
Land with Home for Sale in Southbury, Connecticut
40 Oleson Dr, Southbury, CT 06488
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.
Location
- Street address
- 40 Oleson Dr
- County
- New Haven County
- Zip code
- 06488
- 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 |
|---|---|---|---|---|
| June 26, 2026 | Under contract | $549,000 | — | CTMLS |
| June 4, 2026 | Price drop | $549,000 | $16,000 -2.8% | CTMLS |
| May 15, 2026 | New listing | $565,000 | — | CTMLS |





































