55 Winterset Drive

Taxes: $5,655 (2026)

About this home

Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

Property details

Sewer

On-Site

Style

Cape, Modified

Water

City/Town Water

Cooling

Central Air, Ductless Mini-Split System

Heating

Electric Baseboard, Hot Air Gravity

Type

Detached

Flooring

Tile, Wall to Wall Carpet, Hardwood

Road type

Public

Appliances

Wall Oven, Dishwasher, Microwave, Countertop Range, Refrigerator, Washer, Dryer, Washer / Dryer Combo

Master Bath

Yes

Construction

Aluminum

Roof

Aluminum

Garage

Attached, Under, Garage Door Opener, Side Entry

Lot

Corner, Paved Drive

Parking

1-10 Spaces

Basement

Full, Finished, Walk Out, Interior Access, Garage Access, Exterior Access

Electric

200 Amps

Exterior

Deck, Patio, Professional Landscaping

Interior

Security System, Cable Available, French Doors