40 Oleson Drive, Southbury, Connecticut

$530,000

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5

Beds

2

Baths

2,040

Square feet

2.90

Acres

About 40 Oleson Drive

Just minutes from Main Street, shopping, restaurants, state parks, I-84, and everyday conveniences, this 5BR home is tucked away at the end of a private road on 2.9 beautiful wooded acres. Located approximately 85 miles from NYC, the property offers privacy, and plenty of room to explore, garden, entertain, or simply enjoy the peaceful natural setting. A covered front porch welcomes you into a spacious foyer where hardwood flooring extends throughout much of the home. The sun-filled living rm features oversized windows, built-in bookshelves, and a wood stove, creating a warm and comfortable gathering space. A highlight of the floor plan is the 3BRs on the main level, including the primary bedroom, 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, a dining rm, a full bath, & a bright four-season rm w/large sliders overlooking the wooded landscape. Upstairs are two additional BRs and a half bath with potential for future expansion. The unfinished basement offers workshop space, laundry & mechanical areas, a storage rm suitable for a wine or root cellar, & access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open areas for recreation, stone walls, multiple outbuildings & woodsheds (as is). *seller is offering with an acceptable offer up to a $10,000 seller concession towards buyer's closing costs (mortgage rate buy down & escrows)*.

Features of 40 Oleson Drive

MLS® # 24207493
Price $530,000
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

Features Generator, Storm Windows
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, Concrete Floor

Exterior

Exterior Wood
Exterior Features Shed, Porch, Barn, 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 September 16th, 2026
Days on Market 20
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 October 7th, 2026 at 12:29am EDT.