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55 Winterset Drive
Chatham MA 02633 US

$2,295,000

Active Listing ID 22603375
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4 bed
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4,066 square feet
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4.00 Bath (3 Full , 1 Half)
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Lot: 1.94 Acres
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Single Family Residence

$2,295,000

Active Listing ID 22603375
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55 Winterset Drive Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. 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, 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 AC 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.

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Property Features

  • Facts
  • Lot Size: 1.94 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Private Yard
  • Floor Covering: Carpet, Hardwood
  • Roof Type: Asphalt, Shingle
  • Heating Fuels: Natural Gas
  • Additional Features
  • Basement
  • Fireplace
  • Patio

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 2295000
  • unparsedaddress: 55 Winterset Drive
  • postalcity: Chatham
  • stateorprovince: MA
  • country: US
  • postalcode: 02633
  • bathroomsfull: 3
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 1.94
  • lotsizeunits: Acres
  • lotsizearea: 1.94
  • livingarea: 4066
  • livingareaunits: Square Feet
  • latitude: 41.694159
  • longitude: -69.977027
  • listagentfullname: Janet Stuart
  • listagentemail: janet.stuart@nemoves.com
  • listagentkey: 3yd-CCIAORMA-U24253
  • listagentmlsid: U24253
  • listagentpreferredphone: 6175153824
  • listagentofficephone: 6175153824
  • listofficekey: 3yd-CCIAORMA-CBRES
  • listofficemlsid: CBRES
  • disclaimer: Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CCIAORMA
  • yearbuilt: 1970
  • listingcontractdate: 2026-07-12
  • listagenturl: https://www.coldwellbankerhomes.com
  • countyorparish: Barnstable
  • parcelnumber: CHAT M:0011G B:0074 L:H108-0
  • elementaryschooldistrict: Monomoy
  • middleorjuniorschooldistrict: Monomoy
  • highschooldistrict: Monomoy
  • appliances: Water Heater
  • cooling: Central Air
  • constructionmaterials: Shingle Siding
  • flooring: Carpet, Hardwood
  • heating: Natural Gas
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 3
  • parkingtotal: 14
  • parkingfeatures: Open, Off Street
  • roof: Asphalt, Shingle
  • waterfrontyn: False
  • franchiseaffiliation: Coldwell Banker Real Estate
  • interiorfeatures: Central Vacuum, Recessed Lighting, Kitchen Island, Breakfast Bar, Eat-in Kitchen
  • exteriorfeatures: Private Yard
  • architecturalstyle: Contemporary, Cape Cod
  • rooms: Bathroom 3, Bedroom 2, Bedroom 1, Bedroom 4, Bathroom 1, Bathroom 2, Basement, Bedroom 3, Bathroom 4
  • patioandporchfeatures: Patio, Deck
  • speciallistingconditions: Standard
  • basement: Finished, Walk-Out Access, Full
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -69.97703, 41.69416
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-CCIAORMA-22603375", "OpenHouseEndTime": "2026-09-18 14:30:00", "OpenHouseId": "10235125", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-09-18 13:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Coldwell Banker Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"janet.stuart@nemoves.com", "ListBrokerageCity":"Hanover", "ListBrokerageCountry":"US", "ListBrokerageEmail":"karen.hover@cbrealty.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Coldwell Banker Realty", "ListBrokeragePhone":"(508) 962-6990", "ListBrokeragePostalCode":"02339", "ListBrokerageStateOrProvince":"MA", "ListBrokerageUnitNumber":"Suite 105 Hanover", "ListBrokerageUnparsedAddress":"2053 Washington Street", "ListBrokerageWebsiteUrl":"https://www.coldwellbankerhomes.com", "ListOfficeAddress1":"4650 Rte. 28 ", "ListOfficeAddress2":"Suite 105 Hanover", "ListOfficeBrokerMlsId":"CBRES", "ListOfficeCity":"Cotuit", "ListOfficeCountry":"US", "ListOfficeEmail":"karen.hover@cbrealty.com", "ListOfficePostalCode":"02635", "ListOfficeStateOrProvince":"MA", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, Chatham, MA", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/55-Winterset-Dr_Chatham_MA_02633_M40761-41651?f=listhub&s=CCIAORMA&m=22603375&c=rexren", "MLSModificationTimestamp":"2026-10-02 21:05:18", "Neighborhoods":[{"Description":null, "Name":"Great Hills"}], "PostalCode":null, "RoomCount":8, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":5655, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/2/2026 9:15:37 PM GMT
Source Updated Date: 10/9/2026 12:55:37 AM GMT

Courtesy of: Janet Stuart, Coldwell Banker Realty, janet.stuart@nemoves.com

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.