Vineyard Haven Real Estate

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Search all listings for sale in this Martha's Vineyard villages. Vineyard Haven is considered the island’s most year-round community. Find properties on the historic streets of Main and William Street, as well as on West Chop, Lake Tashmoo, Lagoon Pond, and Vineyard Sound.

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575 Chappaquonsett Road, Vineyard Haven, MA

MLS Number 33192

  • Residential
  • Square Feet 2446
  • Bedrooms 6
  • Bathroom 3
  • Half Bath 1

Waterfront on Lake Tashmoo. Also known as "The Peg House", this 6 bedroom home is located on over 8 acres abutting 60+ acres of conservation land. The home was carefully designed and built to take advantage of water views from almost every room. The first floor holds two bedrooms, one of which is the master bedroom positioned on its own side of the home to provide for the utmost in privacy. The kitchen and dining room are open to the living room which flows seamlessly on to a large screened-in porch. The second floor boasts 4 bedrooms, two of which maintain water views, and 2 full bathrooms. The property also features direct water access to Lake Tashmoo, with a small dock perfect for launching kayaks and paddle boards, and a private beach on the north shore just a short walk or paddle away.

Listed by Wallace & Co. Sotheby's

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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124 Skiff Avenue, Vineyard Haven, MA

Price$375,000

Est. Mortgage: $/month

MLS Number 33550

  • Condominium
  • Village Lagoon
  • Square Feet 611
  • Bedrooms 2
  • Bathroom 1

This meticulously maintained condo is located in the Causeway Harborview Association with a short walk to town and ferry. There is a distant view of the Vineyard Haven Harbor from your living room window and the community pool is near your back door. This is a fabulous association to be part of and one of the least expensive properties to live year round on Martha's Vineyard. The association has outdoor grilling, picnic tables and coin-operated laundry. Very low maintenance and upkeep for the property owner and this unit comes fully furnished so it is move-in ready! Enter the front door and pass through the galley style kitchen which leads you into the living room and dining area. There are two comfortable bedrooms and a full bath. A parking spot is included where you can keep your on-island car. A great investment for year round or seasonal living.

Listed by Martha's Vineyard R.E.

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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24 Union Street, Vineyard Haven, MA

MLS Number 33599

  • Commercial
  • Village Downtown
  • Bathroom 1

Great opportunity to own a prime commercial building in a high traffic location. Good views of the harbor, a great location for the right business. Very close to the Steamship Authority dock. Potential for expansion in the second floor attic space. (Current tenant's business is not included).

Listed by Cronigs Real Estate

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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8 Sagamore Avenue, Vineyard Haven, MA

Price$4,475,000

Est. Mortgage: $/month

MLS Number 33185

  • Residential
  • Village West Chop
  • Square Feet 1847
  • Bedrooms 4
  • Bathroom 2

Breathtaking views from this ideally situated 4-bedroom home overlooking Vineyard Sound, the Elizabeth Islands, and Mink Meadows Pond. Enjoy majestic sunsets from almost every room in the house and especially from the 1,112-s.f. deck! The combined living room and dining area feature expansive windows and sliders, all with panoramic views. This is easy living, with a den or fourth bedroom on a quiet lower level. A classic contemporary, it offers maximum privacy on 2.45 acres, convenient to Mink Meadows Golf Club, West Chop Woods nature preserve, the West Chop Club community, and downtown Vineyard Haven. A birdwatcher's dream, the peaceful tranquility and wildlife of the protected pond area are mesmerizing. Owned, loved, and well-maintained by the same family for over 55 years, this is a rare opportunity to purchase north shore waterfront with panoramic views of sunsets and ferry watching plus direct water access to a West Chop Trust beach. Please call listing office for more beach information. Heat is solar-assisted panels with electric backup.

Listed by Viewpoints

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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62 Weaver Court, Vineyard Haven, MA

Price$1,495,000

Est. Mortgage: $/month

MLS Number 33549

  • Residential
  • Village Lagoon
  • Square Feet 4557
  • Bedrooms 3
  • Bathroom 4

IDYLLIC ISLAND RETREAT. Privately set on 1.2-acres of beautiful landscaped grounds and gardens, this classically styled New England colonial is an idyllic retreat for gathering family and friends and creating many years of treasured Vineyard memories! Built as a dream home by an accomplished builder/owner, this meticulous home offers over 4500 square feet of living space perfectly designed for easy living and entertaining. The home has plenty of extra space to comfortably accommodate guests -- including an expansive third-floor living space with views of Vineyard Haven Harbor PLUS another private living space above the attached garage. The warm and inviting first floor living areas open out onto an expansive mahogany deck, perfect for alfresco dining and entertaining during the summer months and there is also room to install an in-ground pool (Conservation Commission approvals in-hand). Vineyard Haven Village is just a mile away -- offering convenient access to ferries, restaurants, shopping, movie theaters and more! Enjoy a brisk walk into town for your morning coffee or breakfast at Art Cliff Diner or The Black Dog. Savor quiet afternoon walks at the nearby Land Bank Ramble Trail Preserve. Stroll to the nearby public beach and boat launch on The Lagoon and launch your kayak, canoe or paddle board for an enjoyable afternoon out on the water. This beautifully crafted home embodies all the best of island living and is ideal for seasonal or year round living, a multi-generational retreat or a great vacation rental property. An exceptional home -- at an exceptional value!!

Listed by Point B Realty LLC

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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, Vineyard Haven, MA

Price$3,300,000

Est. Mortgage: $/month

MLS Number 33574

  • Residential
  • Village West Chop
  • Square Feet 2072
  • Bedrooms 4
  • Bathroom 2

**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. Comes with a plan and approval from the board of health for a new 5 bedroom septic. This house could not be replicated today in its current location. Don't miss this opportunity!

Listed by Elevated Realty LLC

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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, Vineyard Haven, MA

Price$3,000,000

Est. Mortgage: $/month

MLS Number 31993

  • Residential
  • Village Downtown
  • Square Feet 5534
  • Bedrooms 7
  • Bathroom 6

Majestic water view property in the heart of the William Street Historic District with superb Bracketed-Italianate style, known as the Captain Benjamin Cromwell House and later the Clough House. This commanding period home with perfectly proportioned cross gable and cupola, is year-round, impeccably renovated and maintained, and in move-in condition. Amenities include 6 bedrooms, 5 baths, oil heat, a/c,1,100+/- s.f. third floor loft, cupola, and cabin/guest house with studio bedroom, kitchenette, full bath,a/c, Rinnai heat, 2 car garage, outside shower, and original out house on .66 manicured grounds. As the captain of the Island Line transportation service between New Bedford, the Vineyard, and Nantucket with his steam-powered side-wheelers, the Eagle's Wing and later the Monohansett, this property was an emblem of Captain Cromwell's success and enhanced by its prominent physical setting with surrounding ornate caste iron fencing. The architecture, water views, spacious front veranda approximately 440 s.f., interior spaces with 9' and 10' ceilings, crown molding, gleaming antique wood floors, horse hair plaster, and history will captivate the attention of the most discerning buyer. The original village of Holmes Hole became the town of Vineyard Haven in 1871 and later the town of Tisbury. William Street was the second street originally laid out by the village in approximately 1831. The William Street Historic District is unique in that it has consistently maintained its look with its historic 19th century homes. Truly a rare, in-town opportunity with access to the park, deep water dock, beach, harbor, and clay tennis courts only steps away. In summary, this property needs to be seen to be fully appreciated. Please read floor descriptions for more details.

Listed by Viewpoints

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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83 Main Street, Vineyard Haven, MA

Price$2,250,000

Est. Mortgage: $/month

MLS Number 33532

  • Residential
  • Village Downtown
  • Square Feet 2513
  • Bedrooms 3
  • Bathroom 2

Historic waterfront home, renovated in 1997, with spectacular views of extensive gardens and Vineyard Haven Harbor. This unique property offers the convenience and congeniality of an in-town location, as well as a private sanctuary, where almost an acre of land slopes gracefully to a private beach. A two bedroom home that "lives" like three, with more than 2500 sf of living space. A breezy open plan, renovated to provide all modern amenities, features a large eat-in kitchen, dining room and living room, all with harbor views. Both second floor bedrooms, one with a deck also offers expansive views of the harbor, dotted in season with anchored sailboats. The substantial Master Bedroom Suite, with two gable ends permits ample space for a king size bed, spacious sitting/TV area, built-in desk, ensuite bath and even a large ficus tree. Many windows, french doors and skylights provide beautiful light throughout the house. Relax on the large decks, upstairs and down, while enjoying great views and harbor activities before strolling to dinner or theater in town. All this and three private parking spaces. It's no wonder this property has enjoyed excellent vacation rental history. This property has an approved 4-bedroom septic. NOTE: Interior photos show the house as it appears currently as well as how it appeared furnished.

Listed by Coldwell Banker Landmarks

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 Uncatena Terrace, Vineyard Haven, MA

Price$1,425,000

Est. Mortgage: $/month

MLS Number 32770

  • Residential
  • Village Lambert's Cove
  • Square Feet 2012
  • Bedrooms 3
  • Bathroom 2

Relax and unwind in Lower Makonikey - the perfect location offering a private, up-island atmosphere yet not far from town, with access to a lovely association beach. The contemporary home is attractive and has been well maintained by the single owner. Maximum views of the lush landscape are achieved through large expanses of glass and all rooms boast high ceilings and are filled with abundant light. Also enjoy peaks of the Vineyard Sound from the second floor landing and deck. An open concept layout with spacious kitchen, dining area and living room, first floor master suite and two second floor guest bedrooms, the home is ideal for living the vineyard lifestyle.

Listed by Sandpiper Realty

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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, Vineyard Haven, MA

Price$1,750,000

Est. Mortgage: $/month

MLS Number 33393

  • Residential
  • Village Lambert's Cove
  • Square Feet 3540
  • Bedrooms 3
  • Bathroom 3

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

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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 A VisitAsk A QuestionMore Details