Chilmark Real Estate

Types of homes in Chilmark include ranch style homes, charming cottages, traditional farmhouses, vacation homes, and old family homesteads. Real estate in Chilmark offers access to fishing, beaches, and miles of trails. Chilmark's coastline is very dramatic, ranging from the sloping sandy beaches of the south shore to the rocky coast of the north shore.

Contact us to ask questions or schedule a tour, or scroll down to browse all Chilmark real estate on Martha’s Vineyard.

Register with us to save your favorite Martha's Vineyard real estate listings and receive notification when similar properties become available.

r=1-12
8 Jethro Lane Chilmark MA

Chilmark, MA8 Jethro Lane

Price$15,000,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Square Feet 7000
  • Bedrooms 7
  • Bathroom 6
  • Half Bath 1

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 Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 MA

Chilmark, MA6 Tilton Cove Way

Price$13,500,000

Est. Mortgage: $/month

MLS Number 36699

  • Residential
  • Square Feet 5638
  • Bedrooms 6
  • Bathroom 5
  • Acreage 3.3

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 Conroy & Company R.E., Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

22 Quitsa Lane Chilmark MA

Chilmark, MA22 Quitsa Lane

Price$9,995,000

Est. Mortgage: $/month

MLS Number 36756

  • Residential
  • Square Feet 3888
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 1

Spectacular and charming; this cottage style home and guest annex is located in one of the most picturesque parts of Martha's Vineyard. This home is full of character with access to private beach just steps from the home and unforgettable ocean views from nearly every vantage point on the property. The main house offers a large gourmet kitchen, amazing patio space for outdoor dining, quaint bedrooms and several entertainment and gathering space. The recently constructed guest annex and garage space is tastefully done with room for overflow family and friends.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

277 North Road Chilmark MA

Chilmark, MA277 North Road

Price$8,950,000

Est. Mortgage: $/month

MLS Number 36814

  • Land
  • Village North
  • Acreage 69.2

The James Cagney Estate - A vast 70-acre estate with multiple building sites on the north shore of Chilmark. This is possibly the last time a real estate asset of this scale ever becomes available on Martha's Vineyard. The property is a world unto itself offering so much of what Chilmark and Martha's Vineyard are rightly famous for - water views, beach access, sun-dappled meadows, shaded forests through which streams and brooks wend, and lichen-covered stone walls. Exploring this estate - actually made up of three contiguous pieces of property - is like traveling through time and offers a window into a Chilmark of days gone by. The property was at one time the summer retreat of movie star Jimmy Cagney whose affection for this place is legendary. The Cagney house dates from the 1700s and is still in its original location along with a second house, studio, and barn. The prime waterview building site is located a distance away and is completely private. Located on a ridge and surrounded by acres of meadows and stone walls, this site offers views of Vineyard Sound and the mainland in the distance. A third building site is situated in another area of wide open meadows. The opportunities to develop this estate are many and varied and are limited only by a buyer's vision. This rare property could be yours to be treasured now and for generations of your family to come - truly a refuge from the exigencies of modern city living.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

277 North Road Chilmark MA

Chilmark, MA277 North Road

Price$8,950,000

Est. Mortgage: $/month

MLS Number 36813

  • Residential
  • Village North
  • Square Feet 2914
  • Bedrooms 6
  • Bathroom 3

The James Cagney Estate - A vast 70-acre estate with multiple building sites on the north shore of Chilmark. This is possibly the last time a real estate asset of this scale ever becomes available on Martha's Vineyard. The property is a world unto itself offering so much of what Chilmark and Martha's Vineyard are rightly famous for - water views, beach access, sun-dappled meadows, shaded forests through which streams and brooks wend, and lichen-covered stone walls. Exploring this estate - actually made up of three contiguous pieces of property - is like traveling through time and offers a window into a Chilmark of days gone by. The property was at one time the summer retreat of movie star Jimmy Cagney whose affection for this place is legendary. The Cagney house dates from the 1700s and is still in its original location along with a second house, studio, and barn. The prime waterview building site is located a distance away and is completely private. Located on a ridge and surrounded by acres of meadows and stone walls, this site offers views of Vineyard Sound and the mainland in the distance. A third building site is situated in another area of wide open meadows. The opportunities to develop this estate are many and varied and are limited only by a buyer's vision. This rare property could be yours to be treasured now and for generations of your family to come - truly a refuge from the exigencies of modern city living.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 MA

Chilmark, MA18 Austin Pasture Road

Price$8,900,000

Est. Mortgage: $/month

MLS Number 34345

  • Residential
  • Village South
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 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 Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

100 Beach Plum Lane Chilmark MA

Chilmark, MA100 Beach Plum Lane

Price$7,995,000

Est. Mortgage: $/month

MLS Number 37236

  • Residential
  • Village North
  • Square Feet 2140
  • Bedrooms 4
  • Bathroom 3

Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside cottages positioned to take advantage of the commanding views of Vineyard Sound, the Elizabeth Islands, Gay Head Lighthouse, Menemsha Pond and the village of Menemsha. This property, once featured on the cover of Architectural Digest, dates to the 1930's and was lovingly renovated and restored by the current owner and Joseph Dick, a well-known and respected architect on the Cape and Islands. The main house features two bedrooms, two baths, living and dining rooms with water views, fireplace, well-appointed kitchen, outdoor rain shower, and a front porch which provides a front row seat to those magical Menemsha sunsets. The guest house has one bedroom and bath, large, open living and dining areas, an ample kitchen, and an outdoor shower. Adjacent to the guest house is a detached, one bedroom cottage. A cottage at the rear of the property contains an office with wide water views and a lower level space currently configured as a personal gym. The last of the five cottages on the property is used for storage of seasonal furnishings. Expansion of the main house is possible with permitting. The property has been approved for a five bedroom septic system (see listing broker for conditions). Mature landscaping, specimen trees and lush perennial gardens surround the property and delight the senses with vivid colors and welcoming floral scents. A short stroll on a deeded path takes one to the historic fishing village of Menemsha, it's seafood and craft shops and the calm waters at Menemsha Beach. A video tour of this property can be found here: https://vimeo.com/video/358902170

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

1 Azalea Lane Chilmark MA

Chilmark, MA1 Azalea Lane

Price$7,500,000

Est. Mortgage: $/month

MLS Number 37179

  • Residential
  • Village South
  • Square Feet 2511
  • Bedrooms 5
  • Bathroom 3

Rarest of the rare - Ocean-view Chilmark home with swimming pool, 440 feet of private ocean beach, and big, beauteous ocean views. The house is being completely renovated and price shown is for the completed product. For buyers interested in purchasing the property at a lower price and taking over the construction project, full documentation is available to show 1) what has been done and how much it cost, 2) what is left to do and how much it will cost, and 3) proposed timeline for the completion of the work. Note that the images shown are of the house BEFORE renovation. Detached garage.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

21 Squibnocket Road Chilmark MA

Chilmark, MA21 Squibnocket Road

Price$4,995,000

Est. Mortgage: $/month

MLS Number 36962

  • Residential
  • Village South
  • Square Feet 2018
  • Bedrooms 4
  • Bathroom 2

Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic beach house has amazing views of the Atlantic and shoreline out to Squibnocket Point. It has been fully renovated with many tasteful, modern enhancements and sustainably-sourced materials, and yet retains some of the most charming elements of its past. The airy floor plan offers a family-friendly open kitchen, living and dining area, a master bedroom, and a guest wing with three more bedrooms. The lower level is finished, adding about 1350 square feet of space including a spacious 30' x 20' recreation room and laundry room. The property is surrounded by stone walls, a bluestone patio facing the Atlantic, and a path to the Pond. Access to the pond is by a newly constructed elevated walkway and there's a new kayak/paddleboard rack. Originally known as the Hilly Mayhew House, this property was for over 80 years the haven for the international modernist painter Vaclav Vytlacil and his family. He created hundreds of seascapes and harbor scenes of the Vineyard, many of which can still be found on the island and around the world. The house comes fully furnished with new, interior designer-sourced furniture and furnishings. Walk to the beach, kayak in the pond, or just sit out on your patio watching the day unfold, osprey fish and surfers ride the waves.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 Road Chilmark MA

Chilmark, MA17 High Mark Road

Price$4,900,000

Est. Mortgage: $/month

MLS Number 37278

  • Residential
  • Village South
  • Square Feet 3883
  • Bedrooms 7
  • Bathroom 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 Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 MA

Chilmark, MA260 South Road

Price$4,195,000

Est. Mortgage: $/month

MLS Number 32807

  • Residential
  • Village South
  • Square Feet 2604
  • Bedrooms 6
  • Bathroom 2

Waterview Chilmark estate sprawling over 6.1 acres with access to Chilmark Pond and an Atlantic Ocean beach. 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 Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 MA

Chilmark, MA129, 139 Old Farm Road

Price$3,675,000

Est. Mortgage: $/month

MLS Number 37095

  • Residential
  • Village North
  • Square Feet 1550
  • Bedrooms 3
  • Bathroom 3

Beauty, privacy and stunning imagination describe the 12 acre Eaton 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 resembling 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 Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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