
Land with Home for Sale in Chatham, Massachusetts
55 Winterset Dr, Chatham, MA 02633
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.
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
- Stories
- 3
- Basement
- Finished, Full, Walk-Out Access
- Water
- Well
- 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, Dining Room, Laundry Room
- 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 |
|---|---|---|---|---|
| July 13, 2026 | New listing | $2,390,000 | — | CCIAOR |










































