55 Winterset Drive
Chatham, MA, 02633
$2,390,000
4 Beds
3.5 Baths
4,066 SqFt
1.94 Acres
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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.

Property Details

Price:
$2,390,000
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:
4,066
Total Sq Ft:
4,066
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
ChathamChathamGreat Hills

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Schools

Interior

Appliances
Natural Gas, Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
4
Flooring
Hardwood, Carpet
Heating
Natural Gas
Interior Features
Central Vacuum, Recessed Lighting, Eat-in Kitchen, Kitchen Island, Breakfast Bar
Laundry Features
Laundry Room

Exterior

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 Aug 01, 2026
57
Single Family Listed
102
Avg DOM
1,117
Avg $ / SqFt
$3,099,098
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 $2,390,000 and features 4 beds, 4 baths, and has approximately 4,066 square feet of living space, and was originally constructed in 1970. The current price per square foot is $588. The average price per square foot for Single Family listings in Chatham is $1,117. The average listing price for Single Family in Chatham is $3,099,098. 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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