Skip to main contentSkip to navigation
1 / 35

Land with Home for Sale in Southbury, Connecticut

40 Oleson Dr, Southbury, CT 06488

$530,000
2.9 acres
Active sale
ago
Est $3,265/mo

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 New York City, 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 three bedrooms 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, and a bright four-season room with large sliders overlooking the wooded landscape. Upstairs are two additional bedrooms and a half bath with potential for future expansion. The unfinished lower level offers workshop space, laundry & mechanical areas, a storage rm suitable for a wine or root cellar, and access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open areas for recreation, scenic stone walls, multiple outbuildings & woodsheds (conveyed as is), and ample parking. Significant improvements completed 2023-2026. See remarks addendum. Improvements include a new roof (2023), furnace (2023), well pump, tank, and cap (2024), pool liner, pump, and filter (2024), and a new septic tank with two distribution boxes (2026). A whole-house Generac generator and newer gutters provide additional 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.

2,040
Sq feet
5
Beds
1
Full bath
1
1/2 bath
1963
Built

Location

Street address
40 Oleson Dr
Zip code
06488
Elevation
573 feet
Coordinates
41.4756, -73.1845

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

Open houses

DateBeginsEndsAppt neededRemarks
Sept 27, 202612:00 PM2:00 PMNo

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

NameType
PomperaugHigh

Listing history

DateEventPriceChangeSource
Sept 16, 2026New listing$530,000CTMLS
Subscribe to listing updates

Payment calculator

This 2.9-acre property is located at 40 Oleson Dr in Southbury, CT 06488. The property is available for sale, priced at $530,000. It has a 2,040 square foot 5-bedroom, 1.5-bath house built in 1963.

Listed by William Pitt Sotheby's Int'l, (203) 796-7700

Checked 1 hour agoUpdated Source

Report listing issue

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Contact listing agent Rules
By submitting, I agree to the terms of use and to be contacted by real estate professionals. Message and data rates may apply.
Contact