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95 Stonewall Road Chilmark MA 02535

Chilmark, MA95 Stonewall Road

Sale Price$10,250,000

Sold

MLS Number 34135

  • Residential
  • Mls Status Closed
  • Village South
  • Bedrooms 6
  • Bathroom 5.5

Paradise is located at the magical intersection of the Atlantic Ocean and Stonewall Pond. A true seaside retreat, this 4-acre property with main house and guesthouse welcomes you to an enchanted life. Massive sliding glass doors that showcase truly unparalleled views grace nearly every room. Interior space flows out to decks, past a sprawling lawn to beautiful Stonewall Beach and tranquil Stonewall Pond. You'll enjoy the amenities at the main house with its chef's kitchen, living room with fireplace, 4-bedrooms and 4.5-baths. The guesthouse with fieldstone fireplace offers an intimate setting steeped with Vineyard charm. Short paths lead to swimming, kayaking, surfing, the treats of summer. In the category of a property that embodies the spirit of the Vineyard, this is top of the class. Enjoy the virtual tours of these properties found in the external links section.

Listed by Cassie Courtney of Wallace & Co. Sotheby's

Listing Sold by Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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55 King Point Way Edgartown MA 02539

Edgartown, MA55 King Point Way

Sale Price$10,189,494

Sold

MLS Number 43916

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 6.5
  • Acreage 4.19

Located waterfront on Edgartown Great Pond, this under-construction home on 4.1 acres features 9000 sq ft of living space, a stunning contemporary design, and sweeping water views. In addition to the 4-bedroom main house, there is a detached exercise/wellness structure, garage barn, and swimming pool. ****Sale price reflects unfinished condition of premises****

Listed by LINK of LINK

Listing Sold by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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44 Green Hollow Road Edgartown MA 02539
Sold

MLS Number 40403

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 2
  • Acreage 1.14

This charming 4-bedroom cottage with detached garage and guest house is located in the very desirable mid-harbor area of Edgartown Harbor. The property is over an acre and offers unobstructed views over the rolling lawn to nearly 100 ft of harbor frontage and a private dock. The current cottage could be restored or if one desires a new larger home could be built. The property has been approved for a 6,000 sf / 5-bedroom home and carriage house with apartment above. This offering represents a rare opportunity to own a harbor front property with the ability to build new.

Listed by Gerrett Conover of Landvest MV

Listing Sold by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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Off Moshup Trail Aquinnah MA 02535

Aquinnah, MAOff Moshup Trail

Sale Price$10,000,000

Sold

MLS Number 38856

  • Land
  • Mls Status Closed
  • Acreage 32

Not listed in LINK Mutiple lots with both Pond and Ocean Frontage

Listed by LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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53 South Water Street Edgartown MA 02539
Sold

MLS Number 36023

  • Residential
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 3
  • Bathroom 4.5

Exquisite Edgartown Harbor waterfront property with deep water pier and sweeping views from the outer harbor to Chappaquiddick to Katama Bay. Built in 2002, this home sparkles like new with a grandeur, finishes, and craftsmanship of earlier times. A perfect home for entertaining, enter through a lovely foyer that opens to a gracious living and dining great room with fireplace harborside, and a beautifully equipped gourmet kitchen and casual dining to your left. Expansive master bedroom balcony, ground floor porch, lower level brick patio, large patio, spacious lawn and long deep water dock welcome the outdoors. The center of town is just a short stroll along South Water Street.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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68 North Water Street Edgartown MA 02539
Sold

MLS Number 35647

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 6
  • Acreage 0.31

An expansive compound in the heart of Edgartown village does not come to the market very often. A stunning renovation by Stern McCafferty Architecture + Interiors has yielded a home that seamlessly blends the old and new, the historic with the contemporary. Light, bright, and with the highest levels of finished detail, the home is filled with details to remind you that you are in one of the most richly historic communities in all of New England. Just look out the front windows and watch the yachts pass between the beautiful waterfront homes and it calls to mind that only a few generations ago it was whaling vessels that dominated the water views and the homes themselves belonged to successful ship's captains. The 4,100 s.f. main house and 660 s.f. guest house with sweeping lawn, lovely manicured gardens and oversized swimming pool is an oasis in bustling North Water Street with its brick sidewalks, traditional streetlights, and signature Greek Revival homes. Step inside and you enter a sophisticated home with a contemporary sensibility. Sleek modern furniture and furnishings are juxtaposed with traditional architectural details. In keeping with the modern desire for an open plan living there is lots of space for gatherings of friends and family. There are four large bedrooms with three baths - one of which is a master ensuite with office, and on the third level, a large sleeping and play space for younger kids, also with a full bath. The swimming pool is set within the beautiful gardens and is one of the largest pools in the village at 42' x 18'. At the far end of the property is a charming two-bedroom cottage and garage. A parking court is accessed off a private lane on Morse Street which is large enough to park an abundance of cars. The property is a gem in the crown of historic North Water Street.

Listed by Bonnie Pierce of Wallace & Co. Sotheby's

Listing Sold by Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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3 Dunes Road Edgartown MA 02539

Edgartown, MA3 Dunes Road

Sale Price$10,000,000

Sold

MLS Number 32383

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 6.5
  • Acreage 1.5

Ideally situated just steps from South Beach, Three Dunes Road embodies coastal luxury at its finest. This stunning home is the perfect blend of seaside comfort and classic sophistication. Stepping inside, the residence is beautifully appointed, and the outside amenities create a resort-like compound. Interior and exterior spaces flow seamlessly making a perfect environment for entertaining and relaxation. Don't miss this opportunity, where every detail is a testament to unparalleled luxury.

Listed by Courtney Marek of Sandpiper Realty

Listing Sold by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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52 Mill House Way Vineyard Haven MA 02568
Sold

MLS Number 36702

  • Residential
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 6
  • Bathroom 7

This gracious, impeccably detailed, three-story air conditioned home with guest house and garage overlooks Vineyard Haven harbor towards the East Chop lighthouse, steps away from its own sandy beach and an easy stroll to downtown Vineyard Haven. Thoughtfully sited and designed, the 5,787- sf house on 1.55 acres includes four bedrooms, an expansive living and dining room, and multiple porches with spectacular water views. A graceful gambrel designed house was built in 2004 which incorporates an abundance of windows, red cedar shingles, and copper gutters. The first floor boasts an open living room with a dramatic fieldstone fireplace and a wall of French doors with views of the harbor. The gourmet kitchen adjoins a screened in porch for that perfect sunset dinner. Enjoy multiple outside sitting areas including a porch, another screened in porch and an outside kitchen and dining table on a sunny bluestone terrace. The second floor has a breathtaking master suite with an enviable master bathroom. Completing the second floor are three more bedrooms en suite and two sitting rooms. A third floor with large open spaces and sweeping views, especially from the widow's walk, will entice you for that afternoon read. Additional amenities include a full walkout basement with wet bar, an exercise room, a media room, plus a state of the art wine cellar and an elevator. This is a very special offering! No rentals in place, there is still time to be in the house this summer. Easy to show.

Listed by Bobbi Reed of Viewpoints

Listing Sold by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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117 North Water Street Edgartown MA 02539
Sold

MLS Number 35468

  • Residential
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 7
  • Bathroom 3.5

CLASSIC CAPTAIN'S HOME WITH DEEP WATER DOCK ON EDGARTOWN HARBOR. Located on prestigious North Water Street and in the heart of historic Edgartown Village, this premier harborfront home combines the best of in-town and waterfront living, with the advantages of a deep water dock on Edgartown Harbor. Built in 1998, the home was designed using historic house plans from the 1800's and its traditional style blends perfectly within the neighborhood of historic sea captain's homes. On the harborfront side of the home, there are two expansive decks with panoramic views across the harbor to Chappaquiddick Island and Nantucket Sound creating an idyllic outdoor living and entertaining spot with the Edgartown Lighthouse as the picture-perfect backdrop. There are a total of SEVEN BEDROOMS making the property an exceptional retreat for hosting family and friends (current owners are using the first-floor bedroom as a Family/TV Room). As an extra bonus, the property features wonderful attributes of historic village homes, such as the four wood-burning fireplaces and the widow's walk, which is the perfect place for enjoying the Fourth of July fireworks or a perfect starlit summer light. The professionally landscaped yard features beautiful perennial gardens and an expansive lawn that stretches to meet a sandy shoreline at the harbor's edge. The property boasts an impressive rental history and furnishings are available separately for a turnkey purchase opportunity.

Listed by Wendy Harman of Compass | Point B

Listing Sold by Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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 Squibnocket Road Chilmark MA 02535

Chilmark, MA2 Squibnocket Road

Sale Price$9,525,000

Sold

MLS Number 41941

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 5.5
  • Acreage 4.5

CHILMARK SOUTH SHORE WATER VIEWS. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a day at Lucy Vincent Beach or on the boat. Pick up some local oysters and lobster rolls in Menemsha and then head home to enjoy a perfect summer sunset on the patio overlooking Menemsha Pond and the Elizabeth Islands. The home is pristine and private with many unique features that make it the perfect place from which to enjoy all that up-Island has to offer. The chef's kitchen and dining area are serene, bright, and functional. The main floor living spaces feature unparalleled Chilmark panoramas with views of South Shore beaches, Quitsa and Menemsha Ponds, and the Vineyard Sound. A stately wood-burning stone fireplace centers the living room which overlooks the expansive lap pool and stone patio area with dining space for outdoor enjoyment. The stunning main house has 4 bedrooms and 3 1/2 baths. The primary bedroom, on the main level, has its own fireplace, ensuite bathroom, walk-in closet, and direct access to the outdoor shower. This rare up-Island property also includes a secluded guest house with a well-appointed kitchen, two ensuite bedrooms, and a spacious living area with wood burning fireplace. A one-car garage on the property is a plus for storing all of your Island toys such as surfboards, beach gear, and the Island car. This Chilmark retreat also features deeded access for small boat pick-up and drop-off on Menemsha Pond, just across the way. Close to the Chilmark General store, Chilmark Tavern, Beetlebung Farm Stand, and the Chilmark Community Center for your convenience. However you like to spend your days, at the beach, by the pool, grilling with a crowd, or curled up with a good book in front of the fire, you can do it all at this one-of-a-kind Chilmark property. The co-listing agent is related to the Seller.

Listed by Tina Miller- 508-561-0042 of Compass | Point B

Listing Sold by Conroy & Company R.E., Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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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40 Gaines Way Edgartown MA 02539

Edgartown, MA40 Gaines Way

Sale Price$9,523,000

Sold

MLS Number 42527

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.46

Not listed in LINK.

Listed by Alison Rich Stearns of Carroll & Vincent R.E.

Listing Sold by Carroll & Vincent R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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.

Ask A QuestionMore Details

40 & 44 Meetinghouse, 19 & 25 Old Farms Trail Edgartown MA 02539
Sold

MLS Number 39090

  • Residential
  • Mls Status Closed
  • Bedrooms 8
  • Bathroom 7
  • Acreage 13.55

Historic Edgartown farm overlooking significant acreage of picturesque pastures owned by the Nature Conservancy. Located on Meetinghouse Way, this beautiful 1800's farmhouse has been meticulously restored to showcase the original beams, wide plank hardwood floors, and two large fireplaces. On the ground level, the charm of the historic renovation blends seamlessly in with the significant addition, which offers a modern, spacious kitchen, cathedral ceilings, and sweeping views of the open fields. Completing the addition are two guest rooms with private baths, and a sitting room, located in a separate wing of the house. The farm is made up of a total of four independent lots, each with their own rights for construction. The main house lot has three residential structures: the historic home, a bunkhouse, and a free-standing one-bedroom farmhand cottage. In addition to a barn, there is a lovely pool adjacent to the main house, a duck pond, and fenced pastures. One of the independent lots has a newly constructed barn designed for multiple uses and includes an unfinished apartment on the second level. This parcel also has the right to build an additional main house, which would have significant views of the fields. 19 & 25 Old Farms Trail are vacant parcels currently used as pastures with significant frontage to the Nature Conservancy's open fields. 19 Old Farm Trail has a conservation restriction limiting the building envelope to a specific 10,000 sq. ft location on the site. There is also a restriction on the size of the home and is limited to 5-bedrooms. There is no restriction on selling the four parcels separately, although this offering is for the entire farm and not individual pieces.

Listed by Cassie Courtney of Wallace & Co. Sotheby's

Listing Sold by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* 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.

Virtual TourAsk A QuestionMore Details

Based on information submitted to LINKMV as of June 14, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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