
Land with Home for Sale in Chatham, Massachusetts
55 Winterset Dr, Chatham, MA 02633
Wonderfully renovated and expanded Contemporary Cape set back at the end of a quiet cul-de-sac on just under two acres offering total privacy and nature at every turn. As part of Great Hill, this home includes deeded rights to Lover's Lake for swimming, kayaking, and canoeing just a short footpath away. Features include hardwood floors, lots of windows and french doors for loads of sunlight, open floor plan, vaulted ceilings and multiple decks all perfect for entertaining and large family gatherings. The first floor includes two great rooms each with vaulted beamed ceilings, one with a gas fireplace and one with a wood-burning fireplace, a renovated kitchen with a wall of windows at the kitchen sink overlooking the property, a large dining area, a half bath and a primary suite with ensuite renovated bathroom with large walk-in shower and laundry. Off the great room is a large wraparound deck with gas connection for the grill and room for full dining, lounging and taking in the professionally landscaped grounds, sprawling flower beds and quaint stone walls. Off the other great room and connecting with the kitchen is another deck overlooking the property with a perfect spot for morning coffee, reading and relaxing. On the second floor is a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath with shower and separate spa tub. The lower level has a bedroom with sitting area and full window, a full bath, another laundry, and walk-out access to a stone patio with custom stone wraparound seating and a built-in gas fire-pit. Enjoy brand new Bosch heating system, central a/c, central vac, attached 2 car garage, gas connection and town water. Key location with easy access to Route 6 for commuting off cape and the outer cape areas.yet a 5-minute drive to Chatham Village, Chatham Light, Lighthouse Beach, Chatham Bars Inn, Seaside Links Golf Course, and Hardings Beach. Steps to tennis courts, pickleball courts and the Chatham Scenic Bike Loop connecting to the Cape Cod Rail Trail bike path. House comes fully furnished.
Location
- Street address
- 55 Winterset Dr
- County
- Barnstable County
- Zip code
- 02633
- Community
- Great Hills
- School district
- Monomoy
- Elevation
- 47 feet
Directions
Old Queen Anne Road to Winterset Drive, house located at the end on the left.
Property details
- Acreage
- 1.94 acres84,506 sq ft
- Zoning
- R60
- MLS #
- CCIAOR 22603375
- Posted
Property taxes
- 2026
- $5,655
Expenses
- Homeowner Association Fee
- $75 annually
Parcels
- CHAT M:0011G B:0074 L:H108-0
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
- Franchise
- Coldwell Banker Real Estate
Lot
- Features
- Corner Lot
Exterior
- Parking Spaces
- 14
- Parking
- Off Street, Open
- Pool
- Deck, Patio
- Features
- Private Yard
Structure
- Style
- Cape Cod, Contemporary
- Stories
- 3
- Basement
- Finished, Full, Walk-Out Access
- Water
- Public
- Sewer
- Septic Tank
- Heating
- Natural Gas
- Cooling
- Central Air
- Materials
- Shingle Siding
- Roof
- Asphalt, Shingle
Interior
- Room Count
- 8
- Rooms
- Basement, Bathroom x 4, Bedroom x 4
- Flooring
- Carpet, Hardwood
- Fireplaces
- Yes
- Appliances
- Water Heater
- Features
- Breakfast Bar, Central Vacuum, Eat-In Kitchen, Kitchen Island, Recessed Lighting
Property utilities
| Category | Type | Status |
|---|---|---|
| Gas | Natural Gas | Connected |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Oct 2, 2026 | Back on market | $2,295,000 | — | CCIAOR |
| Sept 24, 2026 | Under contract | $2,295,000 | — | CCIAOR |
| Sept 11, 2026 | Price drop | $2,295,000 | $95,000 -4% | CCIAOR |
| July 13, 2026 | New listing | $2,390,000 | — | CCIAOR |










































