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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 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.

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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: Shingle, Asphalt
  • 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: 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
  • architecturalstyle: Cape Cod, Contemporary
  • rooms: Bedroom 4, Bedroom 2, Bedroom 3, Bedroom 1, Bathroom 3, Bathroom 4, Bathroom 2, Basement, Bathroom 1
  • patioandporchfeatures: Deck, Patio
  • speciallistingconditions: Standard
  • basement: Full, Walk-Out Access, Finished
  • 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": "2026-10-24 12:00:00", "OpenHouseId": "12617745", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-10-24 10:30:00", "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":"2026-10-22 12:54:02", "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: 10/22/2026 10:31:16 PM GMT
Source Updated Date: 10/23/2026 11:01:19 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.