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

Questions about buying a home in Chilmark? Call Landmarks Real Estate: 508-693-6866

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12 Peaked Hill Road

Chilmark, MA12 Peaked Hill Road

Price$1,895,000

Est. Mortgage: $/month

MLS ID 38614

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 1.5
  • Acreage 1.3

A much loved family cottage located on the highest point on the island on a quiet paved drive off Middle Road less than a mile from Beetlebung Corner. Part of this 3 season home was a former WWII Navy barracks and has been in the same family for generations. Bring your imagination and renovate to enjoy spectacular views from a potential second floor or expand up the hill for more elevation with potential to see all of Chilmark’s south shore and the ocean beyond.

Listed by Natalie Conroy of Conroy & Company R.E., Inc.

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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: 2.8% last updated on Jul 29, 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 38565

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

This magnificent waterfront home sited on 6.4 acres sits atop the dramatic Wequobsque cliffs. On Chilmark's coveted South Shore, this home boasts ownership of over 350 feet of private beach with access from your staircase in the backyard. The home has a 5-bedroom and 4-bath wing. Attached by a screened-in porch, is the large gathering kitchen with ceiling beams, tall columns and an open, airy design. Enjoy meals in the dining area with ocean views. Dine on the large outdoor deck facing the Ocean. On the west side of the property sits the barn with a half bath and a loft that can be used as an office or extra sleeping area. There is wet bar, ping-pong table, large screen TV and sofa. There's space to install a wood stove. The home has a new full basement and HVAC system. A very large one car garage below the barn completes the property. This is your opportunity to own your dream home on the waterfront on Chilmark's South Shore.

Listed by Grace Hagerty of Grace Hagerty Real Estate Inc

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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: 2.8% last updated on Jul 29, 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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8 Drive Way

Chilmark, MA8 Drive Way

Price$2,650,000

Est. Mortgage: $/month

Active With Contract

MLS ID 38298

  • Residential
  • Bedrooms 4
  • Bathrooms 2.5
  • Acreage 4.7

Middle Road Water View: This fabulous location, just off Middle Road, and not far from Beetlebung Corner, offers views of the lush countryside extending south to the blue waters of the south shore. The residence, designed by noted architect Milton Klein, has modern lines, a minimalist white interior with bleached bamboo floors, a wall of glass sliders with southern exposure and a high ceiling in the Great Room which encompasses living, dining and kitchen. The main level master suite has a separate office space and en suite bathroom. Off the Great Room is a large deck also leading to the screened porch which has access from the kitchen. The lower level floor plan has a family room with built in cabinets for storage and media, glass sliders out to deck and 2 outdoor showers, 3 guest bedrooms, a full bathroom plus powder room, closet laundry room, and utility room. The house is designed with plenty of built-in drawers and cabinets. The 4.7 acre site provides plenty of room for expansion. It is less than two miles to Lucy Vincent Beach and less than 1 mile to the Chilmark Store. Mini-Split A/C in Great Room and Master Bedroom. House heated by both Gas FHW and Electric, and also receives good solar gain from south side. See attached deed for covenants and view maintenance.

Listed by Patty Kendall of Kendall & Kendall

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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146 Quenames Road

Chilmark, MA146 Quenames Road

Price$26,500,000

Est. Mortgage: $/month

MLS ID 36389

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathrooms 8.5
  • Acreage 60.4

One of the largest single residential lots in Chilmark, this exceptional 60 acre offering includes 800 +/- feet of direct, breath-taking Atlantic Ocean front. This Martha’s Vineyard estate offer multiple homes including a new farmhouse, main house and bunk house. A private drive leads you past beautiful farmland, open fields, down past Quenames Pond and over the dune down to the sandy beach. The residences and grounds offer endless options in this simply stunning private oceanfront estate.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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22 Tabor Hills

Chilmark, MA22 Tabor Hills

Price$1,695,000

Est. Mortgage: $/month

Pending

MLS ID 38274

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathrooms 2.5
  • Acreage 3.1

Beautifully kept three bedroom contemporary home, set amongst 3 acres of rolling Chilmark land. The first floor is all wood floors, a spacious first floor master bedroom, with large bathroom and walk-in closet space as well as an open layout plan for the living/dining and spacious kitchen area all add to the comfort of this home. Enjoy dinners on the screened in porch, or reading a back on the back deck overlooking the large yard and wooded surroundings. A First floor laundry area, a half bathroom, a small office area, as well as a 2 car garage complete the first floor. Upstairs you will find 2 more large bedrooms that share a full bathroom. This home gets amazing light, the living room is lined with windows, making it a wall of glass to enjoy the Chilmark landscape. This home has a 5 bedroom septic in place, yet it is only a 3 bedroom home so the potential already exists to add more bedrooms either by finishing the walk out basement area, an addition or a detached bedroom, so many options!

Listed by Julianna Flanders of Flanders Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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$8,950,000

Est. Mortgage: $/month

MLS ID 36784

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 3.5
  • Acreage 1

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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$8,950,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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$5,200,000

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: 2.8% last updated on Jul 29, 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 August 5, 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."