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55 Winterset Drive Chatham MA 02633 | MLS #22603375

55 Winterset Drive
Chatham, MA, 02633
$2,295,000
4 Beds
3.5 Baths
4,072 SqFt
1.94 Acres
MLS #22603375 image #0
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

Price:
$2,295,000
MLS #:
22603375
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Hills
Neighborhood:
chatham
Listed Date:
Jul 12, 2026
Finished Sq Ft:
4,072
Total Sq Ft:
4,072
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
ChathamChathamGreat HillsMonomoy

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Schools

School District:
Monomoy

Interior

Appliances
Natural Gas, Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
4
Flooring
Hardwood
Heating
Natural Gas
Interior Features
Central Vacuum, Recessed Lighting

Exterior

Architectural Style
Cape Cod, Contemporary
Association Amenities
Beach Access
Construction Materials
Shingle Siding
Fencing
Partial
Garage Spaces
2
Lot Features
Corner Lot
Parking Features
Direct Access, Garage Door Opener, Off Street, Paved
Parking Spots
14
Parking Total
14
Patio And Porch Features
Deck, Patio
Roof
Asphalt, Shingle
Stories
3

Financial

HOA Fee
$75
HOA Fee Frequency
Annually
Tax Year
2026
Taxes
$5,655

Map

Community

Subdivisions in Chatham

Market Summary

Current real estate data for Single Family in Chatham as of Nov 12, 2026
48
Single Family Listed
122
Avg DOM
15,627
Avg $ / SqFt
$3,249,073
Avg List Price

Property Summary

    Located in the Great Hills subdivision, 55 Winterset Drive Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $2,295,000 and features 4 beds, 4 baths, and has approximately 4,072 square feet of living space, and was originally constructed in 1970. The current price per square foot is $564. The average price per square foot for Single Family listings in Chatham is $15,627. The average listing price for Single Family in Chatham is $3,249,073. To schedule a showing of MLS#22603375 at 55 Winterset Drive in Chatham, MA, contact your Gibson Sotheby’s Int’l Realty agent at 5084327856.

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55 Winterset Drive
Chatham, MA