About 40 Oleson Drive
Surrounded by nature, the property provides 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 fill the space with natural light. A key advantage is the three bedrooms on the main level, 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, dining room, full bath, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms and a half bath with potential for expansion. The unfinished lower level includes 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 ample parking. Major updates include a new roof (2023), furnace (2023), well equipment incl pump/tank (2023), newer gutters, and new septic tank and 2 distribution boxes (August 2026). A whole house Generac generator provides added peace of mind. Possible building lot-buyer to do their due diligence. Set at the end of a private road on 2.9 wooded acres, this 5BR home offers privacy, space, and exceptional potential.
Features of 40 Oleson Drive
| MLS® # | 24174641 |
|---|---|
| Price | $535,000 |
| Bedrooms | 5 |
| Bathrooms | 2.00 |
| Full Baths | 1 |
| Half Baths | 1 |
| Square Footage | 2,040 |
| Acres | 2.90 |
| Type | Single Family For Sale |
| Style | Cape Cod, Other |
| Status | Active |
Community Information
| Address | 40 Oleson Drive |
|---|---|
| Area | N/A |
| City | Southbury |
| County | New Haven |
| State | Connecticut |
| Zip Code | 06488 |
Amenities
| Parking Spaces | 4 |
|---|---|
| Parking | Tandem, Under House Garage, Driveway |
| # of Garages | 2 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | Yes |
| Pool | Vinyl, In Ground Pool |
Interior
| Interior Features | Auto Garage Door Opener |
|---|---|
| Appliances | Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer |
| Heating | Hot Air, Oil |
| Cooling | None |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Has Basement | Yes |
| Basement | Full, Unfinished, Storage, Garage Access, Interior Access |
Exterior
| Exterior | Wood |
|---|---|
| Exterior Features | Shed, Porch, Gutters, Stone Wall |
| Lot Description | Secluded, Treed, Level Lot |
| Roof | Asphalt Shingle |
| Foundation | Concrete |
School Information
| Elementary | Per Board of Ed |
|---|---|
| Middle | Memorial Middle School |
| High | Pomperaug |
Additional Information
| Date Listed | May 11th, 2026 |
|---|---|
| Days on Market | 117 |
| Zoning | R-60 |
| RE / Bank Owned | No |
Listing Details
| Office | William Pitt Sotheby's Int'l |
|---|
