55 Winterset Drive, Chatham, MA 02633 (MLS# 22603375)

55 Winterset Drive, Chatham, MA 02633

$2,295,000

Property Type: Residential Bedrooms: 4 Baths: 4 Square Footage: 4,066 Lot Size (sq. ft.): 84,506 Status: Active

Current Price: $2,295,000 List Date: 10/02/2026 Last Modified: 10/23/2026

Overview

Description

Renovated and expanded Contemporary Cape at the end of a cul-de-sac on just under two acres allows for a unique amount of privacy while being less than a five minute drive to Chatham Village, Chatham Lighthouse, the Chatham Bars Inn and all that Chatham has to offer. As part of Great Hill Estates, this home has deeded rights to Lover's Lake for swimming, kayaking and canoeing. This home offers large open spaces perfect for entertaining and large gatherings. The first floor has a family room with vaulted beamed ceiling and wood burning fireplace open to a kitchen with large island and dining area, another large living room with gas fireplace open to a wraparound deck for grilling, dining and enjoying the views of nature looking out over the property. Enjoy a first floor primary with ensuite bathroom including laundry and a half bath. Upstairs are two more bedrooms, one as a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath. The lower level has a be ... (Read more)

Supplements: garage, brand new Bosch heating system and newer roof. Just steps away from the Cape Cod Rail Trail Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

Open Houses

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Listing Details MLS# 22603375

Contract Info

Original List Price: 2390000
List Price/SqFt: 564.44

Legal and Taxes

Street #: 55
Street Name: Winterset
Street Suffix: Drive
County: Barnstable
Town: Chatham
Village: Chatham
State: MA
Zip Code: 02633
Tax ID: CHAT M:0011G B:0074 L:H108-0
Estimated Annual Taxes: 5655
Tax Year: 2026
Building Assessments: 1152900
Total Assessment: 1540900
Underground Fuel Tank: No
Lead Base Paint: Unknown
Flood Ins Required: Not Verified
Mass Use Code: 101 - Residential, single family
Nitrogen Sensitive Area: No

General Property Info

Comp Sale YN: No
Region: Lower Cape
Sub-Area: West Chatham
Subdivision: Great Hills
School District: Monomoy
Zoning: R60
Property Sub-Type: Single Family Residence
Year Built: 1970
Renovated: Yes
Year Renovated: 2000
Total Finished Space: 4066
Field Card SqFt: 3366
Additional Finished Space: 700
Additional SqFt Source: Owner
Total Rooms: 8
Stories: 3
Private Pool: No
Private Dock: No
Leased Land: No
Lot Size SqFt: 84506
Lot Size Source: Field Card
Acres: 1.94
Association: Yes
Fee Amount: 75
Fee Frequency: Annually
Membership Required: No
Assoc Fee Year: 2026
Garage: Yes
# of Cars: 2
# of Parking Spaces: 14
Year Round: Yes
Bedrooms - Total: 4
Baths - Full: 3
Baths - Half: Yes
Baths - Total: 4
Golf Course Front: No
Golf Course View: No
Waterfront: No
Waterview: No
Miles to Beach: 0 - .1
Mi. to Beach Comments: .1 miles to Lover's Lake beach
Fireplace: Yes
# Fireplaces: 4
Property Includes Recording Devices: No

Baths Per Level

Basement Baths: Yes
Baths - Level 1: 2
Baths - Level 2: Yes

Convenient To

Convenient to Water Body 1: Lovers Lake
Convenient to Water Body 2: Hardings Beach

Sewer

Septic Tank Description: Title V Above Ground

More Information

DPR Eligibility

DPR Eligible: No

Room Types

Bedroom 2 Level: Second
Bedroom 3 Level: Second
Bedroom 4 Level: Basement
Dining Room Level: First
Kitchen Level: First
Laundry Level: First
Living Room Level: First
Primary Bedroom Level: First

Property Features

Street Description: Cul-De-Sac; Paved Special Listing Cond: Standard Architectural Style: Cape Cod; Contemporary Year Built Desc: Actual Basement Description: Finished; Full; Garage Access; Interior Access; Walk-Out Access Foundation Details: Poured Lot Features: Corner Lot Association Fee Incl: Beach Access Garage Description: Direct Access; Garage Door Opener; Under Parking Features: Off Street; Paved Convenient To: Bike Path; Cape Cod Rail Trail; Conservation Area; Golf Course; House of Worship; Major Highway; Marina; Medical Facility; Public Tennis; School; Shopping Floors: Carpet; Hardwood Interior Features: Central Vacuum; Recessed Lighting Patio And Porch Features: Deck; Patio Exterior Features: Private Yard Fencing: Partial Roof Description: Asphalt; Shingle Siding Description: Shingle Sewer: Septic Tank Heating: Hot Water Cooling: Central Air Fuel Type: Natural Gas Water: Public Hot Water: Water Heater Hot Water Source: Natural Gas Room Types: Bedroom 2; Bedroom 3; Bedroom 4; Dining Room; Kitchen; Kitchen/Dining Combo; Laundry; Living Room; Living/Dining Combo; Primary Bedroom

Room Information

Room Name	Level
Primary Bedroom	First
Bedroom 2	Second
Bedroom 3	Second
Bedroom 4	Basement
Laundry	First
Living/Dining Combo
Dining Room	First
Kitchen/Dining Combo
Living Room	First
Kitchen	First

Documents

Home Inspection Disclosure ›

Lead Paint Disclosure ›

Septic Inspection ›

Listing Office: Coldwell Banker Realty

Listing Agent: Janet Stuart

Last Updated: October - 23 - 2026

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