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55 Winterset Drive$2,390,000For Sale

$2,390,000
For Sale
NEXT
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.

8/23/2026 12:30PM - 2:00PM EDT

4
beds

4
baths

4,072 Sq.Ft. LIVING AREA

1.94 Acres lot

Features & Amenities

Interior

  • total bedrooms4
  • Total bathrooms4
  • full bathrooms3
  • half bathroom1
  • Laundry room First Floor, Gas Dryer Hookup
  • Flooring Tile, Carpet, Hardwood
  • Fireplace Family Room, Living Room, Bedroom
  • APPLIANCES Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
  • other interior Features Bathroom

Area & Lot

  • Status For Sale
  • OPEN HOUSE

    8/23/2026 12:30PM - 2:00PM EDT

  • Living Area4,072 Sq.Ft.
  • Total Area4,072 Sq.Ft.
  • Lot Area1.94 Acres
  • MLS® ID73548377
  • TypeResidential
  • YEAR BUILT1970
  • Architecture StylesCape, Contemporary
  • Water FrontageLake/Pond, 0 to 1/10 Mile To Beach, Beach Ownership(Private)
  • Elementary SchoolChatham
  • Middle SchoolChatham
  • High SchoolMonomoy

Exterior

  • Garage Space2.0
  • water SourcePublic
  • utilitiesfor Gas Range, for Gas Dryer, Outdoor Gas Grill Hookup
  • roofShingle
  • lot featuresCorner Lot
  • parkingAttached, Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street
  • HEAT TYPEBaseboard, Natural Gas
  • AIR CONDITIONINGCentral Air, Ductless
  • sewerPrivate Sewer
  • SubstructureConcrete Perimeter
  • security FeaturesSecurity System
  • other exterior FeaturesDeck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup

Financial

  • Sales Price$2,390,000
  • Real Estate Tax $5,655/yr
  • HOA $75/yr
  • Zoning res
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