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.

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: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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

138 & 138B State Road Chilmark MA

Chilmark, MA138 & 138B State Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 36861

  • Residential
  • Village South
  • Square Feet 2558
  • Bedrooms 5
  • Bathroom 4

This is an amazing Chilmark waterfront property that sits between Stonewall and Nashaquitsa ponds just past Hariffs Bridge. A 3 bedroom main house and 2 bedroom guest house occupy 4 acres of private natural land, and include access to Stonewall pond and Stonewall beach. The "Lenom" property has been in the same family since the 1970's and is being offered for the first time in over 50 years. The year-round main home has been lovingly maintained over the years and AC was added in 2017, the whole house interior was painted in 2020 which has transformed the space and emphasizes the cathedral height living room and the impressive central stone fireplace. Glass doors and three large picture windows surround the dining area to maximize the water views and summer indoor/outdoor living and entertaining. There's also a lovely patio directly off from the dining area to enjoy the outdoor space. The open kitchen has views over to 'Quitsa pond and was fully renovated in 2013 and painted in 2020. Upstairs there's a loft/TV space and also a great viewing roof deck to enjoy sunrises and sunsets and 360 degree water views all day long. The master bedroom is nicely separated from the other 2 guest bedrooms and there are three bathrooms in total, plus an outdoor shower. The guest cottage was converted from the original boathouse to a comfy one bed plus loft bedroom escape right at the water's edge. The upstairs living room with deck that overlooks the pond, bathroom, (with a second water view outdoor shower), and compact open kitchen/dining make this a great space for extra guests or extended family to stay. A new 2 bed septic has been designed and approved for this building. The property has been a popular rental with many repeat families enjoying the homes for generations.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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

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: 2.99% last updated on Jul 30, 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

15 Lake Road Chilmark MA

Chilmark, MA15 Lake Road

Price$3,000,000

Est. Mortgage: $/month

MLS Number 25297

  • Residential
  • Village South
  • Square Feet 1980
  • Bedrooms 5
  • Bathroom 2

Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads... these are just some of the features of this extraordinary property new to market for the first time in nearly fifty five years. This architect designed modern Cape Cod home with five bedrooms and two and one half baths on nearly three acres can be your summer place. Swim, kayak, row or clam in Nashaquitsa Pond, surf at Squibnocket or relax and enjoy the unspoiled, crowd free beach at Zacks in Aquinnah (with membership).

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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

27, 30, 31 Tower Lane Chilmark MA

Chilmark, MA27, 30, 31 Tower Lane

Price$2,950,000

Est. Mortgage: $/month

MLS Number 35757

  • Residential
  • Village North
  • Square Feet 4967
  • Bedrooms 6
  • Bathroom 3

Over 63 acres in Chilmark. As you turn off of Middle Road you are met by a cobblestone driveway that leads you through 7+acres of conservation land and up to the towering Carriage House archway that is the entryway to this majestic property. Emerging through the archway you are greeted by a unique assemblage of structures including the contemporary main house, guest house, and studio. These are surrounded by old stonewalls and newer detailed stonework that creates a harmonious balance between old farmland and new modern design. The Main House contains 4-bedrooms, large open living space and a rooftop deck. The nearby Guest House with 2-bedrooms and full kitchen overlooks raised bed gardens and rolling hills. Also located on the property is another 2-bedroom cottage with a full kitchen and an unfinished pool with pool house. On the far side of the property is over 45 acres of conservation land including portions of the Tiasquam River, all creating the utmost in privacy. There is potential to build one more single-family home on a portion of the property, or simply update the existing structures and enjoy the pristine land that surrounds you. The options for this property are many and varied.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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

34 Old Farm Road Chilmark MA

Chilmark, MA34 Old Farm Road

Price$2,650,000

Est. Mortgage: $/month

MLS Number 36974

  • Residential
  • Village South
  • Square Feet 3800
  • Bedrooms 4
  • Bathroom 4

An absolute lovely home, nestled on over 3 acres in the woodlands of Chilmark. This home has updated details that make for incredible comfort and relaxation. Gourmet kitchen equipped with state of the art appliances, granite counters, cherry and tile flooring, that over looks dining area with cozy fireplace. The open living room is perfect for family gatherings and movie nights, or a cozy spot for reading your favorite book by the fireplace. First floor master suite offers a fireplace and private bath. Second floor has three additional bedrooms with private bathrooms. Steps away from kitchen entrance is a fantastic outdoor, screened in dining area, perfect for family gatherings and entertaining. Other features include a beautifully landscaped yard, expansive farmer's porch, new azek gutters, 2 HVAC systems, 2 hot water heaters, water filtration system and a 2nd well. A must see home to appreciate!

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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