40 Oleson Drive
Southbury, Connecticut 06488
- Beds
- 5
- Baths
- 1 | 1
- SqFt
- 2,040
- Acres
- 2.90
- Year Built
- 1963
- Property Type
- Single Family

Matt Caiola
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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 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.
Key Facts
- City/Town
- Southbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod,Other
- Year Built
- 1963
- Days on Market
- 0 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
Active Listings
46
25 under contract
Median List Price
$739,400
46 active listings
Median Closed Price
$623,500
172 sales
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
$530,000
vs $739,400 median
28.3% below median
Price / Sq Ft
$260
vs $276 median
5.8% below median
Days on Market
0 days
vs 39 days median
39 days fresher 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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$2,753
- Property Taxes$557
- Insurance$177
- 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
- 0
- MLS #
- 24207493
- MLS Status
- Active
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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 9:30 PM UTC.