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

55 Winterset Drive, Chatham, MA 02633

$2,390,000

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

Current Price: $2,390,000 List Date: 7/13/2026 Last Modified: 9/02/2026

Overview

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.

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Listing Details MLS# 22603375

Contract Info

Original List Price: 2390000
List Price/SqFt: 587.8

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

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: Well 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 ›

Listing Office: Coldwell Banker Realty

Listing Agent: Janet Stuart

Last Updated: September - 02 - 2026

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