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55 Winterset Drive, 
Chatham, MA 02633

$2,295,000


4

Beds


4

Baths


4,066

Sq Ft


Single Family

Active

Listed by

Janet Stuart

Last updated:

September 19, 2026, 04:52 PM

MLS#

22603375

Source:

CAPECOD

Company Logo

About This Home

55 Winterset Drive

Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central air conditioning throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1970

Subdivision & Development:

Great Hills

Price Summary

2,295,000

$564 per Sq. Ft.

MLS #:

22603375

Last Updated:

September 19, 2026, 04:52 PM

Added:

2 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4


Structure

Structure

Building Area:

4,066 Sq. Ft.

Year Built:

1970


Lot

Lot Size (Sq. Ft):

84,506


Finances & Disclosures

Finances

Price:

$2,295,000

Price per Sq. Ft:

$564 per Sq. Ft.

55 Winterset Drive
MLS Logo
Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Coldwell Banker Realty include the name of the listing broker. Neither the listing company nor Coldwell Banker Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.