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Land with Home for Sale in Chatham, Massachusetts

55 Winterset Dr, Chatham, MA 02633

$2,390,000
2 acres
Active sale
ago
Est $12,689/mo

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.

4,066
Sq feet
4
Beds
3
Full baths
1
1/2 bath
1970
Built

Location

Street address
55 Winterset Dr
Zip code
02633
Community
Great Hills
School district
Monomoy
Elevation
47 feet
Coordinates
41.6942, -69.977

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

CategoryTypeStatus
GasNatural GasConnected

Listing history

DateEventPriceChangeSource
July 13, 2026New listing$2,390,000CCIAOR
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This 1.94-acre property is located at 55 Winterset Dr in Chatham, MA 02633. The property is available for sale, priced at $2,390,000. It has a 4,066 square foot 4-bedroom, 3.5-bath house built in 1970.

Listed by Coldwell Banker Realty, (508) 962-6990

Checked 2 hours agoUpdated Source

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