40 Oleson Drive
Southbury, Connecticut 06488
Reduced from $565,000
- Beds
- 5
- Baths
- 1 | 1
- SqFt
- 2,040
- Acres
- 2.90
- Year Built
- 1963
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Set at the end of a shared private driveway on 2.9 wooded acres, this 5BR home presents a unique opportunity for those seeking privacy, space, and the chance to create something truly their own. Surrounded by natural beauty, the property offers 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 bring in natural light. A notable advantage of the home's layout is the presence of three bedrooms on the main level, offering flexibility for single level living, guests, home office space, 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 space that may accommodate future expansion to a full bath or laundry area. Ample closet space is found throughout. The unfinished lower level provides additional flexibility with 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 abundant parking.
Key Facts
- City/Town
- Southbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod,Colonial
- Year Built
- 1963
- Days on Market
- 77 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
- $5,318 / Annually
Market Snapshot
The Southbury Market
Single Family · trailing 12 months
Active Listings
34
35 under contract
Median List Price
$632,450
34 active listings
Median Closed Price
$632,500
164 sales
Median Days on Market
31
34 active listings
Median $ / Sq Ft
$287
34 active listings
Sale-to-List Ratio
100.0%
164 sales
How this home compares
List Price
$549,000
vs $632,450 median
13.2% below median
Price / Sq Ft
$269
vs $287 median
6.3% below median
Days on Market
77 days
vs 31 days median
46 days longer than median
Based on 34 active and 164 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of July 28, 2026.
Location
40 Oleson Drive, Southbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,799
- Property Taxes$443
- Insurance$183
- 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,Colonial
- 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 GarageDrivewayPrivateSharedPaved
- 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
- Level Lot
Listing & Financials
- Property Taxes
- $5,318 / Annually
- Days on Market
- 77
- MLS #
- 24174641
- 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 7/28/2026. 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 7/28/2026 at 5:25 AM UTC.