Price Reduced 2.83%

$549,000 ($269.12 per sqft)

Est. Mortgage $2,669/mo *

Quick Pre-Approval

Listing courtesy of Liz Newnham (203) 994-4123, William Pitt Sotheby's Int'l (203) 796-7700


Open House Schedule

07/12/2026
12:00 PM to 2:00 PM
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Price History

$565,000
5/11/2026

$549,000
6/4/2026


40 Oleson Drive, Southbury, CT, 06488

40 Oleson Drive, Southbury, CT, 06488

9 rooms

5 beds

1 Full / 1 Half baths

1963

Cape Cod, Colonial

2,040 sqft

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. Recent improvements include a new roof (2023), furnace (2023), well equipment (2023), gutters (2024). For added peace of mind, the home is equipped with a whole house Generac generator. Offering a rare combination of privacy, character, and potential, this Southbury property is ready for its next owner to bring their vision and personal touches. Conveniently located just minutes from Exit 15, shopping, restaurants, Main Street, nearby lakes, and the movie theater.


Status:

Active

Type:

Single-family residential

Laundry Remarks:

Lower Level

Zoning:

R-60

Garage:

2-car Tandem, Under House Garage, Driveway

Heating:

Hot Air

Cooling:

None

Basement:

Full, Unfinished, Storage, Garage Access, Interior Access

Parking:

4-car

Acreage:

2.9

Est. Taxes:

$5,318

Assessment

$219,740

Lot Description:

Level Lot

Elementary School:

Per Board of Ed

Middle School:

Regional District 15

High School:

Pomperaug

Days on Market:

54

Appliances:

Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Pool:

Vinyl, In Ground Pool

MLS #:

24174641


Community Info

School Info

Walk Score

Mass Transit

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