Chilmark Homes for Sale

Types of homes in Chilmark include waterfront estates with private docks, cozy beach cottages, Cape styles, and more. The community is home to the fishing village of Menemsha, Squibnocket Beach, and Peaked Hill, which is the Island’s summit. Find homes for sale in Chilmark below.

Houses for Sale in Chilmark MA

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39 Prospect Hill Road

Chilmark, MA39 Prospect Hill Road

Price$3,750,000

Est. Mortgage: $/month

Active With Contract

MLS ID 38968

  • Residential
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 3.3

Stunning sunset water views from this hilltop home will delight the senses from morning to night. At 207 feet above sea level, the rolling and interesting 3.3 acre parcel has spectacular views overlooking many acres of gorgeous stonewall lined fields, a small duck pond, and a glimpse of Noman's and includes Menemsha bight and the Vineyard Sound. On the top of the hill it is perched high enough that the views actually go almost 40 miles over the tops of the Elizabeth Islands to the Newport bridge and mainland north. A comfortable 4 bedroom home designed to accommodate family and friends has an open kitchen living room area walking out to the deck. Great for parties and gatherings the heart of the home is an updated kitchen and a great place to meet and of course the sunsets are exquisite- as is watching the weather patterns over Aquinnah and the Islands. This is the first time this home has been for sale since its construction and there is plenty of room to envision improvements and additions. Built by Island builder Colin White in 1980, this family home has been a cherished heirloom for 4 generations of the current owners family and it will be for you as well.

Listed by Jim Feiner of Feiner Real Estate

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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31 & 33 Flanders Lane

Chilmark, MA31 & 33 Flanders Lane

Price$2,250,000

Est. Mortgage: $/month

Pending

MLS ID 38899

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 2

Light filled main and guest house set on two beautiful acres designed by post war pioneer architect William Smull known for his mid-century houses.With views of Menemsha Pond, Vineyard Sound and Aquinnah and within walking distance to Menenmsha Harbor, fish markets, and Menemsha Beach. Included is deeded access to Menemsha Pond where you can leave your skiff, kayaks or paddle boards for use on the pond.The main house has two bedrooms, two baths and open kitchen/dining/living area with large deck to enjoy the view. Guest house is entirely self-contained with one bedroom, kitchen, bath and two sitting areas yet is accessible from the main house by a charming foot bridge over the stream. Large yard with lily pond, grape vines and blueberry bushes.

Listed by Brenda Codding of Up Island Realty

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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86 Menemsha Cross Road

Chilmark, MA86 Menemsha Cross Road

Price$1,200,000

Est. Mortgage: $/month

Pending

MLS ID 38909

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathrooms 1
  • Acreage 3.6

Charming 1930's cottage located within walking distance of Menemsha harbor & village. This well maintained home has island character and history. Lovely ancient stonewall along western boundary line. The home is situated off the main road which affords privacy. Expansion possibility is limited to 25% of total square footage of existing building - approximately 300 sq. feet. An amazing opportunity to live in the town of Chilmark! REQUESTING ALL 'HIGHEST & BEST' OFFERS TO BE SUBMITTED BY TUESDAY,OCTOBER 19TH AT 3PM.

Listed by Julianna Flanders of Flanders Real Estate

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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53 Wequobsque Road

Chilmark, MA53 Wequobsque Road

Price$4,250,000

Est. Mortgage: $/month

MLS ID 38570

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathrooms 4.5
  • Acreage 6.4

Waterfront in Chilmark with Private Ocean Beach. This home on 6 acres nestled atop the magnificent Wequobsque Cliffs on Chilmark's south shore was built by one of the island's finest builders, John Early Construction. The home enjoys views of the Atlantic Ocean and private ownership of over 300 ft of white sand beach (Note: Seller has installed brand-new beach stairs.) There are 5 bedrooms spread over 4000 square feet with several separate living spaces including the "party barn" that makes up the west wing of the property. Look no further if your dream is to own a home waterfront on Chilmark's south shore. Click the "Documents" tab for full architectural plans including floor plans.

Listed by Andrew McElhinney of Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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31 Tower Lane

Chilmark, MA31 Tower Lane

Price$8,700,000

Est. Mortgage: $/month

MLS ID 38491

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathrooms 5.5
  • Acreage 3.7

Located in the Tower Farm neighborhood in Chilmark, this property is a masterpiece of light and design. An exceptional new to-be-built 5-bedroom and 5.5-bath modern style beach house nestled among 55+ acres of conservation area. Generously entertain family and guests in the open kitchen/family floor plan lined with oversized windows which overlook the lively outdoor landscape, stone walls and Conservation land beyond. This turn-key home will feature state-of- technology, sustainable materials and solar. The outdoor spaces include expansive decking, outdoor grill kitchen, lavish gardens, and proposed reflecting pool. Tower Farm Chilmark invites the senses to a realm of well-being and pleasurability. (Construction to begin 2021)

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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, MA20 Eliot Avenue

Price$7,900,000

Est. Mortgage: $/month

MLS ID 36784

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 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: 3.1% last updated on Nov 24, 2021
* 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, MA20 Eliot Avenue

Price$7,900,000

Est. Mortgage: $/month

MLS ID 38217

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 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: 3.1% last updated on Nov 24, 2021
* 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, MA1 Pondmark

Price$4,700,000

Est. Mortgage: $/month

MLS ID 38183

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

Turn onto country lane and make first turn to right. Drive past Norwegian Pine and many mature plantings and follow stately stone walls up past an open field overlooking the pond. The gentle slope takes you past the garden to a parking area. The white cottage sits on top of the knoll with sweeping views looking out over Keith farm and beyond to the ocean. From the living room the light brightens the large room with vaulted ceilings and a fireplace with a copper chimney hood.You can walk out on the deck for breakfast and watch the cows, geese, horses or the calming motion of the sea. You can lay in bed and take it all in from the king size bed and wall of windows facing south. There is room for a guest house or barn in this private setting. There are walking trails on Old North Road or a trail to Menemsha Crossroads. Go back in time to a slower way of life in this old style Chilmark retreat.

Listed by Elise LeBovit of Gay Head Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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 Middle Road

Chilmark, MA135 Middle Road

Price$2,950,000

Est. Mortgage: $/month

MLS ID 37541

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathrooms 2
  • Acreage 7.1

A quintessential 1950s cottage situated on the highly sought after area of Middle Road in Chilmark. Consisting of a main house, guest house, garage and storage shed on 7.1 total acres. Would make a great family compound. A Landbank walking trail abuts property. Property is being sold "AS IS." Septic upgrade plan completed, but not installed.

Listed by Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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 Ebens Lane

Chilmark, MA34 Ebens Lane

Price$7,650,000

Est. Mortgage: $/month

MLS ID 37882

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathrooms 5.5
  • Acreage 3.9

An exceptional new 5-bedroom and 5.5-bath single-story modern style farmhouse nestled among 55 acres of conservation area in Chilmark. Generously entertain family and guests in the open kitchen/family floor plan with 10’-foot ceilings. Designed with entertaining and relaxation in mind, this beautiful timeless design offers expansive views that immediately connects you with nature in a private setting. The artfully designed landscape will feature custom planters, a lively outdoor grill kitchen and pool overlooking views of the Conservation Area beyond. Places like landscapes to experience and inhabit; to welcome guests and feel welcomed ourselves in beautiful, comfortable outdoor surroundings. Tower Farm Chilmark invites the senses to a realm of well-being and pleasurability. [Construction to begin 2021]

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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 November 30, 2021 . 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."