About 40 Oleson Drive
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 (as is). *seller is offering with an acceptable offer up to a $10,000 seller concession towards buyer's closing costs (mortgage rate buy down & escrows)*.
Features of 40 Oleson Drive
| MLS® # | 24207493 |
|---|---|
| Price | $530,000 |
| 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
| Features | Generator, Storm Windows |
|---|---|
| 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, Concrete Floor |
Exterior
| Exterior | Wood |
|---|---|
| Exterior Features | Shed, Porch, Barn, 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 | September 16th, 2026 |
|---|---|
| Days on Market | 20 |
| Zoning | R-60 |
| RE / Bank Owned | No |
Listing Details
| Office | William Pitt Sotheby's Int'l |
|---|
