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.

96 Menemsha Cross Road

Price$950,000

Est. Mortgage: $/month

MLS ID 33992

  • Residential
  • Square Feet 1546
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Meticulously maintained Cape style home and 2 car garage is move in ready! This home is charming and offers a lovely setting. This home has had tremendous updates in recent years; some of which include new kitchen, new furnace, new roof, upgraded insulation and so much more! A master bedroom and full bathroom on the first floor with spacious living room, small office, updated kitchen and a formal dining area that is surrounded by large windows to allow the room much natural light. Three additional bedrooms and a full bathroom upstairs. The well manicured and mature plantings that surround the house add more appeal and character to this home. A simple distance to Menemsha and also to Chilmark center and Lucy Vincent beach. With a wonderful rental history as well!

Listed by Flanders Real Estate

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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10 Rumpus Ridge

Price$750,000

Est. Mortgage: $/month

MLS ID 33533

  • Residential
  • Square Feet 1000
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.5

Close to Chilmark Center, this three bedroom, two bathroom home is pleasantly sited on a quiet lane. It is ready for a new owner to repair & refurbish it for the next chapter!

Listed by Flanders Real Estate

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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21 Squibnocket Road

Price$4,375,000

Est. Mortgage: $/month

MLS ID 33963

  • Residential
  • Square Feet 1833
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic cottage 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, a guest wing with three more bedrooms, and a 30'x20' recreation room. The property offers 1.11 acres surrounded by stone walls, a bluestone patio facing the Atlantic, and a path to the Pond (with rights to build an elevated walkway). 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

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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114 Middle Road

Price$2,375,000

Est. Mortgage: $/month

MLS ID 33858

  • Residential
  • Square Feet 3951
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

This masterfully-crafted home was built in 2010 with high quality materials and finishes of paramount importance. There is custom paneling, mill work, and cabinetry gracing each and every room. Start with the open concept floor plan - enter first the foyer with a coat closet, powder room, and gorgeous staircase. Then the living room with cathedral ceiling and impressive stone fireplace, a lovely dining area, and a spectacular chef's kitchen with top-tier appliances - Wolf stove top and microwave, 2 Viking ovens and warming drawer, Fisher Paykel refrigerator, dishwasher, washer, and dryer. Off the living room is the master bedroom suite with its own library with fireplace, dressing room with fireplace, and stunning bathroom with a claw-foot soaking tub, double vanity, and tiled shower. Off the kitchen is the year-round sun room or den, a butler's pantry, laundry, and 2-car heated garage. Upstairs you have 2 more bedrooms each with high-end bathrooms. Outside there are stone walls and patios and a charming fountain - all designed for relaxing. Plus a deck perfect for outdoor dining. It should be noted there is a 4-bedroom septic system so the den could be used as a bedroom if desired. So many options at this unique home. It's a must see!

Listed by Viewpoints

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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130 South Road

Price$1,295,000

Est. Mortgage: $/month

MLS ID 33794

  • Residential
  • Square Feet 2746
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 2.3

Once a two story barn, this 2200 square foot space was converted to a 3-br residence some years ago and still retains much of its original character. Formerly known as the Fenner barn, the exposed beams, trusses and original wood walls and ceiling were thoughtfully preserved to retain the antiquity and essence of the original Barn. An open style living concept, the residence offers two sunrooms, open kitchen/living dining area with stone fireplace and a main level master bedroom. Two more bedrooms on the second floor and another loft style living area with book cases and another stone fireplace - known as 'the music room'. Surrounding gardens and mature plantings on 2.3 acres complement the simplicity and charm of the interiors. A 1-br guest house (556 sf) at the rear of the property offers additional sleeping space for guests, family or an income producing property.

Listed by Tea Lane Associates

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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24 North Slope Lane

Price$1,475,000

Est. Mortgage: $/month

MLS ID 33844

  • Residential
  • Square Feet 1640
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Sweet location with surprising views over the Vineyard Sound. The lot is a form A which has not been recorded given the Seller would like the future owner to determine if they want the property in its entirety (6.7 acres) or this 3.9 acre parcel which has already been surveyed. A new well would need to be installed for this home. The septic has a Title V system for four bedrooms however this can be expanded with additional soil testing. The house could be used spiffed up for seasonal use until a new owner has time to design a new home with strong Elizabeth Island and sunset views.

Listed by Tea Lane Associates

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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68 Meeting House Road

Price$1,950,000

Est. Mortgage: $/month

MLS ID 33760

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 6.16

Charming four bedroom Cape with beach key to the sandy shores of Black Point. Sited on over six pristine acres, some of which is held in conservation, complete with stone walls, rolling hills, and meadow. The well-built home offers the perfect layout for comfortable summer living, with an open floor plan and large screened in porch. Distant water views and endless star gazing is achieved from the rooftop deck. The epitome of Island living.

Listed by Sandpiper Realty

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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27, 30, 31 Tower Lane

Price$3,500,000

Est. Mortgage: $/month

MLS ID 33303

  • Residential
  • Square Feet 4967
  • Bedrooms 6
  • Bathrooms 3
  • Acreage 63.3

This is a unique property like no other! Located off of Middle Road on over 63 acres (much of which are conservation restricted), this amazing property has been used as a family compound. Offering an architecturally designed main house, a charming guest house, a caretaker's cottage, additional outbuilding as well as an unfinished in ground pool and pool house. This property, while exceptional, it is in need of maintenance and updating. Being sold "as is", this property needs to be seen to be appreciated.

Listed by Flanders Real Estate

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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34 High Mark

Price$1,950,000

Est. Mortgage: $/month

MLS ID 33598

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 1.8

Enter into this home and be immediately stunned by the wide open expansive South Shore Atlantic views! This vintage home is reminiscent of mid century architecture and offers a lovely open floor plan with an expansive deck facing the views. The master bedroom and a full bathroom is also on this level. The lower level of the home features 3 more bedrooms and a full bathroom as well as an additional living room space, great for the kids! Glass doors and windows to let the natural light flow in. Only a short distance to Chilmark center, Menemsha and Lucy Vincent beach.

Listed by Flanders Real Estate

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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7 Black Point Road

Price$1,960,000

Est. Mortgage: $/month

MLS ID 33729

  • Residential
  • Square Feet 2120
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Come see this charming architect designed retreat with main house & two connecting guest wings, set on 5.5 pristine acres plus 17,424 SF deeded Atlantic Ocean Beach lot valued at $303,000 included with sale for a total acreage of 5.9 acres (SEE Comments/directions). Impeccably maintained the property is designed for relaxing and enjoying the unpretentious beauty of Black Point and the beach. The great room with banks of sliding doors beacons you the deck & patio. Ocean breezes & the sound of the surf gently wake you in the morning & help you drift off to sleep. The evening sky will make an Astronomer out of you. Main house features the great room, dining area, kitchen, laundry, pantry, master, full bath & outdoor shower. 1st guest wing has 2 BR'S, full bath with outdoor shower. Built in 2007 the 2nd guest wing has living area, BR, bath and outdoor shower. With town permitting you can add a guest house & pool. While you feel miles away you are still less than 10 minutes to Alley's store.

Listed by Point B Realty LLC

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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