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: 6.7% last updated on Sep 29, 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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94 Menemsha Inn Road Chilmark MA 02535

Chilmark, MA94 Menemsha Inn Road

Price$9,650,000

Est. Mortgage: $/month

MLS Number 40010

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4
  • Acreage 5.6

Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large enclosed sun porch off the kitchen to enjoy meals and family time and is adjoined by a breakfast nook. Three (3) Bedrooms are located on the upper level. The primary bedroom is complete with a balcony to enjoy sunrises and sunsets. The 4th bedroom is on the first floor next to a full bathroom. The basement is a finished area with an additional living area.

Listed by Julianna Flanders of Flanders Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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94 Menemsha Inn Road Chilmark MA 02535

Chilmark, MA94 Menemsha Inn Road

Price$9,650,000

Est. Mortgage: $/month

MLS Number 40039

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 5.6

This waterfront 4 bedroom 2.5 bath quality custom home and detached 1 bedroom, 1 bath guest studio are sited on 5.6 pristine acres. Enjoy spectacular water views and magnificent sunsets from almost every room as well as from the stone terrace, screened porch and master bedroom balcony. This is a finely crafted home with many wonderful details including salvaged heart pine floors and beautiful old beams. Relax amidst the gardens, expansive lawn and mature trees as you take in the beauty around you or go for a leisurely stroll to Menemsha Village. A short path leads to 340 feet of private waterfront on the Vineyard Sound where one can swim peacefully in the calm waters.

Listed by Abby Rabinovitz of Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

Pending

MLS Number 39416

  • Residential
  • Mls Status Pending
  • 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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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

Pending

MLS Number 36784

  • Residential
  • Mls Status Pending
  • 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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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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15 Red Valley Road Chilmark MA 02535

Chilmark, MA15 Red Valley Road

Price$6,100,000

Est. Mortgage: $/month

MLS Number 40004

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3
  • Acreage 3.6

Glorious views spanning over Nashaquitsa and Menemsha Pond to the Vineyard Sound and Elizabeth Islands. This sweet Vineyard home is situated up high overlooking open meadows, old stone walls with multiple views to the Atlantic Ocean. Located in beloved Blacksmith Valley and enjoyed by the same family for over sixty years -this is a rare opportunity. With 3.6 acres of open, rolling land, classic Chilmark stonewalls and beach plum bushes, this charming 5 bedroom home with an existing pool, sits on a ridge and offers views from Noman's Land to the Edgartown shoreline. The property also includes a garage for vehicle and boat storage at the edge of the property. Squibnocket Beach is around the corner as well as an opportunity to join Zack's Cliffs for Blacksmith Valley residents. The property includes deeded access to Quitsa Pond and a small dock area where kayaks and a sunfish can be stored. Boating, swimming, fishing and bird watching are right outside your door.  This is a special opportunity for a Buyer who appreciates and understands what this location has to offer.

Listed by Elle Lash of Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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$4,400,000

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: 6.7% last updated on Sep 29, 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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4 Tilton Road Chilmark MA 02535

Chilmark, MA4 Tilton Road

Price$3,950,000

Est. Mortgage: $/month

Pending

MLS Number 39831

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 2
  • Acreage 3.2

Steps from the beach, this beloved home is a great opportunity to own in Spring Point overlooking association conservation land out to the Vineyard Sound, Elizabeth Islands and the Aquinnah Lighthouse. This location is an easy stroll to a private beach on the North Shore of Chilmark where residents enjoy miles of maintained walking trails throughout the association. The Spring Point Association has view preservation as a top priority and works with each homeowner to maintain their water view which is critical to maintain a strong investment. This is a lovely property, close to the beach and extremely private. Well oriented for sunsets and all day sun as the deck faces West. A casual, tidy and refreshing home that incorporates nature and the significant water views from most all rooms. Four bedrooms, two full baths, large expansive deck, open floor plan and an easy stroll to the beach! PLEASE NO DRIVEBYS, TENANTS IN PLACE. We have specific times we can get in. Tennis membership available for $5000. Two private tennis courts for members within Spring Point.

Listed by Jill Napior of Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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2 Rockrose Path Chilmark MA 02575

Chilmark, MA2 Rockrose Path

Price$2,295,000

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. This is Chilmark's best value at $2,295,000. Owner in residence, 24 hours notice for showings. No drivebys.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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10 Mollys Way Chilmark MA 02535

Chilmark, MA10 Mollys Way

Price$1,750,000

Est. Mortgage: $/month

MLS Number 39908

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.2

A special spot with a charming water view cottage in the heart of Menemsha. An opportunity that does not present itself often. Quintessential Menemsha cottage, built in 1926, still retains the character of original summer home. Loved by the same family for decades, it can now be yours. Welcoming screened porch with views of Menemsha Pond, Vineyard Sound & beyond. Enjoy Menemsha and stunning sunsets in the western sky from the privacy of your porch away from the crowds or join in the fun and never have to find a parking space! Close to beach, harbor, shops, restaurants & fish markets. Three bedrooms, kitchen with pantry, open living dining area with fireplace, one and a half baths and outside shower. The walkout basement is finished, including a half bath and laundry area as well. The finished basement is included in the square footage of the ELA. Last but not least, you gain access to Lucy Vincent and Squibnocket beaches. There is currently summer water supplied by Menemsha Water Company. It is possible to hook onto winter water for an additional fee and a Menemsha Water Company Stock must be purchased at closing. Please call listing broker for further details and bi-annual fees to MWC. This home is being sold "AS IS".

Listed by Deb Hancock of Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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2 Creek Hill Chilmark MA 02535

Chilmark, MA2 Creek Hill

Price$1,600,000

Est. Mortgage: $/month

Pending

MLS Number 39820

  • Residential
  • Mls Status Pending
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.2

You won’t miss a beat at this classic two-bedroom one bath cottage located in the heart of Menemsha! The perfect escape, overlooking the harbor, with a second-floor salon, providing front-row seats to watch the renowned sunsets. Just steps away from Dutcher’s Dock, the beach, restaurants, galleries, and of course, all the fresh fish your heart could desire, allowing you to become fully immersed in the culture and lifestyle of this picturesque bustling fishing village. A home filled with character and history, waiting to be enjoyed!

Listed by Katherine Donahue of Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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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: 6.7% last updated on Sep 29, 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 October 5, 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."