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Chilmark Properties

A somewhat isolated community, Chilmark is known for its rustic beauty, rolling 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.

15 Hewing Field Marthas Vineyard 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

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Gosnold Way Marthas Vineyard 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

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27 Clambelly Road Marthas Vineyard 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

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

8A Clambelly Road Marthas Vineyard 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

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22 Blackberry Lane Marthas Vineyard MA

Chilmark MA22 Blackberry Lane, North

Price$1,325,000

Est. Mortgage:$/month

MLS Number 27938

  • Residential
  • Village Chilmark
  • Square Feet 1965
  • Bathroom 2
  • Bedrooms 3

A picturesque Vineyard home is set on 3.8 acres off Tea Lane in Chilmark. One of only two homes situated on a private drive bordered with stonewalls and mature plantings. This property is in the middle of old growth woodlands with a stream below that you can enjoy peacefully from your open deck or enclosed sunroom. This pristine home opens up to a custom built gourmet wood finished kitchen with granite countertops by Island craftsman Tom Tate. There is a beautiful fireplace in the living room to warm you on the cool Vineyard nights. Custom built bookcases and a soothing greenhouse solarium are just part of this very special home. Your family and friends will find very comfortable gathering places in this "up island" residence that is the very soul of old Vineyard living. Distant waterview site for a potential guesthouse.

Listed by Sandpiper Realty, Inc.

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

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19 North Tabor Farm Road Marthas Vineyard MA

MLS Number 28029

  • Residential
  • Village Chilmark
  • Square Feet 2700
  • Bathroom 3
  • Bedrooms 3

This lovely, welcoming home on six acres exudes charm and character. It has been thoughtfully expanded over time to suit island living with the addition of a screened porch/sunroom, mudroom, and a first floor master suite with private patio. Additionally, The detached two-bay garage plus expansive studio, office and storage allows for flexible use to fit your needs. The property offers mature gardens and beautiful stonework throughout the yard including a potting shed built into the natural grade of the land. The neighboring conservation land provides privacy and trails. Walk down the quiet country road to your neighboring farmstand at North Tabor Farm. This is a sweet, up-island experience.

Listed by Sandpiper Realty, Inc.

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

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76 Menemsha Inn Road Marthas Vineyard MA

MLS Number 28118

  • Residential
  • Village Chilmark
  • Square Feet 340
  • Bathroom 1
  • Bedrooms 2

This romantic seaside cottage sits on the bluff overlooking Vineyard Sound and offers breathtaking waterviews, spectacular sunsets, a 125' private beach, a creek, and is one of only a handful of waterfront properties along the North Shore that is walking distance to Menemsha Village. With this gem of a spot, the value is in the land, the views and natural setting. At this pristine and unspoiled parcel, one can build a new home of their dreams of up to three bedrooms. This is as good as it gets!

Listed by Sandpiper Realty, Inc.

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

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22 Tabor Hills Marthas Vineyard MA

Chilmark MA22 Tabor Hills

Price$1,275,000

Est. Mortgage:$/month

MLS Number 28025

  • Residential
  • Village Chilmark
  • Square Feet 2375
  • Bathroom 2
  • Bedrooms 3

Beautifully kept three bedroom contemporary home, set amongst 3 acres of rolling Chilmark land. The first floor is all wood floors, a spacious first floor master bedroom, with large bathroom and walk-in closet space as well as an open layout plan for the living/dining and spacious kitchen area all add to the comfort of this home. Enjoy dinners on the screened in porch, or reading a back on the back deck overlooking the large yard and wooded surroundings. A First floor laundry area, a half bathroom, a small office area, as well as a 2 car garage complete the first floor. Upstairs you will find 2 more large bedrooms that share a full bathroom. This home gets amazing light, the living room is lined with windows, making it a wall of glass to enjoy the Chilmark landscape. This home has a 5 bedroom septic in place, yet it is only a 3 bedroom home so the potential already exists to add more bedrooms either by finishing the walk out basement area, an addition or a detached bedroom, so many options!

Listed by Sandpiper Realty, Inc.

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

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134 South Road Marthas Vineyard MA

Chilmark MA134 South Road, South

Price$825,000

Est. Mortgage:$/month

MLS Number 28014

  • Residential
  • Village Chilmark
  • Square Feet 2344
  • Bathroom 2
  • Bedrooms 4

Set nicely back from South Road in a nestle of towering trees, this bright and sunny one-level home is full of character and charm. It's a happy home with a variety of inviting living spaces and well-designed for privacy for family and houseguests. The spacious sun room is the heart of the home when the winter sun is low while the roomy deck is easily accessed from both the eat-in kitchen with bay window and the lovely, formal dining room. The living room's a natural for entertaining with fireplace and ample seating. A sizable loft above the 2-car garage offers opportunity for the artist, writer or overflow guests.

Listed by Sandpiper Realty, Inc.

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

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

73 Tabor House Road Marthas Vineyard MA

Chilmark MA73 Tabor House Road

Price$450,000

Est. Mortgage:$/month

MLS Number 27648

  • Land
  • Village Chilmark
  • Acreage 3.6000

Enjoy the privacy of your woodsy terrain with the added benefit of abutting over 47 acres of Land Bank property! Conveniently located & ready for your vision. This parcel will include an approved six bedroom septic design and well.

Listed by Coldwell Banker Landmarks

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

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

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