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40 Oleson Drive
Southbury CT 06488 US

$535,000

Active Listing ID 24174641
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5 bed
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2,040 square feet
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2.00 Bath (1 Full , 1 Half)
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Lot: 2.90 Acres
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Other

$535,000

Active Listing ID 24174641
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40 Oleson Drive Surrounded by nature, the property provides room to explore, garden, entertain, or simply enjoy a peaceful setting while remaining close to everyday conveniences. A covered porch welcomes you inside where hardwood flooring runs through much of the home. The living room features built in bookshelves, a wood stove, and large windows that fill the space with natural light. A key advantage is the three bedrooms on the main level, offering flexibility for single level living, guests, a home office, or multigenerational needs. The main level also includes an eat in kitchen with a large pantry, dining room, full bath, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms and a half bath with potential for expansion. The unfinished lower level includes workshop space, laundry and mechanical areas, a storage room suitable for a wine or root cellar, and a two car tandem garage. Outside you'll find an inground pool with a new liner (2024), multiple outbuildings and wood sheds (conveyed as is), and ample parking. Major updates include a new roof (2023), furnace (2023), well equipment incl pump/tank (2023), newer gutters, and new septic tank and 2 distribution boxes (August 2026). A whole house Generac generator provides added peace of mind. Possible building lot-buyer to do their due diligence. Set at the end of a private road on 2.9 wooded acres, this 5BR home offers privacy, space, and exceptional potential.

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Property Features

  • Facts
  • Lot Size: 2.90 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 1
  • 1/2 Bathrooms: 1
  • Exterior Finish: Shed, Porch, Gutters, Stone Wall
  • Additional Features
  • Basement
  • Fireplace
  • Patio

School Information

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

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 535000
  • unparsedaddress: 40 Oleson Drive
  • postalcity: Southbury
  • stateorprovince: CT
  • country: US
  • postalcode: 06488
  • bathroomsfull: 1
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 2.9
  • lotsizeunits: Acres
  • lotsizearea: 2.9
  • livingarea: 2040
  • livingareaunits: Square Feet
  • latitude: 41.475578
  • longitude: -73.184507
  • listagentfullname: Liz Newnham
  • listagentemail: lnewnham@wpsir.com
  • listagentkey: 3yd-CTMLS-7758
  • listagentmlsid: 7758
  • listagentpreferredphone: 2039944123
  • listagentofficephone: 2037967700
  • listofficekey: 3yd-CTMLS-PSOTH120
  • listofficemlsid: PSOTH120
  • 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: 1963
  • listingcontractdate: 2026-05-11
  • listagenturl: http://www.williampitt.com
  • countyorparish: New Haven
  • elementaryschool: Per Board of Ed
  • highschool: Pomperaug
  • appliances: Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 4
  • waterfrontyn: False
  • franchiseaffiliation: Sotheby's International Realty
  • interiorfeatures: Auto Garage Door Opener
  • exteriorfeatures: Shed, Porch, Gutters, Stone Wall
  • architecturalstyle: Cape Cod, Other
  • rooms: Bedroom 5, Bedroom 1, Basement, Bathroom 1, Bedroom 4, Bedroom 2, Bathroom 2, Bedroom 3
  • patioandporchfeatures: Porch
  • basement: Unfinished, Full
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.18451, 41.47558
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-CTMLS-24174641", "OpenHouseEndTime": "2026-09-12 13:00:00", "OpenHouseId": "9661803", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-09-12 11:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • 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":"lnewnham@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":"67 Federal Road, Suite 103 ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"PSOTH120", "ListOfficeCity":"Brookfield", "ListOfficeCountry":"US", "ListOfficeEmail":"aunger@wpsir.com", "ListOfficePostalCode":"06804", "ListOfficeStateOrProvince":"CT", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family For Sale, Cape Cod, Other, Southbury, CT", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/40-Oleson-Dr_Southbury_CT_06488_M35651-69267?f=listhub&s=CTMLS&m=24174641&c=rexren", "MLSModificationTimestamp":"2026-09-10 21:41:02", "Neighborhoods":[], "PostalCode":null, "RoomCount":9, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":6687, "TaxDescription":null, "TaxYear":"2027"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 9/12/2026 4:09:22 PM GMT
Source Updated Date: 9/13/2026 12:45:22 AM GMT

Courtesy of: Liz Newnham, William Pitt Sotheby's Int'l, lnewnham@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.