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$499,900
52 Days On Site

40 Oleson Drive
Southbury, CT 06488

For Sale|Single Family Residence|Active Under Contract
5
Beds
2
Total Baths
1
Full Bath
1
Partial Bath
2,040
SqFt
$245
/SqFt
1963
Built
County:
New Haven
Listing courtesy of Liz Newnham of William Pitt Sotheby's Int'l Office Phone: (203) 796-7700 Broker Contact: (203) 994-4123

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1-860-573-4349
40 Oleson Drive40 Oleson Drive40 Oleson Drive40 Oleson Drive
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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. The property is being sold in its present, "as-is" condition. Significant improvements already done. New roof (2023), furnace (2023), septic tank (2026). New well pump/tank/cap (2024). New pool liner (2024). A whole-house Generac generator provides peace of mind. The property may offer subdivision potential, subject to municipal approvals. Buyers should perform their own due diligence regarding any development possibilities. Surrounded by nature, this home is ready for its next owner to make it their own.

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Listing Snapshot
Price 
$499,900
Days On Site 
52 Days
Bedrooms 
5
Inside Area (SqFt) 
2,040 sqft
Total Baths 
2
Full Baths 
1
Partial Baths 
1
Lot Size 
2.9 Acres
Year Built 
1963
MLS Number 
24207493
Status 
Active Under Contract
Property Tax 
$6,687
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
2 days agoListing updated with changes from the MLS
2 days agoStatus changed to Active Under Contract
3 weeks agoPrice changed to $499,900
2 months agoListing first seen on site
General Features
Acres 
2.9
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
2
Parking 
PavedGarage Door OpenerPrivateTandemDriveway
Parking Spaces 
4
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Total 
2040
Style 
Cape CodOther
Water Source 
Well
Zoning 
R-60
Interior Features
Appliances 
DishwasherDryerRangeOvenRefrigeratorWasherElectric Water HeaterRange Hood
Basement 
FullStorage SpaceUnfinishedConcrete
Fireplace 
Yes
Fireplaces 
1
Heating 
OilForced Air
Interior 
Entrance Foyer
Window Features 
Storm Window(s)
Bedroom 
Dimensions - 10.7 x 9Level - Main
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Exterior Features
Construction Details 
Wood SidingFrame
Lot Features 
LevelWooded
Other Structures 
Barn(s)Shed(s)Workshop
Patio And Porch 
Porch
Pool Features 
Outdoor PoolVinylIn Ground
Roof 
Asphalt
Windows/Doors 
Storm Window(s)
Community Features
Community Features 
GolfTennis Court(s)
Schools
School District
Unknown
Elementary School
Per Board of Ed
Middle School
Memorial Middle School
High School
Pomperaug
Listing courtesy of Liz Newnham of William Pitt Sotheby's Int'l Office Phone: (203) 796-7700 Broker Contact: (203) 994-4123



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Last checked: 2026-11-08 04:43 AM UTC.

Neighborhood & Commute
Source: Walkscore
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