55 Winterset Drive, Chatham, MA 02633

• 4 beds |
• 4 baths |
• 4,066 sqft

Property Description

Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private 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, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Home is being offered fully furnished if desired.

Listing Status:

Active

Date Added:

July 13, 2026

Data Last Updated:

July 31, 2026 at 3:36AM

Listing Office:

Coldwell Banker Realty : 508-862-8021

Listing Agent:

Janet Stuart : 617-515-3824

MLS ID:

22603375

Interior

• General: Central VacuumRecessed LightingEat-in KitchenKitchen IslandBreakfast Bar
• Appliances: Natural GasWater Heater
• Laundry: Laundry Room
• Basement: FinishedFull
• Flooring: HardwoodCarpet
• A/C: Central Air
• Heating: Natural Gas
• Fireplace: FireplaceFireplaces: 4

Exterior

• Parking: Direct AccessGarage Door OpenerOff StreetPavedParking spaces: 14

Construction

• Roofing: AsphaltShingle
• General: Shingle Siding3

Location

• HOA Amenities: Beach Access75.0Annually
• Originating MLS: Cape Cod & Islands Association of REALTORS®
• County: Barnstable

Lot

• Zoning: CHAT M:0011G B:0074 L:H108-0
• Fencing: Partial

Utilities

• Water: Well

Financial

• Source: Cape Cod & Islands Association of REALTORS®