Chilmark Homes For Sale

Chilmark is arguably the island’s most beautiful town with a 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 Landmarks, we specialize in helping buyers find the perfect vacation home on Martha’s Vineyard. Learn more about Chilmark. View all real estate for sale on the Vineyard here.

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Chilmark Real Estate For Sale on Martha's Vineyard

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39 Prospect Hill Road

Chilmark, MA39 Prospect Hill Road

Price$3,750,000

Est. Mortgage: $/month

Active With Contract

MLS ID 38968

  • Residential
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 3.3

Stunning sunset water views from this hilltop home will delight the senses from morning to night. At 207 feet above sea level, the rolling and interesting 3.3 acre parcel has spectacular views overlooking many acres of gorgeous stonewall lined fields, a small duck pond, and a glimpse of Noman's and includes Menemsha bight and the Vineyard Sound. On the top of the hill it is perched high enough that the views actually go almost 40 miles over the tops of the Elizabeth Islands to the Newport bridge and mainland north. A comfortable 4 bedroom home designed to accommodate family and friends has an open kitchen living room area walking out to the deck. Great for parties and gatherings the heart of the home is an updated kitchen and a great place to meet and of course the sunsets are exquisite- as is watching the weather patterns over Aquinnah and the Islands. This is the first time this home has been for sale since its construction and there is plenty of room to envision improvements and additions. Built by Island builder Colin White in 1980, this family home has been a cherished heirloom for 4 generations of the current owners family and it will be for you as well.

Listed by Jim Feiner of Feiner Real Estate

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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31 & 33 Flanders Lane

Chilmark, MA31 & 33 Flanders Lane

Price$2,250,000

Est. Mortgage: $/month

Pending

MLS ID 38899

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 2

Light filled main and guest house set on two beautiful acres designed by post war pioneer architect William Smull known for his mid-century houses.With views of Menemsha Pond, Vineyard Sound and Aquinnah and within walking distance to Menenmsha Harbor, fish markets, and Menemsha Beach. Included is deeded access to Menemsha Pond where you can leave your skiff, kayaks or paddle boards for use on the pond.The main house has two bedrooms, two baths and open kitchen/dining/living area with large deck to enjoy the view. Guest house is entirely self-contained with one bedroom, kitchen, bath and two sitting areas yet is accessible from the main house by a charming foot bridge over the stream. Large yard with lily pond, grape vines and blueberry bushes.

Listed by Brenda Codding of Up Island Realty

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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86 Menemsha Cross Road

Chilmark, MA86 Menemsha Cross Road

Price$1,200,000

Est. Mortgage: $/month

Pending

MLS ID 38909

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathrooms 1
  • Acreage 3.6

Charming 1930's cottage located within walking distance of Menemsha harbor & village. This well maintained home has island character and history. Lovely ancient stonewall along western boundary line. The home is situated off the main road which affords privacy. Expansion possibility is limited to 25% of total square footage of existing building - approximately 300 sq. feet. An amazing opportunity to live in the town of Chilmark! REQUESTING ALL 'HIGHEST & BEST' OFFERS TO BE SUBMITTED BY TUESDAY,OCTOBER 19TH AT 3PM.

Listed by Julianna Flanders of Flanders Real Estate

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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, MA22 Quitsa Lane

Price$4,100,000

Est. Mortgage: $/month

Pending

MLS ID 38250

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathrooms 4.5
  • Acreage 3.5

AUCTION HAS STARTED! Bid October 22-27. Currently Listed for $11M. No Reserve. Showings Daily 1-4PM & by Appointment. Settle into island life with 180-degree ocean views. Outdoor entertaining dining, lounging, and entertaining spaces span two sides of the estate, maximizing your expansive water views. Explore your private beach only steps from your property. Inside, 22 Quitsa Lane is quaint and comfortable, with rustic hardwood floors and beamed ceilings. A large open kitchen and living room function for entertaining or summer family life. Your private guest house makes it easy to share this gorgeous setting with your friends and family. There are lots of places to relax on this 3.5-acre estate, from the side patio and garden decorated with mature flowering plants to the expansive oceanfront lawn ideal for games of flag football or catch. Whether you want to soak up the sun or steal away in the shade, this Cape Cod-style property has just what you need.

Listed by Julianna Flanders of Flanders Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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82 South Road

Chilmark, MA82 South Road

Price$1,495,000

Est. Mortgage: $/month

Pending

MLS ID 38778

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 3.05

Chilmark- Located just across the town line, you’ll find this simply charming, recently renovated three-bedroom home. The interior is calm and cozy and has been updated throughout, including the addition of a large primary suite. The three-acre parcel, and six-bedroom septic system, would allow for easy expansion if more space was desired. Convenient to all Island amenities, with access to Chilmark’s highly coveted beaches, what more could you be waiting for in an up-island retreat!

Listed by Katherine Donahue of Sandpiper Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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51 State Road

Chilmark, MA51 State Road

Price$1,900,000

Est. Mortgage: $/month

Pending

MLS ID 38795

  • MultiFamily
  • Mls Status Pending
  • Bedrooms 5
  • Bathrooms 4
  • Acreage 0.7

Two for one! Chilmark Village newly built classic Vineyard Colonial situated in a peaceful serene setting with established plantings that provide plenty of privacy all around. 3 bedrooms, 2.5 bath new Colonial with open plan kitchen , dining, living and family room, gleaming wood floors and modern kitchen. The back patio/deck overlooks the ancient stone walls PLUS two bedroom detached studio with large deck provides many possibilities. Peek of the Atlantic, Chilmark landscape and in the distance a Church steeple gives this property a charming in-town feel.

Listed by Rebecca V Conroy of Conroy & Company R.E.,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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53 Wequobsque Road

Chilmark, MA53 Wequobsque Road

Price$4,250,000

Est. Mortgage: $/month

MLS ID 38570

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathrooms 4.5
  • Acreage 6.4

Waterfront in Chilmark with Private Ocean Beach. This home on 6 acres nestled atop the magnificent Wequobsque Cliffs on Chilmark's south shore was built by one of the island's finest builders, John Early Construction. The home enjoys views of the Atlantic Ocean and private ownership of over 300 ft of white sand beach (Note: Seller has installed brand-new beach stairs.) There are 5 bedrooms spread over 4000 square feet with several separate living spaces including the "party barn" that makes up the west wing of the property. Look no further if your dream is to own a home waterfront on Chilmark's south shore. Click the "Documents" tab for full architectural plans including floor plans.

Listed by Andrew McElhinney of Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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31 Tower Lane

Chilmark, MA31 Tower Lane

Price$8,700,000

Est. Mortgage: $/month

MLS ID 38491

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathrooms 5.5
  • Acreage 3.7

Located in the Tower Farm neighborhood in Chilmark, this property is a masterpiece of light and design. An exceptional new to-be-built 5-bedroom and 5.5-bath modern style beach house nestled among 55+ acres of conservation area. Generously entertain family and guests in the open kitchen/family floor plan lined with oversized windows which overlook the lively outdoor landscape, stone walls and Conservation land beyond. This turn-key home will feature state-of- technology, sustainable materials and solar. The outdoor spaces include expansive decking, outdoor grill kitchen, lavish gardens, and proposed reflecting pool. Tower Farm Chilmark invites the senses to a realm of well-being and pleasurability. (Construction to begin 2021)

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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20 Eliot Avenue

Chilmark, MA20 Eliot Avenue

Price$7,900,000

Est. Mortgage: $/month

MLS ID 36784

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 3.5
  • Acreage 0.6

Spectacular Stonewall Pond and beyond! Experience a sense of privacy and peacefulness while enjoying panoramic ocean & pond views. Each of the three bedroom suites have a connection to an outside space. The master bedroom has extraordinary views and includes an open sitting room and fireplace, as well as a private balcony to take in the sounds of the ocean. The large and open kitchen has recent upgrades with expansive area for dining. Adjacent to the living room is a lovely sitting room currently used as an office. Truly an experience of special living on the Vineyard.

Listed by Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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20 Eliot Avenue

Chilmark, MA20 Eliot Avenue

Price$7,900,000

Est. Mortgage: $/month

MLS ID 38217

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 3.5
  • Acreage 0.6

Surrounded by nature, this is a South Shore waterfront sanctuary. The presence of the peaceful placid pond combined with the power of the ocean and the sound of the waves is part of the special experience of living here. It has a particular sense of privacy and peacefulness. Hidden away on a quiet road of lilacs and summer cottages, the yard is defined by stone walls, lush gardens, natural art objects and several outdoor patios. Just beyond the lawn is a sandy path for easy access to the ocean and pond. The feeling inside the tasteful home is one of understated pleasing ambience. There are three bedroom suites and the ability to create a fourth. Each of the bedrooms has a connection to an outside space, two have pond and ocean views and one bedroom includes a sleeping loft space. The large and open kitchen which was recently renovated has a vaulted ceiling and an expansive dining space. Natural light and views of the pond fill the room and glass doors lead to the outdoor patios. The library with fireplace and a wall of windows to the water also serves as a formal dining room. In the living room, the dramatic height and spectacular views of the ocean and pond give you an expansive sense of water. The views from the adjacent sunroom have an intimacy and this room is currently used as an office and sitting room. The primary bedroom suite has extraordinary panoramic views and is a retreat that includes an open sitting room and fireplace as well as a private balcony and bathroom. The character of this property, its authenticity, vistas and connection to the natural landscape all combine to create a truly unique experience.

Listed by Meg Bodnar of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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"Based on information submitted to MA_LINKMV as of November 28, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."