Aquinnah Homes for Sale

About the Town

AQUINNAH (formerly known as Gay Head) is the island’s “outermost” town, at the western tip. It’s also the smallest town in Massachusetts, with roughly 400 year-round residents. The landscape is valued for its rugged beauty, punctuated by boulder-strewn beaches, the colorful Aquinnah cliffs and the historic Gay Head Light, overlooking a sparkling panorama of the sea. Commerce is lightly present in a handful of souvenir shops, eateries and inns. The Aquinnah Cultural Center celebrates the heritage of the Wampanoag Tribe of Gay Head (Aquinnah), whose presence on the island dates back some 5,000 years.

Aquinnah contains the subareas below. Click the links to learn more about each area.  For more information about the town, visit the Town of Aquinnah official website.

Aquinnah Circle  |  North Shore  |  South Shore

Aquinnah Real Estate Listings

If you would like to view one of the properties below, please contact us online or call 508-693-6866. To stay-up-to-date on your favorite listings and searches, please register with our site. You'll receive automated emails as new Aquinnah homes are listed.

Renting in Aquinnah? Visit our Aquinnah Rentals page to browse available vacation rentals.

3 East Pasture Lane

Price$4,500,000

Est. Mortgage: $/month

MLS ID 31791

  • Residential
  • Square Feet 2310
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 6

Boasting one of the most spectacular views in Aquinnah, this home is poised on 6 acres and majestically resides over the Menemsha Pond and Vineyard Sound. With expansive living space spanning three levels, the four bedroom home has simply breathtaking views, manicured grounds and wonderful outdoor entertaining spaces. Two master suites and two additional bedrooms, open living floor plan and views from nearly every room of this home!

Listed by Flanders Real Estate

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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10 Moshup Trail

Price$2,900,000

Est. Mortgage: $/month

MLS ID 31263

  • Residential
  • Square Feet 1152
  • Bedrooms 5
  • Bathrooms 1
  • Acreage 0.7

This is the Vineyard dream and a once in a lifetime opportunity - a quintessential beach cottage is nestled in the dunes off Moshup Trail enveloped by the sights, sounds and smell of the ocean. Just a short walk to the sand and surf, this iconic house is a mid-century modern color block design inspired by artist Piet Mondriaan, and offers updated kitchen, new well and septic system. The water views from the main living areas are spectacular, while other angles of the dunes and lighthouse are equally enchanting. This is a truly magical and unique setting, the expansive, sandy stretch of the south shore just over the dune is a quiet deeded beach, spanning over 530 feet, that acts as your own private retreat after hours. Take full advantage of the cool sea breeze, tranquility and simplicity of this incomparable setting available for the first time ever.

Listed by Tea Lane Associates

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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10 Deer Path

Price$2,475,000

Est. Mortgage: $/month

MLS ID 32185

  • Residential
  • Square Feet 1903
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 8.86

This extraordinary Aquinnah property is located across the street from Moshup Beach with a private grassy path leading the way from house to ocean. The beloved 4-bedroom cottage is situated perfectly to absorb the water views, meadow setting and peacefulness of this truly special spot on the island. Offering rare privacy for this area and a beautiful entrance down a country road bordered by stone walls, the house is set on almost 9 acres with a garden area and detached garage, all in close proximity to the Aquinnah Circle and the Gay Head Lighthouse. The original section of the house was a former Coast Guard Boathouse which was moved to the site in 1938 by the same family who has soaked up the sun and surf here ever since. This property has all the elements to create your summer perfection.

Listed by Tea Lane Associates

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Beach Plum Way

Price$2,300,000

Est. Mortgage: $/month

MLS ID 32370

  • Multi-Family
  • Village North
  • Location 41.344906,-70.815451
  • Bedrooms 7
  • Bathrooms 5

This private family compound is located on four acres in Aquinnah, offering many decks and vantage points of the view of the Vineyard Sound and Elizabeth Islands beyond. There are seven total bedrooms and five full baths, offering almost 5,000 sq. ft. of interior living space. Both homes have gourmet kitchens with stainless steel appliances, hardwood floors and central air. There is a stunning two-story beach stone fireplace in the main house. Property offers a great rental history. A wonderful private summer oasis!

Listed by Vineyard Select Properties

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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23 Oxcart Road

Price$2,250,000

Est. Mortgage: $/month

MLS ID 31710

  • Residential
  • Square Feet 950
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 3.7

Relax with the calming sounds of nature at this wonderfully simple Ox Cart Road camp in Aquinnah. While the private beach access lay at your doorstep, you can enjoy sunset views, bird watching, dogfish bar fishing and the lulling sound of the ocean. An open floor plan, spacious deck areas and an interesting layout. The enduring appeal of this property is reminiscent of times gone by. An escape surrounded by the beauty of the Vineyard.

Listed by Flanders Real Estate

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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61 Moshup Trail

Price$2,000,000

Est. Mortgage: $/month

MLS ID 31517

  • Residential
  • Square Feet 1096
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 2

Perched high on Moshup Trail this casual 3 bedroom 2 bath year round home commands breathtaking views of the rugged Aquinnah shore line . Easy 3 minute walk to Philbin Beach, just across the road. Plenty of parking, plus garage and walk out basement. Spacious decks for casual out door living. Potential for 1000 sq ft expansion with permits. Property is being sold "as is".

Listed by Mary Jo Goodrich Island Properties Inc.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Lighthouse Road

Price$1,995,000

Est. Mortgage: $/month

MLS ID 30002

  • Residential
  • Square Feet 2332
  • Bedrooms 4
  • Bathrooms 4
  • Acreage 4

Offered for the first time in nearly 50 years, this 4 bedroom, 4 bath, contemporary home is sited on four acres at 22 Lighthouse Road. Spanning over 2,300 square feet on two levels, this home provides views across Vineyard Sound to the Elizabeth Islands, Menemsha Bight and Chilmark's north shore. Entertain friends and guests in the spacious living room with sky lit, cathedral ceilings, fireplace and wide water views. An open kitchen and dining area lead to a sunlit porch where one can also enjoy the views to the Sound and the property's inground, heated swimming pool. The upper floor of this home is complete with a grand master bedroom overlooking the Sound with a large ensuite whirlpool bath, multiple closets, spaces for an au-pair and a large family room with kitchenette and laundry. The lower floor of this home provides three additional bedrooms and bathrooms, an office, a workshop and guest quarters. In addition to the pool, there are multiple decks and outdoor spaces to enjoy. Other amenities include hardwood flooring, a house generator, outdoor shower, air conditioning and two car garage. Water views are protected with ownership of 1.8 acres across Lighthouse Road that may also be able to be developed with permitting. Summer fun can be found at two included private, association beaches, South Shore Beach, located off Moshup Trail, an Atlantic Ocean beach, and Vineyard Sound Beach, located off Oxcart Road. Adjoining 13.7 acres available separately. See 5-106 Lighthouse Road.

Listed by Russell Maloney Real Estate

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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2 Pilots Landing

Price$1,980,000

Est. Mortgage: $/month

MLS ID 31823

  • Residential
  • Square Feet 1385
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 3.2

A sublime contemporary take on the perfect beach house, or, the absolutely perfect year round retreat. Designed by award winning architect Charles Rose, whose ultra modern concept of three living area pavilions separated by grass courtyards and a roof deck with sweeping ,excellent views,of the Vineyard Sound and Elizabeth Islands, satisfies all the senses.The central locus is living room, dining room and kitchen.The front of the building is immense glass sliding doors, with large screen doors which can slide into place to convert the living room into a screened porch in communion with the gardens outside.The master suite and bath is separated by its own courtyard for privacy.Two additional bedrooms and full bath guest house has its own grassy courtyard to define its area apart.The house is designed to accommodate multi functions while preserving privacy in each area.A private path leads to one of the Island's most coveted north shore beaches This seaside gem has won many accolades and can be viewed in publications: Barefoot Beach Houses, Metropolitan Home, The Houses of Martha's Vineyard, to name a few. Definitely delve into the amazing and savvy body of work for Charles Rose Architects at www.charlesrosearchitects.com. For those who want to enjoy the views, the beach and a very special communion with Nature in one of its most sacred places.

Listed by Feiner Real Estate

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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5 Sea Mist Lane

Price$1,950,000

Est. Mortgage: $/month

MLS ID 28415

  • Residential
  • Square Feet 2800
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 2

Aquinnah's Best Water view. Gorgeous hilltop contemporary home with dramatic 180 degree water views is now available to the discerning buyer. Walk across the street to your private ocean side beach. See and hear the waves crashing from this lofty Moshup Trail location which offers one of the finest beaches in the world. Architect designed and built with an eye for details, this solid, comfortable home has lots of space for the whole family. The living room has a two sided fireplace and wood stove. There are wood floors, mahogany trim and tile in every bathroom. The sunset views from the kitchen, living room and master bedroom are beyond compare. This destination house is where you want to be. When you buy this house you also buy a lifestyle. If you're ready to put a lot more fun in your life this is the house for you.

Listed by Feiner Real Estate

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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5 Sea Mist Lane

Price$1,950,000

Est. Mortgage: $/month

MLS ID 31707

  • Residential
  • Bedrooms 4
  • Bathrooms 2

This is a property that simply cannot be duplicated; the site that this house sits on commands the most spectacular views of the Atlantic ocean anywhere on Moshups Trail .And included are deeded rights to a private Atlantic beach, within walking distance. The house is solidly built, and diligently maintained,by the current owner, builder. Certainly, enjoy it as is or re model to your hearts content within this lovely contemporary foot print.. Because of changing regulations , this house could probably not be duplicated today, which makes this an extremely valuable offering. The owner has priced this to sell. If it`s summer fun you are looking for, this one must be seen!!

Listed by Metes & Bounds

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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