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Wonderfully renovated and expanded Contemporary Cape set back at the end of a quiet cul-de-sac on just under two acres offering total privacy and nature at every turn. As part of Great Hill, this home includes deeded rights to Lover's Lake for swimming, kayaking, and canoeing just a short footpath away. Features include hardwood floors, lots of windows and french doors for loads of sunlight, open floor plan, vaulted ceilings and multiple decks all perfect for entertaining and large family gatherings. The first floor includes two great rooms each with vaulted beamed ceilings, one with a gas fireplace and one with a wood-burning fireplace, a renovated kitchen with a wall of windows at the kitchen sink overlooking the property, a large dining area, a half bath and a primary suite with ensuite renovated bathroom with large walk-in shower and laundry. Off the great room is a large wraparound deck with gas connection for the grill and room for full dining, lounging and taking in the professionally landscaped grounds, sprawling flower beds and quaint stone walls. Off the other great room and connecting with the kitchen is another deck overlooking the property with a perfect spot for morning coffee, reading and relaxing. On the second floor is a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath with shower and separate spa tub. The lower level has a bedroom with sitting area and full window, a full bath, another laundry, and walk-out access to a stone patio with custom stone wraparound seating and a built-in gas fire-pit. Enjoy brand new Bosch heating system, central a/c, central vac, attached 2 car garage, gas connection and town water. Key location with easy access to Route 6 for commuting off cape and the outer cape areas.yet a 5-minute drive to Chatham Village, Chatham Light, Lighthouse Beach, Chatham Bars Inn, Seaside Links Golf Course, and Hardings Beach. Steps to tennis courts, pickleball courts and the Chatham Scenic Bike Loop connecting to the Cape Cod Rail Trail bike path. House comes fully furnished.

More Info

Basic Information

  • Bedrooms4
  • Mls StatusActive
  • Bathroom4
  • 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 Spaces10
  • 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 Date10/20/2026
  • Property SubTypeSingle Family Residence
  • Virtual TourView Tour

Location

  • 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
  • View Count1

Map Location

Driving Directions

Listed by Janet Stuart of Coldwell Banker Realty - Concord

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