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Chilmark Cottages

Search with Sanpiper Realty, Inc. to find current cottages for sale in Martha's Vineyard's town of Chilmark. Look through a variety of listings to find your new home. Register with us to save your favorite properties, and you can get email updates when new listings match your search criteria.

Chilmark Cottages for Sale

For more information, questions, or to schedule a showing, please contact Sandpiper Realty today!

You can also search all homes or homes under $500k for sale in Chilmark.

138 & 138B State Road Chilmark MA

Chilmark, MA138 & 138B State Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 36861

  • Residential
  • Square Feet 2558
  • Bedrooms 5
  • Bathroom 4
  • Acreage 4

This is an amazing Chilmark waterfront property that sits between Stonewall and Nashaquitsa ponds just past Hariffs Bridge. A 3 bedroom main house and 2 bedroom guest house occupy 4 acres of private natural land, and include access to Stonewall pond and Stonewall beach. The "Lenom" property has been in the same family since the 1970's and is being offered for the first time in over 50 years. The year-round main home has been lovingly maintained over the years and AC was added in 2017, the whole house interior was painted in 2020 which has transformed the space and emphasizes the cathedral height living room and the impressive central stone fireplace. Glass doors and three large picture windows surround the dining area to maximize the water views and summer indoor/outdoor living and entertaining. There's also a lovely patio directly off from the dining area to enjoy the outdoor space. The open kitchen has views over to 'Quitsa pond and was fully renovated in 2013 and painted in 2020. Upstairs there's a loft/TV space and also a great viewing roof deck to enjoy sunrises and sunsets and 360 degree water views all day long. The master bedroom is nicely separated from the other 2 guest bedrooms and there are three bathrooms in total, plus an outdoor shower. The guest cottage was converted from the original boathouse to a comfy one bed plus loft bedroom escape right at the water's edge. The upstairs living room with deck that overlooks the pond, bathroom, (with a second water view outdoor shower), and compact open kitchen/dining make this a great space for extra guests or extended family to stay. A new 2 bed septic has been designed and approved for this building. The property has been a popular rental with many repeat families enjoying the homes for generations.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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22 Quitsa Lane Chilmark MA

Chilmark, MA22 Quitsa Lane

Price$9,995,000

Est. Mortgage: $/month

MLS Number 36756

  • Residential
  • Square Feet 3888
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 1

Spectacular and charming; this cottage style home and guest annex is located in one of the most picturesque parts of Martha's Vineyard. This home is full of character with access to private beach just steps from the home and unforgettable ocean views from nearly every vantage point on the property. The main house offers a large gourmet kitchen, amazing patio space for outdoor dining, quaint bedrooms and several entertainment and gathering space. The recently constructed guest annex and garage space is tastefully done with room for overflow family and friends.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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 Greenhouse Lane Chilmark MA

Chilmark, MA18 Greenhouse Lane

Price$997,000

Est. Mortgage: $/month

MLS Number 36663

  • Residential
  • Square Feet 2100
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.4

Quintessential waterfront cottage overlooking Martha's Vineyard's hottest surf destination on the south shore. What a great place to spend some time and enjoy this classic and wonderful home listening to the sounds of the surf and sea. 3 comfortable bedrooms and a delightful kitchen lead to a living room centered around a great field stone fireplace with views from every room. The property may be used as is for some time and then be converted into a private beach access ideal for surfers and beach goers alike. This is a magical location where time stands still.

Listed by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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7 Clambelly Road Chilmark MA

Chilmark, MA7 Clambelly Road

Price$1,475,000

Est. Mortgage: $/month

MLS Number 36342

  • Residential
  • Square Feet 1876
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.5

This charming Chilmark cottage offers unexpected water views of the Vineyard Sound. Private and tranquil, the two bedroom, two bath main house and separate two bedroom guest suite, and garage is nestled in the woods off of Tea Lane on Chilmark's North Shore. The main house features an open concept living space comprised of a great room, open kitchen, and dining area with high ceilings, wide planked hardwood floors, an impressive stone fireplace and a wall of windows looking out onto an expansive view of the Sound. The main house has two bedrooms, both facing the water, and two bathrooms, designed with a warm post and beam style that fits so well in the natural beauty of the Chilmark woods. The property has a spacious two car garage with a guest suite above which offers two bedrooms, a bathroom, and study space. The property has a six bedroom septic in place offering the possibility for expansion. The house was built to be a three season home, but the Seller is currently installing additional insulation and a heat pump. This is a wonderful investment opportunity for a Chilmark Buyer looking for a special view at a great price.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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15 Doctors Creek Path Chilmark MA

Chilmark, MA15 Doctors Creek Path

Price$1,500,000

Est. Mortgage: $/month

MLS Number 36279

  • Residential
  • Square Feet 989
  • Bedrooms 3
  • Bathroom 1
  • Half Bath 1

You can "see for miles and miles and miles and miles" from this uniquely located Chilmark beach cottage that includes deeded access to 7 acres of pristine South Beach on the Atlantic Ocean! 180 degree water views looking easterly over Chilmark Pond, to the Barrier Beach and beyond and westerly over the Atlantic to Nomans Land. Simply Stunning! Colorful Sunsets! The cottage is a cozy camp with beach stone fireplace; used seasonally. This is a "one of kind" south shore location that is not often available for purchase. Short distance to the shores of Chilmark Pond from the cottage where you can wade across, in the summer, to the boardwalk that leads to your private access to South Beach! Included is an approved septic design for a 3 bedroom system. Buyer is responsible for installation. Enjoy the "camp" as it is or use your vision to rebuild/remodel. A special place on this beautiful island.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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 MA

Chilmark, MA260 South Road

Price$4,195,000

Est. Mortgage: $/month

MLS Number 32807

  • Residential
  • Square Feet 2604
  • Bedrooms 6
  • Bathroom 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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 MA

Chilmark, MA27, 30, 31 Tower Lane

Price$2,950,000

Est. Mortgage: $/month

MLS Number 35757

  • Residential
  • Square Feet 4967
  • Bedrooms 6
  • Bathroom 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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

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