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Set up high on just under two acres in Chatham's Great Hill, this sun-filled 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy and views of nature all year long. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central air conditioning throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.

More Info

Basic Information

  • Bedrooms4
  • Mls StatusContingent
  • Bathroom4
  • Contingency Pending P&S
  • Lot Features Corner Lot
  • Parcel Number 2260871

Tax Information

  • Tax Assessed Value $1,540,900
  • Tax Year 2026
  • Taxes$5,655

School Information

  • High School Monomoy
  • Elementary SchoolChatham
  • High SchoolMonomoy Regional
  • Junior HighChatham

Parking

  • Parking Spaces14
  • Covered Spaces 2
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features
    • Attached
    • Garage Door Opener
    • Garage Faces Side
    • Off Street
    • Paved Drive
    • Under

Rooms

  • Bathroom 1 First
  • Bathroom 2 First
  • Bathroom 3 Second
  • Bathrooms Total Decimal 3.5
  • Bedroom 2 Second
  • Bedroom 3 Second
  • Bedroom 4 Basement
  • Dining Room Main, First
  • Family Room First
  • Full Bath3
  • Half Baths1
  • Kitchen First
  • Living Room Main, First
  • Main Level Bedrooms 1
  • Master Bedroom Main, First

Basic Information

  • List Price$2,295,000
  • MLS Number73548377
  • Modification Date09/29/2026
  • Property SubTypeSingle Family Residence
  • PurchaseContractDate09/22/2026
  • Virtual TourView Tour

Location

  • SubdivisionGreat Hill
  • Address55 Winterset Drive
  • Building Number55
  • CountyBarnstable
  • StateMA
  • StreetWinterset Drive
  • TownChatham
  • Zip02633

Building

  • Attached Garage YN Yes
  • BasementFull, Finished, Walk-Out Access, Interior Entry, Garage Access
  • Building Area Units Square Feet
  • Construction Materials Frame
  • Door Features Insulated Doors, French Doors
  • FireplaceYes
  • Fireplace Features Family Room, Living Room, Bedroom
  • Fireplaces Total 4
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Patio And Porch Features Deck, Patio
  • Property StyleCape, Contemporary
  • Rooms8
  • Utilities For Gas Range, For Gas Dryer, Outdoor Gas Grill Hookup
  • Window Features Insulated Windows
  • Year Built1970
  • Year Built Details Actual
  • Year Built Source Public Records

Property

  • Acreage1.94

Interior

  • Flooring Tile, Carpet, Hardwood
  • Interior Features Bathroom

Exterior

  • Exterior Features Deck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup
  • RoofShingle

Utilities

  • Cooling Central Air, Ductless
  • Cooling YN Yes
  • Electric 200+ Amp Service
  • Heat SystemYes
  • Heating Baseboard, Natural Gas
  • Sewer Private Sewer
  • Water Source Public

Property Information

  • Square Feet4,072
  • Building Area Source Public Records
  • Living Area 4,072
  • Lot Size Square Feet 84,506
  • Lot Size Units Acres

Amenities

  • Amenities
    • Bike Path
    • Conservation Area
    • Golf
    • Highway Access
    • House of Worship
    • Marina
    • Medical Facility
    • Park
    • Public School
    • Shopping
    • Tennis Court(s)
    • Walk/Jog Trails
  • Appliances IncludedGas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
  • Security Features Security System

Water Body

  • Miles to Beach0.1
  • Waterfront Features Lake/Pond,0 to 1/10 Mile To Beach, Beach Ownership(Private)

Other

  • Association Fee $75
  • Association Fee Frequency Annually
  • Association YN Yes
  • Date Listed07/11/2026
  • Farm Land Area Units Square Feet

Map Location

Driving Directions

Listed by Janet Stuart of Coldwell Banker Realty - Concord

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