55 Winterset Drive, Chatham, MA 02633 (MLS # 22603375)
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Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.
| DAYS ON MARKET | 97 | LAST UPDATED | 10/2/2026 |
|---|---|---|---|
| TRACT | Great Hills | YEAR BUILT | 1970 |
| COMMUNITY | Chatham | GARAGE SPACES | 2.0 |
| COUNTY | Barnstable | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| PRICE HISTORY | |
| Prior to Sep 11, '26 | $2,390,000 |
|---|---|
| Sep 11, '26 - Today | $2,295,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Water Heater |
| AREA | Chatham |
| BASEMENT | Finished, Full, Yes |
| CONSTRUCTION | Shingle Siding |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Natural Gas |
| HOA DUES | 75|Annually |
| INTERIOR | Central Vacuum, Recessed Lighting |
| LOT | 1.94 acre(s) |
| LOT DESCRIPTION | Corner Lot |
| PARKING | Direct Access, Garage Door Opener, Off Street, Paved |
| STORIES | 3 |
| STYLE | Cape Cod, Contemporary |
| SUBDIVISION | Great Hills |
| TAXES | 5655 |
| WATER | Public |
| ZONING | R60 |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with Coldwell Banker Realty
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