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81 Main Street
Chester CT 06412 US

$550,000

Pending Listing ID 24172804
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2 bed
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2.00 Bath (2 Full)
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Lot: 0.15 Acres
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Other

$550,000

Pending Listing ID 24172804
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81 Main Street Discover the perfect blend of mid-century character and modern efficiency in the heart of Chester Village. This impeccably maintained home offers a vibrant "walk-to-everything" lifestyle, just steps from award-winning dining, boutiques, and the theater. Officially a 2-bedroom home per town records, the layout offers incredible flexibility. The main level features a stunning den currently utilized as a primary suite. This light-filled space features a private, fully renovated ensuite full bath and a handsome armoire for storage, offering a sophisticated retreat for those seeking first-floor living. Note: This serves as the primary bath for the main level, enhancing the "suite" feel of the space. Upstairs, you will find two additional well-appointed rooms and a second fully renovated full bath, providing ample space for guests or a home office. The home's infrastructure has been flawlessly upgraded, featuring a new 50-year roof, on-demand propane heat/hot water, and an electric heat pump for heating and cooling (A/C on the first floor). The updated eat-in kitchen is a chef's delight, while the professional landscaping and beautiful stone patio create a private oasis for outdoor entertaining. Rarely does a home combine such high-end mechanical peace of mind with the undeniable charm of a downtown location. Turn-key and ready for its next chapter-experience the best of Chester right outside your front door.

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Property Features

  • Facts
  • Lot Size: 0.15 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 2
  • Cooling System: Heat Pump, Window Unit(s)
  • Exterior Finish: Gutters, Garden Area, Patio
  • Heating Fuels: Heat Pump (Heating), Other (Heating)
  • Additional Features
  • Basement
  • Patio

School Information

  • School
  • Per Board of Ed(Elementary)
  • Per Board of Ed(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 550000
  • unparsedaddress: 81 Main Street
  • postalcity: Chester
  • stateorprovince: CT
  • country: US
  • postalcode: 06412
  • bathroomsfull: 2
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.15
  • lotsizeunits: Acres
  • lotsizearea: 0.15
  • livingarea: 1128
  • livingareaunits: Square Feet
  • latitude: 41.402416
  • longitude: -72.448184
  • listagentfullname: Susan Woods
  • listagentemail: swoods@wpsir.com
  • listagentkey: 3yd-CTMLS-WOODSS
  • listagentmlsid: WOODSS
  • listagentpreferredphone: 2032158676
  • listagentofficephone: 2032456700
  • listofficekey: 3yd-CTMLS-PSOTH50
  • listofficemlsid: PSOTH50
  • 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: 1950
  • listingcontractdate: 2026-05-08
  • listagenturl: http://www.williampitt.com
  • countyorparish: Middlesex
  • elementaryschool: Per Board of Ed
  • highschool: Per Board of Ed
  • appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • cooling: Heat Pump, Window Unit(s)
  • heating: Heat Pump (Heating), Other (Heating)
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • waterfrontyn: False
  • franchiseaffiliation: Sotheby's International Realty
  • interiorfeatures: Open Floor Plan
  • exteriorfeatures: Gutters, Garden Area, Patio
  • architecturalstyle: Cape Cod
  • rooms: Bathroom 1, Bathroom 2, Bedroom 1, Bedroom 2
  • patioandporchfeatures: Patio
  • basement: Crawl Space
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -72.44818, 41.402416
  • 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":"swoods@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":"696 Boston Post Road ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"PSOTH50", "ListOfficeCity":"Madison", "ListOfficeCountry":"US", "ListOfficeEmail":"rmorrell@wpsir.com", "ListOfficePostalCode":"06443", "ListOfficeStateOrProvince":"CT", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Chester, CT", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/81-Main-St_Chester_CT_06412_M47638-46681?f=listhub&s=CTMLS&m=24172804&c=rexren", "MLSModificationTimestamp":"2026-05-16 11:54:09", "Neighborhoods":[], "PostalCode":null, "RoomCount":5, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":5503, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 5/16/2026 12:04:56 PM GMT
Source Updated Date: 6/4/2026 12:54:43 AM GMT

Courtesy of: Susan Woods, William Pitt Sotheby's Int'l, swoods@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.