Recently Listed Open House 10/3 12pm - 2pm
40 Oleson Drive
Southbury, CT, 06488 $ 530,000
Bedrooms5 Baths1.1 Sq 2,040 Monthly Estimate*
$ 3,346
for $530,000 with 5 bedrooms and 1 full bath, 1 half bath. This 2,040 square foot home was built in 1963 on a lot size of 2.9.
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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Open House
10/3/2026 12:00 PM - 2:00 PM
40 Oleson Drive Southbury, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesGeneralZoning R-60
Neighborhood N/A
County New Haven
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 2.9
Directions GPS Friendly. Route 67 to Painter Road to Oleson Drive. Oleson Drive is a private road. House is down the private road on the right. Please drive slowly.
High School Pomperaug
City Southbury
Elementary School Per Board of Ed
Sq Ft Total 2040
DOM 14
Year Built 1963
Exclusions As Per Inclusion/Exclusion Rider
Style Cape Cod Other
Year Built Source Public Records
Pool Description Vinyl In Ground Pool
Energy Features Generator Storm Windows
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InteriorCooling System None
Total Rooms 8
Basement Description Full Unfinished Storage Garage Access Interior Access Concrete Floor
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ExteriorWater Source Private Well
Lot Description Secluded Treed Level Lot
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* Excluded FeaturesList ByWilliam Pitt Sotheby's Int'lBroker
Affordability Calculator
- Monthly Principal & Interest
- $3,346
- Monthly Property Taxes
- $557
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Southbury, CT
Average List Price $777,548
Percent of Sale Price 47%
About Southbury, CT 19,982 Population
8% Since 2002
$ 84,270 Median Income
52.98 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
3042222 Elementary School
3042695 Middle School
Pomperaug High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 9/16/2026 | $530,000 | | Listed Price |