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!

771 Main Street Vineyard Haven MA

Vineyard Haven, MA771 Main Street

Price$15,750,000

Est. Mortgage: $/month

MLS Number 36645

  • Residential
  • Square Feet 5408
  • Bedrooms 7
  • Bathroom 4
  • Half Baths 1

Grand Waterfront Estate - This original 1900's West Chop home has been updated and expanded through the years to result in one of the finest harbor front properties on the Island. Meticulously maintained, this beautiful home includes a private beach with 80 ft. private dock, mooring and panoramic water views allowing you to watch the summer boating activity and the ferry crossings each day. The large open and well-appointed kitchen features top of the line Subzero and Viking appliances, wine cooler, an oversized center island, and butler's pantry, with seating for ten in the nearby dining room. A comfortable den with TV, formal living room, and billiard room surround the kitchen and make up most of the first floor. A favorite space might be the sunroom surrounded by windows with doors leading to a large covered porch and sundeck. A front and rear staircase lead to the second floor where you will find the flawlessly decorated guest bedrooms and the elegant master suite. This water-facing bedroom provides an office area, his + her baths, walk-in closet and a wrap around sundeck with outdoor shower. Water views can be seen from almost everywhere in this home and is complimented by the neighboring beachfront nature preserve. The landscaped lawn and gardens, patio, decks, and porches provide ample places for you to soak up the salt air and enjoy your Vineyard vacation. The privacy of West Chop provides a perfect respite from the mainland.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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1005 Main Street Vineyard Haven MA

Vineyard Haven, MA1005 Main Street

Price$13,900,000

Est. Mortgage: $/month

MLS Number 35775

  • Residential
  • Square Feet 5050
  • Bedrooms 9
  • Bathroom 7
  • Half Baths 1

Presenting one of the most outstanding real estate assets on Martha's Vineyard. 1005 Main Street was built in 1891 and purchased in 1948 by the Singer family who have owned it since. The setting is front and center in West Chop and includes a large private beach and 210-degree views so expansive that you can enjoy sunrises and sunsets from the same chaise lounge on the deck. The views are extremely active with ferries and fishing boats passing in the distance, sailboat races, and at closer range smaller craft including perhaps your own children in a laser or kayak. There are 8 large bedrooms, 7 full baths, and a 2-bedroom apartment in the lower level. The home still exudes olde worlde charm despite all 5,050 sq ft having been completely renovated between 1995 and 2005 with new insulation, HVAC system, and updated plumbing and electric. The 400 ft of private beach is a rare asset, and the walkway down to it has been trod by many who have come to love this home and incomparable setting. Of course, with its multiple decks and spectacular views, the home has always been a prime location for entertaining friends and family and so it is helpful to have so much parking - eight spaces plus a two-car garage. The sea wall assures that this property will be here for future generations. Owners may apply separately for membership at the West Chop Club, which offers a wide range of amenities, including use of nearby "middle pier" for loading and unloading.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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14 and 22 Cataumet Avenue Vineyard Haven MA

MLS Number 36803

  • Multi-Family
  • Village West Chop
  • Bedrooms 11
  • Bathroom 8
  • Half Baths 1

EXQUISITE WEST CHOP BEACHFRONT ESTATE - This rare and exquisite beachfront estate features 200 feet of direct frontage on West Chop Trust Beach and is comprised of three 1900's homes with charming architectural details of the era. Privately sited on 1.56 park-like acres, the property features exquisite landscaped grounds with mature trees and plantings, gorgeous perennial gardens and a magnificent lawn that stretches to meet the edge of the shoreline. The five-bedroom MAIN HOUSE was perfectly designed for entertaining and to enjoy the amazing views and sunsets across Vineyard Sound. The enchanting one-bedroom GUEST COTTAGE is loaded with charm -- and the nearby STUDIO building offers a fitness retreat with dry sauna. Sitting along the front row, the majestic five-bedroom BEACH HOUSE is a classic, turn-of-the-century shingle-style home with an expansive wraparound deck and front-row views across the sound. This rare beachfront estate offers an idyllic setting for gathering family and friends to create special experiences and treasured memories for years to come. Located within walking distance to the West Chop Club, within close proximity to Mink Meadows Golf Club and just two miles to downtown Vineyard Haven, this property offers all the essentials for a perfect island lifestyle. NOTE: This property is being offered as a combined ensemble as shown here -- or the two properties may also be purchased separately. See LINK listings #36795 and #36796 for more details.

Listed by Point B Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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52 Mill House Way Vineyard Haven MA

Vineyard Haven, MA52 Mill House Way

Price$11,500,000

Est. Mortgage: $/month

MLS Number 36702

  • Residential
  • Village Downtown
  • Square Feet 7101
  • Bedrooms 6
  • Bathroom 6

This gracious, impeccably detailed, three-story air conditioned home with guest house and garage overlooks Vineyard Haven harbor towards the East Chop lighthouse, steps away from its own sandy beach and an easy stroll to downtown Vineyard Haven. Thoughtfully sited and designed, the 5,787- sf house on 1.55 acres includes four bedrooms, an expansive living and dining room, and multiple porches with spectacular water views. A graceful gambrel designed house was built in 2004 which incorporates an abundance of windows, red cedar shingles, and copper gutters. The first floor boasts an open living room with a dramatic fieldstone fireplace and a wall of French doors with views of the harbor. The gourmet kitchen adjoins a screened in porch for that perfect sunset dinner. Enjoy multiple outside sitting areas including a porch, another screened in porch and an outside kitchen and dining table on a sunny bluestone terrace. The second floor has a breathtaking master suite with an enviable master bathroom. Completing the second floor are three more bedrooms en suite and two sitting rooms. A third floor with large open spaces and sweeping views, especially from the widow's walk, will entice you for that afternoon read. Additional amenities include a full walkout basement with wet bar, an exercise room, a media room, plus a state of the art wine cellar and an elevator. This is a very special offering!

Listed by Viewpoints

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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

Vineyard Haven, MA1153 Main Street

Price$10,499,000

Est. Mortgage: $/month

MLS Number 33535

  • Residential
  • Village West Chop
  • Square Feet 5345
  • Bedrooms 8
  • Bathroom 6

This three-story shingle-style air conditioned 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, open lawns, and most importantly multiple possible sites for a pool. 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. This private community affords easy access to beaches, independence and activities for all members, and an appealing lifestyle away from the hustle and bustle of other parts of the island. We are happy to provide all the wonderful amenities available in the West Chop area.

Listed by Viewpoints

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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

Vineyard Haven, MA1153 Main Street

Price$10,499,000

Est. Mortgage: $/month

MLS Number 33954

  • Residential
  • Village West Chop
  • Square Feet 5345
  • Bedrooms 8
  • Bathroom 6

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 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 a 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 a wine cellar, family room or gym. The home was fully air conditioned in 2019 and there is potential to add a pool. Directly in front of the property is a beautiful private conservation trust protected beach ideal for sunning, swimming, tide rides to the dock, kayaking, fishing and of course breathtaking water views and dreamy sunsets. This is a rare opportunity to buy in the heart of West Chop. Privately located, yet close to Mink Meadows Golf, the Vineyard Haven Yacht Club and conveniently close to ferry service, hospital and town center restaurants and shops. West Chop is a unique Vineyard community where families have enjoyed the fellowship of friends and neighbors for generations. See further description under "Comments/Directions" for the benefits of being part of the West Chop community in this special North Shore setting.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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22 Cataumet Avenue Vineyard Haven MA

Vineyard Haven, MA22 Cataumet Avenue

Price$7,250,000

Est. Mortgage: $/month

MLS Number 36795

  • Residential
  • Village West Chop
  • Square Feet 3849
  • Bedrooms 5
  • Bathroom 4

BEACHFRONT BLISS ON WEST CHOP. Quietly set on private lane in West Chop and bordering 167 feet of beachfront, this charming 1900's summer home enjoys superlative front-row water views and evokes images of quintessential Vineyard summer days spent living by the sea . . . fishing, clamming, doing “tide rides” down the shoreline, riding bicycles, reading books and more. This turn-of-the-century, shingle-style home features classic architectural details of the era and features an open first-floor living area that opens out onto an expansive wraparound deck overlooking gorgeous park-like grounds and a sandy path that meanders through beach grass to West Chop Trust Beach. Framed between blue skies and sparkling blue waters Sound of Vineyard, this charming seaside home is a perfect place to gather family and friends and create treasured memories for years to come. Located within walking distance to the West Chop Club, within close proximity to Mink Meadows Golf Club and just two miles to downtown Vineyard Haven, this property offers all the essentials for a perfect island lifestyle. NOTE: This rare beachfront retreat is part of a larger 1.56-acre, three-home estate, which is being offered as a combined ensemble for $13,490,000. See LINK ID#36803 for more details.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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31 Lamberts Cove Road Vineyard Haven MA

MLS Number 35174

  • Residential
  • Village Tashmoo
  • Square Feet 5732
  • Bedrooms 6
  • Bathroom 6

Tashmoo Farm, originally built before the Revolutionary War, has been meticulously and tastefully restored to preserve the historic character and grandeur. This gracious home is in pristine condition and now features 6 bedrooms, 5 full baths, 3 half baths, several sitting rooms, a more formal living room, dining room and family room. All new heating and A/C. The newly renovated kitchen includes 2 Sub Zero refrigerators, a Bosche dishwasher, Thermador double ovens and a five burner stove top. Many complimenting features include original moldings, 7 fireplaces, wide pine and fir floors and all new windows. A har-tru tennis court, gunite pool and a delightful pool house were added in the late 1990's. The pool house is accessible to both tennis and pool through oversized doors that lead to private patios covered by a pergola. It's is well equipped for entertaining with grill area and wet bar, a changing room and full bath. Beautifully landscaped grounds with expansive lawns overlooking rolling meadows, extensive perennial gardens surrounded by stone walls offers exceptional privacy. Access to Lake Tashmoo and the association dock.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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14 Cataumet Avenue Vineyard Haven MA

Vineyard Haven, MA14 Cataumet Avenue

Price$6,950,000

Est. Mortgage: $/month

MLS Number 36796

  • Residential
  • Village West Chop
  • Square Feet 3822
  • Bedrooms 6
  • Bathroom 3

WEST CHOP BEACHFRONT CHARMER WITH GUEST COTTAGE and STUDIO. Sited on a quiet and private lane in West Chop, this wonderful 1900's gem is sited on an acre of exquisite park-like grounds that border the West Chop Trust Beach, creating a special and private sanctuary near the sea. Boasting delightful and charming architectural features of the era, the home offers a warm and inviting style -- as well as spacious indoor and outdoor living areas ideal for entertaining family and friends. The property is comprised of a 5-Bedroom Main House, a 1-Bedroom Guest Cottage and a separate Studio with fitness room and dry sauna. The property can be enjoyed as-is or transformed into a signature waterfront compound (conceptual renderings are available). Located within walking distance to the West Chop Club, within close proximity to Mink Meadows Golf Club and just two miles to downtown Vineyard Haven, this property offers all the essentials for a perfect island lifestyle. NOTE: This special West Chop property is part of a larger 1.56-acre, three-home estate, which is also being offered as a combined ensemble for $13,490,000. See LINK ID#36803 for details.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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20 West Chop Lane Vineyard Haven MA

Vineyard Haven, MA20 West Chop Lane

Price$6,250,000

Est. Mortgage: $/month

MLS Number 35038

  • Residential
  • Village West Chop
  • Square Feet 4704
  • Bedrooms 7
  • Bathroom 5

Panoramic views over Vineyard Sound and the Elizabeth Islands, frontage on Mink Meadows Pond, and a tranquil wooded setting with beautiful mature plantings make this 3.53-acre property feel like a secluded and serene island retreat. A relaxed gathering spot for family and friends, the 4,704-SF house includes seven bedrooms and four-and-a-half baths, separate guest quarters, screened porch, two-car garage, and nearly 2,000 SF of outdoor decking. The great room anchors the house with its soaring cathedral ceiling, brick fireplace, and a wall of windows framing the dramatic sunset water views. The light, airy kitchen is outfitted with a spacious white granite island and countertops, Gaggenau ovens and cooktop, and walk-in pantry. Custom built-in shelves and cupboards throughout provide lots of storage space. Enjoy easy access to the sandy Mink Meadows association beach, along with preferential member status at Mink Meadows golf course. Nearby are West Chop Woods 85-acre nature reserve, Lake Tashmoo, the West Chop community, and Vineyard Haven Yacht Club. Making the most of its peaceful, private location and panoramic views, this beautifully crafted home, with renovation design by renowned island architect Ben Moore, has room for everyone, inside and out. Please call listing office for details on flexible financing.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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37 Pasture Gate Road Vineyard Haven MA

Vineyard Haven, MA37 Pasture Gate Road

Price$5,250,000

Est. Mortgage: $/month

MLS Number 37071

  • Residential
  • Village Tashmoo
  • Square Feet 7604
  • Bedrooms 5
  • Bathroom 4

THE PERFECT VINEYARD RETREAT THAT HAS IT ALL! This property offers all the room you need for today's "stay-at-home" environment. There are wings, lofts, and a private guest suite above the garage, providing a myriad of independent locations and common areas to gather at the beginning and end of the day. The grand entrance sets the tone of this Vineyard estate located on 3.15 acres of land. The home overlooks pastoral fields with surrounding woodlands to create a peaceful setting to retreat amid the dynamics of today's world. The pool area and custom-designed pool house provide an expansive outdoor living space full of sun and fresh air. The owners chose the location in the Tashmoo Association because of the amenities of the community, which provides tennis, a dock, beach, and the proximity to Vineyard Haven Village. An up-Island property in a down-Island location. A grand foyer invites you to the living room on the right with fireplace and French doors to the back patio. The dining room connects the living room to the kitchen, which is more than generous with a breakfast area overlooking the gardens and pool. Open from the kitchen is a custom family/sunroom with views over the fields and horse farm beyond. Behind the kitchen and powder room is a classic study that can convert from a workspace to a den for a social gathering or to watch the game. There are four bedrooms in the main house on the second floor and a third-floor loft. A guest suite is located above the two-car garage with private access. One of the dramatic additions is another living room with fireplace, vaulted, lighted ceiling, bar and powder room with French doors to the pool. The sale also includes a beach lot (32C/4 and 32D/4) just before the opening to Lake Tashmoo with beach access on the Lake and the Sound. Boating from the association dock to your private location, anchoring your boat for a picnic, or digging clams for dinner puts the frosting on the cake or the Vine in Vineyard. If 7,604 sf is not quite enough for your new "stay-at-home" lifestyle, the renovated 2 bedroom cottage at 19 Chappaquonsett is also available as is the horse farm at 67 Lamberts Cove Road.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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645 Lamberts Cove Road Vineyard Haven MA

MLS Number 36604

  • Residential
  • Village Lambert's Cove
  • Square Feet 7050
  • Bedrooms 5
  • Bathroom 5

This commanding, 11+ acre estate offers so much to be appreciated. The spacious hilltop home has gracious and serene interiors, with outstanding water views from nearly every room of its 4 levels. With 3 living rooms and 5 bedrooms, there is room here for everyone to join in the fun, while the 7,000 square feet of living space was designed to allow for plenty of options for quiet moments - to work in the extraordinary 2nd floor office, workout in the 4th level gym, or simply while away a lazy day watching the ferries come and go or imagining yourself out there with the fishermen on Middle Ground and cheering them on to bring in a big one. The rest of the gang can swim and play in the pool, create a grand feast in either the indoor or the outdoor kitchen, head down the hill to the association beach or have a game of hide and seek in the acres of woodland and meadow. Oh, and don't forget those sunsets - or the 4th of July fireworks that can be seen fired off from Woods Hole to Hyannis! On the practical side, the property is comprised of 3 conforming lots on which other homes can be built or which can be sold separately. The undulating landscape invites the creation of outdoor "rooms", while affording absolute privacy from neighbors and traffic from Lambert's Cove Road. You are only a 10-minute drive to all of Main Street's conveniences while feeling light years away from bustling crowds. Offered fully furnished and equipped, much of the artwork, both inside and in the sculpture park, will be made available to the buyer by separate purchase.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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