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55 Winterset Drive
Chatham MA 02633 US

$2,390,000

Active Listing ID 22603375
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4 bed
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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

$2,390,000

Active Listing ID 22603375
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55 Winterset Drive Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

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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: Hardwood, Carpet
  • Roof Type: Shingle, Asphalt
  • Heating Fuels: Natural Gas
  • Additional Features
  • Basement
  • Fireplace
  • Patio

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 2390000
  • 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: Hardwood, Carpet
  • heating: Natural Gas
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 3
  • parkingtotal: 14
  • parkingfeatures: Off Street, Open
  • roof: Shingle, Asphalt
  • waterfrontyn: False
  • franchiseaffiliation: Coldwell Banker Real Estate
  • interiorfeatures: Central Vacuum, Recessed Lighting, Kitchen Island, Breakfast Bar, Eat-in Kitchen
  • exteriorfeatures: Private Yard
  • rooms: Bedroom 3, Bathroom 1, Basement, Bedroom 1, Bathroom 2, Bedroom 4, Bedroom 2, Bathroom 4, Laundry Room, Dining Room, Bathroom 3
  • patioandporchfeatures: Deck, Patio
  • speciallistingconditions: Standard
  • basement: Walk-Out Access, Full, Finished
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -69.97703, 41.69416
  • 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":"SINGLE_FAMILY - 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":"2026-07-13 19:07:22", "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: 7/13/2026 7:17:02 PM GMT
Source Updated Date: 7/15/2026 12:46:44 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.