55 Winterset Drive
Chatham, MA, 02633
$2,295,000
4 Beds
3.5 Baths
4,072 SqFt
1.94 Acres
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Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham’s most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover’s Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham’s bustling village & ocean beaches. May be sold furnished.

Property Details

Price:
$2,295,000
MLS #:
22502257
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Hills Estates
Listed Date:
May 6, 2025
Finished Sq Ft:
4,072
Total Sq Ft:
4,072
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
Great Hills EstatesMonomoy

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Schools

School District:
Monomoy

Interior

Appliances
Dishwasher, Washer, Washer/ Dryer Stacked, Refrigerator, Gas Range, Microwave, Electric Dryer, Gas Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Fireplaces Total
4
Flooring
Hardwood, Carpet, Tile, Other
Heating
Hot Water, Other
Laundry Features
Laundry Room, In Basement

Exterior

Architectural Style
Cape Cod, Other
Community Features
Deeded Beach Rights
Construction Materials
Shingle Siding
Exterior Features
Garden
Parking Features
Basement
Parking Spots
6
Roof
Asphalt, Pitched, Flat

Financial

HOA Frequency
Annually
Tax Year
2025
Taxes
$5,179

Map

Community

Market Summary

Current real estate data for Single Family in Chatham as of Sep 04, 2025
83
Single Family Listed
119
Avg DOM
996
Avg $ / SqFt
$3,184,042
Avg List Price

Property Summary

    Located in the Great Hills Estates 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 $996. The average listing price for Single Family in Chatham is $3,184,042. To schedule a showing of MLS#22502257 at 55 Winterset Drive in Chatham, MA, contact your Pleasant Bay Realty agent at (774) 209-1428.

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