$2,295,000
-4.0% from original list of $2,390,000 · September 11, 2026
55 Winterset Drive, Chatham, MA 02633
4 bedrooms
3 Full Baths
1 Half Bath
4,066 Sq Ft
1.94 acres
2 Car Garage
MLS# 22603375 · Residential / (Single Family Residence)
Listed: 07/12/26 (listing data as of 09/22/26 at 6:59 pm)
Listed: 07/12/26 (listing data as of 09/22/26 at 6:59 pm)
- Hardwood Floors
- Built-Ins
- Cul-de-Sac
- Kayaking
- 1st Floor Primary Bedroom
- Central A/C
- 4 Fireplaces
- Renovated 2000
- 2-Car Garage
About This Property
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, 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 AC 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.
Property Details
Property TypeResidential
(Single Family Residence)
(Single Family Residence)
StatusFor Sale
MLS Number22603375
Year Built1970
Annual Taxes$5,655 (2026)
Total Assessment$1,540,900
Square Footage4,066
Price/Sq Ft$564/sq ft
Additional Finished Space700 sqft
Lot Size1.94 acres
Total Rooms8
Bedrooms4
Full Baths3
Half Baths1
RenovatedYes
Year Renovated2000
Heat Source
Natural Gas
Add'l Heating
Forced Hot Water
Cooling A/C
Central Air
Association Fee
$75.00 (Annually)
Association Fee Includes
Beach Access
Garage Spaces2
Days on Market72
WaterfrontNo
Miles to Beach0 - .1
Fireplaces4
Lot Features
Corner Lot
Bedroom Details
Primary Bedroom
- First Floor
- Private Full Bath
- Laundry Areas
Bedroom 2
- Second Floor
- Office/Sitting Area
Bedroom 3
- Second Floor
Bedroom 4
- Basement Floor
Living Area Details
Living Room
- First Floor
- French Door
- Shared Half Bath
- Recessed Lighting
- Wood Flooring
- Cathedral Ceiling(s)
- Beamed Ceilings
Dining Room
- First Floor
- French Door
- Shared Half Bath
- Recessed Lighting
- Wood Flooring
Kitchen
- First Floor
- French Door
- Recessed Lighting
- Kitchen Island
- Wood Flooring
- Granite Counters
- Breakfast Bar
Laundry
- First Floor
Convenient To
- Bike Path
- Cape Cod Rail Trail
- Conservation Area
- Golf Course
- House of Worship
- Major Highway
- Marina
- Medical Facility
- Public Tennis
- School
- Shopping
- Convenient to Lovers Lake
- Convenient to Hardings Beach
Exterior Features
- Private Yard
Interior Features
- Central Vacuum
- Recessed Lighting
Location
Sold History
55 Winterset Drive last sold
April 10, 2023 for $1,770,000
Listed At
$1,795,000
Sale / List
98.6%
Days on Market
2
Nearby Listings
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Listing Courtesy of: Janet Stuart / Coldwell Banker Realty
