Oak Bluffs, MA 02557
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  /20

  $1,450,000

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

  5 Seth's Path, Oak Bluffs, MA 02557

  Desirable picturesque Deer Run location. Just steps from the bike path, this centrally located home is a perfect island retreat. You can enjoy the multi level deck and patio overlooking a wonderful in ground pool. The large lot provides for plenty of room for gardening or games and backs up to an idyllic open field. This house is perfectly set back off of the small cul de sac. Wonderful

  Robin Perschel Feiner Real Estate

  5 Seth's Path, Oak Bluffs, MA 02557
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  /39

  $2,495,000

  • 5 Beds
  • 2.5 Baths
  • 2,577 Sq Ft

  16 Atlantic Ave, Oak Bluffs, MA 02557

  East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

  Katherine Donahue Sandpiper Realty Inc

  16 Atlantic Ave, Oak Bluffs, MA 02557
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  /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
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  $4,895,000

  • 7 Beds
  • 4.5 Baths
  • 5,320 Sq Ft

  8 Fresh Pond Rd, Oak Bluffs, MA 02557

  The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

  Jarrett Hurwitz Keller Williams Realty

  8 Fresh Pond Rd, Oak Bluffs, MA 02557
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  $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
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  $674,000

  • Land
  • 0.49 Acre
  • $1,375,510 per Acre

  56 Holmes Hole Rd, Oak Bluffs, MA 02568

  Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either

  Marilyn Moses Ocean Park Realty, Inc.

  56 Holmes Hole Rd, Oak Bluffs, MA 02568
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  $487,000

  • Land
  • 0.23 Acre
  • $2,122,004 per Acre

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568

  Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for buildings of any size. Water and electric are nearby.

  Jim Joyce Carroll & Vincent R.E.

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
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  $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
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  $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 is less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal—close to restaurants, shopping, and the ferry. The three-bedroom home offers a comfortable and functional layout. The first floor features a spacious living room with a wood-burning fireplace, an adjacent dining room, and a fabulous

  Stephanie Roache Donnelly + Co.

  169 Clover Hill Dr, Vineyard Haven, MA 02568
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  $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
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  /12

  $4,400,000

  • Land
  • 4.8 Acres
  • $916,667 per Acre

  0 Eastville Ave Unit 147.2 / 3 / 4 / 5 /6, Oak Bluffs, MA 02568

  EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS. THESE LOTS ARE ALREADY SUBDIVIDED. Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor. NEW Shared Use Path runs along Eastville Avenue, when finished will link Vineyard Haven and Oak Bluffs for walking and cycling. Septic

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  0 Eastville Ave Unit 147.2 / 3 / 4 / 5 /6, Oak Bluffs, MA 02568
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  /23

  $969,000

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  67 12th St S, Edgartown, MA 02539

  QUICK CLOSING POSSIBLE! Ideal for employee housing, first time home buyers or investment.This ranch style 3 bedroom home centrally located in a quiet neighborhood is close to the bike path with easy access to town and beaches. Sited on a 12,000 square foot parcel with a spacious privately enclosed yard and mature gardens. First floor includes an efficient galley kitchen with a quaint dining area.

  Brenda Galligan Karen M. Overtoom R.E.

  67 12th St S, Edgartown, MA 02539
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  $6,795,000

  • 3 Beds
  • 2.5 Baths
  • 2,589 Sq Ft

  57 Hines Point Rd, Vineyard Haven, MA 02568

  Lily Hill - a rare Hines Point offering that includes a waterfront home with exquisite views, a deep water mooring and dock, and 130 feet of private fine-sand beach. Poised on a knoll on the western shore of the Lagoon, Lily Hill evokes a more peaceful time with sweeping views of the sky and water. Enjoy a swim at your private beach morning, noon or night. Watch the play of light across the water

  Elissa Lash Tea Lane Associates

  57 Hines Point Rd, Vineyard Haven, MA 02568
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  $1,495,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  47 E Chop Dr Unit 5, Oak Bluffs, MA 02568

  East Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, this 1-bedroom, waterfront condominium unit, the "Captain's Quarters", features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new

  Perry Patterson MV Luxury Homes

  47 E Chop Dr Unit 5, Oak Bluffs, MA 02568
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  $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
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  /23

  $1,790,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  11 Beach Rd, Oak Bluffs, MA 02557

  Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

  Alan Schweikert Ocean Park Realty Inc

  11 Beach Rd, Oak Bluffs, MA 02557
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  $425,000

  • Land
  • 0.23 Acre
  • $1,845,419 per Acre

  0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568

  Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district and more... Included on the "Sea View Bluffs Subdivision Plan of Land" and recorded with

  Rosemary Byrd Ocean Park Realty Inc

  0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
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  $1,295,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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  $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
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  $1,495,000

  • Land
  • 3.01 Acres
  • $496,678 per Acre

  11 Beach Pebble Rd, West Tisbury, MA 02568

  Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

  Cassie Bradley Wallace & Co. Sotheby's International Realty

  11 Beach Pebble Rd, West Tisbury, MA 02568
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  $1,095,000

  • 3 Beds
  • 1.5 Baths
  • 1,487 Sq Ft

  12 Wheelhouse Way, Oak Bluffs, MA 02557

  Custom-built 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, charming town centers and year-round ferries. Features include a large primary bedroom, a convenient first floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower--perfect for indoor-outdoor living.

  Dawn Bellante Sandpiper Realty Inc

  12 Wheelhouse Way, Oak Bluffs, MA 02557
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  $1,425,000

  • Land
  • 3.01 Acres
  • $473,422 per Acre

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

  The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

  Elissa Lash Tea Lane Associates

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
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  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,983 Sq Ft

  157 Ben Chase Rd, West Tisbury, MA 02575

  You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

  Madelyn Silvia Wallace & Co. Sotheby's

  157 Ben Chase Rd, West Tisbury, MA 02575
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  $1,095,000

  • 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 bathroom,

  Andrew McElhinney Compass LLC

  9 Bayview Ave, Oak Bluffs, MA 02568

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