
Land with Home for Sale in Southbury, Connecticut
40 Oleson Dr, Southbury, CT 06488
Just minutes from Main Street, shopping, restaurants, state parks, I-84, and everyday conveniences, this 5BR home is tucked away at the end of a private road on 2.9 beautiful wooded acres. Located approximately 85 miles from NYC, the property offers privacy, and plenty of room to explore, garden, entertain, or simply enjoy the peaceful natural setting. A covered front porch welcomes you into a spacious foyer where hardwood flooring extends throughout much of the home. The sun-filled living rm features oversized windows, built-in bookshelves, and a wood stove, creating a warm and comfortable gathering space. A highlight of the floor plan is the 3BRs on the main level, including the primary bedroom, offering flexibility for single-level living, guests, a home office, or multigenerational needs. The main level also includes an eat-in kitchen with a large pantry, a dining rm, a full bath, & a bright four-season rm w/large sliders overlooking the wooded landscape. Upstairs are two additional BRs and a half bath with potential for future expansion. The unfinished basement offers workshop space, laundry & mechanical areas, a storage rm suitable for a wine or root cellar, & access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open areas for recreation, stone walls, multiple outbuildings & woodsheds. The property is being sold in its present, "as-is" condition. Significant improvements already done. New roof (2023), furnace (2023), septic tank (2026). New well pump/tank/cap (2024). New pool liner (2024). A whole-house Generac generator provides peace of mind. The property may offer subdivision potential, subject to municipal approvals. Buyers should perform their own due diligence regarding any development possibilities. Surrounded by nature, this home is ready for its next owner to make it their own.
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 private road. House is down the private road on the right. Please drive slowly.
Property details
- Acreage
- 2.9 acres
- Zoning
- R-60
- MLS #
- CTMLS 24207493
- Posted
Property taxes
- 2027
- $6,687
Details and features
Listing
- Type
- Residential
- Franchise
- Sotheby's International Realty
Lot
- Features
- Level Lot, Secluded, Treed
Exterior
- Parking Spaces
- 4
- Pool
- Porch
- Features
- Shed, Porch, Barn, Gutters, Stone Wall
Structure
- Style
- Cape Cod
- Basement
- Concrete, Full, Unfinished
- Water
- Private
Interior
- Room Count
- 8
- 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 |
|---|---|---|---|---|
| Nov 5, 2026 | Under contract | $499,900 | — | CTMLS |
| Oct 15, 2026 | Price drop | $499,900 | $30,100 -5.7% | CTMLS |
| Sept 16, 2026 | New listing | $530,000 | — | CTMLS |


































