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.

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42 South Ridge Road

Chilmark, MA42 South Ridge Road

Price$1,850,000

Est. Mortgage: $/month

MLS ID 36139

  • Residential
  • Square Feet 3951
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Spectacular post and beam home set among rolling Chilmark hills. This house sits beautifully on the land and is tucked into two knolls. The pastoral views are endless. Gaze out the large window wall and watch the magnificent sunset views. Or gather in one of the two porches for entertaining a crowd. Enjoy the cathedral ceiling, large windows and fireplace in the living which then flows seamlessly to the open dining and kitchen area. The master bedroom suite is on the first floor complete with a comfortable library. Several generous bedrooms are on the second floor with room for extra guests in the office or loft area. This home has top of the line heating and cooling systems and is supplemented by a vast array of solar panels. Newly painted garage and garage floor with room for two cars is right off the entryway. Association tennis is right down the street. This is an incredible opportunity to surround yourself with privacy and beauty and to enjoy the wonderful Chilmark Beaches.

Listed by Karen M. Overtoom R.E.

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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42 South Ridge Road

Chilmark, MA42 South Ridge Road

Price$1,850,000

Est. Mortgage: $/month

MLS ID 36101

  • Residential
  • Square Feet 3951
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

A special opportunity for a hill top post and beam with stunning sunset views across the Chilmark Valleys. Built in 2002 by Yankee Barn, this well constructed, spacious and bright home was designed as the "dream house" for the current owners. The thoughtful attention to design, space and proportion are obvious. The house is packed with charm, imbued with character and has many extra details like a generator and solar panels. Master suite with soaring ceilings on the first floor allows for easy living when the home is less than full. Radiant heat is under the whole first floor and there is AC for those hot summer days. Drive in garage keeps you dry. A petite fish pond with waterfall behind the home brings a calming din to the morning sounds as you enjoy the day. Step out of the gardeners room onto your breakfast patio for the morning sun. The rolling meadow below has lots of opportunity for flowers and there is plenty of property for an orchard, a pool (after 2 years) and there is a great guest house spot, allowable after 5 years in Chilmark. This home is priced very accurately, packed with value and will be one of the fastest homes to sell this season. It could not be rebuilt for the price it is being offered. Sellers can not close until mid June but the good news is it just got painted and needs nothing! For the outdoor lovers, this home is located in the center of a massive trail system and has wonderful biking, and hiking opportunities out the back door with literally miles of trails that enable you to wander for hours and end up at some of the hidden gems of Chilmark.

Listed by Feiner Real Estate

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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260 South Road

Chilmark, MA260 South Road

Price$4,195,000

Est. Mortgage: $/month

MLS ID 32807

  • Residential
  • Square Feet 2604
  • Bedrooms 6
  • Bathrooms 2
  • Half Bath 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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27, 30, 31 Tower Lane

Chilmark, MA27, 30, 31 Tower Lane

Price$2,950,000

Est. Mortgage: $/month

MLS ID 35757

  • Residential
  • Square Feet 4967
  • Bedrooms 6
  • Bathrooms 3
  • Acreage 63.3

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

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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277 North Road

Chilmark, MA277 North Road

Price$12,500,000

Est. Mortgage: $/month

MLS ID 35612

  • Residential
  • Square Feet 2914
  • Bedrooms 6
  • Bathrooms 3
  • Half Bath 1

With a sweeping entrance through an expansive farm field, walking and riding trails, woodlands, pond, beach access, and total privacy, this feels like one of the exclusive home associations on the island, but this is yours all unto your own. Almost 70 acres of storied history, seclusion and a mile of stone walls throughout the property exude the authentic character of this long beloved farm in Chilmark. Past the antique post and beam barn, a granite bridge over Roaring Brook leads you to the back meadows and a beautiful ridgeline with strong views of the Vineyard Sound and the Elizabeth Islands. From this rise, the vista over the open meadows surrounding the ridge out to the rolling treetops of the north shore is equally enchanting and a landscape like no other on the island. Ride horses on the extensive trails throughout the property and out to the Sound for a swim. Even on your way to your beach, the Vineyard's past whispers to you as you pass the old brickyard. This is an extraordinary situation in which to create your island estate. This is the place James Cagney loved “beyond words” for the freedom and peace it provided. (PLEASE NOTE: There are 2 houses and a detached bedroom which are not habitable as is.)

Listed by Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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8 Jethro Lane

Chilmark, MA8 Jethro Lane

Price$15,000,000

Est. Mortgage: $/month

MLS ID 35593

  • Residential
  • Square Feet 7000
  • Bedrooms 7
  • Bathrooms 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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3 Fulling Mill Road

Chilmark, MA3 Fulling Mill Road

Price$995,000

Est. Mortgage: $/month

MLS ID 35606

  • Residential
  • Square Feet 1728
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.7

Custom built home set hillside with lovely terraced gardens, patio and glacial rocks. Ample family space on two levels. Bright and fully equipped kitchen opens onto the screened porch for dining alfresco. The en-suite master bedroom opens to private deck. Propane heat, fireplace and central AC. Great location just minutes to Beetlebung Corner and Lucy Vincent Beach.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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18 Austin Pasture Road

Chilmark, MA18 Austin Pasture Road

Price$8,900,000

Est. Mortgage: $/month

MLS ID 34345

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathrooms 3
  • Acreage 16.38

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: 3.6% last updated on Jan 23, 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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2 Rockrose Path

Chilmark, MA2 Rockrose Path

Price$1,695,000

Est. Mortgage: $/month

MLS ID 35538

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 1.6

This four bedroom, three bath home with ocean views and a private, south shore beach, is located on Rockrose Path off of 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 (under construction), and plenty of storage space. This property is being sold with access to a private Atlantic Ocean beach, Thumb Cove, and access to a dock on Chilmark Pond for launching of a small boats, kayaks, and paddle boards. This home is being sold "as is"....bring your architect and builder for renovation and expansion plans! Furnishings available separately.

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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68 Meeting House Road

Chilmark, MA68 Meeting House Road

Price$1,725,000

Est. Mortgage: $/month

MLS ID 35318

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 6.16

Lovely four bedroom on six acres of rolling hills and meadow. Portion of land held in conservation, Open floor plan with a large screened in porch. New Windows installed in 2019. For virtual tour, please copy and paste in a new tab the following link: virtual tour https://my.matterport.com/show/?m=XwSejuiNXGN&brand=0

Listed by Flanders Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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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