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 real estate on Martha’s Vineyard. Our team has decades of experience in the local real estate market, so contact us to get started.

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5 Herring Run

Price$3,200,000

Est. Mortgage: $/month

MLS ID 30966

  • Residential
  • Square Feet 1284
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 3

Simply charming home that enjoys one of the most breathtaking views you will ever see. Perched high on a hill, the views of Menemsha Pond, Vineyard Sound, the Elizabeth Islands beyond and the nearby marshlands with their abundant bird life are simply mesmerizing. 3 Acres of land with Deeded rights to a sandy Menemsha Pond cove that is shared by just 4 households and which you access down a short, pretty, winding path. Perfect for swimming, fishing and boating. A new well and a 5-bedroom septic have been installed. The newly-refreshed home has open living spaces that all enjoy the water views and there are 3 comfortable bedrooms and 2 tiled baths. Enjoy this Chilmark classic just as it is - or renovate to your heart's desire. * Land Assessment and Taxes are an approximation because lot is being re-configured.

Listed by Karen M. Overtoom R.E.

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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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15 Lake Road

Price$3,000,000

Est. Mortgage: $/month

MLS ID 25297

  • Residential
  • Square Feet 1927
  • Bedrooms 5
  • Bathrooms 2
  • Acreage 2.7

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

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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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11 Howell Lane

Price$2,850,000

Est. Mortgage: $/month

MLS ID 29242

  • Residential
  • Square Feet 4000
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 4.68

Nestled down Flanders Lane, this spacious, post-and-beam custom built contemporary home has an open and airy interior. This 4.68 acre property is the ideal retreat. Featuring four bedrooms, three and a half bathrooms (each with heated towel racks) and lovingly maintained landscapes. The Gourmet kitchen has top of the line appliances, 8 burner gas stove, built in booths as well as a formal dining area. Relax in the sauna, or read a book by the large brick fireplace in the living room. The outdoor space is perfect for entertaining company on the stone patio with views of the rolling backyard. A beautifully constructed outdoor shower and fully fenced expansive garden with raised beds also adorn this property. An Expansive attached garage (With radiant heated floors!), workshop, and so many other details embellish this home. All of this, plus only a short distance to swim, clam or kayak at your own private access on Menemsha Pond. With 200' of deeded frontage on Menemhsa pond and area for boat storage on the shore. This home is in immaculate condition with impeccable craftsmanship and is turnkey for you and your family. Ask about the permit for a pool!

Listed by Flanders Real Estate

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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 Boston Hill Road

Price$2,850,000

Est. Mortgage: $/month

MLS ID 31742

  • Residential
  • Square Feet 2500
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 3.5

This 3.5 acre home with beautiful grounds, waterviews of Menemsha pond, Vineyard sound and Squibnocket point has a light filled interior rising above the in-ground pool. The center of the home with soaring cathedral ceilings has a unique open staircase rising to the second floor Master bedroom en-suite with study and private sunning deck. Creative designed open living, kitchen and dining areas overlook the pool from every room. 6 bedroom septic for 2 additional bedrooms or guest house.

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

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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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15 Valley Lane

Price$2,600,000

Est. Mortgage: $/month

MLS ID 32252

  • Residential
  • Square Feet 4976
  • Bedrooms 6
  • Bathrooms 5
  • Acreage 3

End-of-the-road privacy off Old Farm Rd in Chilmark. As you enter through an attractively designed entrance to this property, you'll discover a contemporary farmhouse enveloped in a landscape with vibrant, mature perennials and lush lawns with a wooded backdrop and conservation land beyond. Enter into a dramatic, over-sized living-dining area with beach stone fireplace. Walking through to the left, Patrick Ahearn has designed a gorgeous master bedroom and bath that opens through French doors to both a screened porch and open deck. Circle through the other way to a connecting first floor study/TV room. To the right of the living area is a sensational gourmet kitchen loaded with amenities. Three bedroom/bath suites are located on the second floor. A 2-room detached bedroom is located over a 2-car garage. This is a comfortable year-round house, and one that will accommodate family and friends for many summers filled with great memories. Don't miss the video, see link below!

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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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7 Black Point Road

Price$2,100,000

Est. Mortgage: $/month

MLS ID 31969

  • Residential
  • Square Feet 2120
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 5.9

Come see this charming architect designed retreat with main house & two connecting guest wings, set on 5.5 pristine acres plus 17,424 SF deeded Atlantic Ocean Beach lot valued at $303,000 included with sale for a total acreage of 5.9 acres (SEE Comments/directions). Impeccably maintained the property is designed for relaxing and enjoying the unpretentious beauty of Black Point and the beach. The great room with banks of sliding doors beacons you the deck & patio. Ocean breezes & the sound of the surf gently wake you in the morning & help you drift off to sleep. The evening sky will make an Astronomer out of you. Main house features the great room, dining area, kitchen, laundry, pantry, master, full bath & outdoor shower. 1st guest wing has 2 BR'S, full bath with outdoor shower. Built in 2007 the 2nd guest wing has living area, BR, bath and outdoor shower. With town permitting you can add a guest house & pool. While you feel miles away you are still less than 10 minutes to Alley's store.

Listed by Laer Realty Partners

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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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24 Bassett Place Road

Price$2,100,000

Est. Mortgage: $/month

MLS ID 31720

  • Residential
  • Square Feet 1473
  • Bedrooms 4
  • Bathrooms 1
  • Acreage 15.8

Chilmark Pond front cottage with Atlantic Ocean views and private beach lot. YOU CAN'T BE CLOSER TO CHILMARK POND. Unique waterfront summer house with outstanding ocean and pond views on Chilmark Pond. Very private. Nature preserve setting on 15 acres surrounded by marsh lands, heron and osprey.Nothing between you, the pond and ocean. Big deck for dining and relaxation. Shared dock on the pond. Private ownership in Atlantic Ocean beach short boat ride away.

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

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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 Rockrose Path

Price$1,755,000

Est. Mortgage: $/month

MLS ID 30666

  • Residential
  • Square Feet 1973
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 1.6

This is a ranch style summer cottage set high on Rockrose Path (off King's Highway) with wide views of Chilmark Pond and the Atlantic Ocean beyond. A private Atlantic Ocean beach lot, Thumb Cove, is included with the sale of this home. Master suite with full bath, three additional bedrooms, and second full bath, cathedral ceilings, sleep loft, large wraparound mahogany decking provides plenty of seating area for taking in ocean views and starlit skies. This home has an outdoor shower, wood burning stove, insulation, whole house fan, and basement storage. Easy expansion possibilities for larger kitchen and additional master suite with terrific views possible. Furnishings, motor boat and Sunfish available separately.

Listed by Russell Maloney Real Estate

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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 Hewing Field

Price$1,550,000

Est. Mortgage: $/month

MLS ID 31822

  • Residential
  • Square Feet 4652
  • Bedrooms 10
  • Bathrooms 6
  • Acreage 4.5

This is a compound for someone with a dream. Whether to connect family and friends in comfort the year round, to host workshops, to garden, to conduct a professional practice or pursue creative endeavors - there's ample room to do it all here. With the treasure of Chilmark beaches to enjoy, it's just a scenic 5-minute drive from Alley's. Tucked away on a hilltop meadow bordered by conservation land, an extensive trail network beckons just steps from the decks leading down to the mossy banks of the Tiasquam. Besides the space and versatility here, the main house has extra insulation in the interior walls for an added sense of quiet, a 2015 Buderus 7-zone heating system, three stairways to the second floor, additional attic and basement rooms, an attached 2-car garage and a generator. There's great privacy between the dwellings and a general sense of sanctuary and expansiveness on these bright acres. PLEASE NOTE: As of 11/17/17, this price reflects a temporary reduction. If a Buyer is able to close before 1/31/18, the price will apply. Otherwise the property will be taken off the market and reintroduced in Spring 2018.

Listed by Tashmoo Realty

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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 South Road

Price$1,450,000

Est. Mortgage: $/month

MLS ID 31585

  • Residential
  • Square Feet 2877
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 1

Classic features blend seamlessly with modern sensibilities in this expanded Cape Cod-style home. With double the square footage of the original and updated for the 21st-century lifestyle (including a first-floor master suite), this home is perfect for year-round living or as an all-seasons Vineyard retreat. The property adjoins acres of untouched woods, providing ample privacy, while remaining easily accessible throughout the year on a town-maintained paved road. First floor consists of formal living room with fireplace, separate dining room, master suite with large sitting room and private screened-in sunroom, laundry room, additional bedroom and bath, kitchen, 650 sq. ft. mahogany deck for outdoor entertaining, and sun-filled, 530 sq. ft. great room with 14' ceiling, exposed antique beams and radiant floor heating for the ultimate in winter comfort. Second floor contains two large bedrooms with cozy dormer alcoves, and full bath. Oversized two-car garage with built-in work bench. 1500 sq. ft. basement provides lots of storage space, additional refrigerator and freezer, and second laundry room. The many updates and improvements include new well, architectural-shingle roof, cedar-siding shingles, HVAC, Title V septic system, top-quality insulation, upgraded electrical and plumbing, and energy-efficient Marvin windows and French doors throughout. This home is turn key. Fully furnished with just a few exceptions!

Listed by Up Island Realty

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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 A VisitAsk A QuestionMore Details