40 Oleson Drive, Southbury, Connecticut

$535,000

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5

Beds

2

Baths

2,040

Square feet

2.90

Acres

About 40 Oleson Drive

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 incl pump/tank (2023), newer gutters, and new septic tank and 2 distribution boxes (August 2026). A whole house Generac generator provides added peace of mind. Possible building lot-buyer to do their due diligence. Set at the end of a private road on 2.9 wooded acres, this 5BR home offers privacy, space, and exceptional potential.

Features of 40 Oleson Drive

MLS® # 24174641
Price $535,000
Bedrooms 5
Bathrooms 2.00
Full Baths 1
Half Baths 1
Square Footage 2,040
Acres 2.90
Type Single Family For Sale
Style Cape Cod, Other
Status Active

Community Information

Address 40 Oleson Drive
Area N/A
City Southbury
County New Haven
State Connecticut
Zip Code 06488

Amenities

Parking Spaces 4
Parking Tandem, Under House Garage, Driveway
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool Yes
Pool Vinyl, In Ground Pool

Interior

Interior Features Auto Garage Door Opener
Appliances Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Air, Oil
Cooling None
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Unfinished, Storage, Garage Access, Interior Access

Exterior

Exterior Wood
Exterior Features Shed, Porch, Gutters, Stone Wall
Lot Description Secluded, Treed, Level Lot
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Per Board of Ed
Middle Memorial Middle School
High Pomperaug

Additional Information

Date Listed May 11th, 2026
Days on Market 117
Zoning R-60
RE / Bank Owned No

Listing Details

OfficeWilliam Pitt Sotheby's Int'l

Listing Map

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Listing information last updated on September 10th, 2026 at 9:27am EDT.