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40 Oleson Drive
Southbury CT 06488 US

$530,000

Active Listing ID 24207493
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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

$530,000

Active Listing ID 24207493
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40 Oleson Drive Just minutes from Main Street, shopping, restaurants, state parks, I-84, and everyday conveniences, this 5BR home is tucked away at the end of a private road on 2.9 beautiful wooded acres. Located approximately 85 miles from New York City, the property offers privacy, and plenty of room to explore, garden, entertain, or simply enjoy the peaceful natural setting. A covered front porch welcomes you into a spacious foyer where hardwood flooring extends throughout much of the home. The sun-filled living rm features oversized windows, built-in bookshelves, and a wood stove, creating a warm and comfortable gathering space. A highlight of the floor plan is the three bedrooms on the main level, including the primary bedroom, 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, a dining rm, a full bath, and a bright four-season room with large sliders overlooking the wooded landscape. Upstairs are two additional bedrooms and a half bath with potential for future expansion. The unfinished lower level offers workshop space, laundry & mechanical areas, a storage rm suitable for a wine or root cellar, and access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open areas for recreation, scenic stone walls, multiple outbuildings & woodsheds (conveyed as is), and ample parking. Significant improvements completed 2023-2026. See remarks addendum. Improvements include a new roof (2023), furnace (2023), well pump, tank, and cap (2024), pool liner, pump, and filter (2024), and a new septic tank with two distribution boxes (2026). A whole-house Generac generator and newer gutters provide additional peace of mind. The property may offer subdivision potential, subject to municipal approvals. Buyers should perform their own due diligence regarding any development possibilities. Surrounded by nature, this home is ready for its next owner to make it their own.

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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, Barn, Gutters, Stone Wall
  • Additional Features
  • Basement
  • Fireplace
  • Patio

School Information

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

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 530000
  • 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: 2026-09-16
  • 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, Barn, Gutters, Stone Wall
  • architecturalstyle: Other, Cape Cod
  • rooms: Bedroom 1, Basement, Bedroom 5, Bedroom 4, Bedroom 3, Bathroom 2, Bedroom 2, Bathroom 1
  • patioandporchfeatures: Porch
  • basement: Full, Unfinished, Concrete
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.18451, 41.47558
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-CTMLS-24207493", "OpenHouseEndTime": "2026-09-19 13:00:00", "OpenHouseId": "10077525", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-09-19 11:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
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Listing Changed: 9/19/2026 11:07:40 PM GMT
Source Updated Date: 9/22/2026 12:44:47 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.