$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
4,072 Sq Ft
1.94 acres
2 Car Garage
MLS# 22603375 · Residential / (Single Family Residence)
Listed: 07/12/26 (listing data as of 11/6/26 at 9:59 pm)
Listed: 07/12/26 (listing data as of 11/6/26 at 9:59 pm)
- Hardwood Floors
- Primary Suite
- Laundry Room
- Kayaking
- 1st Floor Primary Bedroom
- Central A/C
- 4 Fireplaces
- Renovated 2000
- 2-Car Garage
About This Property
Exceptional Great Hill Estates retreat being offered fully furnished, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short foot path away. Located on a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out. A first-floor primary suite features ensuite bath and laundry for convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent great rooms with vaulted beamed ceilings and fireplaces. A wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs are two bedrooms and a full bath, including one bedroom with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, another laundry area, and direct access to a stone patio with custom seating and gas fire pit. Additional highlights include central ac, hardwood floors, two-car attached garage and new Bosch heating system. Close to Chatham Village, Lighthouse and Hardings beaches, bike path and tennis courts.
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 Footage4,072
Price/Sq Ft$564/sq ft
Additional Finished Space706 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 Market117
WaterfrontNo
Miles to Beach0 - .1
Fireplaces4
Lot Features
Corner Lot
Bedroom Details
Primary Bedroom
- First Floor
- Closet(s)
- Laundry Areas
- Private Full Bath
Bedroom 2
- Second Floor
- Closet(s)
- Office/Sitting Area
- Wood Burning Fireplace
Bedroom 3
- Second Floor
- Closet(s)
Bedroom 4
- Basement Floor
- Closet(s)
Living Area Details
Living Room
- First Floor
- Beamed Ceilings
- French Door
- Gas Fireplace
- Hardwood Flooring
- Recessed Lighting
Dining Room
- First Floor
- French Door
- Hardwood Flooring
- Recessed Lighting
Kitchen
- Granite Counters
- Hardwood Flooring
- Recessed Lighting
Laundry
- Basement Floor
Family Room
- First Floor
- Beamed Ceilings
- Ceiling Fan(s)
- Hardwood Flooring
- Wood Burning Fireplace
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
