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MLS 24207493 For Sale Open House Updated September 20, 2026
Open House An open house is scheduled — contact us for times.
40 Oleson Drive

Southbury, Connecticut 06488

$530,000
On market 3 days
40 Oleson Drive
1 / 35

About This Property

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 New York City, 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 three bedrooms 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, and a bright four-season room with large sliders overlooking the wooded landscape. Upstairs are two additional bedrooms and a half bath with potential for future expansion. The unfinished lower level offers workshop space, laundry & mechanical areas, a storage rm suitable for a wine or root cellar, and access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open areas for recreation, scenic stone walls, multiple outbuildings & woodsheds (conveyed as is), and ample parking. Significant improvements completed 2023-2026. See remarks addendum.

Property Details

Interior

Heat
Hot Air — Oil
Cooling
None
Fireplaces
1
Basement
Full,Unfinished,Storage,Garage Access,Interior Access,Concrete Floor
In-Law Apartment
No
Interior Features
Auto Garage Door Opener

Exterior & Lot

Roof
Asphalt Shingle
Construction
Construction
Pool
Vinyl,In Ground Pool
Exterior Features
Shed Porch Barn Gutters Stone Wall
Lot Description
Secluded Treed Level Lot
Garage & Parking
Tandem Under House Garage Driveway

Utilities & Systems

Water Source
Private Well
Sewer
Septic
Energy Features
Generator Storm Windows

Community & Schools

Elementary
Per Board of Ed
Middle
Memorial Middle School
High
Pomperaug
Nearby Amenities
Basketball Court Golf Course Health Club Lake Library Medical Facilities Park Tennis Courts

Appliances

Included
Oven/Range Range Hood Refrigerator Dishwasher Washer Dryer

40 Oleson Drive

Southbury , Connecticut 06488

$530,000

On market 3 days

Beds
5
Baths
2
SqFt
2,040
Type
Single Family
County New Haven
Garage 2
Rooms -
Lot Size 2.90 Acres
Property Tax $6,687
Assessed Value $263,270
Year Built 1963
Style Cape Cod,Other
Zoning R-60
Parking Spaces 4

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
Open the full mortgage calculator →

Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: PSOTH120.

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