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: 3.6% last updated on Aug 15, 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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37 Pasture Gate Road

Price$5,250,000

Est. Mortgage: $/month

MLS ID 33630

  • Residential
  • Square Feet 7604
  • Bedrooms 5
  • Bathrooms 4
  • Half Bath 2

A prestigious home designed by a meticulous owner. The property has evolved over the years in updates and numerous expansion projects. When you love where you live, a property such as this is the result. The owners chose the location in the Tashmoo Association because of the tranquil pastoral setting overlooking the grazing fields, the amenities of the community which provides tennis, a dock, beach and the proximity to Vineyard Haven Village. With 3.15 acres of land, there was more than adequate room to create a spacious estate setting. As you approach the house, the feeling of relaxed elegance is apparent. It is evident that the expansive home with 7,604 sf of living space will offer room for all. The surrounding landscape and natural, wooded space create an exceptional setting. The details in the house abound from the formal living room and dining room, the large well-designed kitchen, the newer addition year round sun porch, the beautiful den to retreat to, and the newest addition, a contemporary incredible living room/dining room with fireplace and custom designed ceiling, to name a few highlights. An extensive pool area has room for many lounge chairs and tables for dining along with a pool house. A fifth bedroom suite is above the oversized 2 car garage. The second floor is dedicated to the en suite master bedroom, three guest rooms, and a superior bonus room with high ceilings and large windows. A finished third floor is there for your interpretation. 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 you need more space for your family compound, the renovated, fully furnished cottage on 1.06 A at 19 Chappaquonsett (54C/ 2) is also available at $1.5M. See photos attached to this listing. This property provides all the components to establish a family estate for generations to come on this magical Island of Martha's Vineyard.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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 146' 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: 3.6% last updated on Aug 15, 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: 3.6% last updated on Aug 15, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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$2,950,000

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: 3.6% last updated on Aug 15, 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 harbor view property offers living at its best in a vibrant area of well maintained and preserved period homes just one block to Main Street or Owen Park's deep water dock, beach, bandstand, and boat moorings. Enjoy all the benefits with the village mere steps away, clay tennis courts around the corner, and two blocks to the Tisbury school. The Steamship ferry dock is ultra convenient for commuters and excursions to the mainland. Located in the heart of William Street, this Bracketed-Italianate style gem is known as the Capt. Benjamin Cromwell House and was carefully sited on the highest point of the property. Perfectly proportioned cross gable and cupola, impeccably renovated and updated throughout, features include 6 bedrooms, 5 baths, chef's kitchen, oil heat, a/c, spacious finished attic with soaring peaks. Don't forget the adorable cabin guest house with its climbing roses plus the two car garage while overlooking the .66 acre manicured grounds. Skip over to Owen Park to your dinghy or kayak, grab a morning swim or stretch on the beach, or simply soak up a magical sunrise or reflective sunset while the sea ebbs and flows nearby. As the captain of the old 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. The architectural details, water views, spacious veranda, gleaming wood floors, 9' ceilings, crown molding, and more will captivate the attention of the most discerning buyer. The historic port of Holmes Hole became Vineyard Haven in 1871 and later Tisbury. William Street was the second street laid out by the village in 1831 and has consistently maintained its look. Truly a rare, in-town, luxury opportunity, in turn-key condition - a property which needs to be seen to be appreciated. Furnishings available separately.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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: 3.6% last updated on Aug 15, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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733 Main Street

Price$3,250,000

Est. Mortgage: $/month

MLS ID 33134

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

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

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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48 Sandpiper Lane

Price$1,299,000

Est. Mortgage: $/month

MLS ID 32353

  • Residential
  • Square Feet 2260
  • Bedrooms 4
  • Bathrooms 3
  • Half Bath 1

WEST CHOP - Elegant and uniquely styled home in desirable Tashmoo Woods, on the last remaining lot within view of Mink Meadows Golf Course. This home has tremendous curb appeal. Front entrance via a vestibule, creating a nice transition into the home. Main living level has an Open Floor Plan, 9 foot high ceilings, striking 'two over two' oversized windows, Custom Trim Detail, Wood Burning fireplace and Wide Oak flooring throughout. Living room flows seamlessly to the dining area and kitchen. Large Custom Kitchen with Cream Cabinets (including oversized upper cabinets and numerous roll out shelves) beautiful mink colored Quartz counter tops, complementary Sea Glass backsplash and Stainless Steel appliances with a Cook's gas stove. Kitchen looks out over back yard and woodlands towards Mink Meadows and is adjacent to the garage for ease of access with groceries! Ground Floor Master Suite with Custom Trim and Wainscoting throughout, Walk in Closet, Double Vanity, Large Custom Tiled shower with Seamless Glass door. Upstairs to the Second Master Bedroom Suite, also with a Double Vanity, Quartz counters, Custom Closets, Custom Tiled floors and Shower with Seamless Glass Enclosure, Separate Water Closet and Custom Trim Detail! Two additional guest bedrooms share a bathroom with Tiled Tub and Wainscoting. Access to large storage area over garage. Second floor also has Wide Oak Flooring throughout, not a carpet in sight!! Multi zone Central Air-conditioning and forced hot air Heat. Full Basement. Front porch with Mahogany deck and Blue Stone Patio in rear yard off dining area. Mahogany clad Outdoor shower. Tashmoo Woods has numerous amenities including Association Tennis, Swimming Pool, Clubhouse, Dock and Private Beach Access. Minutes to Lake Tashmoo, Mink Meadows Golf, West Chop Club, Vineyard Haven Yacht Club, Restaurants, Shopping and Ferry. Move in ready. Empty and easy to show!

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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