55 Winterset Drive, Chatham, MA 02633

Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
55 Winterset Drive,Chatham, MA 02633
$2,295,000
  • 4 Beds
  • 4 Baths
  • 4,072 sq. ft.
  • Single family
  • Active
Upcoming open houses
  • Sat, Nov 15
    11:00 am - 02:00 pm
Listed by: tara j schiffmann
Office: bayview real estate
MLS#:22502257
Source:CAPECOD

Price summary

  • Price:$2,295,000
  • Price per sq. ft.:$563.61
  • Monthly HOA dues:$6.25

About this home

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop

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Home facts

  • Year built:1970
  • Listing ID #:22502257
  • Added:185 day(s) ago
  • Updated:November 15, 2025 at 04:49 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:4
  • Full bathrooms:3
  • Living area:4,072 sq. ft.

Heating and cooling

  • Heating:Hot Water

Structure and exterior

  • Roof:Asphalt, Flat, Pitched
  • Year built:1970
  • Building area:4,072 sq. ft.
  • Lot area:1.89 Acres

Schools

  • Middle school:Monomoy
  • Elementary school:Monomoy

Utilities

  • Sewer:Private Sewer

Finances and disclosures

  • Price:$2,295,000
  • Price per sq. ft.:$563.61
  • Tax amount:$5,179 (2025)
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