Vineyard Haven Homes For Sale

Vineyard Haven, MA, (also known as Tisbury) is the gateway to Martha’s Vineyard with the only year-round ferry service to and from the mainland. Vineyard Haven Real Estate is situated around the historic, colonial harbor with great restaurants, shops and more. This lovely, convenient town offers a great selection of homes for sale with both beachfront and lakefront property thanks to the real estate on Lake Tashmoo and Lagoon Pond. Learn more about Vineyard Haven. We take great pride in our ability to connect you with your perfect Martha’s Vineyard vacation home. 

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1153 Main Street

Price$11,750,000

Est. Mortgage: $/month

MLS ID 33535

  • Residential
  • Square Feet 5345
  • Bedrooms 8
  • Bathrooms 6
  • Half Bath 1

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 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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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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71 Stoney Hill Road

Price$4,395,000

Est. Mortgage: $/month

MLS ID 33865

  • Residential
  • Square Feet 5598
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 2

Designed to afford expansive and protected views, the upscale property at 71 Stoney Hill Road is adjacent to Malabar Horse Farm. It consists of a 5 bedroom post and beam home and matching barn. Both are architectural masterpieces created by master craftsmen. The home was designed by Phil Regan of Hutker Architects and built by Jim Cranston of Offshore Timber Framing. It centers around a 1,000sf open living, dining, and kitchen area anchored by a floor to ceiling stone fireplace at one end and a chef's kitchen and pantry complex at the other. The home is surrounded by over seven acres of bucolic nature in fields, meadows, and woodlands. Adjacent to the property is over 200 acres of MV Land Bank property, giving complete privacy and tranquility with no visible neighbors. This location has access to Land Bank walking trails as well as island bike paths. Expansive and protected views from anywhere in the house provide manicured yet natural grounds for the discerning buyer. In addition, both the barn and the house have newly installed solar roof systems which create an electric surplus during the year. The entire home is also set up as wheelchair accessible with a large elevator to access the bottom floor. The main house is level with the surrounding property negating the need for entrance steps. Much of the home has custom built-in cabinetry and woodwork created by a master Island craftsman, Ken Lobdell. The finished product must be seen to be appreciated; it's as spectacular as the day it was finished.

Listed by Priestley Smadbeck & Mone

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS ID 33742

  • Residential
  • Square Feet 7046
  • Bedrooms 5
  • Bathrooms 4
  • Half Bath 2

VINEYARD HAVEN HARBOR WATERFRONT WITH A POOL - A premier location on Vineyard Haven Harbor with expansive views of all the activity. Set back on 1.7A, with 150' of private beach, this property offers a spectacular pool, surrounding landscaping, and a 5 bedroom, 7,046 sf home, 2 car garage impeccably designed by premier architect, Patrick Ahearn. A dramatic foyer separates the casual side of the house from the more formal rooms. The spacious kitchen to the left, with a view of the Harbor, incorporates a casual sitting area with fireplace and a separate bar area. Wide French doors open to a large porch with stone fireplace, where you will enjoy the smell of the ocean, breezes, and feeling of what summer is all about on the Vineyard. The outstanding dining room overlooks the entire harbor and is centrally located beyond the foyer. The south wing of the first floor includes the formal living room with fireplace, all season porch, and study. The second floor is devoted to the master suite and guest quarters with broad views which deliver varying angles of the Harbor. A long balcony hallway leads to the master suite on the right with an over sized walk in closet, bath and French doors overlooking the lawn and pool to the Harbor beyond. Next to the master suite is a stairway to the widows' walk and the Harbor and stars. The north wing of the house is devoted to three guest bedrooms. A fifth bedroom studio is above the 2 car garage, with sleeping quarters, bath, living space, and kitchenette. It has a private access from the garage or accessed from the guest suite on the second floor. A stunning property with stunning views with proximity to town and the ferry.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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246 Tashmoo Avenue

MLS ID 33779

  • Residential
  • Square Feet 2214
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 1

Potential, Potential, Potential!!! This well maintained, year round colonial 3 bedroom home sits on a lot large enough to have either a 600 sqft guest house, or a garage with a 1 bedroom apartment above. High ceilings, a living room, a family room, formal dining room, kitchen, breakfast nook, and mud room with half bath are all on the first floor. On the second floor you'll find the Master suite, complete with walk-in closet and bathroom, two more bedrooms and a hall bath. The walkout basement boasts an office, 10' high ceilings, and is waiting to be finished off to create more living space. Hardwood floors, ample closet space, new 4 bedroom septic, and access to Tashmoo Opening Beach & community tennis courts are all a part of this lovely home.

Listed by Martha's Vineyard Seacoast Properties

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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84 Quinsigamond Avenue

MLS ID 33741

  • Residential
  • Square Feet 1515
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 1.2

This versatile four level home maximizes space for easy, fun living. Enjoy an open combination/living room/kitchen that opens up to an expansive deck, ideal for summer dining and entertaining. "Treetops" features a special room at the very top of the woods, perfect for the afternoon nap or reading! This low maintenance home is a perfect summer getaway in an ideal location tucked away off Main St. The 1.2 acre lot abuts 85 acres of conservation land and jogging paths.. Close proximity to the West Chop Club, Mink Meadows Golf Club, Lake Tashmoo, and Vineyard Haven are an added bonus! This is a perfect home for the sports enthusiast with easy access to fishing, swimming, clamming, bike riding , and of course, a leisurely walk with views of the Sound.

Listed by Viewpoints

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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16 Mariner Road

Price$879,000

Est. Mortgage: $/month

MLS ID 33702

  • Residential
  • Square Feet 2627
  • Bedrooms 6
  • Bathrooms 4
  • Acreage 0.2942

SURPRISING! SIX Bedroom, FOUR Bathroom, Four LEVEL home with a LEGAL apartment, walk up ATTIC and a GARAGE, in excellent condition. This large Single family home with Accessory Apartment has been tastefully renovated, with a lovely front yard, huge back yard and a wonderful deck for entertaining. Main level has three different living spaces including a large eat in kitchen with painted cabinets, granite counters, movable island and stainless steel appliances. Open plan kitchen and dining area is so large it accommodates a dining table for up to 10, as well as banquette seating! There's also, a living room and a den/tv room, a full bath and a laundry area in terrific mudroom. Upstairs there are Four bedrooms including a Master with an Ensuite complete with jet/soaking tub and shower. Three generous sized guest bedrooms share a full bathroom. Walk up to a huge, bright, functional Attic space. Back on the main living level, the dining area leads out to an enormous mahogany deck with Outdoor Shower overlooking a huge back yard. APARTMENT: Two bedroom accessory apartment on lower level with interior access and walk-out to 'patio' area and back yard. Open plan living room, kitchen with dining area and a full bath. Garage can be used for storage, has a separate entrance and a room above which would make a terrific home office. Walking distance to Tisbury School, town and Ferry. This is a lot of house and must be seen. Title 5 Certification for a 6 Bedroom system in place.

Listed by Alisan Lohan-Conway Properties

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

Price$3,100,000

Est. Mortgage: $/month

MLS ID 33574

  • Residential
  • Square Feet 2072
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

Price$2,795,000

Est. Mortgage: $/month

MLS ID 31993

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

Location, Location, Location! Walk or bike to everything. This majestic water view property offers living at its best in a vibrant area of well maintained and preserved period homes, one block to Main Street and Owen Park with deep water dock, beach, bandstand, and town moorings. Enjoy all the benefits with the village mere steps away, clay tennis courts around the corner, and two blocks to the elementary school. The ferry dock is ultra convenient for commuters and excursions to the mainland. Located in the heart of William Street with Bracketed-Italianate style, this beauty is known as the Capt. Cromwell House, later the Clough House. Perfectly proportioned cross gable and cupola, impeccably renovated throughout, 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. Skip over to Owen Park to your boat or go for a swim and picnic or enjoy magical sunrise and sunset from the cupola. The two car garage, original out house, and his and her 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 the Captain'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 with 9' and 10' ceilings, crown molding, gleaming wood floors, and history will captivate the attention of the most discerning buyer. The historic port 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. Truly a rare, in-town, luxury opportunity. In summary, this property needs to be seen to be fully appreciated. Furnishings available separately.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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77 Massabesic Avenue

Price$1,525,000

Est. Mortgage: $/month

MLS ID 33393

  • Residential
  • Square Feet 3540
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

Enjoy stunning water views from every room of this charming three bedroom Vineyard Haven home. Tucked away off lower Lambert's Cove Road, this post and beam styled house is nestled on over three acres in Lower Makonikey and boasts substantial views of Vineyard Sound from the first and second level. There are many sweet interior details including three fireplaces, a loft space, and a fully finished walk out basement which provides additional living space. The property also offers access to the association's private North shore beach. The house has been thoughtfully maintained by the current owner including new skylights, roof, downspouts, red cedar shingles and new roof. The graceful trees behind the home have been regularly topped and pruned to maintain the broad, deep view. The property offers ample outdoor spaces with deck and patio overlooking gently wooded land, open lawn space, as well as lovely plantings .

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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161 Sandpiper Lane

MLS ID 33338

  • Condominium
  • Village West Chop
  • Square Feet 1780
  • Bedrooms 2
  • Bathrooms 3

A wonderful opportunity to purchase a property in Tashmoo Woods, a private community of single family homes and condominiums on more than 100 acres in Vineyard Haven. This well appointed townhouse is bright, open and spacious with large windows, a fireplace, and a cathedral ceilings. The sun-filled living room opens onto a raised deck with a peaceful view of the surrounding woods. The condominium also features a charming eat-in kitchen, separate dining area, full bathroom, and cozy bonus room (currently being used as a home office) on the main level. A master suite and guest bedroom, both with ensuite bathrooms and ample closet space make up the second floor. Adding to the living space is a finished walkout basement, currently being used as a family room and space for overflow guests. This home was built as part of Phase One of Tashmoo Woods, which means it offers additional features like charming built-in shelving and a full walk out basement. Central air, a garage, and outdoor shower are other features of the unit. The home has been well cared for and has a strong rental history. The association boasts a community pool, tennis courts, a private boat landing and dock onto Lake Tashmoo, walking trails and access to both town and association beaches. Nearby is Mink Meadows Golf Club and the port of Vineyard Haven for dining and shopping. The Property Owners Association takes care of the condo exterior, the roads, and community spaces (pool, tennis courts, beach access) so you can enjoy all the Island has to offer with less of the stress of property ownership.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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