Chilmark Real Estate

Types of homes in Chilmark include ranch style homes, charming cottages, traditional farmhouses, vacation homes, and old family homesteads. Real estate in Chilmark offers access to fishing, beaches, and miles of trails. Chilmark's coastline is very dramatic, ranging from the sloping sandy beaches of the south shore to the rocky coast of the north shore.

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Menemsha Water View

Chilmark, MA 02535

Listing Number 2-MWV

  • Non-MLS Vacation Rentals
  • Property Name Menemsha Water View
  • Maximum Occupants 6
  • Type Vacation Rental
  • Sleeps 6

Beautiful three bedroom, three bath, water view home overlooking the salt marsh and Menemsha Pond. Open living/dining/kitchen area facing the water with views on the entry level along with two bedrooms with ensuite  baths. The kitchen is well equipped and has granite tile countertops. Upper level master bedroom area with ensuite bath and private deck. Two flat screen televisions, one in the living room and the other in master bedroom area. Other amenities include central AC, a dishwasher, washer/dryer, cable TV, Internet, a BBQ grill, and an outdoor shower. Linens, towels, beach towels & chairs also provided. Landscaped with traditional Vineyard stone walls, red brick walkway, shrubs, trees and perennial gardens. This lovely home is just moments from Menemsha Village. Enjoy the restaurants, shops, fish markets, Menemsha Beach, and the awesome Menemsha sunsets without having to find a parking space!. Please contact for availability and rates

Listed by Hancock Real Estate

$
$
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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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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Charming Chilmark Rental

Chilmark, MA 02535

Listing Number 1-CCR

  • Non-MLS Vacation Rentals

One of the most charming properties in Chilmark. A lovely parcel with gently rolling contours overlooking Chilmark Pond and the South Shore. The main house, guesthouse and playhouse are located on a large private lot in Chilmark. The main house has three bedrooms and two baths, the guesthouse has two bedrooms, one and one-half baths. Rental includes Chilmark Pond and and Atlantic beach access. Centrally located, easy access to the center of Chilmark, as well as West Tisbury Farmer’s market. Please call for rates and availability.  

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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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Menemsha Bridge House

Chilmark, MA 02535

Listing Number 2-MBH

  • Non-MLS Vacation Rentals
  • Bathroom 3
  • Maximum Occupants 8
  • Bedrooms 4
  • Type Vacation Rental

Beautiful four bedroom home near Menemsha Village.  Open living/dining/kitchen area on first floor along with full bath and king bedroom.   Second floor has master bedroom with king bed, full bath and private deck, along with two other bedrooms that share a full bath.   Enjoy the outdoor living areas whether your on one of the decks, screened in porch or the patio.  House is well equipped , central AC, outdoor shower and propane grill.   Please contact for availability and rates.

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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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South Shore Water Front

Chilmark, MA 02535

Listing Number 1-SSWF

  • Non-MLS Vacation Rentals
  • Bathroom 4
  • Bedrooms 4
  • Type Vacation Rental

Four bedroom contemporary waterfront home on the Atlantic.  Outstanding views, path to beach, lap pool, expansive decks, great vacation location. Please call for availability and rates.

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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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Panoramic Water Views

Chilmark, MA 02535

Listing Number 1-PWV

  • Non-MLS Vacation Rentals
  • Bathroom 5
  • Bedrooms 6
  • Type Vacation Rental

Spectacular six bedroom contemporary home with panoramic views of the Vineyard Sound. Please call for availability and rates.

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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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Spectacular Colonial Home ~ South Road

Chilmark, MA 02535

Listing Number 1-SCHSR

  • Non-MLS Vacation Rentals
  • Maximum Occupants 10
  • Bedrooms 5
  • Type Vacation Rental
  • Sleeps 10

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach!  The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern, Chilmark Community Center, etc.).  It is also a short ride to Menemsha Village (fishing, fish markets, galleries, restaurants, and sunsets on the beach). This 1713 Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to honor its past while embracing today’s contemporary lifestyle.  The house is fully air- conditioned and has Wi-Fi, high speed Internet and cable TV.  A beautiful three-season porch was added to the back of the house.  It is a relaxing place to sit, read, play a game, watch TV, or simply observe what is going on outside.  The porch leads to a bluestone patio with a teak dining table with seating for 8 under a market umbrella along with a number of chairs to relax in and a gas grill.  Adjacent to the patio is a large private outdoor shower.  The house is surrounded by an expansive lawn bordered by stonewalls.    The house is remarkably open on the first floor.  The porch leads into a fully equipped cook’s kitchen with high-end appliances, quartz countertops and an island with seating.  The dining room has a farmer’s table that seats up to 10 along with an additional sitting area by the fireplace. The library/media room is a cozy place to sit and talk, read by the fireplace, or binge watch that show you just never got to last year on a large flat screen TV. The final room downstairs is the first, of two, en suite master bedrooms (queen bed).  It has a fireplace, flat screen TV, and a marble and tile bathroom.  A French door leads from this bedroom to the bluestone patio.  The central hallway contains a half bath and two stairways that lead to the second floor where you will find four additional bedrooms, (two queens, one twin and an en suite king), a full laundry and a large bathroom with an oversized tub/shower.  The 2nd floor master bedroom (king bed) has a flat screen TV, an attached walk-in closet and en suite marble and tile bath.  High quality linens and towels are provided throughout the house. The real bonus of this house is its key to Hancock Beach—located approximately 1.5 miles from the house down a private road.  Hancock Beach is a premier private South Shore ocean beach adjacent to Chilmark Pond so that both can be enjoyed.  Tenants can bring kayaks to the pond to explore this beautiful, unspoiled environment. Tenants also have access to Chilmark town beaches—Lucy Vincent and Squibnocket.  Beach chairs, towels, umbrellas and coolers are all provided. Please call for availability and rates.    

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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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Menemsha Cottage

Chilmark, MA 02535

Listing Number X32532334

  • Non-MLS Vacation Rentals
  • Bathroom 2
  • Property Name Menemsha Cottage
  • Maximum Occupants 4
  • Bedrooms 2

Enchanting waterviews over the saltmarsh and the sand dunes of Menemsha Beach with water views of the Vineyard Sound, with the Elizabeth Islands and sunsets as a backdrop. This newly renovated two bedroom, two bath home is charming with all the comforts of home in a unique location near Menemsha Village.  Open kitchen/dining/living area with large deck that also connects to the master bedroom. A great spot for morning coffee... This wonderful cottage also has AC, wifi, outdoor grill and outdoor shower to make your vacation even more enjoyable. Please call for availability and rates  

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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

South Shore Water View with Pool

Chilmark, MA 02535

Listing Number X64844175

  • Non-MLS Vacation Rentals
  • Bathroom 4
  • Maximum Occupants 10
  • Bedrooms 5
  • Type Vacation Rental

Spectacular five bedroom, water view home with pool. Open living /dining area with walk out to large deck with a well furnished outdoor dining area.   Plenty of outdoor living to be enjoyed whether in the pool or poolside, sitting around the fire pit at night or playing tennis on the private court.   Rental also comes with Chilmark Pond access and south shore beach access across the Pond. Please call for rates and availability.  

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* 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