55 Winterset Drive, Chatham, MA 02633 (MLS # 22603375)
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Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & 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. Possible subdivision opportunity.
| DAYS ON MARKET | 15 | LAST UPDATED | 7/12/2026 |
|---|---|---|---|
| TRACT | Great Hills | YEAR BUILT | 1970 |
| COMMUNITY | West Chatham | GARAGE SPACES | 2.0 |
| COUNTY | Barnstable | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Gas Water Heater |
| AREA | West Chatham |
| BASEMENT | Finished, Full, Interior Entry, Yes |
| CONSTRUCTION | Shingle Siding |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Hot Water |
| HOA DUES | 75|Annually |
| INTERIOR | Breakfast Bar, Recessed Lighting |
| LOT | 1.94 acre(s) |
| LOT DESCRIPTION | Cul-De-Sac, Near Golf Course, On Golf Course |
| PARKING | Basement |
| SEWER | Septic Tank |
| STORIES | 3 |
| STYLE | Cape Cod, Contemporary |
| SUBDIVISION | Great Hills |
| TAXES | 5655 |
| WATER | Private, Well |
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Listed with Coldwell Banker Realty
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