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!

1115 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1115 Main Street

Price$11,950,000

Est. Mortgage: $/month

MLS Number 38728

  • Residential
  • Mls Status Active
  • Bedrooms 11
  • Bathroom 8.5
  • Acreage 0.3145

Step back in time as you explore the old-world charm of this West Chop waterfront grande dame overlooking Vineyard Sound, the Elizabeth Islands, and Woods Hole. Built in 1893 and meticulously maintained and updated over the past century, the much-loved 7,026-sf Victorian home includes many original hand-crafted architectural details. The expansive great room with exposed beams and windows on three sides offers panoramic water views with truly magnificent sunsets, and the adjacent reading room faces a cozy wood-burning fireplace with a door to the covered porch. Flooded with morning light, the kitchen – convenient to the entry mudroom and butler’s pantry/laundry room – features a six-burner Wolf stove, soapstone counters, and sunny breakfast area. Each of the three floors includes a spacious main bedroom with an en-suite bath and expansive water views, for a total of three primary bedroom suites. The fully renovated basement addition – with an underground hallway and door leading to the beach path – also includes two bedrooms, totaling eleven throughout the house. Two bedrooms have fireplaces, and custom built-ins provide plenty of storage. Outside, beautifully crafted stone walls, a south-facing stone terrace, and mature perennial landscaping create a tranquil seaside retreat on .31 acres, with convenient proximity to the West Chop Club and Mink Meadows Golf Club. There’s no shortage of nearby things to do, from tennis and golf to swimming and sailing, but perhaps this property’s greatest appeal is its sense of timelessness, the charm and allure of a bygone era. With only a handful of owners over the generations, now is the rare opportunity to make summers at “Pierside” a part of your family’s history.

Listed by Emily Flake of Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

1005 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1005 Main Street

Price$11,600,000

Est. Mortgage: $/month

MLS Number 38460

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathroom 7
  • Acreage 0.8333

Welcome to 1005 Main St! Located at the northern tip of Martha's Vineyard comes one of the most beautiful oceanfront properties on the entire island. A 5,050 square foot estate with an incredible deck, private beach, lovely painted floors and a ton of space for entertainment is now on the market. A feeling of privacy and peace surrounds this property due to the amazing landscaping, views, and unique character that this home brings. Come watch the sunset from the very spacious and freshly painted deck and be taken away into the immersive environment of the immaculate surroundings. Call and set up an appointment today!

Listed by Ryan Knoechelman of Rovi Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

14 & 22 Cataumet Avenue Vineyard Haven MA 02568

MLS Number 38212

  • Residential
  • Mls Status Active
  • Bedrooms 11
  • Bathroom 8
  • Acreage 1.55

This magical beachfront estate is located in the heart of the exclusive West Chop community on a double lot with 200 feet of beach dune frontage. There are four classic shingle style structures complimenting the property of which all enjoy enchanting views across the expansive rolling lawns and gardens to the beach and breathtaking sunset views over the Vineyard Sound. There are two, turn of the century, five-bedrooms homes, each with extraordinary character including wrap-around porches and 2nd floor balconies. Additionally, there is a charming 1-bedroom/1-bath guest house with cathedral ceiling living room and fireplace, and a studio building offering a fitness area and sauna. This unique compound, set within mature vegetation offering complete privacy, beautiful gardens and specimen trees is just a short walk to the West Chop Club with Mink Meadows Golf Club and downtown Vineyard Haven just minutes away. This is a very special Vineyard property that must be seen if considering the best waterfront offerings.

Listed by Gerrett Conover of Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

52 Mill House Way Vineyard Haven MA 02568

Vineyard Haven, MA52 Mill House Way

Price$10,900,000

Est. Mortgage: $/month

Pending

MLS Number 36702

  • Residential
  • Mls Status Pending
  • Village Downtown
  • Bedrooms 6
  • Bathroom 7

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! No rentals in place, there is still time to be in the house this summer. Easy to show.

Listed by Bobbi Reed of Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

1153 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1153 Main Street

Price$9,500,000

Est. Mortgage: $/month

MLS Number 38206

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 6.5
  • Acreage 0.59

Beautifully sited on a winding, private lane and overlooking pristine North Shore West Chop, conservation trust protected beach, this elegant seaside home flawlessly combines the refined lifestyle of its 1896 origins with a modern style. Meticulously maintained and completely renovated, it is move-in ready for you to enjoy wide, panoramic views of Vineyard Sound and the Elizabeth Islands, dramatic sunsets, natural light, and a fine, sandy beach made for memorable summer days and nights. The house features a first floor that openly flows from an eloquent entrance foyer through dining, living and kitchen areas, and ending up on the most incredible spacious covered porch taking in the magical views of always entertaining boating and fishing activity lawn, gardens, and the Sound. Coastal living has never been easier with its 8 BRs and 6.5 BAs that will make filling this open and airy waterfront home with the happy sounds of summer vacations and family gatherings a breeze. The property is wonderfully landscaped with many specimen trees, nicely framing the lawn and gardens and there is potential to add a swimming pool. Mink Meadows Golf Course and downtown Vineyard Haven are only minutes away. A truly amazing Vineyard property in one of the few remaining N. Shore Martha’s Vineyard private communities!

Listed by Gerrett Conover of Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

47 and 31 Hatch Road Vineyard Haven MA 02568

Vineyard Haven, MA47 and 31 Hatch Road

Price$7,450,000

Est. Mortgage: $/month

MLS Number 37396

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 7
  • Bathroom 6

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 Alyssa Halisky of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

31 Lamberts Cove Road Vineyard Haven MA 02568
Open House

MLS Number 35174

  • Residential
  • Next Open House: Sat 09/25 10:00 am. to 1:00 pm.
  • Mls Status Active
  • Village Tashmoo
  • Bedrooms 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. Additional 3.30 acre parcel. Please inquire. BUYER'S BROKER MUST BE PRESENT AT ALL SHOWINGS AND APPOINTMENTS.

Listed by Brenda Galligan of Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

733 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA733 Main Street

Price$5,450,000

Est. Mortgage: $/month

MLS Number 37140

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 4
  • Bathroom 3.5

Brand-New West Chop Waterfront-Sweeping water views, spectacular sunrises, and a private 143-foot sandy beach anchor this brand-new waterfront home overlooking Vineyard Haven harbor, the East Chop lighthouse, and Nantucket Sound in the distance. Exquisitely finished and move-in ready, this four-bedroom, three-and-a-half bath home with gourmet kitchen features nearly 900 SF of water view outdoor living space with expansive covered porches on the main floor and upstairs. An airy, light-filled open floor plan allows for relaxed ease of movement between the spacious entryway, living room, and kitchen and dining areas, with amenities galore. Enjoy state-of-the-art kitchen appliances, including a wine fridge and pebble ice maker, mudroom/laundry room with its own entrance, sunny outdoor shower and changing area, a built-in propane grill, and plenty of storage areas. Built to current FEMA safety standards, its elevated position dramatically enhances the views and offers ample storage space on the ground level for kayaks, bikes, surfboards, and fishing gear. Two waterview master bedrooms – one on the first floor and another upstairs – include en-suite marble-tiled bathrooms and double closets. Another upstairs bedroom features a beautiful view of the outer harbor, and a fourth bedroom accommodates bunk beds for four. Centering the upstairs bedrooms and full bath is an open sitting area with a wall of French doors offering access to a covered porch overlooking the water, sandy beach, and nearby West Chop Meadow. With its elegant and serene décor, central air conditioning, and furnishings by Vineyard Decorators – available for purchase separately –this 2,581-SF house on .9 acres is ready for immediate occupancy. The private sandy swimming beach with its calm, clear waters and the spectacular water views are clearly the star attraction, but the thoughtful attention to design, details, and craftsmanship make this house a place you will appreciate for its easy living and low maintenance for years to come. The location is superb – close to downtown, Vineyard Haven Yacht Club, Mink Meadows Golf Club, West Chop Club, the 83-acre West Chop Woods nature preserve, and the iconic 1891 West Chop lighthouse. Sailing, tennis, walking and running trails, biking, swimming, fishing, children’s activities, and more are close at hand. Contact listing agent for house plans and details about club memberships. Enjoy the perfect Vineyard summer from your sparkling new, waterfront aerie!

Listed by Emily Flake of Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

71 Stoney Hill Road Vineyard Haven MA 02568

Vineyard Haven, MA71 Stoney Hill Road

Price$5,100,000

Est. Mortgage: $/month

MLS Number 37393

  • Residential
  • Mls Status Active
  • Village Central
  • Bedrooms 5
  • Bathroom 4

Incredible opportunity to own a magnificent home on just over 7 professionally landscaped acres (by Vineyard Gardens and Jerimiah Brown.), nestled in a quiet wooded area of Vineyard Haven. Main house is a beautifully designed post and beam home, 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 2,480sq. ft. massive post and beam barn with concrete floors has been used for special occasion gatherings and additional storage. 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 Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

137 Massasoit Avenue Vineyard Haven MA 02568

Vineyard Haven, MA137 Massasoit Avenue

Price$5,100,000

Est. Mortgage: $/month

MLS Number 38416

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 0.87

Spacious West Chop House with Waterviews - The huge, sun-dappled porch on this family-friendly house, set within the West Chop “loop” in Vineyard Haven, is the perfect place to relax and watch the ferries sailing back and forth to Martha’s Vineyard. Just inside, the soaring great room – with its vaulted ceiling, exposed beams, hardwood floors, expansive windows, and views out to Nantucket Sound – offers a warm and welcoming gathering space. Five bedrooms, three-and-a-half bathrooms, a spacious eat-in country kitchen with adjacent dining room, and plenty of sitting areas throughout allow this much-loved home to accommodate a swell of visiting family and friends with room to spare. The bright and airy master suite upstairs has magnificent northeast views over the water, with a cathedral ceiling, comfortable sitting area, walk-in closet, and full bath. Near the master suite are a walk-through study and den/bedroom, another full bath, and a light-filled bedroom. There are two spacious bedrooms downstairs, together with a third full bath and a half bathroom. Built in 1988 and renovated in 2002, the house has mini-splits, a gas furnace, irrigation, and an outdoor shower, comfortable for year-round living and well-suited for holiday gatherings. Tucked away from Main Street atop a grassy slope overlooking the water, the house is set on .87 acres of quiet woodland and open lawn bordered by a stone wall and meadow plantings. It’s a rare offering in this location, right across the street from the West Chop Club’s Middle Pier and swimming beach. Close by are the West Chop Club, Vineyard Haven Yacht Club, Mink Meadows Golf Club, the 83-acre West Chop Woods nature preserve, and the classic 1891 West Chop lighthouse. Sailing, tennis, walking and running trails, biking, swimming, fishing, children’s activities, and more are close at hand. Please note that 125 Massasoit, an abutting property, is also for sale at $3.1M so enjoy a compound in the heart of West Chop. Contact listing agent for details about club memberships.

Listed by Bobbi Reed of Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

87 Bellevue Avenue and 0 Howard Street Vineyard Haven MA 02535

MLS Number 38276

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3
  • Acreage 2.96

This extraordinary waterfront home sits on a bluff overlooking beautiful Lagoon Pond with views spanning from Eastville Point Beach to the south and Vineyard Haven Harbor and beyond to the north. This is a one-of-a kind property with expansive views, privacy, yet easy access to Vineyard Haven. The home is sited on a total of 3 acres of land, rare for waterfront property, with a landscaped lawn, lush gardens and plantings around the home, a fire pit, hammocks, rope swing and shady, green oak trees. The property features a total of 270 feet of beachfront on Lagoon Pond. The home is a classic Victorian, built in the 1870’s as part of the Innisfall Inn, a summer resort that attracted actors, opera singers, and musicians. The home has been thoughtfully renovated to include updated amenities. The kitchen has been expanded, including a loft above; and an 800 square foot master bedroom suite including private bath, walk-through closet, and an office alcove with Lagoon views added. The generous porch was enlarged to wrap around the new living space, including a painting porch with a sink nestled into the garden. The exterior gable filigree trim and porch of the new construction were carefully matched to the original design of 150 years ago. A guest cottage and storage shed were built as well as two spacious outdoor showers under a floral arbor. The property includes a large parking area and Tesla charger. The interior of the house radiates happiness, with cheerful accents of color grounded by crisp white paint. The charming character of the home remains with the exposed joists, board walls, open ceilings, keeping the feel of the Victorian cottage intact. In Celtic, “Innisfall” means “the abode of peace and rest”, an accurate description of the tranquility and beauty of this property. Downtown Vineyard Haven is a 15 minute walk or short bike ride on the very lightly trafficked Weaver Lane. The waterfront has a nice beach for swimming, canoeing, kayaking, and deep water boating. The property consists of two adjacent lots, so a second home could be built to create a very private family compound, or the lot could be sold to another buyer, or kept as an expansive lawn. A second septic system was installed to facilitate permitting of a second home. The home sits on a 1.57 acre lot with 120 feet of beachfront, and the adjoining second lot is 1.39 acres with 150 feet of beachfront.

Listed by Cassie Bradley of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

125 Massasoit Avenue Vineyard Haven MA 02568

Vineyard Haven, MA125 Massasoit Avenue

Price$3,100,000

Est. Mortgage: $/month

MLS Number 36566

  • Residential
  • Mls Status Active
  • Village West Chop
  • 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 Emily Flake of Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

"Based on information submitted to MA_LINKMV as of September 24, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."