Skip to main contentSkip to navigation
1 / 39

Land with Home for Sale in Southbury, Connecticut

40 Oleson Dr, Southbury, CT 06488

$565,000
2.9 acres
Active sale
ago
Est $3,153/mo

Tucked away at the end of a shared private driveway, this 5BR home sits on 2.9 private wooded acres offering a peaceful setting with room to explore and enjoy the outdoors. A covered front 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, creating a warm and inviting gathering area. The main level includes an eat in kitchen with a large pantry, a dining room, a full bath, three bedrooms, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms along with a half bath offering potential for expansion into a full bath or laundry area. There is ample closet space throughout. The unfinished lower level includes a workshop area, laundry and mechanical space, a storage area that could also serve as a potential wine or root cellar and a two-car tandem garage. Outside, the level property features an inground pool with a new liner (2024), multiple outbuildings, and wood sheds. Recent improvements include a new roof (2023), furnace (2023), well equipment (2023), gutters (2024), and interior paint (2025). A whole house Generac generator provides added peace of mind. This wonderful property, offering privacy and natural surroundings, is ready for its next owner to bring their vision and personal touches.

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

Location

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

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

NameType
PomperaugHigh

Listing history

DateEventPriceChangeSource
May 15, 2026New listing$565,000CTMLS
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 for $565,000. It has a 2,040 sq ft 5 bedroom, 1 bath house built in 1963.

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

Checked 2 hours 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