Vineyard Haven Homes for Sale

Many know Vineyard Haven as the village with the ferry, and although that does provide plenty of convenience, Vineyard Haven has a unique character that perfectly blends the past and present. You will find delicious restaurants, shops, and nature through out Vineyard Haven. 

Browse Homes for Sale in Vineyard Haven

Below you will find all real estate currently for sale in Vineyard Haven. See a property you love? Contact us to schedule a time to tour the property. Save your favorite Vineyard Haven listings and receive updates when similar listings become available by registering with us!

1153 Main Street Vineyard Haven MA

Price$11,750,000

Est. Mortgage: $/month

MLS Number 33954

  • Residential
  • Square Feet 5345
  • Bedrooms 8
  • Bathroom 6
  • Half Baths 1

Located on a winding private road, this original 1896 West Chop waterfront home was completely renovated to exacting standards in 1992. With 8 bedrooms and 6 and a half bathrooms, and a classical layout with formal and informal areas in which to relax and pass the time, this home encompasses all that this desirable location provides for multi-generational family gatherings and summer memories at West Chop. A stately front entrance leads to the formal living room with adjoining separate sitting room, with fireplace, that opens to the expansive water facing porch providing active views of the Vineyard Sound and additional entertaining space to while away a lazy summer afternoon. The home offers an exceptional combination of elegant charm and modern amenities including the large gourmet kitchen breakfast room, with Wolf and Sub Zero appliances, bespoke cabinetry and a butler's pantry that leads through to the formal dining room. The staircase leads to a large master suite with full bath, office and balcony overlooking the water. Three further bedrooms and 2 additional bathrooms occupy the remainder of the second floor with 4 further bedrooms and 3 baths on the third floor. The huge walk out basement was created during the renovation, and could be finished to create living space for wine cellar, family room or gym. Air Conditioning has been installed throughout for 2019. Walk from the house through established perennial gardens to the beautiful sandy beach for easy swimming, tide rides to the pier and docks and enjoyment of the water. This is a rare opportunity to buy in the heart of the West Chop community. Contact us for more information about this special North Shore private setting with opportunities for beaches, tennis, golf, and more.

Listed by Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1153 Main Street Vineyard Haven MA

Price$11,750,000

Est. Mortgage: $/month

MLS Number 33535

  • Residential
  • Square Feet 5345
  • Bedrooms 8
  • Bathroom 6
  • Half Baths 1

This three-story shingle-style home on Vineyard Sound, an easy walk to the West Chop Club, epitomizes the relaxed elegance of late 19th-century seaside living. Beautifully restored and decorated, the 5,345-sf house ideally located on a peaceful private road, includes eight bedrooms, multiple formal and informal gathering areas, and wide porches with spectacular water views. A superb example of traditional coastal New England architecture with its cedar shingles and abundance of windows, gables, and gambrels, this meticulously maintained house was built in 1897 and renovated in the early 1990s, paying tribute to its historical detail while adding many amenities. A spacious gourmet kitchen, outfitted with high-end appliances, adjoins a casual dining/lounging area and connects through a butler's pantry to the formal dining room. Two living rooms, one with a large fireplace, comfortably accommodate a large gathering. The expansive master suite includes a balcony with water views, brick fireplace, spacious master bath, and adjoining sitting room and office. The .59-acre property makes the most of its dramatic setting with graceful perennial gardens and open lawns. A private path leads to the West Chop Trust's north shore beach for lazy days in the sun, tide rides, and fishing. Just two miles from the center of Vineyard Haven, a West Chop classic similar to this home rarely comes on the market, and provides the perfect setting to create memories of your own for generations to come.

Listed by Viewpoints

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$
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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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721 Main Street Vineyard Haven MA

Price$6,950,000

Est. Mortgage: $/month

MLS Number 30721

  • Residential
  • Square Feet 3037
  • Bedrooms 4
  • Bathroom 4
  • Half Baths 1

This spectacular waterfront West Chop home with panoramic views looking out across the Vineyard Sound will take your breath away. A true beach home featuring 110 feet of private beach with dock and mooring, and positively the best swimming on the island! The great room with cathedral ceilings and floor to ceiling windows captures the boat activity in every direction. Easy living here with one wing with master and guest ensuite bedroom. A newly renovated state of the art eat-in kitchen just off the great room makes this the perfect home for entertaining. One bedroom and den is found off the kitchen with separate exterior access to an outdoor shower. A huge bonus here, and something that could not be duplicated today, is the quaint detached bedroom complete with a kitchenette and living room area. Additional garage and basement, perfect for storing the kayaks, beach toys and bikes! This is a very special offering, furniture may be purchased separately, all you need is your bathing suit!

Listed by Viewpoints

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$
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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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275 South Farm Road Vineyard Haven MA

Price$5,700,000

Est. Mortgage: $/month

MLS Number 29771

  • Residential
  • Square Feet 3067
  • Bedrooms 5
  • Bathroom 3
  • Acreage 6.4

Not all vineyard waterfront properties are the same. This waterfront estate on the shores of Lake Tashmoo is truly unique. Located on 6.4 acres of woods, the house is on a point of land with water on three sides. There is a main house and several outbuildings. The property is landscaped with two circular drives, brick walkways and over 700 feet of deepwater frontage on Lake Tashmoo. A sandy beach is a few steps away from the front porch. It slopes gently into the water and is ideal for young children. There is a plentiful supply of shellfish just off the property. There is a family of otters, a pair of ospreys that live near the shore and an occasional sighting of harbor seals. It is a bird watcher's paradise. The house has five comfortably sized bedrooms, two of which have their own outside entrances and private decks. The master bedroom and bath occupies the entire second floor of the house, and has the utmost privacy. It has a loft, built-in bureaus, a fireplace and a wraparound outside deck. The living room has fireplace, wood paneling, yellow pine floors and a cathedral ceiling with skylights. A glass wall opens into a screened porch, a favorite place to dine in the summer. The dining room is connected to the kitchen by a set of French doors. It has yellow pine floors, wood paneling and wraparound windows. There is also a family room with a very private screened porch overlooking the dock. The entire house is very bright and cheerful with skylights and an abundance of windows. Have you been searching for Vineyard waterfront properties with a deep water dock? Search no more! Don't miss the opportunity to own this stunning Lake Tashmoo property.

Listed by Jampel Associates

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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122 Kuffies Point Way Vineyard Haven MA

MLS Number 31874

  • Residential
  • Square Feet 4034
  • Bedrooms 4
  • Bathroom 4
  • Half Baths 1

Waterfront on Lake Tashmoo with sweeping water views. This highly sophisticated home with deeded north shore beach access was built by Mark Baumhofer and bears all the hallmarks of a luxury residence. The design blends rustic elements with contemporary styling, all to dramatic effect. Privacy is assured with three of the four bedrooms being bedroom suites, one upstairs and two semi-detached. The lush landscape by renowned Tea Lane Nursery is all-organic. Custom details include plaster walls, CWM copper-clad windows, doors and windows made from the highest grade Tahitian mahogany, radiant floors, and a 23 ft ceiling height in the Great Room. The property abuts 50 acres of Sheriff's Meadow conservation land to the west, and to the east, a 6-acre parcel that cannot be subdivided. A 42-acre farm lies immediately to the south. The 150-ft north shore beach to which owners have deeded access is reachable via a quiet country road or by kayak, canoe, or paddleboard. This beach offers excellent swimming and beautiful sunsets. Please view imagery and request a specifications sheet for more information on this spectacular property.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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78 Hines Point Vineyard Haven MA

Price$3,500,000

Est. Mortgage: $/month

MLS Number 33998

  • Residential
  • Square Feet 2825
  • Bedrooms 4
  • Bathroom 4
  • Half Baths 1

78 Hines Point, designed by Breese Architects and built in 2008 by Holmes Hole Construction, features 2800+/- square feet of living space on two levels with water views from every room. Two master suites flank each end of the first floor with a central gathering space between…the kitchen, dining and living room with wood burning fireplace. The second level holds two bedrooms with en suite baths. A screened porch with wood burning fireplace is the perfect room to catch the sunsets over Vineyard Sound. Outdoor areas include parking for four cars, irrigated gardens and landscape, outdoor showers, wide flagstone patios and steps down to the beach. A dock at water's edge eases the launching of kayaks, paddle boards and other watercraft for summer enjoyment. Hines Point is within walking distance to the ferries, fish market, restaurants, theaters, shopping and all of the amenities that Vineyard Haven has to offer. 78 Hines Point is offered furnished. The abutting property at 104 Hines Point is offered separately.

Listed by Russell Maloney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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733 Main Street Vineyard Haven MA

Price$3,250,000

Est. Mortgage: $/month

MLS Number 33134

  • Residential
  • Square Feet 2081
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.91

This contemporary A-frame located by Sheriff's Meadow in West Chop has unsurpassed views over the Meadow towards the Cape and the Sound and over 145 feet of private beach looking out towards East Chop and the outer harbor. The detached guest house is complete with office, kitchen, bedroom and bath which could not be duplicated today. The main 3 br. house enjoys a 415 sq. ft. deck and a 96 sq. ft. porch area to view all the summer boat activity. This house could be part of a magnificent waterfront compound with the purchase of 741 Main St. next door. This is a very special spot and a rare opportunity.

Listed by Viewpoints

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27 Hatch Road Vineyard Haven MA

Price$3,199,000

Est. Mortgage: $/month

MLS Number 34794

  • Residential
  • Square Feet 3875
  • Bedrooms 6
  • Bathroom 4
  • Half Baths 1

Set in West Chop's most coveted enclave, this newly constructed Hatch Road compound has so much to offer. Move right in and enjoy three floors of beautifully designed living in the main house, which includes generous water views from multiple vantages. The first level provides a warm greeting and comfortable ease, with connected and open living, dining, and kitchen spaces. Master suites are readily available on the first and second levels, and the third level offers the home's fifth bedroom. Complementing the water view decks are a screened porch and bluestone patio. Thoughtfully engineered, the home includes elements of high performance design and efficiency, including quartz and granite countertops, Thermador appliances, tankless hot water heater, Anderson windows, state of the art insulation, and more. A detached two-car carriage house with beautiful full guest apartment above completes the compound. Expansive lawns and superb hardscape bring the buildings together harmoniously. And, while there is room for a pool, the grounds between the main and carriage houses unify the property in an exemplary way, with several noteworthy trees and mature plantings striking all the right chords. For swimming, kayaking and more, access to VH harbor is approx. 500' away via Hatch Road and Cleveland Ave. For a newly built and turn-key option in one of Martha's Vineyard's absolutely best locations, look no farther!

Listed by Compass

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Harbor View Lane Vineyard Haven MA

Price$3,100,000

Est. Mortgage: $/month

MLS Number 33574

  • Residential
  • Square Feet 2072
  • Bedrooms 4
  • Bathroom 2
  • Half Baths 1

**RECENTLY INSTALLED 5 BEDROOM SEPTIC ** Rare opportunity to own this vintage, dutch colonial waterfront home situated atop a West Chop bluff offering unparalleled views of Vineyard Haven Harbor, East Chop, and Vineyard Sound. Elevated above a secure bluff, enjoy breathtaking views with your friends and family from every vantage point! This unique property has its own private white sand beach with a private stairway and swimming dock, which was completely rebuilt in the spring of 2015. Enjoy the feeling of seclusion from your oasis within walking distance of shopping, restaurants, the ferry and all that downtown Vineyard Haven has to offer. Also includes a detached one car garage, lush landscaping and grass, mature trees and an extra downstairs toilet and shower for after beach use (not included in 2.5 bath figuring). Owned by a single family since 1955 and while it has been updated over the years, the original charm of this delightful home remains entirely intact. This house could not be replicated today in its current location. Don't miss this opportunity!

Listed by Elevated Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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56 Hatch Road Vineyard Haven MA

Price$2,995,000

Est. Mortgage: $/month

MLS Number 34941

  • Residential
  • Square Feet 2325
  • Bedrooms 4
  • Bathroom 3
  • Half Baths 2

Ready for summer use! Close to downtown on a quiet side street, this 2,325-SF house with water views and magical morning light is steps away from a secluded beach overlooking the town's outer harbor. With three en-suite bedrooms upstairs and a downstairs den, first-floor and upper decks facing the water, and proximity to the Vineyard Haven Yacht Club and West Chop, this architect-designed contemporary offers comfortable and convenient summer living. The open floor plan flows around a floor-to-ceiling central fireplace, with expansive windows and plenty of built-in storage. The .20-acre corner lot features mature landscaping and a large sunny lawn with a field stone wall. Other amenities in this beautifully renovated home include a spacious garage, central air, unfinished basement, and an airy, light-filled mudroom.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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108 William Street Vineyard Haven MA

Price$2,795,000

Est. Mortgage: $/month

MLS Number 31993

  • Residential
  • Square Feet 5534
  • Bedrooms 7
  • Bathroom 6
  • Acreage 0.657

Reduced & Ready for Sale! Location, Location, Location in the historic seaside village of Vineyard Haven. This majestic water view property offers living at its best in a vibrant area of year-round, well maintained and preserved period homes, one block to Main Street and Owen Park with deep water dock, beach, bandstand, and town moorings. Enjoy magical sunrise and moon rise over the ocean. All the benefits of in-town ownership are mere steps away plus clay tennis courts and the elementary school. The ferry dock is ultra convenient for commuters and excursions to the mainland. Located in the heart of the William Street Historic District with Bracketed-Italianate style, this beauty is known as the Captain Benjamin Cromwell House, later as the Clough House. Perfectly proportioned cross gable and cupola, impeccably renovated and maintained, features include 6 bedrooms, 5 baths, oil heat, a/c, spacious vaulted third floor loft, and cupola, plus guest cabin studio-style with kitchenette, full bath, a/c unit, and Rinnai heat. A two car garage, original out house, and his & hers outside shower complete the .66 acre manicured grounds. As the captain of the Island Line transportation service with steam-powered side-wheelers, the Eagle's Wing and later the Monohansett, this property was an emblem of Captain Cromwell's success and enhanced by its prominent physical setting with surrounding decorative caste iron fencing and grounds. The architecture, water views, spacious front veranda, interior spaces with 9' and 10' ceilings, crown molding, gleaming antique wood floors, and history will captivate the attention of the most discerning buyer. The original village of Holmes Hole became the Town of Vineyard Haven in 1871 and later Tisbury. William Street was the second street laid out by the village in approximately 1831 and has consistently maintained its look with its historic 19th century homes. Truly a rare in-town opportunity. Furnishings available separately. In summary, this property needs to be seen to be fully appreciated. Please see floor descriptions for more detail.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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92 Main Street Vineyard Haven MA

Price$2,100,000

Est. Mortgage: $/month

MLS Number 34789

  • Residential
  • Square Feet 6330
  • Bedrooms 7
  • Bathroom 6
  • Half Baths 1

The Captain Dexter House, ca. 1843, has a storied history. Originally owned by one of the Island whaling captains, this home has had several iterations, including the most recent in 2004 when a 3 story addition completed the restoration of this charming historic residence set in the heart of the seaside village of Vineyard Haven. The restoration included the preservation of the original architectural details while bringing the home into the present century with the addition of the country kitchen including a large center island and top of the line appliances, informal dining area and family room with a fireplace and access to the garden patio. Conveniences include a walk-in pantry, powder room and full bath, and laundry room. Formal and informal living areas can be found throughout the house as well as seven bedrooms and six and one-half baths. There are five working fireplaces including the master bedroom suite. All mechanical systems have been completely updated including central AC. Exterior living areas feature a balcony off the second floor sitting area, covered porch with views of the harbor, newly fenced bluestone patio with mature plantings, tiered perennial gardens and private parking for 3 cars. Theater, restaurants, boating and the beach are within footsteps of this gracious in-town residence. Walk to the library and elementary school. Offered fully furnished with a list of exclusions, attached. Substantial rental history.

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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