
Land with Home for Sale in Southbury, Connecticut
40 Oleson Dr, Southbury, CT 06488
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.
Location
- Street address
- 40 Oleson Dr
- County
- New Haven County
- Elevation
- 573 feet
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.
Property details
- Acreage
- 2.9 acres
- Zoning
- R-60
- MLS #
- CTMLS 24174641
- Posted
Property taxes
- 2026
- $5,318
Details and features
Listing
- Type
- Residential
- Franchise
- Sotheby's International Realty
Lot
- Features
- Level Lot
Exterior
- Parking Spaces
- 4
- Pool
- Porch
- Features
- Shed, Porch, Gutters, Stone Wall
Structure
- Style
- Cape Cod, Colonial
- Basement
- Full, Unfinished
- Water
- Private
Interior
- Room Count
- 9
- Rooms
- Basement, Bathroom x 2, Bedroom x 5
- Fireplaces
- Yes
- Appliances
- Dishwasher, Dryer, Oven/Range, Range Hood, Refrigerator, Washer
- Features
- Auto Garage Door Opener
Nearby schools
| Name | Type |
|---|---|
| Pomperaug | High |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| May 15, 2026 | New listing | $565,000 | — | CTMLS |






































