Open House 5/16 11am - 2pm
40 Oleson Drive
Southbury, CT, 06488 $ 565,000
Bedrooms5 Baths1.1 Sq 2,040 Monthly Estimate*
$ 3,479
for $565,000 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.
Tucked away at the end of a shared private driveway, this 5BR home sits on 2.9 private wooded acres offering a peaceful setting with room to explore and enjoy the outdoors. A covered front 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, creating a warm and inviting gathering area. The main level includes an eat in kitchen with a large pantry, a dining room, a full bath, three bedrooms, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms along with a half bath offering potential for expansion into a full bath or laundry area. There is ample closet space throughout. The unfinished lower level includes a workshop area, laundry and mechanical space, a storage area that could also serve as a potential wine or root cellar and a two-car tandem garage. Outside, the level property features an inground pool with a new liner (2024), multiple outbuildings, and wood sheds. Recent improvements include a new roof (2023), furnace (2023), well equipment (2023), gutters (2024), and interior paint (2025). A whole house Generac generator provides added peace of mind. This wonderful property, offering privacy and natural surroundings, is ready for its next owner to bring their vision and personal touches. Enjoy a peaceful Southbury setting just minutes from Exit 15, shopping, restaurants, Main Street, nearby lakes, and the movie theater.
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Open House
5/16/2026 11:00 AM - 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
Single Family Coming Soon
FeaturesGeneralZoning R-60
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 2.9
Directions GPS Friendly. Route 67 to Painter Road to Oleson Drive. Oleson Drive is a shared private road/driveway. House is down the driveway on the right. Please drive slowly and do not block shared driveway.
High School Pomperaug
City Southbury
Elementary School Per Board of Ed
Sq Ft Total 2040
Year Built 1963
Exclusions As Per Inclusion/Exclusion Rider
Style Cape Cod Colonial
Year Built Source Public Records
Pool Description Vinyl In Ground Pool
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InteriorCooling System None
Total Rooms 9
Basement Description Full Unfinished Storage Garage Access Interior Access
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ExteriorWater Source Private Well
Lot Description Level Lot
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* Excluded FeaturesList ByWilliam Pitt Sotheby's Int'lBroker
Affordability Calculator
- Monthly Principal & Interest
- $3,479
- Monthly Property Taxes
- $443
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% 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 $861,172
Percent of Sale Price 52%
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 |
|---|
| 5/11/2026 | $565,000 | | Listed Price |