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. 

8 Snail Road, Chilmark, MA

Price$17,750,000

Est. Mortgage: $/month

MLS Number 28958

  • Residential
  • Square Feet 6967
  • Bedrooms 6
  • Bathroom 5
  • Half Baths 2

Majestically perched 120 feet above the Atlantic Ocean, the magnificent Chilmark House is an award-winning triumph of design and execution. Designed by Seattle architect Rick Sundberg, Falmouth landscape architect Steve Stimson and built by master builder Andrew Flake, the house flows continuously between interior and exterior spaces. A comfortable yet luxurious seaside retreat that celebrates panoramic ocean views of the South Shore and Chilmark Pond. This home features gracious skylights, huge windows and wonderful detail in both design and materials. Oak and radiant-heated limestone floors, marble baths, precast concrete fireplace mantles and top quality appliances support a relaxed yet sophisticated experience for residents and guests. Views from the grand entrance encompass the ocean and infinity pool. The foyer leads past an exquisitely appointed dining room to the great room with soaring ceilings, floor to ceiling windows and an oversized wood burning fireplace. The impeccable attention to detail is highlighted in the chef's kitchen with sitting area, fireplace and custom casework. Heated infinity pool, half-basketball court, large screened porch and outdoor terraces provide a breezy and beautiful venue for all. This secluded residence and 2 bedroom guest cottage sit on 9.5 acres of wooded hillside and includes access to a private Atlantic Ocean beach accessed by boat across Chilmark Pond from your private dock. A presidential paradise, this estate served as the 2013 summer White House. An exquisite Vineyard home!

Listed by Wallace & Co. Sotheby's

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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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22 Austin Pasture Road, Chilmark, MA

Price$7,800,000

Est. Mortgage: $/month

MLS Number 31818

  • Residential
  • Square Feet 3358
  • Bedrooms 4
  • Bathroom 3
  • Acreage 22.9

22 acres in Chilmark with a well designed home that truly resonates with the land. Commanding views over Squibnocket Pond, south shore barrier beaches and the Atlantic Ocean. A three bedroom main house and a one bedroom guest house are sited privately on a south facing slope taking advantage of the best this property has to offer. Ultimate privacy with an exceptional location. Exclusive access to Squibnocket Pond with two little private islands included (Strawberry Island and Gull Island). Paddle board and kayak around this pristine pond and enjoy the quiet and calm that comes with living in this natural environment.This is truly a once in a lifetime opportunity for a discerning Buyer. Click on the link for a drone video of the property.

Listed by Tea Lane Associates

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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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51 Squibnocket Farm Road, Chilmark, MA

Price$7,500,000

Est. Mortgage: $/month

MLS Number 31990

  • Residential
  • Square Feet 3200
  • Bedrooms 4
  • Bathroom 2
  • Half Baths 1

Set in one of the wildest, most natural open landscapes on the island, this converted 1830s Dutch barn in Squibnocket Ridge Farm is unlike any other home on the island. Just steps from the beach and Squibnocket Pond, surrounded by conservation land, tranquility and miles of private shoreline, this home combines rustic historic character with modern kitchen, baths, and utilities/systems. 32-ft high ceilings in the soaring living room, water views, screened porch and expansive outdoor living space including lawn, gardens, trails. This is a truly extraordinary property.

Listed by Tea Lane Associates

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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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51 Squibnocket Farm Road, Chilmark, MA

Price$7,500,000

Est. Mortgage: $/month

MLS Number 32000

  • Residential
  • Square Feet 3225
  • Bedrooms 4
  • Bathroom 2
  • Half Baths 1

Quintessential Chilmark property located in one of the finest coastal enclaves in the entire Northeast, only 16 home sites on 500+ acres of private and natural seaside lands. Renovated 1830's barn with soaring ceilings, exposed beams and modern kitchen amenities. One-of-a-kind property with deeded rights to miles of private, south-facing sandy beaches and pond-side trails.

Listed by Rooney & Company

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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

Price$6,500,000

Est. Mortgage: $/month

MLS Number 30425

  • Residential
  • Square Feet 3241
  • Bedrooms 5
  • Bathroom 3
  • Half Baths 1

This waterfront 4 bedroom 2.5 bath impeccable 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 Tea Lane Associates

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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

Price$6,500,000

Est. Mortgage: $/month

MLS Number 30472

  • Residential
  • Square Feet 3241
  • Bedrooms 5
  • Bathroom 3
  • Half Baths 1

This elegant, architect-designed main house and guest house is steeped in privacy at the end of a picturesque Chilmark Lane. A private path leads you to the private North shore beach frontage that is provided by this property. With remarkable views of the Vineyard sound, Elizabeth Islands, and endless sunsets this lovingly maintained property has much to offer. The four bedroom main house is in excellent condition with a spacious, well laid out kitchen and dining space as well as a lovely screened-in porch. A large living room area, with stone fireplace and French doors, leads out to the terrace and ocean views. Vaulted ceilings, spacious bedrooms and an additional living space and bathroom in the lower level plus a detached guest house studio with wonderful sound views add to the appeal of this home. The gardens and manicured outdoor spaces of this land add to the already welcoming and flawless feel of this entire property. Menemsha village is only a short drive away or one could also walk along the shore's edge to get there. This home and property is truly a magical and restful place in which to enjoy the Vineyard.

Listed by Flanders Real Estate

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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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135 State Road, Chilmark, MA

Price$5,750,000

Est. Mortgage: $/month

MLS Number 19770

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathroom 1
  • Half Baths 1

Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the Vineyard. Views from nearly every room of this home over Quitsa and Menemsha Pond. With extremely desirable dock space included, this property has two full private docks and one floating dock only steps from your door. First level of home is a large living area with kitchen all fronted by a large screened in porch. There is also another area that serves as bedroom or could also be used as a den or office space. Upper level has 3 bedrooms, large living room, full bathroom and loft space - great for the young ones. This home is great for entertaining and offers some of the most spectacular views in Chilmark. Enjoy sunset views over the pond...or swim off of the private sandy beach area on the pond which is great for young swimmers and for launching kayaks...All of this just within a short distance of Squibnocket Beach.

Listed by Flanders Real Estate

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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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11 Azalea Lane, Chilmark, MA

Price$5,500,000

Est. Mortgage: $/month

MLS Number 30618

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 4
  • Half Baths 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 Wallace & Co. Sotheby's

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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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3 Eliot Avenue, Chilmark, MA

Price$5,500,000

Est. Mortgage: $/month

MLS Number 31243

  • Residential
  • Square Feet 4696
  • Bedrooms 5
  • Bathroom 3
  • Half Baths 1

Enjoy incomparable water and landscape views, exquisite sunrise and sunsets, from this inviting and sophisticated home, designed and built by one of the Island's best,Tom Tate, is uniquely situated in the landscape in one of Chilmark's most exclusive areas. Reclaimed lumber and wood beams are discreetly incorporated into the details throughout the house to give an enduring and timeless affect. The open floor plan captures views from different bodies of water and landscape elements. A gourmet kitchen with Gaggenau stove, Sub-zero and built-in Fisher & Paykel dishwasher, lends itself as a perfect place to entertain guests next to a stone fireplace and dining area. There are five bedrooms and an additional family room on the lower level that leads out to a stone patio with hot tub. The exterior details are intriguing with professional hardscaping in abundance. Very convenient location to beaches, shopping, and restaurants. Steps away is access to your deeded beach rights on the south shore and boat launch at Quitsa pond. Come see and experience this property for yourself.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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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225 State Road and 3 Clam Point Cove Road, Chilmark, MA

MLS Number 26642

  • Residential
  • Square Feet 3190
  • Bedrooms 6
  • Bathroom 3
  • Half Baths 1

This antique homestead with barn was built around 1850 and is sited on six magnificent acres with stunning water views overlooking Quitsa and Menemsha Ponds on out to the Vineyard Sound and the Atlantic Ocean. Walk down a quiet path to seventy seven feet of private shoreline on Quitsa Pond where one can paddle boat, kayak and sail out to Menemsha and the Vineyard Sound. The property consists of two abutting three acre parcels. The six bedroom homestead parcel offers a piece of Chilmark history and holds the potential for a wonderful restoration. With special permit the antique barn, currently used as a garage, could become an art studio, detached bedroom or eventual guest house. The abutting buildable waterfront lot offers the opportunity to create an amazing new home on a spectacular site. Recently engineered, the waterfront lot is approved by the Board of Health for six bedrooms. This is a wonderful offering for the buyer who is looking for a unique and special property. Preliminary design sketches are available upon request. Note: The Assessors Map does not reflect the current configuration of this property. Clam Point Cove Rd., which originally bisected the waterfront lot, has been moved to the north western boundary of the homestead lot and no longer divides this six acre property. The move opens up a prime building area on the waterfront lot. (see building site document) and allows for two homes on this six acres with spectacular water views as well as privacy . The waterfront parcel can be purchased separately for $2,800,000, the homestead can be purchased separately for $2,495,000 (see individual listings) or both can be purchased together at the reduced price of $4,995,000.

Listed by Tea Lane Associates

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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 Eliot Avenue, Chilmark, MA

Price$4,000,000

Est. Mortgage: $/month

MLS Number 30462

  • Residential
  • Square Feet 1714
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.65

Leave it all behind when you arrive at this magical location with stunning views of both the Atlantic Ocean and Stonewall Pond. One of the Island's most brilliant settings and an immensely fascinating location where Stonewall Pond meets the Atlantic barrier beach. A path to the beach is just footsteps from an elegantly simple dwelling with lots of glass and decks. This is an incomparable location and must be experienced! The property includes a detached shed and a Stonewall beach lot. Aerial video can be found under External Links.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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 Chockers Lane, Chilmark, MA

Price$3,900,000

Est. Mortgage: $/month

MLS Number 32231

  • Land
  • Village North
  • Acreage 9.27

Exquisite piece of Chilmark available with frontage on Menemsha Pond. This gorgeous parcel has already been staked, surveyed, and the well and septic are already complete and in place! The expansive views of Menemsha Pond and beyond include the Vineyard Sound and Elizabeth islands inclusive of sunset views. Build your dream home and explore the beauty of all that Chilmark has to offer.

Listed by Flanders Real Estate

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on May 25, 2017
* 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