Back 40 Oleson Drive
Active

40 Oleson Drive

Southbury CT 06488

5
2
4
2040 sq. ft.
2.9 ac.
Single-Family
Currently for sale - view listing

Overview

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.

Features

5 bedrooms
2 bathrooms
4 carspaces
2 garage spaces
2040 sq. ft. floor area
2.9 ac. lot size
Single-Family

Happy sellers in Southbury

88%
88% of sellers in Southbury reported that their sale price either exceeded or met their price expectations.

Southbury stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 10 reviews in Southbury over the last 12 months.

Local market activity for 5 bedroom single-family properties in Southbury

In the last 12 months, 15 five-bedroom single-family properties similar to 40 Oleson Drive, have been sold.

This represents a 16% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

© 2026 RateMyAgent