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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31 Tower Lane

Chilmark, MA31 Tower Lane

Price$7,100,000

Est. Mortgage: $/month

MLS ID 37882

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

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.

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

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$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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40 Blueberry Ridge Lane

Chilmark, MA40 Blueberry Ridge Lane

Price$1,500,000

Est. Mortgage: $/month

MLS ID 37977

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 3.7

Located in the beautiful Blueberry Ridge Association off North Rd, this traditional 4-bedroom home delights us with many appealing upgrades. The spacious, eat-in chef's kitchen is clearly the heart of the home. Decks on both the front and back of the house provide attractive transitional areas to relax and enjoy the quiet country setting abutting Sheriff's Meadow property. This is a great year-round home or the vacation home that is nicely located for easy access to Menemsha and the center of town. Of course, this house provides entree to the beautiful Chilmark south shore beaches as well. Major full house renovations done in 2011, additional upgrades in 2015.

Listed by Cassie Bradley of Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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92 Kings Highway

Chilmark, MA92 Kings Highway

Price$1,450,000

Est. Mortgage: $/month

Active With Contract

MLS ID 37915

  • Residential
  • Village South
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 1.9

Set in the heart of Chilmark's largest continuous trail system off King's Highway, this comfy, bright and airy contemporary home is a great place to enjoy your Vineyard lifestyle. This great vacation home was designed with high ceilings, a wonderful stone fireplace and an open floor plan . There are 4 spacious and bright bedrooms, 2 updated baths and an unfinished basement area with workbenchand storage ready for your personal touch. The spacious deck wraps around 2 sides of the house and there is a smaller private deck off the master bedroom. There are literally miles of trials in every direction for great walking, mountain biking or adventures in the woods. The centralized location is midway between Alleys and the Chilmark beaches.

Listed by Jim Feiner of Feiner Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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 Smith Lane

Chilmark, MA1 Smith Lane

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS ID 37899

  • Residential
  • Mls Status Pending
  • Village South
  • Bedrooms 4
  • Bathrooms 4.5

One Smith Lane is a four bedroom, four and one half bath, home located just above Beetlebung Corner and Chilmark’s town center with easy access to Chilmark and Menemsha beaches. Built in 1998 and renovated in 2017, this home is suitable for year round living with air source heat pumps and air conditioning. Interiors feature a large family / television room with wood burning fireplace, a first floor primary bedroom suite, large upper level open kitchen, living and dining rooms, a lower level with two bedrooms and two new, full baths, laundry, and an adjacent, separate wing with an additional, spacious primary bedroom suite with marble bathroom, jacuzzi tub and second laundry. Most rooms open to ample outdoor wooden decking. There are two outdoor showers, a stone patio and room for a pool in the yard. A three car garage provides plenty of space for vehicles and storage. Mature landscaping, specimen plantings, gardens by Carly Look and hardscape by Morgan Stone and Landscaping complete the grounds at One Smith Lane.

Listed by Russell Maloney of Russell Maloney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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17 High Mark

Chilmark, MA17 High Mark

Price$4,900,000

Est. Mortgage: $/month

MLS ID 37278

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 7
  • Bathrooms 5

17 High Mark, built in 1928, sits atop Highmark Hill near the center of Chilmark. There’s a plaque on the wall in the kitchen commemorating the original owner, architect, builders and neighbors of this estate which reads 'High Mark House – Abode of Ennobling Vision'. This unique Chilmark property is now exclusively offered for the first time in 49 years. Spread across 10.4 acres, the property consists of two parcels. The first parcel is 6.7 acres in size and holds the living quarters. The second parcel is 3.7 acres in size and provides a wide buffer to the main homesite or a suitable lot for further development. Structures on the larger parcel include the main house, guest house, detached bedroom, artist studio or playhouse, in ground pool with outdoor shower and dressing room, tennis court, detached two car garage and long shed workshop. Water views to the Atlantic Ocean, Menemsha Pond, and Nomans Land are seen from many of the rooms of the main house and guest house. The grounds hold specimen plantings in a park like, private setting with wide and long front and rear yards. The main house has both primary and guest bedroom suites, living room with large fireplace, dining room with ample seating for ten, office and gallery, kitchen and laundry room. The lower level has a library/media room (or another bedroom), full bath, utility room, cedar closet and multiple storage rooms. The guest house is 800 square feet with 3 bedrooms, full bath, an eat in kitchen and laundry. The detached bedroom is the perfect bunk house with views to the Atlantic. It is rare to find an estate property in Chilmark that has the features of this compound already in place . Many of the existing amenities found on this property (guest house, pool, etc.) allow for immediate enjoyment without special zoning permits and years of in town residency. Ample acreage provides room for building expansion or relocation.

Listed by Russell Maloney of Russell Maloney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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37 North Abels Hill Road

Chilmark, MA37 North Abels Hill Road

Price$3,475,000

Est. Mortgage: $/month

Pending

MLS ID 37032

  • Residential
  • Mls Status Pending
  • Village South
  • Bedrooms 4
  • Bathrooms 3

An uncommon opportunity in Abels Hill. A sweet year round 4 bedroom home that offers strong south shore Atlantic Ocean and Chilmark Pond views. Renovated in the 90's and well maintained with an easy floor plan that expands out to the large deck and looks over a meadow to the ocean beyond. Wood floors, open beams, high ceilings and so much sunlight! 2 Loft style bedrooms and 2 additional bedrooms on the first floor with a total of 3 bathrooms. The open living space has four sets of glass sliding doors that open to the water views and make this feel like a real vacation home. Central AC plus a mini-split in one of the lofts. There is also a brick fireplace in the living room. Plus a garage to store your on island car. This is a solid year round home in one of the most desirable areas of Chilmark. Private access to the exclusive sandy south shore beach of Abels Hill. Zip around in your boat, kayak and paddle board all across Chilmark Pond and have a game of tennis on the three private courts the association offers.

Listed by Jill Napior of Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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129, 139 Old Farm Road

Chilmark, MA129

Price$3,675,000

Est. Mortgage: $/month

MLS ID 37095

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 3
  • Bathrooms 3.5

Beauty, privacy and stunning imagination describe the 12 acre estate with 325 yards of ancient stone walls weaving through a meadow landscape with an extraordinary 2,800 sq ft architectural Greenhouse supported by a charming post and beam 925 sq ft guest house and a 600 sq ft beautiful comfortable living barn. Designed like a cross, this advanced high-tech contemporary Greenhouse may have other uses such as a personal residence. It resembles a cathedral with a soaring angular roof line in perfect symmetry. It was built by Rough Brothers, the preeminent and largest manufacturer of greenhouses world wide. Rough does extensive research and designs systems and controls for conservatories, public and private gardens, US Dept of Agriculture and Forestry, major universities, Projects completed for NY Botanical Gardens, National Botanical Gardens in Washington DC, MIT University and Huntington Garden and Museum. Equipped with the most advanced temperature control system, it houses dozens of exotic and rare plants, trees, grasses, vegetables and flowers. The 12 acres have beautiful meadows, endless trees, dense brush and hundreds of healthy mature heirloom blueberry bushes. The property abuts the 300+ acres of Roth Woodlands and Waskosim's Rock and Tiasquam Valley Reservations extending uninterrupted from North Road to Middle Road.

Listed by Robert Kenney of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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6 Tilton Cove Way

Chilmark, MA6 Tilton Cove Way

Price$13,500,000

Est. Mortgage: $/month

MLS ID 36699

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 6
  • Bathrooms 5

Perfectly sited on a slight bluff overlooking upper Chilmark pond to the Atlantic. Kayak or canoe from your dock to the private beach access. Superbly appointed , this 6 bedroom custom built home offers the finest in craftsmanship and materials including Lew French stone work and patios. There are few words that can adequately describe the feeling that exists in this location. The roar of the ocean and the glorious sunrises, the privacy, the view of nature’s world serene and safe. Exclusively offered.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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239 State Road

Chilmark, MA239 State Road

Price$2,450,000

Est. Mortgage: $/month

MLS ID 36769

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 3
  • Bathrooms 2

A Charming summer home with magnificent, uninterrupted views of Menemsha Pond, Vineyard Sound, and on a clear day the Elizabeth Islands, in the distance. The property comes with access to Short Beach; a private beach 10 minutes away by foot and just a few minutes by car. The beach comes with small boat launching rights. The house has great cross breezes on warm days and a fireplace for when it's chilly. It has been in the same family for over 60 years and has been called "Windhover" based on the Gerard Manley Hopkins poem by that name. The property is on what is now considered an undersized lot, but is grandfathered in for zoning purposes. Property is located close to State Road, but has extensive privacy with natural brush surrounding the perimeter.

Listed by Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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2 Rockrose Path

Chilmark, MA2 Rockrose Path

Price$1,288,000

Est. Mortgage: $/month

MLS ID 36863

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 4
  • Bathrooms 3

This four bedroom, three bath home with ocean views is located on Rockrose Path off Meetinghouse Road in Chilmark. This heated, year round house is sited on one and a half acres in a private setting with a large front yard and easy to care for landscaping. The open living room, dining area and kitchen have direct views to the Atlantic. The master bedroom and bath also have ocean views. The lower level of the home has one bedroom and one full bath, large laundry room and plenty of storage space. Architectural plans are available for renovation or rebuild. Owner motivated to sell. Furnishings available separately. Access to a deeded, private Atlantic Ocean beach at Thumb Cove is also available separately (follow this link: http://vineyard.mylinkmls.com/Listings/36865).

Listed by Russell Maloney of Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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 April 13, 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."