Luxury Waterfront Real Estate on Martha’s Vineyard

Each waterfront property on Martha’s Vineyard is truly unique. Luxury waterfront homes on the island offer an alluring range of amenities, including boathouses, private docks, guest houses, private beaches, and spectacular views of Lake Tashmoo, Edgartown Harbor, the Lighthouse, and Katama Bay.

Martha’s Vineyard, the largest and one of the most picturesque islands in New England, has some of the most beautiful waterfront properties.

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50 Oyster Watcha Road, Edgartown, MA

Price$12,950,000

Est. Mortgage: $/month

MLS Number 31928

  • Residential
  • Square Feet 3922
  • Bedrooms 6
  • Bathroom 4
  • Acreage 11.5

Ideally and prominently positioned on the southernmost peninsula of Oyster Pond, this perfectly idyllic compound, among the most spectacular on Martha's Vineyard, awaits. With over 1,200 feet of private waterfront on Oyster Pond and access to over 2,200 feet of prime sandy Atlantic beach, the pristine waters of the pond and ocean set the tone for pure relaxation. The property features beautifully constructed and impeccably maintained residences for family, friends, and guests, with a 4 bedroom main house, 2 bedroom guest house, and charming boathouse, all clad in cedar shingles and elegantly landscaped. Views from both residences are jaw-dropping with a true “wow” factor. From the main house the pond, barrier dunes, and Atlantic Ocean are beautifully framed, with the sounds and scent of the ocean readily on hand. Water views from the guest house are pristine and natural, displaying the dunes and Atlantic beyond the westernmost cove of Oyster Pond. The interiors feature bright, open and airy living spaces accented with fir floors and paneling, large central brick fireplaces, high ceilings, comfortable layouts, and ready access to the outdoors. With a parcel of over 11.5 acres, complete with several trails and accesses to the pond, the opportunities for crafting new structures and improvements abound, if desired; offering an unbelievable canvas for one's architect within a most private and distinguished setting. Oyster Watcha Midlands, inclusive of over 450 total acres with vast tracts of conservation lands, private Atlantic beach with ample parking, tennis, and only 15 building lots, is one of the most sought after locations on the Island, carefully protected by covenants and restrictions for the future enjoyment of owners. Within convenient distances of the airport, downtown Edgartown and all of the Vineyard's best amenities, ownership in this neighborhood rarely becomes available, and the experience is second to none.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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96 Beach Road, Edgartown, MA

Price$11,950,000

Est. Mortgage: $/month

MLS Number 33506

  • Residential
  • Square Feet 10804
  • Bedrooms 6
  • Bathroom 6
  • Half Bath 2

This dramatic compound is set amidst 150 acres of conservation land. Completed in 2010, and offering over 10,000 square feet of living space, this five-bedroom / seven-bath custom home affords every amenity with exceptional finishes. Some highlights of this remarkable home include a large chef's kitchen and family room with stone fireplace, a formal dining room and a cathedral ceiling great room with French doors opening onto an expansive bluestone patio. A finished lower level offers a gym with sauna, a billiards room and bar with fireplace, a media room and additional living space. Stunning views from every room in the home overlook Sengekontacket Pond and beyond to Nantucket Sound. The property also offers a three-car garage with one-bedroom carriage house above, an outdoor kitchen, screened porch with fireplace and a luxurious infinity edge pool, spa and pool house - all situated on more than 150 feet water frontage with mooring.

Listed by Landvest MV

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$
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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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 33954

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

Located on a winding private 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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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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138 and 140 State Road, Chilmark, MA

Price$11,000,000

Est. Mortgage: $/month

MLS Number 33559

  • Residential
  • Square Feet 4600
  • Bedrooms 7
  • Bathroom 6
  • Acreage 5.8

Spectacular 3 home waterfront Chilmark estate on 5.8 acres with private dock on Stonewall Pond. Breathtaking one-of-a-kind views across Stonewall Pond out to the Atlantic from all 3 homes as well as stunning views of Quitsa Pond. Each of the homes is charming and beautifully maintained, with its own Vineyard history. “Lorca” is sited on a 1.2 acre lot (140 State Rd) while “Lenom” and the “Boathouse” are sited on the abutting 4.6 acre lot (138 State Rd). These 3 homes are offered together for the first time in over 50 years. Built in 1939, the original "Lorca" home was expanded in 1973 and renovated over the past 40 years. This year round home evokes old Vineyard charm with modern upgrades and features water views from almost every room. “Lorca” has 3 bedrooms, 2 bathrooms, and light open living spaces with wonderful picture windows through which to enjoy views of the pond and the ocean beyond. Enjoy al fresco dining on the water facing decks then walk down a gentle grassy slope to your own private dock on the pond, surrounded by nature. “Lenom” is the second home with 3 bedrooms and 3 baths. Most recently expanded in 1988, the kitchen and dining area were renovated in 2013 and air conditioning was added in 2017. This year round house has a beautiful stone fireplace, a focal point of the open living/dining area, and a rooftop deck that has wonderful 360 degree views of Stonewall and Quitsa ponds. Nestled between “Lorca” and “Lenom”, on the water's edge, is “The Boathouse”. Built in the early 1970's as a boathouse it was expanded in the 1980s into an additional home with one bedroom and one bathroom plus loft space, full kitchen, living room and lovely outdoor decks over-looking the pond. Each of these homes, with its own unique vistas and water views, is privately situated. Together they create a family compound that allows both separation and the ability to come together so the whole property can be enjoyed by all. Relax in the beauty or enjoy sailing, kayaking, swimming and paddle boarding. The sunrises and sunsets here are breathtaking and watching the moon rise over the pond is spectacular. Just a short walk, boat or drive to nearby private association Stonewall ocean beach. Boat from Stonewall Pond under Hariffs Bridge to Quitsa and Menemsha ponds and then out to the Vineyard Sound. This is an extraordinary property, exclusively offered as a 3 home estate for $11,000,000 or one home (“Lorca”) may be purchased separately for $5,500,000.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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4 Gosnolds Way, Chilmark, MA

Price$10,750,000

Est. Mortgage: $/month

MLS Number 33746

  • Land
  • Village North
  • Acreage 22.75

* Magnificent Waterfront * North Shore Chilmark * Beyond Compare * A unique opportunity to own over 20 acres of unspoiled waterfront in an exclusive private enclave just minutes from Menemsha. Glorious panoramic views of sunsets over the Vineyard Sound and Elizabeth Islands with the iconic Gay Head Lighthouse adding to the magic. Watch the ships sail by as you gaze at the incredible views. Fabulous elevated water view building sites allow you to create the compound you may have imagined, allowing your family to enjoy the peace, quiet, tranquility and astounding beauty of the North Shore of this enchanted isle. Martha's Vineyard ~ located 7 miles off the coast of Cape Cod, 80 miles from Boston and 150 miles from New York ~ this idyllic island is easily accessible ~ yet a world away! Call Listing Broker to experience this piece of paradise.......

Listed by Hancock Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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1 Red Gate Farm Road, Aquinnah, MA

Price$10,000,000

Est. Mortgage: $/month

MLS Number 33456

  • Land
  • Village South
  • Acreage 40.56

Nestled on the shores of picturesque 603±-acre Squibnocket Pond, this pristine, one-of-a-kind 40.56±-acre waterfront retreat looks southeast over the open expanse of calm waters and winding coastline to the Atlantic Ocean beyond the dune-fringed barrier beach that stretches between the pond and the ocean. Two potential homesites on the extensive acreage include one tucked by the 1,009±-foot shoreline of this tranquil oasis, an unspoiled natural refuge for bountiful wildlife in a landscape of breathtaking four-season beauty, featuring many varieties of trees and plants. Also enjoying deeded access to the ocean by boating over the pond, as well as by car, the property has been held by the same family for nearly 40 years as part of the Red Gate Farm compound. The rare setting on the coastline of Aquinnah, the westernmost outpost of Martha's Vineyard, is prized for its unparalleled peace and privacy.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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22 Quitsa Lane, Chilmark, MA

Price$9,995,000

Est. Mortgage: $/month

MLS Number 34036

  • Residential
  • Village South
  • Square Feet 3888
  • Bedrooms 6
  • Bathroom 4

Spectacular and charming; this cottage style home and guest annex is located in one of the most picturesque parts of Martha's Vineyard. This home is full of character with access to private beach just steps from the home and unforgettable ocean views from nearly every vantage point on the property. The main house offers a large gourmet kitchen, amazing patio space for outdoor dining, quaint bedrooms and several entertainment and gathering space. The recently constructed guest annex and garage space is tastefully done with room for overflow family and friends.

Listed by Flanders Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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6 Janes Cove, Edgartown, MA

Price$9,990,000

Est. Mortgage: $/month

MLS Number 32215

  • Residential
  • Village South Shore
  • Square Feet 6925
  • Bedrooms 7
  • Bathroom 7

This beautifully designed and appointed Contemporary Colonial is tucked away on a very private 9.2 acre setting directly on Janes Cove, Edgartown Great Pond with private association south shore beach and tennis courts. Waterviews throughout. Enter the property to the circular drive in front of the Main House.This wonderful House offers a spacious great room/living room with vaulted ceilings, 5 ensuite bedrooms including first floor master with fireplace, sunroom/parlor, family/media room, office/bedroom and finished basement with sauna and full sized recessed wine cooler. There is a separate two car garage with lovely one bedroom apartment above. Natural landscaping, apple trees, children's play area.

Listed by Martha's Vineyard Seacoast Properties

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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Lot 4 at Homers Pond, West Tisbury, MA

Price$9,500,000

Est. Mortgage: $/month

MLS Number 34296

  • Land
  • Village South Shore
  • Acreage 23.7

This 23.7 acre oceanfront parcel offers substantial buildable rights that will offer breathtaking southwesterly views of the Atlantic Ocean, barrier beach, Homers Pond and the cliffs of Squibnocket beyond. There is a existing one-bedroom beach house that could be rebuilt in place as well as a significant main house building site behind. As one of the lots in Homers Pond Association, you commonly own 141 acres of conservation restricted land which provides a majestic entrance to the properties. In addition you are one of 3 lots that commonly own over 46 acres of association land which can be improved to offer any number of usages and represents great value. One can also walk directly from the property through the dunes to access over 1,200 sf of private beach. With engineering and utilities in place, tremendous build ability and the ultimate secluded location, this is an amazing opportunity.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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109 North Water Street, Edgartown, MA

Price$8,650,000

Est. Mortgage: $/month

MLS Number 33763

  • Residential
  • Village Downtown
  • Square Feet 882
  • Bedrooms 2
  • Bathroom 1

This unique Edgartown harbor front parcel offers the rare opportunity to construct a newly built house on historic North Water Street with amazing views of the lighthouse and entrance to the harbor. Complimenting the property is the most charming two-bedroom boathouse just steps to the sandy shoreline. There is a deeded dock slip for a 17-foot boat on the neighboring dock. A very special property that must be seen if considering an inner harbor property acquisition.

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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