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. 

2 Squibnocket Road Chilmark MA 02535

Chilmark, MA2 Squibnocket Road

Price$15,000,000

Est. Mortgage: $/month

MLS Number 39331

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

Sited on 4.5 acres and nestled at the top of the hill you will find this commanding residence flanked with views of the Atlantic Ocean, Menemsha Pond and the Vineyard Sound. Living is seamless both indoors and out at this light, bright and tranquil abode. Sophisticated summer living at its finest, no detail is overlooked in this pristine four-bedroom, three and a half bathroom residence with a two-bedroom, two bath guest house. This Up-Island retreat offers a spacious layout, lap pool, very private guest house and deeded access to Menemsha Pond. Start or end your days doing laps in the pool or venture down to Squibnocket beach, for a swim or surf, just a short distance away. A highly coveted setting with a beach amenity only available to Chilmark residents. This is truly a one of a kind offering that should not be overlooked!

Listed by Madelyn Silvia of Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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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8 Jethro Lane Chilmark MA 02535

Chilmark, MA8 Jethro Lane

Price$11,995,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 8
  • Bathroom 6.5

Stunning Chilmark north shore 4 acre waterfront paradise with wonderful sunsets and unique privacy nestled between a large wooded hill and a 200 acre private estate. The 5 bedroom 4 1/2 bath TWO kitchen main house and 2 bedroom (with 2 dormers) 2 bath guest house enjoy dramatic views of the Elizabeth Islands from the Gay Head Lighthouse to Woods Hole from every room. The property is beautifully manicured with an enchanting contour stretching to the bluff overlooking a dreamy private cove and sandy beach. Four cleared acres are very rare on the heavily wooded north shore. Waterfront values on the rugged, elevated and protected Vineyard north shore are attracting more interest after Hurricane Sandy damaged the low elevation fragile south shore NY, NJ and New England coast line. The property is in the highly desirable 335 acre Spring Point community with 38 home sites with 135 acres of common land, 3/4 mile of private beach, 2 tennis courts and endless dirt roads and trails.

Listed by Robert Kenney of Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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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76 Menemsha Inn Road Chilmark MA 02535

Chilmark, MA76 Menemsha Inn Road

Price$8,900,000

Est. Mortgage: $/month

Pending

MLS Number 39240

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 4
  • Acreage 1.1

WATER VIEW, WATERFRONT, PRIVATE BEACH- nestled above the north shore with spectacular views of the Gay Head Lighthouse, Vineyard Sound, and the Elizabeth Islands. Walk down to your private beach and go for a morning swim, kayak, or paddleboard. Privacy abounds with this spectacular new home, finished in 2021 was designed by Hutker Architects. The masterful quality craftsmanship by Serpa Construction does not disappoint. Engineered to make this home safe and durable for decades to come. Thoughtfully designed with three bedrooms, two primary suites in the main living level, and one lower level bedroom, all with breathtaking oceanfront views. Throughout the house are three full and two-half bathrooms. A comfortable office or den on also on the main level. This contemporary coastal home is move-in ready and is designed inside and out to enjoy everything about life on the Island. The main level enjoys spanning views with an open concept, including a fully equipped modern kitchen. The state-of-the-art STUV fireplace works as a standard fireplace or for chillier evenings it can be operated as a woodstove. The home is a Smart home wired with LED fixtures and a Sonos system throughout, set up to be voice-activated for ease. Walk down to the beach alongside a babbling freshwater stream. Cross the footbridge to a beautiful grassy knoll that sits high above the beach overlooking the Elizabeth Islands. After a late afternoon swim, head up to the top deck for a sunset with a six-person Hotspring hot tub.

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

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$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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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20 Eliot Avenue Chilmark MA 02535

Chilmark, MA20 Eliot Avenue

Price$6,750,000

Est. Mortgage: $/month

MLS Number 39416

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.6

Surrounded by nature, this is a South Shore waterfront sanctuary. The presence of the peaceful placid pond combined with the power of the ocean and the sound of the waves is part of the special experience of living here. It has a particular sense of privacy and peacefulness. Hidden away on a quiet road of lilacs and summer cottages, the yard is defined by stone walls, lush gardens, natural art objects and several outdoor patios. Just beyond the lawn is a sandy path for easy access to the ocean and pond. The feeling inside the tasteful home is one of understated pleasing ambience. There are three bedroom suites and the ability to create a fourth. Each of the bedrooms has a connection to an outside space, two have pond and ocean views and one bedroom includes a sleeping loft space. The large and open kitchen which was recently renovated has a vaulted ceiling and an expansive dining space. Natural light and views of the pond fill the room and glass doors lead to the outdoor patios. The library with fireplace and a wall of windows to the water also serves as a formal dining room. In the living room, the dramatic height and spectacular views of the ocean and pond give you an expansive sense of water. The views from the adjacent sunroom have an intimacy and this room is currently used as an office and sitting room. The primary bedroom suite has extraordinary panoramic views and is a retreat that includes an open sitting room and fireplace as well as a private balcony and bathroom. The character of this property, its authenticity, vistas and connection to the natural landscape all combine to create a truly unique experience.

Listed by Meg Bodnar of Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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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20 Eliot Avenue Chilmark MA 02535

Chilmark, MA20 Eliot Avenue

Price$6,750,000

Est. Mortgage: $/month

MLS Number 36784

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.6

Spectacular Stonewall Pond and beyond! Experience a sense of privacy and peacefulness while enjoying panoramic ocean & pond views. Each of the three bedroom suites have a connection to an outside space. The master bedroom has extraordinary views and includes an open sitting room and fireplace, as well as a private balcony to take in the sounds of the ocean. The large and open kitchen has recent upgrades with expansive area for dining. Adjacent to the living room is a lovely sitting room currently used as an office. Truly an experience of special living on the Vineyard.

Listed by Julianna Flanders of Flanders Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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 Wequobsque Road Chilmark MA 02535

Chilmark, MA53 Wequobsque Road

Price$4,900,000

Est. Mortgage: $/month

MLS Number 39258

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 6.4

This magnificent waterfront home sited on 6.4 acres sits atop the dramatic Wequobsque cliffs. On Chilmark's coveted South Shore, this home boasts ownership of over 350 feet of private beach with access from your staircase in the backyard. The home has a 5-bedroom and 4-bath wing. Attached by a screened-in porch, is the large gathering kitchen with ceiling beams, tall columns and an open, airy design. Enjoy meals in the dining area with ocean views. Dine on the large outdoor deck facing the Ocean. On the west side of the property sits the barn with a half bath and a loft that can be used as an office or extra sleeping area. There is a wet bar, ping-pong table, large screen TV and sofa. There's space to install a wood stove. The home has a new full basement and HVAC system. A very large one car garage below the barn completes the property. This is your opportunity to own your dream home on the waterfront on Chilmark's South Shore.

Listed by Grace Hagerty of Grace Hagerty Real Estate Inc

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$
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$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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 Pondmark Chilmark MA 02535

Chilmark, MA1 Pondmark

Price$4,700,000

Est. Mortgage: $/month

MLS Number 38183

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 4.7

Turn onto country lane and make first turn to right. Drive past Norwegian Pine and many mature plantings and follow stately stone walls up past an open field overlooking the pond. The gentle slope takes you past the garden to a parking area. The white cottage sits on top of the knoll with sweeping views looking out over Keith farm and beyond to the ocean. From the living room the light brightens the large room with vaulted ceilings and a fireplace with a copper chimney hood.You can walk out on the deck for breakfast and watch the cows, geese, horses or the calming motion of the sea. You can lay in bed and take it all in from the king size bed and wall of windows facing south. There is room for a guest house or barn in this private setting. There are walking trails on Old North Road or a trail to Menemsha Crossroads. Go back in time to a slower way of life in this old style Chilmark retreat.

Listed by Elise LeBovit of Gay Head Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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 Meeting House Road & 0 Rockrose Path Chilmark MA 02535

MLS Number 39598

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 6.16

Enchanting four bedroom home in the heart of Chilmark. Set amongst the rolling hills between South and Middle Roads, this private residence exudes timeless charm, surrounded by ancient stone walls, gorgeous trees and fabulous landscape/hardscape. The living space includes a sprawling, open floorplan with central kitchen, stone fireplace and views of rolling meadows. Primary and guest bedrooms are well-appointed and set privately. A rooftop deck offers an ideal vantage for sunsets with south westerly ocean view. Recent upgrades include refinished floors, new windows, paint and an open kitchen design - some elements still in-progress though property offered as-is. Over 6 acres of land and existing 5 bedroom septic offer lots of options for any desired changes (note that 2.56 acres are conservation restricted). Ownership in Chilmark allows access to town residents' only beaches at Squibnocket and Lucy Vincent. Make this your Martha’s Vineyard destination!

Listed by Peyton Wallace of Compass | MV Team

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$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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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26 Pinkletink Road Chilmark MA 02535

Chilmark, MA26 Pinkletink Road

Price$3,495,000

Est. Mortgage: $/month

Pending

MLS Number 39499

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 2
  • Acreage 3

PROSPECT HILL CONTEMPORARY WITH WATER VIEWS. Located off North Road, in the highly-coveted Prospect Hill enclave, this contemporary beach house is set amid a 3-acre natural landscape with rolling fields and perched to enjoy idyllic sunsets and sweeping views across Menemsha Bight to Lobsterville Beach and the Gay Head Lighthouse beyond. The home offers one-level living, designed to maximize the views and indoor-outdoor living with a full wall of sliding glass doors that open out to an expansive 1244-square-foot mahogany deck. The home has been tastefully updated and features beautiful hardwood floors, a wood-burning fireplace, automatic Hunter Douglas® blinds, high-end kitchen appliances, central air, smart home technology with Nest® thermostats and more. Prospect Hill offers private association tennis courts and there is easy access to Menemsha Village plus other favorites like Great Rock Bight Preserve, Menemsha Hills, The Brickyard and more. Note: There is future expansion potential and preliminary plans to site a guest house and pool are available. The property is being offered turnkey with furnishings and contents, making it move-in ready for Summer, 2022. ***OPEN HOUSES are scheduled between 1:00 PM and 3:00 PM on Saturday, 4/23 and Sunday, 4/24***. The Sellers will begin accepting offers at 5:00 PM on Monday, 4/25.

Listed by Wendy Harman of Compass | Point B

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$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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 Middle Road Chilmark MA 02535

Chilmark, MA135 Middle Road

Price$2,950,000

Est. Mortgage: $/month

Pending

MLS Number 37541

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 2
  • Acreage 7.1

A quintessential 1950s cottage situated on the highly sought after area of Middle Road in Chilmark. Consisting of a main house, guest house, garage and storage shed on 7.1 total acres. Would make a great family compound. A Landbank walking trail abuts property. Property is being sold "AS IS." Septic upgrade plan completed, but not installed.

Listed by Julianna Flanders of Flanders Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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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0 Eliot Avenue Chilmark MA 02535

Chilmark, MA0 Eliot Avenue

Price$155,000

Est. Mortgage: $/month

MLS Number 33176

  • Land
  • Mls Status Active
  • Village South
  • Acreage 0.8

Enjoy access to lovely stonewall Beach, south shore Atlantic beach with great swimming and fishing! - not a buildable lot.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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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"Based on information submitted to MA_LINKMV as of May 27, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_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."