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40 Oleson Drive

Southbury, Connecticut 06488

ACTIVE$535,000

Reduced from $565,000

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

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.

Key Facts

City/Town
Southbury
Neighborhood
N/A
Property / Style
Single Family · Cape Cod,Other
Year Built
1963
Days on Market
127 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

39

46 active listings

Median $ / Sq Ft

$276

46 active listings

Sale-to-List Ratio

100.0%

172 sales

How this home compares

List Price

$535,000

vs $739,400 median

27.6% below median

Price / Sq Ft

$262

vs $276 median

5.1% below median

Days on Market

127 days

vs 39 days median

88 days longer than median

Based on 46 active and 172 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of September 16, 2026.

Location

40 Oleson Drive, Southbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,514

per month

  • Principal & Interest$2,779
  • Property Taxes$557
  • Insurance$178
  • 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 Access
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
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedPorchGuttersStone Wall
Lot Description
SecludedTreedLevel Lot

Listing & Financials

Property Taxes
$6,687 / Annually
Days on Market
127
MLS #
24174641
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 9/16/2026. 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 9/16/2026 at 9:40 PM UTC.