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359 Winchester Road
Winchester CT 06098 US

$850,000

Active Listing ID 24208872
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3 bed
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2,943 square feet
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3.00 Bath (3 Full)
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Lot: 7.55 Acres
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Other

$850,000

Active Listing ID 24208872
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359 Winchester Road Breathtaking water views and master craftsmanship await in this pristine Colonial offering nearly 3, 000 SF overlooking serene Highland Lake. This entertainer's dream home opens from an inviting two-story foyer into an airy, open layout where the living and dining rooms are joined by a floor-to-ceiling fieldstone fireplace. The spacious dining room easily accommodates large gatherings and flows seamlessly onto a delightful screened-in porch to enjoy the calm, serene setting with distant lake views. The gourmet kitchen is a master craftsman renovation featuring custom white birch cabinetry, rich soapstone countertops, stone subway tile backsplash, a farmhouse sink with a view, and a Sub-Zero refrigerator. Dedicated home office off front foyer, mudroom, laundry room, and half bath complete the main level. Upstairs features an en-suite primary bedroom, two additional nice-sized bedrooms, and a full guest bath. Accessed via a private second staircase off the kitchen, the expansive 27' x 21' "Skybox" family room (finished over the garage in 2017) boasts its own heating/cooling system, surround sound, and live music performance hook-ups. Property is flanked by a magnificent stone wall, emerald green meadows including a two-stall run-in shed with tack room. Hardwood floors main level, bamboo engineered floors upper level, oversized 2 car garage, walk-out basement. New well pump 2020, new whole house generator 2023. EZ commute to NYC & Boston from this ideal retreat. Rare opportunity.

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Property Features

  • Facts
  • Lot Size: 7.55 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 3
  • Cooling System: Central Air
  • Exterior Finish: Porch-Screened, Underground Utilities, Shed, Barn, Deck, Gutters, Lighting, Stone Wall
  • Heating Fuels: Zoned, Baseboard, Other (Heating), Hot Water(Heating)
  • Additional Features
  • Basement
  • Fireplace
  • Patio

School Information

  • School
  • Batcheller(Elementary)
  • Gilbert(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 850000
  • unparsedaddress: 359 Winchester Road
  • postalcity: Winchester
  • stateorprovince: CT
  • country: US
  • postalcode: 06098
  • bathroomsfull: 3
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 7.55
  • lotsizeunits: Acres
  • lotsizearea: 7.55
  • livingarea: 2943
  • livingareaunits: Square Feet
  • latitude: 41.917751
  • longitude: -73.096826
  • listagentfullname: Catherine McCahill
  • listagentemail: cmccahill@wpsir.com
  • listagentkey: 3yd-CTMLS-MCCAHILC
  • listagentmlsid: MCCAHILC
  • listagentpreferredphone: 8604806760
  • listagentofficephone: 8607771800
  • listofficekey: 3yd-CTMLS-PSOTH00
  • listofficemlsid: PSOTH00
  • disclaimer: Copyright © 2026 SmartMLS, 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: CTMLS
  • yearbuilt: 2000
  • listingcontractdate: 2026-09-22
  • listagenturl: http://www.williampitt.com
  • countyorparish: Litchfield
  • elementaryschool: Batcheller
  • highschool: Gilbert
  • appliances: Electric Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Instant Hot Water Tap, Washer, Dryer
  • cooling: Central Air
  • heating: Zoned, Baseboard, Other (Heating), Hot Water(Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • waterfrontyn: False
  • franchiseaffiliation: Sotheby's International Realty
  • interiorfeatures: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
  • exteriorfeatures: Porch-Screened, Underground Utilities, Shed, Barn, Deck, Gutters, Lighting, Stone Wall
  • architecturalstyle: Colonial
  • rooms: Bathroom 1, Bathroom 3, Basement, Bedroom 3, Bedroom 1, Bathroom 2, Bedroom 2, Laundry Room
  • patioandporchfeatures: Porch
  • basement: Full, Unfinished
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.096825, 41.91775
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"William Pitt Sotheby's International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"cmccahill@wpsir.com", "ListBrokerageCity":"Stamford", "ListBrokerageCountry":"US", "ListBrokerageEmail":"pbreunich@wpsir.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"William Pitt Sotheby's International Realty", "ListBrokeragePhone":null, "ListBrokeragePostalCode":"06902", "ListBrokerageStateOrProvince":"CT", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"170 Washington Blvd", "ListBrokerageWebsiteUrl":"http://www.williampitt.com", "ListOfficeAddress1":"45 E Main Street ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"PSOTH00", "ListOfficeCity":"Avon", "ListOfficeCountry":"US", "ListOfficeEmail":"aohlandt@williampitt.com", "ListOfficePostalCode":"06001", "ListOfficeStateOrProvince":"CT", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family For Sale, Colonial, Winchester, CT", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/359-Winchester-Rd_Winsted_CT_06098_M39470-38272?f=listhub&s=CTMLS&m=24208872&c=rexren", "MLSModificationTimestamp":"2026-09-24 04:05:03", "Neighborhoods":[{"Description":null, "Name":"Winsted"}], "PostalCode":null, "RoomCount":8, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":8400, "TaxDescription":null, "TaxYear":"2027"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 9/24/2026 4:09:50 AM GMT
Source Updated Date: 9/26/2026 12:50:14 AM GMT

Courtesy of: Catherine McCahill, William Pitt Sotheby's Int'l, cmccahill@wpsir.com

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.