55 Winterset Drive
Chatham, MA, 02633
$2,295,000
4 Beds
3.5 Baths
4,072 SqFt
1.94 Acres
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Open House Nov 07, 2026
11:00 – 01:00
Open House Nov 08, 2026
11:00 – 01:00
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

Market Summary

Current real estate data for Single Family in Chatham as of Nov 05, 2026
49
Single Family Listed
122
Avg DOM
1,073
Avg $ / SqFt
$3,313,214
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 $1,073. The average listing price for Single Family in Chatham is $3,313,214. To schedule a showing of MLS#22603375 at 55 Winterset Drive in Chatham, MA, contact your Pleasant Bay Realty agent at (774) 209-1428.

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