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 real estate on Martha’s Vineyard. Our team has decades of experience in the local real estate market, so contact us to get started.

Learn more about Chilmark.

r=1-10
156 South Road

Price$1,485,000

Est. Mortgage: $/month

MLS ID 33282

  • Residential
  • Square Feet 2084
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 5

This quintessential Vineyard retreat is located just 1.5 miles to West Tisbury on a large 5 acre lot on South Road. Upon entering this charming Cape you are immediately greeted with a warm yet dramatic post and beam living room with cathedral ceilings and a wood burning fireplace encased in a custom made floor to ceiling wood surround. This room sets the tone for the rest of the home which is very unique in both layout and architecture.The kitchen includes a small island and an additional room which could be used as a more casual eating area or sitting room. There is a bedroom and a den and bath in this section of the house leading to an inviting long corridor which provides access to the second bedroom and finally the master en suite. Placing a couple of the bedrooms away from the main living areas' is great for groups with small children or elders who might prefer to retire a bit earlier then the rest of the family offering peace and quiet from a busy summer day. The home has a full house generator which is a must have for winter use.The house is sited on a dramatic, park like setting lot which offers many options in terms of landscaping or expansion to the house. In season it offers a large lawn area as well as an expansive area of wild flowers, grape vines and vegetable garden. The large lot enables the buyer to add a guest house, barn, garage, pool, etc with town approvals.

Listed by Jean Kelleher of Kelleher Real Estate Services

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

8 Smith Lane

Price$1,175,000

Est. Mortgage: $/month

MLS ID 33196

  • Residential
  • Square Feet 2089
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

If location is important this is the spot. Just a short drive off State road, this house is an easy bike ride to both town beaches and walking distance to the Chilmark Store and the community center. 2.5 wonderful rolling acres with a large west facing meadow affording tons of privacy and sun. This home has been rented for many years and is available for the first time. Nice sized bedrooms with a real master en-suite, huge living room with sliders out to a very large and almost new mahogany deck, great for lounging and grilling. The super-sized kitchen has tons of potential and would benefit from some updating of appliances and counter tops. This home is a diamond in the rough presenting real opportunity to someone with vision who appreciates a property with special qualities. There is a 2 car garage with plenty of storage and a wonderful palate of interesting land on which to create your vision.

Listed by Feiner, Jim of Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

11 Howell Lane

Price$2,950,000

Est. Mortgage: $/month

MLS ID 33171

  • Residential
  • Square Feet 4000
  • Bedrooms 4
  • Bathrooms 3
  • Half Bath 1

No detail was forgotten in this meticulously maintained Post and Beam custom home down Flanders Lane. A peaceful setting where you can hear the Menemsha bell chiming in the distance. With four spacious bedrooms, 2 of which are master bedrooms, gracious living areas, beautiful outdoor spaces and deeded rights to 200' of Menemsha Pond frontage, this home is a rare find. From the Alaskan cedar shake roof, to the soapstone kitchen counters and sink, the level of quality and craftsmanship is supreme. The finish work of the oversized living room with huge brick fireplace is an ideal resting place for those chilly winter evenings. The cozy TV/Dining area off the kitchen serves as the perfect entertaining space that can spill out onto the stone patio. A brand new 18 x 36 gunnite heated saltwater in-ground pool currently being added to this unique gem of a property, will enhance the already well maintained and beautiful landscapes and gardens surrounding this home. A must see property, too many details and qualities to list. An unparalleled find!

Listed by Flanders, Julianna of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

26 Kenasaoome Way

Price$879,900

Est. Mortgage: $/month

MLS ID 33069

  • Residential
  • Square Feet 702
  • Bedrooms 3
  • Bathrooms 1
  • Acreage 3.2

CHILMARK - Abutting 90 + acres of Conservation Land, this gem of a property has so much to offer, with tons of potential! Located in the lovely Quansoo area, on 3.2 acres of level and wooded land. Currently, a two bedroom, two story home, with an open floor plan and a large wrap around mahogany deck for that Summer living, including an outside shower. Very appealing, large, functional existing additional structure being used as a detached bedroom with cute porch! Three bedroom septic system with Title 5 Certification but lot size allows multiple additional bedrooms. Keep the house as is or take advantage of the lot size, location, by building your dream home and keep existing house as your guest house! Guest house allowed up to 800sq.ft, once town requirements are met. Quansoo Beach is at the 'end of the road', end of Quansoo Road, and can be freely enjoyed at the 'relaxing' time of the year........when the season is over.....(unless you have a key)! Short of that.... Spend your Summer days with a beach pass from the Town of Chilmark for Lucy Vincent and Squibnocket Beaches!!

Listed by Lohan-Conway, Alisan of Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

81 Squibnocket Farm Road

Price$11,600,000

Est. Mortgage: $/month

MLS ID 32757

  • Residential
  • Square Feet 4852
  • Bedrooms 4
  • Bathrooms 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 Kenney, Robert of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

137 Quansoo Road

Price$3,900,000

Est. Mortgage: $/month

MLS ID 32538

  • Residential
  • Square Feet 1476
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 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 Pearlson, Leslie of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

508 North Road

Price$800,000

Est. Mortgage: $/month

MLS ID 32266

  • Residential
  • Square Feet 900
  • Bedrooms 3
  • Bathrooms 1
  • Acreage 0.1

Historically known as the Cooper Gallery, this endearing icon of Menemsha has remained in the same family for years. A 3 bedroom cottage with a wonderful location, centrally located to all things Menemsha has to offer. Large Kitchen space with dining space, spacious living room, full bathroom and a bedroom make up the first floor plus a large deck space. Upstairs is two bright bedrooms with skylights.

Listed by Flanders, Julianna of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

34 Bijahs Way

Price$1,049,000

Est. Mortgage: $/month

MLS ID 32139

  • Residential
  • Square Feet 2293
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Well designed for low maintenance this 4 bedroom home located off Tea Lane in Chilmark has plenty to offer. With over 4 acres and access from 2 different roads a guest house could be added with it's own entrance for total privacy. The open kitchen living floor plan with sliders to a large 25 ft deck offers great entertaining space. Built in bookcases and window seat adds to the charm of the room and tie in nicely with the hardwood floors. The renovated kitchen with a lot of counter space and large pantry provides ample room to create. There are 2 floors of outside decks overlooking the garden area and the walkout basement adds additional living space. Spacious entryway leads to first floor master bedroom and 2 additional bedrooms that share a bath. This home is in excellent condition and ready for summer enjoyment. Seasonal water views from the living room. Many possibilities on this 4+ acre Lot! Easy to show!

Listed by Viglas, Deborah of Carroll & Vincent R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

11 Azalea Lane

Price$5,200,000

Est. Mortgage: $/month

MLS ID 30618

  • Residential
  • Square Feet 3750
  • Bedrooms 5
  • Bathrooms 4
  • Half Bath 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 Jenkins, Mark of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

4 Peases Point Way

Price$995,000

Est. Mortgage: $/month

MLS ID 30444

  • Residential
  • Square Feet 1652
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 1

Located down an idyllic country lane, this beautiful 3 bedroom home offers an inviting open floor plan with cathedral beamed ceilings perfect for entering summer family and friends. Renovated in 2004, updates include a new kitchen with granite counters and new appliances, updated bathrooms, new roof and new outside shower. This charming space flows gracefully out to a spacious sun room leading out to a large back deck. The private, first floor master en-suite includes a large inviting window seat perfect for morning coffee. Two second floor bedrooms and a small loft complete the picture. Located just minutes to Menemsha for an early morning swim or idyllic sunset lobster dinner. Small stained glass insert in front door to be replaced with clear glass. Check out the 3D Tour - https://livetour.istaging.com/590cc123becd360054078dae?ui=true

Listed by Jean Kelleher of Kelleher Real Estate Services

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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