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!

103 Main Street Vineyard Haven MA

Vineyard Haven, MA103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS Number 37110

  • Residential
  • MlsStatus Active
  • Square Feet 7046
  • Bedrooms 5
  • Bathroom 4

THE ULTIMATE WATERFRONT RETREAT - The Vineyard has always been the place to go for R&R, and if you needed it in the past, you certainly need it now. It is the oasis of beauty and tranquility in a vintage community. This property offers the best of the Island. Located on Vineyard Haven Harbor, the home sits on a large 1.7A parcel of land, which provides privacy, spectacular views of harbor activity, yet steps away from the Village for your morning coffee, afternoon shopping, and dinner and theater in the evening. A unique feature is proximity to the ferry to come to and leave the Island easily. Think of it - the kids who will probably be with you a lot more, Mom and Dad, who will visit, and the family workforce can easily use the Vineyard home as "operation center," adjusting to the new lifestyle perfectly. Designed by premier architect Patrick Ahearn, with 7,045 sf, the home is warm and friendly with space to accommodate everyone's needs. The large kitchen with sitting room and fireplace opens to a screened porch. A dramatic stone fireplace is the focal point of the sitting area on the porch with generous room for dining for twelve with views of Harbor activity. This space is the hub of the house. There is a large, quiet office on the first floor for serious work along with a smaller office space off the kitchen. A grand formal dining room with a fireplace and living room is designed for special occasions. Another all-season sun porch on the first floor provides additional space for a variety of activities. The informal and formal areas connect with an outdoor patio. The master bedroom suite with a sitting area occupies the south wing of the second floor and is cleverly separated from the activity of the household. Three more bedrooms are in the north wing of the house. Another expansive deck connects both wings. The views from the first floor are spectacular, and they become panoramic and magnificent on the second floor. There is a guest suite over the two car garage which can be accessed from the outside or the adjoining deck on the second floor. The piece de resistance is the widow's walk offering the most brilliant views. The terraced pool and built-in outside grill overlooking the Harbor complete this perfect Vineyard home.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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$12,999,000

Est. Mortgage: $/month

MLS Number 35775

  • Residential
  • MlsStatus Active
  • Square Feet 5050
  • Bedrooms 9
  • Bathroom 7

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: 2.77% last updated on Jan 21, 2021
* 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$10,900,000

Est. Mortgage: $/month

MLS Number 36702

  • Residential
  • MlsStatus Active
  • 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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$
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$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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$9,999,500

Est. Mortgage: $/month

MLS Number 33954

  • Residential
  • MlsStatus Active
  • 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: 2.77% last updated on Jan 21, 2021
* 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$9,999,500

Est. Mortgage: $/month

MLS Number 33535

  • Residential
  • MlsStatus Active
  • 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: 2.77% last updated on Jan 21, 2021
* 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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47 and 31 Hatch Road Vineyard Haven MA

Vineyard Haven, MA47 and 31 Hatch Road

Price$7,950,000

Est. Mortgage: $/month

MLS Number 37396

  • Residential
  • MlsStatus Active
  • Square Feet 6476
  • Bedrooms 7
  • Bathroom 5

Elegant and refined, this exceptional estate property is sited on 1.3 acres. Located in the coveted Hatch Road neighborhood, this 2 home property boasts incredible architectural detail with all the modern amenities. As you enter the property via a winding gravel drive past an expansive lawn, you come to a setting not found so close to downtown Vineyard Haven. The main house dates back to 1900 and has been meticulously renovated and features a gourmet kitchen open to a dining room with french doors looking out to a rose garden, a spacious first floor master bedroom suite, dramatic great room with 20 foot ceilings with wood detail, and an inviting screened-in porch leading out to a private brick patio. The home features 4 additional guest bedrooms on the second floor. The guest house was designed in 2008 and built by a prominent Martha's Vineyard builder. The wood detail includes aged lumber and the walls are warmly lined with recycled barnwood. Stunning museum quality terrazzo flooring inlaid with wood beams and terrazzo countertops are featured in the spacious great room, gourmet kitchen and dining room. Other guest house amenities include two bedrooms with en suite baths each with stunning wide plank flooring, and a spacious loft perfect for a home office. A home gym/pool house, outdoor kitchen, 2 car-garage and pool complete this rare offering.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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71 Stoney Hill Road Vineyard Haven MA

Vineyard Haven, MA71 Stoney Hill Road

Price$7,300,000

Est. Mortgage: $/month

MLS Number 37393

  • Residential
  • MlsStatus Active
  • Square Feet 9065
  • Bedrooms 10
  • Bathroom 6

Incredible opportunity to have your own family compound on almost 15 acres, nestled in a quiet wooded area of Vineyard Haven. Main house is a beautifully designed post and beam home, sits on 7.17 professionally landscaped acres, by Vineyard Gardens and Jerimiah Brown including 15 zones of irrigation, and a regulation horse shoe pit. Consisting of 5 bedrooms and 3 1/2 baths it's open living at it's finest! Gourmet Chef's kitchen with 48"Sub Zero fir paneled refrigerator and 36" Wolf induction 5 burner stove and pantry with double Thermador ovens and a gorgeous fireplace, living room and dining room. Custom built-in cabinetry throughout house, and cypress ceilings and white ash floors. Two offices, one has a separate outdoor entrance, perfect for a home business. Incredible media room with a 10' screen and overhead projector, 7 speakers and 4 sub-woofers. 4,000 sq. ft. screened in porch built by Johnny Hoy, perfect for entertaining and relaxing. Property is surrounded by over 200 acres of MV Land Bank property with access to Land Bank walking trails. The entire home is set up as wheelchair accessible with a large elevator to access the bottom floor, and entire home is 100% solar powered. A 2,500sq. ft. massive post and beam barn with concrete floors has been used for special occasion gatherings and additional storage. Second dwelling consisting of a 5 BR 3.5 BA, 2 car garage with apartment and is perfect for additional family members. Four stall horse barn completes this compound. Please copy and paste the following link into your browser for virtual tour https://my.matterport.com/show/?m=Ug5DLd5xrhW&mls=1?ts=1

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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
  • MlsStatus Active
  • Square Feet 5732
  • Bedrooms 6
  • Bathroom 6

Why would you need to leave home? this extraordinary estate offers everything one needs for privacy and seclusion in a safe at home setting. Tashmoo Farm has been meticulously and tastefully restored to preserve the historic character and grandeur yet offers all of today's modern amenities. 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, family room and home office. 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 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, association dock and several walking trails. BUYER'S BROKER MUST BE PRESENT AT ALL SHOWINGS AND APPOINTMENTS.

Listed by Karen M. Overtoom R.E.

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$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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

Vineyard Haven, MA733 Main Street

Price$5,890,000

Est. Mortgage: $/month

MLS Number 37140

  • Residential
  • MlsStatus Active
  • Square Feet 2581
  • Bedrooms 4
  • Bathroom 3

VIEWS! VIEWS! VIEWS! Start 2021 off right with this lovely turnkey home on the water that is ready for immediate occupancy! Enjoy spectacular views from 885 square feet of decking and porch overlooking Sheriff's Meadows and the Vineyard Sound. What could be better than living space and dining outside on a pristine deck. With 120 feet of private beach, you will not find better swimming and boat activity on the island. All your amenities are here including a great outside shower, built in grill area with piped propane, mudroom to wash off the sand, and countless spaces outside to read a good book or to dine! First floor master suite with fantastic sunrises and sweeping water views. Combination kitchen and dining, inside or out, plus a living room viewing a 42 foot long deck with the Sound beyond. Upstairs, another master suite with picturesque Sheriff Meadow views, and a porch to enjoy early morning sunrises and coffee. Another 2 bedrooms and full bath plus a sitting area round out the spectacular 2nd floor. This house is ready for the discriminating buyer looking for that move-in ready home, furniture to be negotiated separately. This ideal location is near the 83 acre West Chop Woods, Mink Meadows Golf Club, the West Chop Club, and the Vineyard Haven Yacht Club. Rarely is there a waterfront in this area with such dramatic views and a total renovation. Don't miss your opportunity to have your own slice of paradise anytime you want to escape to the Vineyard or year-round living! Please call listing office for floor plans and renderings from Squash Meadow. Please view listing sheet for landscaping plans! Easy to show!

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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87 Bellevue Avenue Vineyard Haven MA

Vineyard Haven, MA87 Bellevue Avenue

Price$3,600,000

Est. Mortgage: $/month

MLS Number 35371

  • Residential
  • MlsStatus Active
  • Square Feet 2398
  • Bedrooms 5
  • Bathroom 2

This extraordinary waterfront home sits on a bluff overlooking the desirable Lagoon Pond, with views spanning to Eastville Point Beach and Vineyard Haven Harbor beyond. This home is sited on 1.57 acres of landscaped lawn with brilliant green oak trees and features 120 feet of frontage on Lagoon Pond. A stunning example of the perfect blend of historic charm and modern amenities, this classic Victorian style home was built in the 1870s as part of the Innisfail Inn, a summer resort that attracted famous actors, operetta stars, and musicians, who spent their days enjoying the ocean breeze and perfecting their craft with informal concerts on the wrap-around porch. This home has been thoughtfully renovated to include updated amenities. The kitchen was expanded; an eight-hundred-square-foot master bedroom suite including private bath, a walk-through closet, an office alcove, and air conditioning was added; and the porch was enlarged to wrap around the new living space. The interior of the house radiates happiness, with cheerful accents of color grounded by crisp white paint. Yet the vintage character of the home remains with original exposed joists, board walls, and open ceilings, keeping the feel of the Victorian cottage intact. In Celtic, Innisfail means "the abode of peace and rest", an accurate translation to convey the tranquility and beauty of this property. This is a rare opportunity to own a lovingly maintained home with a long and storied history, but most importantly, this elegant home is the perfect property for generations of gatherings for family and friends. This home directly abuts the vacant land for sale at 0 Howard Street. A buyer looking to keep the same feel and privacy that 87 Bellevue currently holds, should also consider buying the adjacent land with almost 150 feet of Lagoon frontage and a 4-bedroom septic in place.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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125 Massasoit Avenue Vineyard Haven MA

Vineyard Haven, MA125 Massasoit Avenue

Price$3,200,000

Est. Mortgage: $/month

MLS Number 36566

  • Residential
  • MlsStatus Active
  • Square Feet 1830
  • Bedrooms 5
  • Bathroom 3

One of a kind saltbox located in the heart of West Chop. Owned and loved by the same family since 1935, this home was erected on its current site in 1930 incorporating portions of an older (late 1700's) house which had been carefully dismantled and transported from Lambert's Cove to the current West Chop site. This is a wonderful opportunity for a new family to embrace a treasured home with peaks of water. This 5 bedroom, 3 bath home embodies simple summer life on Martha's Vineyard, rocking on the back porch, playing tag in the yard, or enjoying a morning or evening tide ride. Properties on "the Loop" rarely come on the market, this classic is not too be missed!

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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4 State Road Vineyard Haven MA

Vineyard Haven, MA4 State Road

Price$2,600,000

Est. Mortgage: $/month

MLS Number 37691

  • Residential
  • MlsStatus Active
  • Square Feet 5430
  • Half Baths 2
  • Acreage 0.4869

Commercial Opportunity - Right Downtown! This flagship building is the anchor to Main Street. Located right in downtown Vineyard Haven, with more than 20 parking spaces, this building is rich with Vineyard history. This charming brick building was constructed in 1929 to house the telephone company. Next tenants included Community Services offices, a Youth Center on the main level, and a hamburger restaurant in the lower level. Most recently, the beloved art and office supply store, Educomp, has called this home since 1986. This building has a total of 8 office spaces. The lower level features more than 1,950 square feet of office space as well as two additional private offices. The second floor has 5 additional office spaces, ranging in size. Three levels of opportunity in the business district of downtown Vineyard Haven. Come take a look at this property that is a cornerstone of Main Street. *Attached floor plans completed by sellers. There are no bedrooms in this building. Information deemed reliable but not guaranteed.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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