55 Winterset Drive Chatham, MA ^$ 2,390,000

55 Winterset Drive

^$ 2,390,000

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55 Winterset Drive

Chatham, MA, 02633

^$ 2,390,000

Bedrooms4 Baths3.1 Sq 4,072

Monthly Estimate*

^$ 15,091

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Single Family Home for sale in Chatham, MA

for $2,390,000 with 4 bedrooms and 3 full baths, 1 half bath. This 4,072 square foot home was built in 1970 on a lot size of 1.94.

Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

Single Family Active

Price

^$ 2,390,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 5,655

Style

Cape,Contemporary

Lot Size

1.94

Year Built

1970

Town/City

Chatham

County/Region

Barnstable

MLS | Web ID

73548377

List By

Janet Stuart

Listing Agent

Coldwell Banker Realty - Concord

Broker

Affordability Calculator

$15,562

Per Month

Monthly Principal & Interest: $15,091
Monthly Property Taxes: $471
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Chatham, MA

Average List Price ^$3,363,436

Percent of Sale Price 41%

About Chatham, MA

6,037 Population

-10% Since 2002

^$69,389 Median Income

60.04 Median Age

13% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
7/11/2026	$2,390,000		Listed Price

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55 Winterset Drive, Chatham, MA, 02633 is a Single Family Home for sale at $2,390,000 with 4,072 sqft and a lot size of 1.94. 55 Winterset Drive has 4 bedrooms, 3.1 baths, and was built in 1970. The property's zip code is 02633 which is in Chatham, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 8/30/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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55 Winterset Drive

Single Family Home for sale in Chatham, MA

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