Chilmark Real Estate Listings

black point beach

Chilmark is one of the most desirable places to own real estate in New England thanks to its beautiful beaches and spectacular homes.

Chilmark Real Estate Statistics:

2017 Tax Rate: $2.68
2016 Tax Rate: $2.75
2016 Average Sale Price: $2,086,827

Learn more about life in Chilmark.

Browse Listings in Chilmark MA

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8 Snail Road, Chilmark, MA

Price$18,000,000

Est. Mortgage: $/month

MLS Number 33672

  • Residential
  • Square Feet 6967
  • Bedrooms 6
  • Bathroom 5
  • Acreage 9.5

Majestically perched 120 feet above the Atlantic Ocean, the magnificent Chilmark House is an award-winning triumph of design and execution. Designed by Seattle architect Rick Sundberg, Falmouth landscape architect Steve Stimson and built by master builder Andrew Flake, the house flows continuously between interior and exterior spaces. A comfortable yet luxurious seaside retreat that celebrates panoramic ocean views of the South Shore and Chilmark Pond. This home features gracious skylights, huge windows and wonderful detail in both design and materials. Oak and radiant-heated limestone floors, marble baths, precast concrete fireplace mantles and top quality appliances support a relaxed yet sophisticated experience for residents and guests. Views from the grand entrance encompass the ocean and infinity pool. The foyer leads past an exquisitely appointed dining room to the great room with soaring ceilings, floor to ceiling windows and an oversized wood burning fireplace. The impeccable attention to detail is highlighted in the chef's kitchen with sitting area, fireplace and custom casework. Heated infinity pool, half-basketball court, large screened porch and outdoor terraces provide a breezy and beautiful venue for all. This secluded residence and 2 bedroom guest cottage sit on 9.5 acres of wooded hillside and includes access to a private Atlantic Ocean beach accessed by boat across Chilmark Pond from your private dock. A presidential paradise, this estate served as the 2013 summer White House. An exquisite Vineyard home!

Listed by Wallace & Co. Sotheby's

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Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 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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81 Squibnocket Farm Road, Chilmark, MA

Price$12,650,000

Est. Mortgage: $/month

MLS Number 32757

  • Residential
  • Square Feet 4852
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.9

Home, water and community are the highlights of this extraordinary property. Award winning architect Bernard Wharton & Allan Shope designed a breathtaking 4 bedroom 4 bath home. Each room enjoys marvelous ocean and meadow views and is complimented by exquisite floor to ceiling design details which make it the most interesting home on the Vineyard. The multi year collaboration of architect, interior designer, builder and owners ceated a home beyond stunning -- this collective genius created a home which is exciting, charming and livable. Like a great artistic masterpiece, it gets better over time. The owners have felt this way every day for 20 years. This exquisite home on 6 private acres embraces the natural wonder of the endless Chilmark, West Tisbury and Edgarown shoreline with the Edgartown Water Tower in clear view 14 miles away. The home and coastline splendor is further enhanced by the private 450+ acre Squibnocket community with 1.5 miles of pond front, 2 miles of ocean front, 300+ acres of conservation and shared with only 12 other homes. 123 of these conservation acres abut this property on one side and 17 conservation acres abut on another side. This paradise is considered the finest waterfront community on the east coast. (see Virtual Tour)

Listed by Tea Lane Associates

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Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 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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Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

94 Menemsha Inn Road, Chilmark, MA

Price$6,500,000

Est. Mortgage: $/month

MLS Number 30472

  • Residential
  • Square Feet 3241
  • Bedrooms 5
  • Bathroom 3
  • Acreage 5.6

This elegant, architect-designed main house and guest quarters are steeped in privacy at the end of a picturesque Chilmark Lane. A private path leads you to the private North shore beach frontage that is provided by this property. With remarkable views of the Vineyard sound, Elizabeth Islands, and endless sunsets this lovingly maintained property has much to offer. The four bedroom main house is in excellent condition with a spacious, well laid out kitchen and dining space as well as a lovely screened-in porch. A large living room area, with stone fireplace and French doors, leads out to the terrace and ocean views. Vaulted ceilings, spacious bedrooms and an additional living space and bathroom in the lower level plus a detached guest annex with wonderful Sound views add to the appeal of this home. The gardens and manicured outdoor spaces of this land add to the already welcoming and flawless feel of this entire property. Menemsha village is only a short drive away or one could also walk along the shore's edge to get there. This home and property is truly a magical and restful place in which to enjoy the Vineyard.

Listed by Flanders Real Estate

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Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

94 Menemsha Inn Road, Chilmark, MA

Price$6,500,000

Est. Mortgage: $/month

MLS Number 30425

  • Residential
  • Square Feet 3241
  • Bedrooms 5
  • Bathroom 3
  • Acreage 5.6

This waterfront 4 bedroom 2.5 bath impeccable custom home and detached 1 bedroom, 1 bath guest studio are sited on 5.6 pristine acres. Enjoy spectacular water views and magnificent sunsets from almost every room as well as from the stone terrace, screened porch and master bedroom balcony. This is a finely crafted home with many wonderful details including salvaged heart pine floors and beautiful old beams. Relax amidst the gardens, expansive lawn and mature trees as you take in the beauty around you or go for a leisurely stroll to Menemsha Village. A short path leads to 340 feet of private waterfront on the Vineyard Sound where one can swim peacefully in the calm waters.

Listed by Tea Lane Associates

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

135 State Road, Chilmark, MA

Price$5,750,000

Est. Mortgage: $/month

MLS Number 19770

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathroom 1
  • Acreage 1.9

Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the Vineyard. Views from nearly every room of this home over Quitsa and Menemsha Pond. With extremely desirable dock space included, this property has two full private docks and one floating dock only steps from your door. First level of home is a large living area with kitchen all fronted by a large screened in porch. There is also another area that serves as bedroom or could also be used as a den or office space. Upper level has 3 bedrooms, large living room, full bathroom and loft space - great for the young ones. This home is great for entertaining and offers some of the most spectacular views in Chilmark. Enjoy sunset views over the pond...or swim off of the private sandy beach area on the pond which is great for young swimmers and for launching kayaks...All of this just within a short distance of Squibnocket Beach.

Listed by Flanders Real Estate

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

140 State Road, Chilmark, MA

Price$5,500,000

Est. Mortgage: $/month

MLS Number 33561

  • Residential
  • Square Feet 2042
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.2

Spectacular waterfront property with private dock on Stonewall Pond. Breathtaking one-of-a kind views across Stonewall Pond out to the Atlantic Ocean as well as stunning views of Quitsa Pond. This magical property is known as the "Lorca" home because the current owners purchased it in 1972 from the Garcia Lorca estate. With modern upgrades, this is a year round home which evokes old Vineyard charm and features water views from almost every room. Built in 1939 "Lorca" was expanded in 1973 and has been been lovingly renovated and maintained over the past 40 years. There are 3 bedrooms and 2 bathrooms, an open living room, kitchen and dining room, an adjacent family room with fireplace and wonderful picture windows to maximize the water views. Dine al fresco on one of the 2 large decks and enjoy magical moon-rises and spectacular sunsets with 360 degree water views from the roof top deck. Stroll down the gently sloping yard to a private dock and enjoy sailing, kayaking, swimming and paddle boarding. Boat from Stonewall Pond under Hariffs Bridge to Quitsa and Menemsha ponds and then out to the Vineyard Sound or take a quiet moment at home to simply relax in the surrounding beauty. The sunrises and sunsets here are breathtaking and watching the moon rise over the pond is spectacular. It's just a short walk (.3 miles), boat or drive to nearby private association Stonewall ocean beach. This is an amazing opportunity to own a very special Chilmark waterfront property that is surrounded by nature.

Listed by Tea Lane Associates

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

11 Azalea Lane, Chilmark, MA

Price$5,200,000

Est. Mortgage: $/month

MLS Number 30618

  • Residential
  • Square Feet 3750
  • Bedrooms 5
  • Bathroom 4
  • Acreage 8

With 425 ft of private ocean beach, this offering deserves its reputation as the "ultimate beach house". The 5-bedroom home has been completely renovated to the highest specifications with a focus on bold contemporary choices to take advantage of the views and setting. The beach stairs provide access to a wide swath of sand that many consider the most beautiful stretch of beach on Martha's Vineyard. To fully appreciate this extraordinary setting, view the images in the "photo gallery" and watch this drone video: https://vimeo.com/175588276

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

3 Eliot Avenue, Chilmark, MA

Price$4,995,000

Est. Mortgage: $/month

MLS Number 32911

  • Residential
  • Square Feet 4696
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.21

A substantial Tom Tate built home on 1.2 acres in Chilmark, designed to work with the landscape to maximize the spectacular water views from almost every window. Experience the most amazing sunrises and sunsets with panoramic views over Nashaquitsa and Menemsha Ponds and the Elizabeth Islands to the North, with Menemsha and Stonewall Ponds and Atlantic beach to the south. At over 4,600 square feet, this fabulous 4/5 bedroom, 3 and a half bathroom home has been thoughtfully designed with both year round living and summer entertaining in mind. The grand entrance foyer separates the master bedroom suite on the south side of the main level from the open living room with feature fireplace and doors to the decks. There's a superb open gourmet kitchen with custom heart pine counter tops and top notch appliances and adjacent large dining space. There are multiple doors to all the outdoor spaces, and decks span the whole length of the home. Two staircases take you down to private guest bedrooms, baths and a great family / hang out space with doors to private hot tub and patio. It's a short stroll to Stonewall Beach and the boat launch on 'Quitsa pond. This property must be seen to be appreciated. Steps away from your own private access to Stonewall beach. Strong rental history.

Listed by Tea Lane Associates

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

2 Chockers Lane, Chilmark, MA

Price$3,900,000

Est. Mortgage: $/month

MLS Number 32231

  • Land
  • Village North
  • Acreage 9.27

Exquisite piece of Chilmark available with frontage on Menemsha Pond. This gorgeous parcel has already been staked, surveyed, and the well and septic are already complete and in place! The expansive views of Menemsha Pond and beyond include the Vineyard Sound and Elizabeth islands inclusive of sunset views. Build your dream home and explore the beauty of all that Chilmark has to offer.

Listed by Flanders Real Estate

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.66% last updated on May 24, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details