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Chilmark Properties

A somewhat isolated community, Chilmark is known for its rustic beauty, Chilmark MA Beach Access Homesrolling land, rambling stone walls, grazing sheep and picturesque beaches. Home to Great Rock Bight Preserve, Menemsha Reservation, Chilmark Chocolates, and many idyllic beaches and ponds. Also in the town of Chilmark is the small fishing village of Menemsha, offering fantastic eateries, a public beach, and the most famous sunset on the island.

Chilmark real estate includes waterfront homes on the South Shore, Vineyard Sound, Menemsha or Squibnocket Ponds, as well as property along scenic Middle Road and North Road, or near the village of Menemsha.

Contact Sandpiper Realty to learn more about one of the Chimark real estate listings below. Register with our site if you would like to stay up to date on your favorite Chilmark properties.

You might also like to browse Katama properties or West Chop properties.

245 North Road, Chilmark, MA

Chilmark MA245 North Road

Price$3,750,000

Est. Mortgage:$/month

MLS Number 28114

  • Residential
  • Village Chilmark
  • Square Feet 4804
  • Bathroom 3
  • Bedrooms 6

This is one of the most charming properties in Chilmark. This beautiful parcel has gently rolling contours strewn with ancient stonewalls that surround a perfectly designed compound, attention has been paid to every detail. It was purchased by the current owners from James Cagney and abuts the original Cagney estate. The main house was originally built in the 1700s. It underwent a major renovation from 1987 to 1990 adding a beautiful kitchen and conservatory. In 2003, the master bedroom, office and mudroom were added. Coming through the entry, you are greeted by a cozy fire-placed living room with warm oak flooring, leading to the private dining room on one side and on the other, a gourmet kitchen/dining area that defies the imagination. The sliding glass doors open to the conservatory with another brick fireplace and floor to ceiling windows that bring the outside in. All of this overlooks your own private pond and the lovely rolling landscape. Today this lovingly restored home consists of+/- 3753 sq ft with four bedrooms, two and one-half baths. The property has many more improvements, a large antique barn with a loft bedroom and many outbuildings. Meticulous landscaping, gorgeous gardens and an orchard enhance the property. An over-sized two-bedroom guesthouse is nearby, augmented with an amazing pool and private tennis court, all priceless amenities that would be hard if not impossible to build today.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

7 Black Point Road, Chilmark, MA

Chilmark MA7 Black Point Road, South

Price$3,000,000

Est. Mortgage:$/month

MLS Number 28612

  • Residential
  • Village Chilmark
  • Square Feet 2016
  • Bathroom 2
  • Bedrooms 4

Classic Chilmark architect designed contemporary on 5.5 acres at Black Point. This simple but elegant 4 bedroom, 2.5 bath home boasts 3 outdoor showers, 2 living areas, deck & patio. Potential for a guest house with town approval. Key to Black Point beach is included. Main living area features vaulted ceiling in the living & dining areas with 2 walls of sliding doors that allow for a close connection to the beauty of the Chilmark landscape. Adjacent to the kitchen is the pantry & laundry. Master bedroom with full bath & access to 1 of the 3 outdoor showers. Across the covered walk way you will find 2 bedrooms with a shared full bath. Adjacent and connected to the guest wing is the 4th bedroom with private sitting area, deck, bath and doorway to your private outdoor shower. There are walking trails through much of the 5.5 acres. Grounds have large stately oaks unique to this property in Chilmark. Down the road, approx 1/2 mile, through the gate is the Black Point Beach parking area.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

30 Shadbush Hollow, Chilmark, MA

MLS Number 28595

  • Residential
  • Village Chilmark
  • Square Feet 1974
  • Bathroom 2
  • Bedrooms 3

Come, visit and be charmed by this wonderful, year-round Chilmark home. Enter through the gracious front hall and find, to your left, the front to back living room which is warmed by a floor to ceiling brick hearth with custom fire screen and which offers direct access out to the patio for ease in entertaining. In addition to the large, eat-in country kitchen, there is a gracious dining room, also with a slider out to the patio. The three bedrooms are all on the second floor with a master not to be missed - having its own custom fireplace and plenty of space for a charming sitting area. The two guest bedrooms complete this floor. This large, custom-built Cape with an "Old Vineyard" feeling is on a very pretty lot that is conveniently located close to Alley's and the West Tisbury Village and adjacent to a wonderful, extensive trail network that accesses acres of conserved property. * Square footage is agent's estimate - assessors' records not recognizing finished second floor.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

20 Davids Way, Chilmark, MA

Chilmark MA20 Davids Way, North

Price$8,500,000

Est. Mortgage:$/month

MLS Number 27605

  • Residential
  • Village Chilmark
  • Square Feet 4450
  • Bathroom 3
  • Bedrooms 3

Stunning contemporary residence, designed with care and respect for the surroundings. Superb quality is apparent throughout this home, affectionately known as "Three Barn Farm", carefully nestled into the landscape 150 feet from Vineyard Sound and your private waterfront. Extraordinary views include Gay Head Lighthouse, Dogfish Bar, the Elizabeth Islands and beyond. Magnificent Menemsha sunsets are yours to enjoy from this exclusive private enclave on Martha's Vineyard. A scenic and lovely walk to Menemsha. A must see for the discerning buyer.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Chilmark Road, Chilmark, MA

Chilmark MAChilmark Road, North

Price$1,970,000

Est. Mortgage:$/month

MLS Number 27596

  • Land
  • Village Chilmark
  • Acreage 7.8800

Site 25, in Seven Gates Farm, is a vacant lot bisected by the Chilmark-West Tisbury town line. 6.3 acres lie in Chilmark and 1.58 acres are in West Tisbury. The cement bound that designates the approved house site has been located and is on the Chilmark portion of the lot. There are potential water views. Some clearing is necessary to determine the possible quality of the views. Seller is seeking permission to clear view channels that should provide distant water scoops. Buyer will be responsible for well, septic testing, utilities. Also Natural Heritage pre-building application if necessary.

Listed by Wallace & Co. Sotheby's

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

85 Quenames Road, Chilmark, MA

Chilmark MA85 Quenames Road, South

Price$2,250,000

Est. Mortgage:$/month

MLS Number 28488

  • Residential
  • Village Chilmark
  • Square Feet 5077
  • Bathroom 3
  • Bedrooms 5

A home for all seasons. Custom 5,000 sq ft residence set within 7 parklike acres and beautifully landscaped gardens.This home features meticulous details, state of the art systems, gourmet kitchen , first floor master suite. Perfect for the Buyer looking for true elegance, but also values privacy and convenience. Quansoo beach key also available to purchase.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

15 Hewing Field, Chilmark, MA

Chilmark MA15 Hewing Field

Price$999,000

Est. Mortgage:$/month

MLS Number 28475

  • Residential
  • Village Chilmark
  • Square Feet 2472
  • Bathroom 2
  • Bedrooms 3

This Chilmark home is perched on a bluff just off of Middle Road. It is a quintessential up-island sanctuary on just over three acres. The home site is clear of trees allowing for plentiful light to stream into the Cape-style home with wood shingle exterior. Woods surround the large lawn and garden providing complete privacy from neighboring homes and a special private forest with winding paths that lead down to additional walking trails.Inside, the hardwood floors and attractive light-colored post and beam throughout the home are delightful to the eye. The open floor plan surrounds a central brick fireplace in the cozy living room. Off the living room, one of the most attractive rooms in the house is the sunken solarium. It has floor to ceiling windows and skylights providing a great sitting space regardless of the season. The kitchen features a butcher's block breakfast island and generous space for cooking. Winter nights and cool summer evenings are warmed by a wood burning stove in the kitchen connected to the back of the brick fireplace. On the second floor the post and beam construction continues accentuating the high gabled ceilings. Each of the bedrooms has skylights providing abundant light into the second floor spaces. Priced to sell at under a million dollars, the opportunity to own this serene slice of Chilmark will not last long.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Gosnold Way, Chilmark, MA

Chilmark MAGosnold Way

Price$9,750,000

Est. Mortgage:$/month

MLS Number 27824

  • Land
  • Village Chilmark
  • Acreage 20.0000

Simply Amazing...A awesome opportunity to own one of the largest tracks of unspoiled land in Chilmark. This 20 acre parcel sits high in the Chilmark Hills with magnificent panoramic views of Menemsha, the Gay Head Lighthouse, Dogfish Bar, the Elizabeth Islands, Vineyard Sound and beyond. Spectacular sunsets year-round from this unique and beautiful location accessed through Prospect Hill off North Road. Situated close to hundreds of acres of Trustees of Reservations Land with miles of walking trails through the Menemsha Hills Reservation. A blank slate where you can create a fabulous compound for you and your family to enjoy for generations to come. Property is sub-dividable into two lots, with proper permitting. Two wells are installed, perk tests completed, septic systems are not installed. Please call for a private showing of this lovely parcel that has only traded hands once in many generations. Just bring your imagination. More photos to come as the weather improves!!!

Listed by Hancock Real Estate

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

27 Clambelly Road, Chilmark, MA

MLS Number 28329

  • Residential
  • Village Chilmark
  • Square Feet 1260
  • Bathroom 2
  • Bedrooms 3

This charming three-bedroom home is privately situated in a storybook setting with stone walls, mature gardens, and expansive lawn. The home is bright and cheery with hardwood floors, a first floor bedroom, a working fireplace and a half-finished lower level with good storage space. From the welcoming entrance into the property where woods open up onto this lovely pastoral setting, to the immaculately maintained home, everything about this property adds to the experience of tranquil living in the heart of Chilmark.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

8A Clambelly Road, Chilmark, MA

Chilmark MA8A Clambelly Road

Price$1,350,000

Est. Mortgage:$/month

MLS Number 28287

  • Residential
  • Village Chilmark
  • Square Feet 3297
  • Bathroom 2
  • Bedrooms 3

Private spacious property tucked in the woods off Tea Lane. Beautiful, south facing sun filled home with professional mature landscape on a large piece of gently sloping land. Surrounded by trails with plenty of room for the entire family. Ground floor master en suite with three spacious closets. Formal living room and dining room, gourmet kitchen with enormous pantry. Mudroom with washer/dryer and sink off the kitchen. Room to expand with over 700 sq ft of unfinished attic space and over 2500 sq. ft of unfinished basement. New mahogany deck off back of house adds to the entertaining space in the summer. 16' x 12' shed with workbench for all your tools & equipment. 5.31 acres is in a conservation restriction with the Town of Chilmark.

Listed by Sandpiper Realty, Inc.

Sandpiper Realty, Inc.
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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