40 Oleson Drive
Southbury, CT, 06488 $ 549,000
Bedrooms5 Baths1.1 Sq 2,040 Monthly Estimate*
$ 3,466
for $549,000 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.
Set at the end of a shared private driveway on 2.9 wooded acres, this 5BR home presents a unique opportunity for those seeking privacy, space, and the chance to create something truly their own. Surrounded by natural beauty, the property offers 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 bring in natural light. A notable advantage of the home's layout is the presence of three bedrooms on the main level, offering flexibility for single level living, guests, home office space, 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 space that may accommodate future expansion to a full bath or laundry area. Ample closet space is found throughout. The unfinished lower level provides additional flexibility with 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 abundant parking. Recent improvements include a new roof (2023), furnace (2023), well equipment (2023), gutters (2024). For added peace of mind, the home is equipped with a whole house Generac generator. Offering a rare combination of privacy, character, and potential, this Southbury property is ready for its next owner to bring their vision and personal touches. Conveniently located just minutes from Exit 15, shopping, restaurants, Main Street, nearby lakes, and the movie theater.
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FeaturesGeneralZoning R-60
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract - Continue to Show
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
DOM 42
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
- $3,466
- Monthly Property Taxes
- $443
- 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 $707,316
Percent of Sale Price 29%
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 |
|---|
| 6/4/2026 | $549,000 | -2.83% | Price Down |
| 5/11/2026 | $565,000 | | Listed Price |