Chilmark Homes For Sale

Chilmark is arguably the island’s most beautiful town with 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 Coldwell Banker 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

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

23 Black Point Road

Chilmark, MA23 Black Point Road

Price$2,900,000

Est. Mortgage: $/month

MLS ID 37327

  • Residential
  • Square Feet 1164
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 3.01

Located near Black Point Beach, this quaint rural setting offers lots of privacy and a wonderful yard for children to play, outdoor games. and mature garden bed. Open Kitchen/living room with soap stone counter tops and an island with granite countertops and storage. Beautiful hardwood floors through out house. Built by South Mountain, this house can be expanded or reduced to guest size, and the property is large enough to create a family compound. Black Point Beach lot available at an additional cost.

Listed by Flanders Real Estate

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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17 Chowder Kettle Lane

Chilmark, MA17 Chowder Kettle Lane

Price$2,450,000

Est. Mortgage: $/month

MLS ID 37199

  • Residential
  • Square Feet 2384
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 0.2

Menemsha -- one of the most desirable locations on the Island. It is an easy walk to the village and to the beach from this sweetly located property. Set at the end of a private cul-de-sac, this remodeled beach themed, sea view cottage oozes with charm. Three bedrooms and two baths are in the two story main house. The second floor consists of a master suite, dressing area, bathroom, water-view office and bonus room with ample storage. A screened in porch and upper and lower decks point the way to terrific sunsets! A one bedroom one bath guest cottage and outdoor shower complete this property. Agent has an ownership interest in home.

Listed by Kendall & Kendall

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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17 High Mark

Chilmark, MA17 High Mark

Price$4,900,000

Est. Mortgage: $/month

MLS ID 37278

  • Residential
  • Square Feet 3883
  • Bedrooms 7
  • Bathrooms 5
  • Acreage 10.4289

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

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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20 Tennis Lane

Chilmark, MA20 Tennis Lane

Price$1,995,000

Est. Mortgage: $/month

MLS ID 37213

  • Residential
  • Square Feet 2673
  • Bedrooms 4
  • Bathrooms 3
  • Half Bath 1

Move right in to this bright and beautiful Chilmark home on 3 private acres off Old Farm Road. There are 4 bedrooms and three and a half bathrooms plus a modern kitchen with high end appliances, large sliders open to the screened porch and two more set of sliders open to the sunny deck. With a contemporary and open floor plan, this home has great entertaining spaces in and out. The large living room has a cathedral ceiling and a modern fireplace which is the focal point, there is lots of natural light. The 2 first floor bedrooms share a full bath as well as access to the outdoor shower, while there is also a powder room for visitors, and the laundry room is also on this level. On the second floor there are two private master suites each with a private bath and one with private balcony. Large clean unfinished basement which could be finished for extra living space. A great second home or rental investment property with strong rental history. Chilmark residents have access to beautiful Lucy Vincent beach and a Squibnocket beaches and the home is a short stroll to the lovely trails at Waskosims Rock land bank property.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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100 Beach Plum Lane

Chilmark, MA100 Beach Plum Lane

Price$7,995,000

Est. Mortgage: $/month

MLS ID 37236

  • Residential
  • Square Feet 2140
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 3.3

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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1 Azalea Lane

Chilmark, MA1 Azalea Lane

Price$7,500,000

Est. Mortgage: $/month

MLS ID 37179

  • Residential
  • Square Feet 2511
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 1

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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37 North Abels Hill Road

Chilmark, MA37 North Abels Hill Road

Price$3,475,000

Est. Mortgage: $/month

MLS ID 37032

  • Residential
  • Square Feet 2082
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 2.3

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 Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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14 Wisteria Lane

Chilmark, MA14 Wisteria Lane

Price$1,825,000

Est. Mortgage: $/month

MLS ID 37137

  • Residential
  • Square Feet 2093
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 1

Magical and stunning setting with a luxurious lawn that stretches between ancient stonewalls to a lovely pond. This family compound has it all- a wonderful sunny setting with a pool out the back, private tennis court below the house and a large yard for anything fun outdoors. Also just across pasture road is the Chilmark softball field where sunday games delight the ballplayers young and old. Landbank properties up the road for miles of hiking or mountain biking. With sun beaming in throughout the day, this 5 bedroom home has great spaces for hanging together or alone, and plenty of opportunities to relax and appreciate the scenic surroundings. A short drive to Chilmark's spectacular beaches, its a home to enjoy for generations.

Listed by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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.

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129, 139 Old Farm Road

Chilmark, MA129, 139 Old Farm Road

Price$3,675,000

Est. Mortgage: $/month

MLS ID 37095

  • Residential
  • Square Feet 1550
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

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: 2.9% last updated on Sep 24, 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.

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21 Squibnocket Road

Chilmark, MA21 Squibnocket Road

Price$4,995,000

Est. Mortgage: $/month

MLS ID 36962

  • Residential
  • Square Feet 2018
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

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: 2.9% last updated on Sep 24, 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