Chilmark MA Real Estate & Homes

Chilmark is a small, rural community on the western end of Martha's Vineyard. You will find lush fields, gorgeous homes, and even sheep! Chilmark mostly consists of residential homes and farmland. Middle Road in Chilmark features one of Martha's Vineyard's most beautiful drives. 

Explore Chilmark Real Estate

Scroll down to view all homes currently for sale in Chilmark. Contact us to schedule a showing, or if you have any questions. Create an account to save favorite listings and to receive email notifications when similar listings become available. 

95 Stonewall Road Chilmark MA

Price$13,500,000

Est. Mortgage: $/month

MLS Number 34135

  • Residential
  • Square Feet 3008
  • Bedrooms 6
  • Bathroom 5
  • Half Baths 1

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 Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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$10,300,000

Est. Mortgage: $/month

MLS Number 33559

  • Residential
  • Square Feet 4600
  • Bedrooms 7
  • Bathroom 6
  • Acreage 5.4

Spectacular 3 home waterfront Chilmark estate on 5.4 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 1.4 acre lot (140 State Rd) while “Lenom” and the “Boathouse” are sited on the abutting 4 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 $10,300,000 or the two parcels may be purchased separately.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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100 Beach Plum Lane Chilmark MA

Price$8,500,000

Est. Mortgage: $/month

MLS Number 35399

  • Residential
  • Square Feet 2140
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.3

Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside cottages positioned to take advantage of the commanding views of Vineyard Sound and the village of Menemsha. This property, once featured on the cover of Architectural Digest, dates to the 1930's and was lovingly restored by the current owner and Joseph Dick, a well-known and respected architect on the Cape and Islands. The main house features two bedrooms, two baths, living and dining rooms with water views, fireplace, well-appointed kitchen, outdoor rain shower, and a front porch which provides a front row seat to those magical Menemsha sunsets and the Elizabeth Islands. The guest house has one bedroom and bath, large, open living and dining areas, an ample kitchen, and an outdoor shower. Adjacent to the guest house is a detached, one bedroom cottage. A cottage at the rear of the property contains an office with wide water views and a lower level space currently configured as a personal gym. The last of the five cottages on the property is used for storage of seasonal furnishings. Mature landscaping, specimen trees and lush perennial gardens surround the property and delight the senses with vivid colors and welcoming floral scents. A short stroll on a deeded path takes one to the historic fishing village of Menemsha, it's seafood and craft shops and the calm waters at Menemsha Beach.

Listed by Russell Maloney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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 Azalea Lane Chilmark MA

Price$8,250,000

Est. Mortgage: $/month

MLS Number 34126

  • Residential
  • Square Feet 2511
  • Bedrooms 5
  • Bathroom 3
  • Half Baths 1

Rarest of the rare - Ocean-view Chilmark home with swimming pool, 440 feet of private ocean beach, and big, beauteous ocean views. The house is being completely renovated and price shown is for the completed product. Note that the images shown are of the house BEFORE renovation. Detached garage.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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18 Spruce Gate Road Chilmark MA

Price$7,750,000

Est. Mortgage: $/month

MLS Number 34218

  • Residential
  • Square Feet 3700
  • Bedrooms 5
  • Bathroom 3
  • Half Baths 1

The best and most coveted location on Martha's Vineyard - Squibnocket Farm. Set within a private, gated +/- 500 acre community that includes over 300 acres of conservation land, extensive private waterfront on Squibnocket Pond, miles of sandy Atlantic beach with towering dunes, and only 12 homes, this turnkey offering melds modern construction and comfort with an idyllic farm-like setting. Stately and elegant, the property residence sprawls peacefully amid surrounding natural beauty. The home was designed and built by Soikkeli & Company, a well-known luxury contractor on the Island. The exterior design evokes traditional New England farmhouse style, with multiple gables and cedar shingles defining the facade. The living space centers on a gorgeous chef's kitchen - soapstone counters, custom farm sink, all new top of the line appliances and fixtures, and a charming pantry are just a few of the outstanding elements found within. Two living rooms flank the kitchen on either side, and the master suite is set perfectly on the first level at the home's southern end. Four additional bedrooms are found on a northerly wing, as is the two-car garage. Views of the ocean, Squibnocket Pond, Noman's Land, and open fields are readily available from many rooms. The house is wired for sound and includes smart home features such as Nest learning thermostats for the AC and heating systems, and sound controlled by HEOS and the Google assistant. The landscape of the property was thoughtfully designed, highlighting ancient stonewalls on the property borders. Along with gracious lawns, flower beds and an organic vegetable garden, the property offers nearly 3 acres of fenced pasture as well as permits for a pool and horse barn. Outdoor living areas to enjoy include an expansive back deck, a superb screened porch with outdoor fireplace, and an outdoor fire pit - ideal for summer evenings or nighttime star-gazing. Ownership in Squibnocket Farm provides access to miles of trails, multiple accesses to Squibnocket Pond, and access to the exquisite homeowners beach, which is home to some of the most stunning sandy beachfront and dunes on the Atlantic seaboard. Squibnocket Farm is a paradise that must been seen to fully experience - a rare enclave of privacy and calm.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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135 State Road Chilmark MA

Price$5,750,000

Est. Mortgage: $/month

MLS Number 19770

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathroom 1
  • Half Baths 1

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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 & 138B State Road Chilmark MA

Price$5,500,000

Est. Mortgage: $/month

MLS Number 34994

  • Residential
  • Square Feet 2558
  • Bedrooms 5
  • Bathroom 4
  • Acreage 4

An amazing Chilmark waterfront property that sits between Stonewall and Nashaquitsa ponds just past Hariffs Bridge. A 3 bedroom main house and 2 bedroom guest house occupy 4 acres of private natural land, and include access to Stonewall pond and Stonewall beach. The "Lenom" property has been in the same family since the 1970's and is being offered for the first time in over 50 years. This year- round home has been lovingly maintained over the years and AC was added in 2017. A lovely cathedral height living room is punctuated with an in impressive stone fireplace for cozy winters and glass doors and three large picture windows to maximize the views and summer indoor/outdoor living and entertaining. The open kitchen was expanded and renovated in 2013 and has views over Nashaquitsa and there's also a great viewing roof deck to enjoy sunrises and sunsets and 360 degree water views all day long. There are three comfy bedrooms and three baths plus an outdoor shower. The "Boathouse" guest cottage was converted from the original boathouse to a comfy one bed plus loft bedroom escape right at the waters edge. A full kitchen, bathroom and living room with ample sleeping spaces make this a great space for extra guests or extended family to stay. A new 2 bed septic has been designed and approved for this building. This one-of-a-kind property is part of a 3 home compound also being offered for sale together for $10,300, 000 ( link id 33559) and the third home "Lorca" is being offered separately for $4,800,000 ( link ID 33561)

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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11 Azalea Lane Chilmark MA

Price$5,200,000

Est. Mortgage: $/month

MLS Number 30618

  • Residential
  • Square Feet 3750
  • Bedrooms 5
  • Bathroom 4
  • Half Baths 1

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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140 State Road Chilmark MA

Price$4,800,000

Est. Mortgage: $/month

MLS Number 33561

  • Residential
  • Square Feet 2042
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.4

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. This one-of-a-kind property is part of a 3 home compound also being offered for sale together for $10,300, 000 ( link id 33559) and the other two homes "Lenom/Boathouse" are being offered separately as well for $5,500,000 ( link ID 34994)

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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21 Squibnocket Road Chilmark MA

Price$4,375,000

Est. Mortgage: $/month

MLS Number 33963

  • Residential
  • Square Feet 2018
  • Bedrooms 4
  • Bathroom 2
  • Half Baths 1

Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic beach house has amazing views of the Atlantic and shoreline out to Squibnocket Point. It has been fully renovated with many tasteful, modern enhancements and sustainably-sourced materials, and yet retains some of the most charming elements of its past. The airy floor plan offers a family-friendly open kitchen, living and dining area, a master bedroom, and a guest wing with three more bedrooms. The lower level is finished, adding about 1350 square feet of space including a spacious 30' x 20' recreation room and laundry room. The property is surrounded by stone walls, a bluestone patio facing the Atlantic, and a path to the Pond (with rights to build an elevated walkway and kayak rack). Originally known as the Hilly Mayhew House, this property was for over 80 years the haven for the international modernist painter Vaclav Vytlacil and his family. He created hundreds of seascapes and harbor scenes of the Vineyard, many of which can still be found on the island and around the world. Walk to the beach, kayak in the pond, or just sit out on your patio watching the day unfold, osprey fish and surfers ride the waves.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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137 Quansoo Road Chilmark MA

Price$3,700,000

Est. Mortgage: $/month

MLS Number 35095

  • Residential
  • Square Feet 1476
  • Bedrooms 3
  • Bathroom 2
  • Half Baths 1

This rare Chilmark waterfront setting is on three acres of graceful land featuring a light-filled home with an intelligent one level layout. Kayak from the private pond front beach to the Atlantic, or enjoy paddle boarding, shell fishing and the sunset right in your front yard. The current home is open and bright, the master suite has its own wing and the two additional bedrooms and bath are on the other side. The house is centered by an open concept kitchen, dining and living room area with a fireplace, and views to the water. The screened porch and extensive decking offer further areas to gather, and the grounds have lovely old oaks and a rolling lawn.This property supports 6 bedrooms and is the perfect palate for a substantial and thoughtful water front home. The property captures intimate pond views, as well as views to the Atlantic Ocean and Quansoo beach. The Island's Great Ponds, over ten acres in size, are salt ponds, and considered some of the best fishing and boating spots on Martha's Vineyard. The Tisbury Great Pond is on the south shore and separated from the ocean by a barrier beach that is opened seasonally to achieve the balance of salinity necessary for the native oysters, clams and many species of fish. For those seeking a quiet and tranquil escape with a quintessential and expansive Martha's Vineyard water view, it doesn't get much better than this. See broker for further details about beach access.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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15 Lake Road Chilmark MA

Price$3,000,000

Est. Mortgage: $/month

MLS Number 25297

  • Residential
  • Square Feet 1927
  • Bedrooms 5
  • Bathroom 2
  • Half Baths 1

Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads... these are just some of the features of this extraordinary property new to market for the first time in nearly fifty five years. This architect designed modern Cape Cod home with five bedrooms and two and one half baths on nearly three acres can be your summer place. Swim, kayak, row or clam in Nashaquitsa Pond, surf at Squibnocket or relax and enjoy the unspoiled, crowd free beach at Zacks in Aquinnah (with membership).

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 2019
* 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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