Vineyard Haven Water View Homes

Scroll down to find current water view homes for sale in Martha's Vineyard, MA's town of Vineyard Haven. Look through a variety of listings including luxury homes, cottages, condos and many more. Register with our site to save your favorite properties, and you can get email updates when new listings match your search criteria. For more information, questions, or to schedule a showing, please contact us today!

1153 Main Street, Vineyard Haven, MA

Price$11,750,000

Est. Mortgage: $/month

MLS Number 33954

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

Located on a winding private dirt 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 multi-generational 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 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 wine cellar, family room or gym. Walk from the house through established perennial gardens to the beautiful sandy beach for easy swimming, tide rides to the pier and docks and enjoyment of the water. This is a rare opportunity to buy in the heart of the West Chop community. Contact us for more information about this special North Shore private setting with opportunities for beaches, tennis, golf, and more.

Listed by Tea Lane Associates

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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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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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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1153 Main Street, Vineyard Haven, MA

Price$11,750,000

Est. Mortgage: $/month

MLS Number 33535

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

This three-story shingle-style 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

{$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: 4.52% last updated on Jul 19, 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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104 Hines Point, Vineyard Haven, MA

Price$2,250,000

Est. Mortgage: $/month

MLS Number 33999

  • Residential
  • Square Feet 1544
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.95

104 Hines Point was designed by Breese Architects and was built Baumhoffer Estes, Inc. in 2015. This three bedroom home, each with en suite bath and direct water views, features 1,544+/- square feet of living space on two levels. The first floor holds two bedrooms, and an open living, dining and kitchen space with wood burning fireplace and views to the Lagoon. The second level, reached by a circular metal stair, holds the third bedroom and bath. A raised flagstone patio overlooks the path and stairs that lead down to the beach. A full height basement with laundry, outdoor shower, irrigated landscape, single car garage and additional parking for three vehicles complete the property. Hines Point is within walking distance to the ferries, fish market, restaurants, theaters, shopping and all of the amenities that Vineyard Haven has to offer. 104 Hines Point is offered furnished. The abutting property at 78 Hines Point Road is offered separately.

Listed by Russell Maloney 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: 4.52% last updated on Jul 19, 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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78 Hines Point, Vineyard Haven, MA

Price$3,500,000

Est. Mortgage: $/month

MLS Number 33998

  • Residential
  • Square Feet 2825
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

78 Hines Point, designed by Breese Architects and built in 2008 by Holmes Hole Construction, features 2800+/- square feet of living space on two levels with water views from every room. Two master suites flank each end of the first floor with a central gathering space between…the kitchen, dining and living room with wood burning fireplace. The second level holds two bedrooms with en suite baths. A screened porch with wood burning fireplace is the perfect room to catch the sunsets over Vineyard Sound. Outdoor areas include parking for four cars, irrigated gardens and landscape, outdoor showers, wide flagstone patios and steps down to the beach. A dock at water's edge eases the launching of kayaks, paddle boards and other watercraft for summer enjoyment. Hines Point is within walking distance to the ferries, fish market, restaurants, theaters, shopping and all of the amenities that Vineyard Haven has to offer. 78 Hines Point is offered furnished. The abutting property at 104 Hines Point is offered separately.

Listed by Russell Maloney 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: 4.52% last updated on Jul 19, 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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88 Hatch Road, Vineyard Haven, MA

Price$10,500,000

Est. Mortgage: $/month

MLS Number 33910

  • Residential
  • Square Feet 4054
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 2

Harborfront Vineyard Haven home with private dock and sandy beach. Boasting over 4,000 sq. ft. of living space, this 5-bedroom home has been meticulously re-built to create a sophisticated modern beach house that is conveniently located just outside of downtown Vineyard Haven. Tucked away on peaceful Hatch Road, just a few yards from the Vineyard Haven Yacht Club, the beautifully landscaped yard rolls gently towards the private beach, deep water dock, and mooring coming this summer. Inside, the large open first floor allows for seamless flow between the kitchen, dining room, and living room, as well as the screened in porch and large deck overlooking the water. The expansive views from the second story master are unmatched. The new fully finished basement is comprised of two bedrooms, each with their own bathroom, and a large open recreational space complete with wet bar. A perfect spot to create lasting memories with family and friends in this picture perfect Martha's Vineyard location.

Listed by Wallace & Co. Sotheby's

{$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: 4.52% last updated on Jul 19, 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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103 Main Street, Vineyard Haven, MA

Price$13,500,000

Est. Mortgage: $/month

MLS Number 33742

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

A matchless property on a matchless Island. A premier location on Vineyard Haven Harbor with expansive views of all the activity, a large 1.7A parcel of land which provides unique privacy, a dramatically designed pool and surrounding landscaping, and a 5 bedroom, 7,046 sf home, 2 car garage impeccably designed by premier architect, Patrick Ahearn. The spaces are designed for casual living or an elegant cocktail party. 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. The many windows gets you closer to the smell of the ocean, breezes and feeling of what summer is all about; beaching, boating, watching the ferry in action, good food and good company. Leaving the casual side of the home and meandering beyond the dining room, the south wing of the first floor includes the formal living room with fireplace, all season porch and study. The different textures in each room, from the paneled study, to the softly toned living room and porch adds an element of contrast. The second floor is devoted to the master suite and guest quarters with broad views which deliver varying angles of the Harbor. A long balconied hallway, a gallery for intriguing art, leads to the master suite on the right with an oversized 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. A highly technical powered hatch opens that space for the “Mary Poppins” view. The north wing of the house is devoted to three guest bedrooms. A fifth bedroom studio is privately located above the 2 car garage. It includes sleeping quarters, bath, living space and kitchenette. It has private access from the garage or can be accessed from the guest suite on the second floor. Located on Main Street, the size of the parcel of land allowed the house to be located behind a well- planted front yard which screens all the activity and still provides a tremendous amount of room on the water side for a patio with built in grill, pool with gracious surround and a broad lawn that rolls directly to the water. The written word and videos are powerful tools however in this instance; this is a property that must be visited.

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: 4.52% last updated on Jul 19, 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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56 Hatch Road, Vineyard Haven, MA

Price$2,995,000

Est. Mortgage: $/month

MLS Number 33807

  • Residential
  • Square Feet 2325
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 2

Close to downtown on a quiet side street, this 2,325-SF house with water views and magical morning light is steps away from a secluded beach overlooking the town's outer harbor. With three en-suite bedrooms upstairs and a downstairs den, first-floor and upper decks facing the water, and proximity to the Vineyard Haven Yacht Club and West Chop, this architect-designed contemporary offers comfortable and convenient summer living. The open floor plan flows around a floor-to-ceiling central fireplace, with expansive windows and plenty of built-in storage. The .20-acre corner lot features mature landscaping and a large sunny lawn with a field stone wall. Other amenities in this beautifully renovated home include a spacious garage, central air, unfinished basement, and an airy, light-filled mudroom.

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: 4.52% last updated on Jul 19, 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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20 West Chop Lane, Vineyard Haven, MA

Price$7,250,000

Est. Mortgage: $/month

MLS Number 33232

  • Residential
  • Square Feet 4704
  • Bedrooms 8
  • Bathroom 5
  • Half Bath 1

Panoramic views over Vineyard Sound and the Elizabeth Islands, frontage on Mink Meadows Pond, and a tranquil wooded setting with beautiful mature plantings make this 3.53-acre property feel like a secluded and serene island retreat. A relaxed gathering spot for family and friends, the 4,704-SF house includes seven bedrooms and four-and-a-half baths, separate guest quarters, screened porch, two-car garage, and nearly 2,000 SF of outdoor decking. The great room anchors the house with its soaring cathedral ceiling, brick fireplace, and a wall of windows framing the dramatic sunset water views. The light, airy kitchen is outfitted with a spacious white granite island and countertops, Gaggenau ovens and cooktop, and walk-in pantry. Custom built-in shelves and cupboards throughout provide lots of storage space. Enjoy easy access to the sandy Mink Meadows association beach, along with preferential member status at Mink Meadows golf course. Nearby are West Chop Woods 85-acre nature reserve, Lake Tashmoo, the West Chop community, and Vineyard Haven Yacht Club. Making the most of its peaceful, private location and panoramic views, this beautifully crafted home, with renovation design by renowned island architect Ben Moore, has room for everyone, inside and out.

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: 4.52% last updated on Jul 19, 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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34 Pond View Way, Vineyard Haven, MA

Price$3,100,000

Est. Mortgage: $/month

MLS Number 33663

  • Residential
  • Square Feet 3884
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 3

When a premier builder builds his own home, he applies all the innovative and state-of-the-art qualities, appointments, and technology he has made for his clients over the years. It becomes the best of the best in every respect. This home is that property. The term "over the top" is applicable here. Combining this with the impeccable taste of his wife is a win/win situation. Not only is the home remarkable but the landscaping, the views, and access to the private beach on the Lagoon enhance an already unique property. There are custom cabinets and woodwork throughout the home, each ceiling has a different height and design, and the study/office curved ceiling made of fir bead board. The 8' high custom entrance door and custom sized windows distinguish the building. Ledge stone used at the outside entrance rolls into the interior dining room, living room, and kitchen. The kitchen is as remarkable as the balance of the house. A pizza oven, 2 dishwashers, a Thermador Column System for refrigeration and floor to ceiling wine cooler further demonstrate the details of the house. The kitchen opens to a comfortable den with wood burning fireplace and corner windows overlooking the water. An efficient built in bar is between the den and living room for easy entertaining. A gracious hall takes you by the covered deck with outdoor dining and the office/den with open views of the Lagoon. The luxurious master suite is in the south wing of the house with a fireplace, private deck and outdoor shower and an exceptionally designed bath, laundry area, and closet space. The lower level has direct water views from every room. It is dedicated to the guest area with two en suite bedrooms, a sitting area, an extraordinary laundry area, closet storage, general storage and access to the two car garage. This description only touches the surface of the incomparable property and the superlative attributes, and has to be seen in person to appreciate the comfortable elegance throughout the home. (4 Bedroom septic system.)

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: 4.52% last updated on Jul 19, 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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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

{$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: 4.52% last updated on Jul 19, 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
  • Square Feet 1847
  • Bedrooms 4
  • Bathroom 2
  • Acreage 2.45

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: 4.52% last updated on Jul 19, 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
  • Square Feet 4557
  • Bedrooms 3
  • Bathroom 4
  • Half Bath 1

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: 4.52% last updated on Jul 19, 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
  • Square Feet 2072
  • Bedrooms 4
  • Bathroom 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. 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: 4.52% last updated on Jul 19, 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
  • Square Feet 5534
  • Bedrooms 7
  • Bathroom 6
  • Acreage 0.657

Majestic single family water view home plus guest house 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: 4.52% last updated on Jul 19, 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
  • Square Feet 2513
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.6709

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: 4.52% last updated on Jul 19, 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
  • Square Feet 2012
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

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

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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
  • Square Feet 3540
  • Bedrooms 3
  • Bathroom 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

{$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: 4.52% last updated on Jul 19, 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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27 Hatch Road, Vineyard Haven, MA

Price$3,199,000

Est. Mortgage: $/month

MLS Number 33426

  • Residential
  • Square Feet 3797
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 1

Rare opportunity to own 3 floors of spectacular water-views! Come view this 6 bedroom, 4 1/2 bath brand new construction on Hatch Road. Custom-built, energy-efficient retreat sited on a wooded and landscaped 3/4 acre lot includes a five-bedroom, three-level home and a detached one-bedroom carriage house. Beautifully styled and fully furnished, the main house features an open floor plan, three floors, and stunning views of Vineyard Haven harbor and East Chop. The main floor boasts 9-foot ceilings and crown molding, a great room with 50-inch HDTV and media room set-up, gas fireplace, a stunning chef's style kitchen with center island, granite and quartz countertops, six-burner Thermador gas range, Thermador microwave and dishwasher, a master suite with large walk-in closet, jetted spa tub, tiled shower, and twin French door access to rear bluestone patio, laundry room with frontload washer and dryer, walk-in pantry and 1/2 bathroom. The dining room exits through French doors to large screened-in porch with a cathedral ceiling, fan, and outdoor speakers. Second floor boasts second master suite with twin walk-in closets, tiled shower, and twin French door access to covered side porch with stunning views of the harbor. Second floor also features bedrooms 3 and 4 with third full bath. Third floor features a Nantucket dormer with spectacular views of East Chop and a sliding glass door that open onto a sun deck with sweeping views of East Chop and Vineyard Haven harbor. Rough-in plumbing on third floor can accommodate another bathroom or wet bar. Third floor can serve as fifth bedroom, office, art studio, or entertainment suite. Rich hardwood floors installed throughout entire house. Ceiling fans in great room, all bedrooms, and covered side porch. Relax in rocking chairs on the Nantucket styled front porch. Three-zone FHA heat and A/C, and expanded outdoor shower. Custom landscaped yard features mature trees including one of the few California Sequoia trees in the northeast. There is plenty of room on the property to add a pool with town approval. Gorgeous private brand new Carriage House over a spacious 2-car garage. Custom designed kitchen, stainless appliances with granite countertops, 1 full bath, 1 queen bedroom, hardwood floors throughout, front load washer and dryer, large living room, cable, wireless, 50-inch HDTV with surround sound, private mahogany deck, and outdoor shower.

Listed by Premier Properties

{$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: 4.52% last updated on Jul 19, 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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741 Main Street, Vineyard Haven, MA

Price$5,695,000

Est. Mortgage: $/month

MLS Number 33416

  • Residential
  • Square Feet 2424
  • Bedrooms 6
  • Bathroom 3
  • Acreage 0.69

Wonderful 6 br. beach home located on a private, sandy beach overlooking the outer harbor and Sheriff's Meadow. One of a kind opportunity to own a home that could not be replicated today. First floor has been renovated with state of the art kitchen opening to informal dining and living room with panoramic waterviews. Casual living with window seats viewing a rolling, manicured lawn and a sandy beach path leading to some of the best swimming on the island. .A private, oversized master with adjoining den abuts the conservation land with private outside access to early morning or late night swims. There is an additional bedroom off the kitchen, again with beautiful waterviews. The second floor is old age charm with 3 bedrooms viewing the Sound. This property is a rare offering with your own private beach and can be packaged with the house next door to form a breathtaking waterfront compound.

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: 4.52% last updated on Jul 19, 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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655 Herring Creek Road, Vineyard Haven, MA

MLS Number 33187

  • Residential
  • Square Feet 928
  • Bedrooms 2
  • Bathroom 1
  • Acreage 1.26

It's all about the beach, stunning sunrises, epic sunsets and the sound of the waves lapping on the shore. Live the Island life in this classic style summer house perched waterfront between Lake Tashmoo and Vineyard Sound. Kayaking, paddle boarding sailing just steps away. Designed for casual vacation living, it's a perfect summer home for generations to come.

Listed by Conroy & Company R.E., Inc.

{$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: 4.52% last updated on Jul 19, 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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733 Main Street, Vineyard Haven, MA

Price$3,250,000

Est. Mortgage: $/month

MLS Number 33134

  • Residential
  • Square Feet 2081
  • Bedrooms 4
  • Bathroom 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

{$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: 4.52% last updated on Jul 19, 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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92 Main Street, Vineyard Haven, MA

Price$2,350,000

Est. Mortgage: $/month

MLS Number 32818

  • Residential
  • Square Feet 6330
  • Bedrooms 7
  • Bathroom 6
  • Half Bath 1

The stately Captain Dexter House is the perfect blend of historic charm and modern amenities. In 2004, a three story addition completed the restoration of this gracious home, and included on the first floor adding a chef's kitchen with oversized island and walk in pantry, full and half bath, dedicated laundry room, large family room with fireplace, formal dining room and wetbar. Two large bedrooms which share a Jack and Jill style bathroom, a second family room and outdoor deck were added to the second floor. Finally, a private staircase to the third floor master suite with views across Vineyard Haven Harbor to East Chop Lighthouse, was added. Other features of the home include 5 fireplaces, an updated mechanical system, Energy Efficient windows, 4 zone heating and 3 zone AC, and private parking. The lovely professionally landscaped grounds and tiered gardens offer multiple areas for gathering, entertaining, or watching the world walk by. Enjoy your morning coffee on the front porch, or entertain friends on the large wrap around porch. The hydrangea filled, beautifully landscaped side patio is serene and private. You are steps away from restaurants, movies, health club, galleries, boutiques and the ferry terminal. This lovely home is being sold furnished with the exception of the attached exclusion list. Consistently strong rental history.

Listed by Wallace & Co. Sotheby's

{$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: 4.52% last updated on Jul 19, 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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201 Mitchell Road, Vineyard Haven, MA

Price$2,500,000

Est. Mortgage: $/month

MLS Number 32707

  • Residential
  • Square Feet 5021
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 2

Private 2.6-acre estate in Mink Meadows with multiple components - main house (3,451 sq ft), swimming pool, 3-bedroom guesthouse (1,540 sq ft), 2-story detached dry studio, and 2-car garage. Extensive landscaping and stonework accentuates the estate feel. The entrance to the half-mile of private association beach is less than 500 yards down a quiet dirt road. There are peeks of Vineyard Sound over the charming golf course views. The field stone chimney is a distinctive landmark for your arriving guests. MAIN HOUSE: There is extensive space for entertaining, including a 600 sq ft great room with cathedral ceiling, 300 sq ft screen porch, 800 sq ft hardwood deck overlooking the golf course, and of course, the beautifully landscaped swimming pool environment with adjacent changing area/outdoor shower. There is a formal dining room for gatherings during the cooler months, as well as an elegant sitting room with fireplace. A dedicated office provides views of the golf course. GUESTHOUSE: A 3-bedroom guesthouse is a rarity, especially one with this much privacy. This one is located almost 200 feet away from the main house, has its own private driveway, and has additional seclusion thanks to mature landscape screening. There is a 600 sq ft main deck overlooking the golf course and woods, and another spacious deck off the master bedroom suite. The guesthouse also has its own outdoor shower and a full basement. STUDIO: The two-level dry studio with hardwood floors is presently being used as a gym and office but it has multiple applications depending on an owner's needs.

Listed by Wallace & Co. Sotheby's

{$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: 4.52% last updated on Jul 19, 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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111 Main Street, Vineyard Haven, MA

Price$3,950,000

Est. Mortgage: $/month

MLS Number 31682

  • Residential
  • Square Feet 3355
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 1

Tucked down an unassuming driveway and invisible from the street, this 19th century Cape is just steps from Vineyard Haven's year-round shopping and cultural center. Terrace after terrace unfolds as you descend toward the waterfront through the lovely 2/3-acre compound, culminating in 68 feet of beach on the inner harbor. The main house, built around 1825, has four bedrooms plus an office/bedroom, three-and-a-half baths and five fireplaces. Harbor views abound from many vantage points, with character-filled features including wide board floors and extensive wainscoting, broad-silled windows, plaster walls and low ceilings. A seven-bedroom septic was installed in 2013. The property boasts many extras: a garden shed, detached one-car garage, large harborview porch with arched beadboard ceiling, and lush, mature gardens. A secret gate provides access to Owen Park with its town wharf and gazebo. Near the harbor is a boathouse with brick fireplace, built-in bunkbeds, barrel-ceilinged interior with natural wood, tiny bath and kitchenette. The peaceful private beach, perfect for crabbing, kayaking and contemplation, crowns this property where future memories are waiting to be made. A mooring is available.

Listed by John Best 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: 4.52% last updated on Jul 19, 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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50 Pine Tree Lane, Vineyard Haven, MA

Price$839,000

Est. Mortgage: $/month

MLS Number 32596

  • Residential
  • Square Feet 1538
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.31

This classic Vineyard cape is located in a peaceful and serene neighborhood on the outer harbor of Vineyard Haven - a stone's throw from Main Street and walkable to downtown. Boasting four bedrooms and two baths this vintage Chilmark style cape is perched on an oversized and private corner lot. The home is bordered by a wooded parcel on the back and mature plantings to the north ensuring a quiet and private lifestyle. This home is warmed by three fireplaces that provide heat and comfort through the shoulder seasons. Directly across the street is your deeded path which provides access to Vineyard Haven Harbor. Savor the filtered views of Nantucket Sound and the Harbor on lazy summer afternoons from the living room. Enjoy lunch and evenings from the screened porch that overlooks the flower garden. The first floor is comprised of the master bedroom, living room, dining room and galley kitchen with adjoining laundry room. Three bedrooms and a second full bath finish the second floor. This home offers a wonderful mix of the best of the Vineyard - location, charm, water access, gardens and an easy walk to shops, galleries and restaurants.

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: 4.52% last updated on Jul 19, 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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