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40 Oleson Drive

Southbury, Connecticut 06488

ACTIVE$499,900

Reduced from $530,000

Beds
5
Baths
1 | 1
SqFt
2,040
Acres
2.90
Year Built
1963
Matt Caiola

Matt Caiola

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Pool2-Car Garage1 FireplacePrice Reduced

About This Home

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).

Key Facts

City/Town
Southbury
Neighborhood
N/A
Property / Style
Single Family · Cape Cod,Other
Year Built
1963
Days on Market
49 days
Beds
5
Baths
1 full · 1 half
Living Area
2,040 sq ft
Lot Size
2.90 acres
Garage / Parking
2 garage · 4 total
Property Taxes
$6,687 / Annually

Market Snapshot

The Southbury Market

Single Family · trailing 12 months

Median Days on Market

53

48 active listings

Median $ / Sq Ft

$290

48 active listings

Sale-to-List Ratio

100.0%

162 sales

How this home compares

List Price

$499,900

vs $799,000 median

37.4% below median

Price / Sq Ft

$245

vs $290 median

15.5% below median

Days on Market

49 days

vs 53 days median

4 days fresher than median

Based on 48 active and 162 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of November 4, 2026.

Location

40 Oleson Drive, Southbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,449

per month

  • Principal & Interest$2,725
  • Property Taxes$557
  • Insurance$167
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Southbury
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Cape Cod,Other
Year Built
1963
New Construction
No/Resale
Living Area
2,040 sq ft

Schools

Elementary
Per Board of Ed
Middle
Regional District 15
High
Pomperaug

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
None
Fireplaces
1
Laundry
Lower Level
Appliances
Oven/RangeRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullUnfinishedStorageGarage AccessInterior AccessConcrete Floor
In-Law Apartment
No
Interior Features
Auto Garage Door Opener
Additional Rooms
FoyerWorkshop

Exterior & Lot

Lot Size
2.90 acres
Zoning
R-60
Garage / Parking
2 garage spaces4 total parking spacesTandemUnder House GarageDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Pool
VinylIn Ground Pool
Construction
Wood
Color
Green
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedPorchBarnGuttersStone Wall
Lot Description
SecludedTreedLevel Lot

Listing & Financials

Property Taxes
$6,687 / Annually
Days on Market
49
MLS #
24207493
MLS Status
Active

Similar Properties

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Listed By

Liz Newnham

(203) 994-4123

William Pitt Sotheby's Int'l

(203) 796-7700

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 11/4/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 11/4/2026 at 2:30 AM UTC.