Chilmark MA Real Estate

black point beach

Chilmark is one of the most desirable places to own real estate in New England thanks to its beautiful beaches and spectacular homes. The area is home to the fishing village of Menemsha and lots of beautiful rural landscapes. You’ll find a variety of contemporary homes, cottages, beach houses, waterfront properties, and custom homes.

Chilmark Real Estate Statistics:

Average Sale Price for Chilmark in 2015: $1,701,202

Average Sale Price for Chilmark in 2019: $2,379,414

Average Sale Price for Chilmark in 2020: $2,584,167

Average Days on Market for Properties Sold in Chilmark for 2020: 308

Chilmark MIL (tax) Rate 2020: 2.86

Learn more about life in Chilmark.

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Browse Listings in Chilmark MA

Call Ocean Park Realty at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour.

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86 Menemsha Cross Road Chilmark MA 02535

Chilmark, MA86 Menemsha Cross Road

Price$1,200,000

Est. Mortgage: $/month

Pending

MLS Number 38909

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 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: 3.05% last updated on Oct 14, 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 MA 02535

Chilmark, MA22 Quitsa Lane

Price$11,000,000

Est. Mortgage: $/month

MLS Number 38250

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 3.5

AUCTION: 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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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 MA 02535

Chilmark, MA82 South Road

Price$1,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38778

  • Residential
  • Bedrooms 3
  • Bathroom 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: 3.05% last updated on Oct 14, 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 MA 02535

Chilmark, MA51 State Road

Price$1,900,000

Est. Mortgage: $/month

Open House

MLS Number 38795

  • MultiFamily
  • Next Open House: Sat 10/23 12:00 pm. to 2:00 pm.
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4

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: 3.05% last updated on Oct 14, 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 MA 02535

Chilmark, MA53 Wequobsque Road

Price$4,250,000

Est. Mortgage: $/month

MLS Number 38570

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 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: 3.05% last updated on Oct 14, 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 MA 02535

Chilmark, MA31 Tower Lane

Price$8,700,000

Est. Mortgage: $/month

MLS Number 38491

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 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: 3.05% last updated on Oct 14, 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 MA 02535

Chilmark, MA20 Eliot Avenue

Price$7,900,000

Est. Mortgage: $/month

MLS Number 36784

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 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: 3.05% last updated on Oct 14, 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 MA 02535

Chilmark, MA20 Eliot Avenue

Price$7,900,000

Est. Mortgage: $/month

MLS Number 38217

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 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: 3.05% last updated on Oct 14, 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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1 Pondmark Chilmark MA 02535

Chilmark, MA1 Pondmark

Price$4,700,000

Est. Mortgage: $/month

MLS Number 38183

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 4.7

Turn onto country lane and make first turn to right. Drive past Norwegian Pine and many mature plantings and follow stately stone walls up past an open field overlooking the pond. The gentle slope takes you past the garden to a parking area. The white cottage sits on top of the knoll with sweeping views looking out over Keith farm and beyond to the ocean. From the living room the light brightens the large room with vaulted ceilings and a fireplace with a copper chimney hood.You can walk out on the deck for breakfast and watch the cows, geese, horses or the calming motion of the sea. You can lay in bed and take it all in from the king size bed and wall of windows facing south. There is room for a guest house or barn in this private setting. There are walking trails on Old North Road or a trail to Menemsha Crossroads. Go back in time to a slower way of life in this old style Chilmark retreat.

Listed by Elise LeBovit of Gay Head Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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135 Middle Road Chilmark MA 02535

Chilmark, MA135 Middle Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 37541

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 2
  • Acreage 7.1

A quintessential 1950s cottage situated on the highly sought after area of Middle Road in Chilmark. Consisting of a main house, guest house, garage and storage shed on 7.1 total acres. Would make a great family compound. A Landbank walking trail abuts property. Property is being sold "AS IS." Septic upgrade plan completed, but not installed.

Listed by Julianna Flanders of Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 October 21, 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."

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