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Land with Home for Sale in Southbury, Connecticut

40 Oleson Dr, Southbury, CT 06488

$549,000
2.9 acres
Pending sale
Under contract

Set at the end of a shared private driveway on 2.9 wooded acres, this 5BR home presents a unique opportunity for those seeking privacy, space, and the chance to create something truly their own. Surrounded by natural beauty, the property offers 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 bring in natural light. A notable advantage of the home's layout is the presence of three bedrooms on the main level, offering flexibility for single level living, guests, home office space, 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 space that may accommodate future expansion to a full bath or laundry area. Ample closet space is found throughout. The unfinished lower level provides additional flexibility with 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 abundant parking.

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

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
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 pending sale. 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 2 hours agoUpdated Source

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