
55 Winterset Drive Chatham — Photo 1 of 39
$2,390,000
Chatham, MA 02633 — Great Hill
Beds
4
Baths
3.5
SqFt
4,072
Style
Single Family
Built
1970
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.
* Analysis is based on 8 actively listed and recently sold comparable properties strictly within Chatham, MA.
Gas Water Heater • Oven • Dishwasher • Microwave • Range • Refrigerator • Washer • Dryer • Washer/Dryer
Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Golf • Medical Facility
4,512
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$85K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
15.9%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
513 housing units permitted in the last 12 months (-50% vs the prior 12 months) — 128 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 4,072 sq ft principal dwelling). Lot size: 84,506 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Janet Stuart
Listing Office: Coldwell Banker Realty - Concord
MLS® Number: 73548377
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