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. 

1 Pondmark Chilmark MA 02535

Chilmark, MA1 Pondmark

Price$4,400,000

Est. Mortgage: $/month

MLS Number 40055

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

Massive Atlantic Ocean views! This 4.7-acre lot with 120-degree views of the Atlantic Ocean over Keith Farm offers the ideal opportunity to create a stunning property with a main house, guesthouse and swimming pool. The current home is ready to make way for the new owner's vision. The property is just one mile to the entrance of Lucy Vincent Beach and half a mile to Beetlebung Corner. It is a mile and a half to Menemsha. The property is criss-crossed with ancient lichen-covered stone walls and has a feeling of having stepped back in time.

Listed by Mark Jenkins of Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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50 South Road Chilmark MA 02535

Chilmark, MA50 South Road

Price$2,695,000

Est. Mortgage: $/month

MLS Number 40343

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3
  • Acreage 6.4

Authentic and lovely Vineyard homestead on over 6 acres with hedgerow borders and stone walls, this is a special and storied piece of island history. The sweeping views over farm fields are stunning, filling the windows with light and the beauty of this natural rural landscape as it has been for hundreds of years. The 1700s post and beam home was originally a "high double house" and became a three-quarter house with an ell in the 1800s. It retains some original features like wainscoting and ancient wide plank floors. The sturdy barn, which was moved to the property in the early 1900s, is ready for it's next chapter as a work barn again, rec space, studio or entertaining spot. This antique Chilmark home awaits its rejuvenation. The property can support an additional house. Property is being sold AS IS.

Listed by Meg Bodnar of Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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2 Rockrose Path Chilmark MA 02575

Chilmark, MA2 Rockrose Path

Price$1,995,000

Est. Mortgage: $/month

MLS Number 39975

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.6

Sited atop a hill to take full advantage of its South Shore Atlantic Views, this 4-bedroom, 3-bath home has vaulted, open plan living spaces that flood the living, dining and kitchen with sunlight. Each of the 4 bedrooms is generous in size and the primary bedroom, with en suite bath, is especially roomy, bright and airy. Tucked away on a beautiful lot with rolling hills, large boulders, mature trees and stone walls. Access to Lucy Vincent beach, Squibnocket beach and Menemsha beach. Quitsa Pond and Menemsha Pond landing is also accessible. Thumb's Cove Beach Lot available for additional $350,000.

Listed by Alyson Parker of Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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 The Aerie Chilmark MA 02535

Chilmark, MA7 The Aerie

Price$1,950,000

Est. Mortgage: $/month

Pending

MLS Number 40227

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 1.5
  • Acreage 3.3

For the artist and nature enthusiast! This cozy post and beam house boasts 3 bedrooms and 1 1/2 baths. Saltillo tile throughout the first floor. Built in shelving and cabinetry for great storage. Close proximity to Menemsha and Chilmark center. Private and peaceful yard with potential for a gardener to add their own touches. Two out buildings provide for additional storage. Garden shed/barn with loft area above and second outbuilding is perfect for a home office, artist studio or guests visiting. Come see this "little house on the Aerie." BEST AND FINAL OFFERS due Monday, November 7 by 4PM.

Listed by Julianna Flanders of Flanders Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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 Tea Lane Chilmark MA 02535

Chilmark, MA21 Tea Lane

Price$1,375,000

Est. Mortgage: $/month

MLS Number 40137

  • Land
  • Mls Status Active
  • Acreage 5.16

Exciting opportunity to build your Chilmark dream home on this private 5.2 acre lot. Located just off Tea Lane, this magical lot features stonewalls, mature trees and a desirable rolling topography. Approved for a 6-bedroom residence, the dramatic ridgeline offers the ideal homesite. The land is mostly surrounded by Martha’s Vineyard Land Bank with easy access to the miles of hiking trails at Tea Lane Farm. Chilmark residents enjoy exclusive access to both Lucy Vincent Beach and Squibnocket Beach on the Atlantic Ocean.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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 January 30, 2023 . 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."