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:
$2,495,000
MLS #:
22502257
Status:
Active
Beds:
4
Baths:
3.5
Address:
55 Winterset Drive
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Hills Estates
City:
Chatham
Listed Date:
May 6, 2025
State:
MA
Finished Sq Ft:
4,072
Total Sq Ft:
4,072
ZIP:
02633
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
Schools
School District:
Monomoy
Interior
Appliances
Dishwasher, Washer, Refrigerator, Microwave, 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
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
Contact Us
Mortgage Calculator
Similar Listings Nearby
- 30 Mill Hill Lane
Chatham, MA$2,950,000
1.89 miles away
- 106 Stage Neck Road
Chatham, MA$2,699,000
1.52 miles away
- 7 Colonial Drive
Chatham, MA$2,550,000
1.64 miles away
- 213 Main Street
Chatham, MA$2,549,000
1.87 miles away
- 25 Menekish Lane
Chatham, MA$2,500,000
1.08 miles away
- 98 Horizon Drive
Chatham, MA$2,375,000
0.03 miles away
- 292 Stage Harbor Road
Chatham, MA$2,300,000
1.45 miles away
- 409 Main Street
Chatham, MA$2,250,000
1.56 miles away
- 331 Riverview Drive
Chatham, MA$1,899,900
1.60 miles away
As a lifelong resident of the outer Cape I was the third generation to pick up the mantel in the family construction business. In my early twenties, I called the Cape my home on weekends as I spent several years working for a variety of off-Cape commercial construction companies. My commercial site supervision resume includes two supermarkets, two HUD projects, a funeral home and a handful of steel industrial buildings as well as various restaurant and office remodels. Prior to striking out on m…
More About Jon
55 Winterset Drive
Chatham, MA
LIGHTBOX-IMAGES
As a lifelong resident of the outer Cape I was the third generation to pick up the mantel in the family construction business. In my early twenties, I called the Cape my home on weekends as I spent several years working for a variety of off-Cape commercial construction companies. My site supervision resume includes two supermarkets, two HUD projects, a funeral home and a handful of steel industrial buildings as well as various restaurant and office remodels.