Chilmark Homes For Sale

Chilmark is arguably the island’s most beautiful town with a rolling rural landscape sandwiched between gorgeous beach-lined coasts to the north and south. Many of the lovely homes for sale in Chilmark are properties lined with classic stone walls across several acres. Real estate in Menemsha, Chilmark’s historic fishing village is very popular thanks to the picturesque sunsets, nearby beaches, and great restaurants. Homes for sale in Chilmark are a great investment, whether you are looking for a vacation home or a place to live year-round. At Landmarks we specialize in helping buyers find the perfect vacation home on Martha’s Vineyard. Learn more about Chilmark. View all real estate for sale on the Vineyard here.

Chilmark Real Estate Listings

if you have any questions about buying a home in Chilmark, call Landmarks Real Estate: 508-693-6866

Save time & effort! Create an account to save your favorite listings & get notifications when similar properties become available.

View by Property Type: Waterfront Homes | Water View Homes | Single Family | Condos

1 Smith Lane

Chilmark, MA1 Smith Lane

Price$1,595,000

Est. Mortgage: $/month

MLS ID 37899

  • Residential
  • Mls Status Active
  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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: 3.02% last updated on Mar 4, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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: 3.02% last updated on Mar 4, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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: 3.02% last updated on Mar 4, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

260 South Road

Chilmark, MA260 South Road

Price$4,195,000

Est. Mortgage: $/month

MLS ID 32807

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 6
  • Bathrooms 3

Waterview Chilmark estate sprawling over 6.1 acres with deeded access to a dock on Chilmark Pond and private Atlantic Ocean beach access. Known as The James Allen House, this historic home has been lovingly maintained by the same family for generations. The landscape is like no other with stonewalls, various species of trees, expansive lawn, and an open field with paths that lead you to Chilmark Pond and beyond. The classic floor plan of the main house offers multiple living spaces with 3 bedrooms, several fireplaces, and beautiful waterviews. This property features multiple other buildings including a 2 bedroom guest cottage, 1 bedroom bunkhouse, garage and garden shed. This is a unique opportunity for a new owner to carry on the proud legacy of this home's historic past. An extraordinary and rare find in the heart of Chilmark.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

8 Jethro Lane

Chilmark, MA8 Jethro Lane

Price$13,000,000

Est. Mortgage: $/month

MLS ID 35593

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 7
  • Bathrooms 6.5

Stunning Chilmark north shore 4 acre waterfront paradise with wonderful sunsets and unique privacy nestled between a large wooded hill and a 200 acre private estate. The 5 bedroom 4 1/2 bath TWO kitchen main house and 2 bedroom (with 2 dormers) 2 bath guest house enjoy dramatic views of the Elizabeth Islands from the Gay Head Lighthouse to Woods Hole from every room. The property is beautifully manicured with an enchanting contour stretching to the bluff overlooking a dreamy private cove and sandy beach. Four cleared acres are very rare on the heavily wooded north shore. Waterfront values on the rugged, elevated and protected Vineyard north shore are attracting more interest after Hurricane Sandy damaged the low elevation fragile south shore NY, NJ and New England coast line. The property is in the highly desirable 335 acre Spring Point community with 38 home sites with 135 acres of common land, 3/4 mile of private beach, 2 tennis courts and endless dirt roads and trails.

Listed by Robert Kenney of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

18 Austin Pasture Road

Chilmark, MA18 Austin Pasture Road

Price$8,900,000

Est. Mortgage: $/month

MLS ID 34345

  • Residential
  • Mls Status Active
  • Village South
  • Bedrooms 5
  • Bathrooms 3

A magical setting on Squibnocket Pond with endless waterviews of Squibnocket Pond, Atlantic Ocean and Nomans Land Island. Perched high up on a hill on over 16 acres of untouched land, sits this inviting Chilmark home that has been crafted to take in the beautiful surroundings and private landscape. The home features wonderful wood throughout, a generous main level with an open living room and a stone fireplace, a built-in window seat, a spacious dining room and a large gourmet kitchen with an over-sized island. The master suite includes a spacious bath and access to a lovely porch overlooking Squibnocket Pond and beyond. A separate guest wing includes 2 additional bedrooms and full guest bath. Oversized windows allow for spectacular waterviews in every direction. The lower level features a comfortable sitting room with a wood stove, 2 guest bedrooms, full bath and access to a one car garage and storage area. Venture down a peaceful footpath to the water's edge and boat, kayak, or paddle board with ease on Squibnocket Pond. With over 16 acres of grounds, this home is sited to take in mesmerizing waterviews and its serene setting is the perfect retreat to create memories for a lifetime.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

"Based on information submitted to MA_LINKMV as of March 8, 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."