
55 Winterset Drive Chatham — Photo 1 of 38
Recent Drop: $95,000
$2,295,000
55 Winterset Drive, Chatham, MA 02633
Chatham, MA 02633 — Great Hill
Beds
4
Baths
3.5
SqFt
4,072
Style
Single Family
Built
1970
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.
Immersive Experience
Market Value Analysis
* Analysis is based on 8 actively listed and recently sold comparable properties strictly within Chatham, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Oven • Dishwasher • Microwave • Range • Refrigerator • Washer • Dryer • Washer/Dryer
Neighborhood
Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Golf • Medical Facility
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,FirstCathedral Ceiling(s), Ceiling Fan(s), Beamed Ceilings, Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled
Dining Room
Lvl Main,FirstFlooring - Hardwood, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Lighting - Sconce
Kitchen
Lvl FirstFlooring - Hardwood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting
Family Room
Lvl FirstCathedral Ceiling(s), Beamed Ceilings, Flooring - Hardwood, Window(s) - Picture, Balcony / Deck, French Doors, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting
Primary Bedroom
Lvl Main,FirstBathroom - Full, Closet, Flooring - Wall to Wall Carpet, Recessed Lighting, Closet - Double
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondCloset, Flooring - Wall to Wall Carpet
Bedroom 4
Lvl BasementCloset, Flooring - Wall to Wall Carpet
Bathroom 1
Lvl FirstBathroom 2
Lvl FirstBathroom 3
Lvl SecondProperty History
$2,295,000
Was $2,390,000
Sep 11, 2026
MLS® 73548377
$2,390,000
Jul 11, 2026
MLS® 73548377
Population
4,512
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$85K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
15.9%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Barnstable County
505 housing units permitted in the last 12 months (-51% vs the prior 12 months) — 123 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
Listing Agent: Janet Stuart
Listing Office: Coldwell Banker Realty - Concord
MLS® Number: 73548377
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