Boston Luxury Condos and Apartments
355 Boylston St / (617) 233-5800

55 Winterset Drive

Chatham, MA ID #73548377

Property Description

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.

Additional Details

  • Status: ACT
  • Type: Single Family, Single Family Residence
  • Zip Code: 02633
  • HOA Fee: $75
  • Taxes: 5,655
  • Acres: 1.94

Parking

  • Garage: 2
  • Garage Capacity: 2
  • Parking: Paved,Attached,Garage Door Opener,Garage Faces Side,Off Street,Garage
  • Parking Spaces: 14

Rooms/Dimensions

  • Total Rooms: 8
  • Has Basement: Yes

Location

Get Directions
Luxury Condo Buildings
Luxury Apartment Buildings
More buildings

Request more Information or schedule a tour of:
55 Winterset Drive, Chatham, MA

When you are ready, please contact us and we will put our unrivaled knowledge of the Boston real estate market to work for you. Whether you are purchasing a luxury home, condo or renting an apartment, we pledge to make your experience as stress free and enjoyable as possible.

For prompt, expert service and answers to all your questions, please send us a message or call anytime at
617-233-5800

* Required Fields.

By submitting your information you agree to our Terms and Conditions and Privacy Policy.

Request Info
Content © 2026 MLS Property Information Network, Inc.
The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Janet Stuart of Coldwell Banker Realty - Concord. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.