Chilmark Homes For Sale

Chilmark is arguably the island’s most beautiful town with rolling rural landscape sandwiched between gorgeous beach-lined coasts to the north and south. Many of the lovely homes for sale in Chilmark are properties lined with classic stone walls across several acres. Real estate in Menemsha, Chilmark’s historic fishing village is very popular thanks to the picturesque sunsets, nearby beaches, and great restaurants. Homes for sale in Chilmark are a great investment, whether you are looking for a vacation home or a place to live year-round. At Coldwell Banker Landmarks we specialize in helping buyers find the perfect vacation home on Martha’s Vineyard. Learn more about Chilmark.

Questions about buying a home in Chilmark?

Call Coldwell Banker Landmarks Real Estate: 508-693-6866

Save time & effort! Create an account to save your favorite listings & get notifications when similar properties become available.

r=1-10
138 & 138B State Road

Price$5,500,000

Est. Mortgage: $/month

MLS ID 34994

  • Residential
  • Square Feet 2558
  • Bedrooms 5
  • Bathrooms 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

8B Clambelly Road

Price$1,275,000

Est. Mortgage: $/month

MLS ID 34950

  • Residential
  • Square Feet 1978
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

CHARMING IN CHILMARK - WITH FULLY PERMITTED COMMERCIAL KITCHEN! Nestled among the rolling hills of Chilmark, this expanded Cape welcomes those who wish to retreat to its magical comfort. The thoughtful design captures the southern light traversing the first floor living area as the day unfolds. The Chef's kitchen, open concept design and large deck allow for an exceptional space in which to entertain. Three outbuildings grace the property allowing for additional storage, gardening tools and a space for simple solitude, play or work. Just minutes away from Lucy Vincent and Squibnocket as well as Alley's and the famous Liz Lemon at 7A. See additional details below.

Listed by Point B Realty LLC

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

33R North Road

Price$750,000

Est. Mortgage: $/month

MLS ID 33959

  • Residential
  • Square Feet 612
  • Bedrooms 2
  • Bathrooms 1
  • Acreage 0.2

Cozy cottage with lots of windows and light set in a very quiet area far off North Road abutting Seven Gates. Lot offers a lovely back and side yard perfect for entertaining. Stone wall border creates a wonderful, rural Chilmark feel yet the lot is just minutes back down to West Tisbury and still offers access to Lucy Vincent and Squibnocket. Acres of Landbank property just minutes from the house. Home is heated, insulated and has a new septic system, updated bathroom, hot water heater and well installed in 2013. There is a spacious 500 sq ft wrap around mahogany deck with seating that provides ample room for your summer guests while entertaining. You could perhaps increase the living space by adding a second floor with town approval. Several weeks are already booked late July thru August for $12,000. Check out the 3D video on sidebar.

Listed by Kelleher R.E.

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

16 Trails End

Price$1,550,000

Est. Mortgage: $/month

MLS ID 34723

  • Residential
  • Square Feet 1113
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 2

One of the unique aspects of this hilltop home is it's location at the top of a rise where it captures the stunning water views looking westerly over the Atlantic to Squibnocket point and the amazing sunsets. Connect with nature within the abutting Land Bank preserve. Several favorite vantage points are the new master suite/office again with those amazing views, the cathedral ceiling living room with gas wood stove and the expansive deck. Free wheeling with a beach Jeep included and a short drive to exclusive Lucy Vincent Beach.. Shed for storage, Out door shower, air conditioning and excellent rental history.

Listed by Conroy & Company R.E., Inc.

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

15 Doctors Creek Path

Price$1,900,000

Est. Mortgage: $/month

MLS ID 34870

  • Residential
  • Square Feet 989
  • Bedrooms 3
  • Bathrooms 1
  • Half Bath 1

You can "see for miles and miles and miles and miles" from this uniquely located Chilmark cottage. 180 degree water views looking easterly over Chilmark Pond, to the Barrier Beach and beyond and westerly over the Atlantic to Nomans Land. Simply Stunning! Colorful Sunsets! Includes a deeded beach lot on South Beach. The cottage is a cozy camp with beach stone fireplace; used seasonally. This is a "one of kind" south shore location that is not often available for purchase. Short walk to the shores of Chilmark Pond from the cottage where you can wade across, in the summer, to the boardwalk that leads to your private access to South Beach! Expansion possibilities still being researched

Listed by RE/MAX on Island

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

3 Little Oak Lane

Price$875,000

Est. Mortgage: $/month

MLS ID 34858

  • Residential
  • Square Feet 1590
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 1.6

Chilmark living - the way it's supposed to be. Located between Middle Road and South Road, this year-round, 3 bedroom, 2 bath home offers Up-Island privacy on 1.6 acres. A gardener's dream, with newly planted raised perennials in a deer resistant enclosure. Centrally located, it is close to “one of the 10 best beaches in North America” - Lucy Vincent Beach; steps away from Fulling Mill Preserve's extensive trail system and dramatic ocean views; minutes away from the Chilmark Store, the Chilmark Community Center and Menemsha. The house has undergone extensive renovations with a new roof, deck and flooring completed in 2015 plus new Corian bathroom sink and vanity, new glass shower doors, 4 new heating/air conditioning ductless Mini-Splits, all new windows, new gutters, all new Moen faucets, new carpet on the lower level, insulated blinds and fresh paint throughout. A lower garden shed and storage has easy access. *Agent is the brother-in-law of the sellers.

Listed by Feiner 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

22 Larsen Lane

Price$1,199,000

Est. Mortgage: $/month

MLS ID 34809

  • Residential
  • Square Feet 1361
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 0.13

Unique opportunity to enjoy the Vineyard the way it use to be on this lovely country lane just steps from the Homeport and Menemsha Pond. Nestled in among vintage cottages this charming, fully renovated home offers all of the amenities buyers are looking for in an expanded Cape with three floors for entertaining family and summer guests. The home offers a beach theme design with its white beadboard wainscoting and offers rich wood floors, ceramic tile floors and baths. The home includes three spacious bedrooms and three full baths as well as a cozy sun room off the kitchen and a large finished basement. Winter water views from upstairs. This location offers your family and guests the unique ability to walk to a day at the beach, watch a Menemsha sunset, go to dinner and never have to get into a car or struggle to find a coveted parking space. Most Furnishings Included. There is over 600 additional sq feet of living space on the lower level that is not included in the square footage listed. Check out the 3D Virtual Tour.

Listed by Kelleher R.E.

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

95 Stonewall Road

Price$13,500,000

Est. Mortgage: $/month

MLS ID 34135

  • Residential
  • Square Feet 3008
  • Bedrooms 6
  • Bathrooms 5
  • Half Bath 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

$
$
%
$/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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

20 Tennis Lane

Price$2,195,000

Est. Mortgage: $/month

MLS ID 34314

  • Residential
  • Square Feet 2673
  • Bedrooms 4
  • Bathrooms 3
  • Half Bath 1

A thoughtfully appointed contemporary home in the center of Chilmark with 4 bedrooms and three and a half bathrooms all of which are newly renovated. This home has great entertaining spaces in and out. The large living room has a cathedral ceiling and a modern fireplace which is the focal point, there is lots of natural light provided by two sets of sliding doors to the deck . Another set of wide sliders opens up from the kitchen to the screened porch with dining area and door to the deck . The bright modern kitchen includes all high end appliances and central island. The 2 first floor bedrooms share a full bath while there is a half bath for guests and laundry room on this level. On the second floor there are two private master suites each with a private bath and one with private balcony. Large clean unfinished basement which could be finished for extra living space. A great second home or rental investment property with strong rental history. Chilmark residents have access to beautiful Lucy Vincent beach and a Squibnocket beaches and the home is within walking distance to lovely trails at Waskosims Rock land bank property.

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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

18 Spruce Gate Road

Price$7,750,000

Est. Mortgage: $/month

MLS ID 34218

  • Residential
  • Square Feet 3700
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details