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Land with Home for Sale in Southbury, Connecticut

40 Oleson Dr, Southbury, CT 06488

$535,000
2.9 acres
Active sale
$14k drop
Est $3,177/mo

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 (2023), newer gutters, and a new septic tank and distribution box to be installed (August 2026). A whole house Generac generator provides added peace of mind. Set at the end of a shared private road on 2.9 wooded acres, this 5BR home offers privacy, space, and exceptional potential.

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 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

Open houses

DateBeginsEndsAppt neededRemarks
Aug 23, 202612:00 PM2:00 PMNo

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
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
Aug 3, 2026Price drop$535,000$14,000 -2.6%CTMLS
July 7, 2026Back on market$549,000CTMLS
June 26, 2026Under contract$549,000CTMLS
June 4, 2026Price drop$549,000$16,000 -2.8%CTMLS
May 15, 2026New listing$565,000CTMLS
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This 2.9-acre property is located at 40 Oleson Dr in Southbury, CT 06488. The property is available for sale, priced at $535,000. 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

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