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- Property Details
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Street View
$499,900
Monthly Est:$2,488
5 Beds
- 2 Baths
1 full bath + 1 half bath
2,040sqft
40 Oleson Dr, Southbury, CT 06488
$499,900
$2,488/moEst:
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Single Family Residence
Built in 1963
$-- HOA
2.9 acres lot
$245/sq.ft
Description
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).
- Houzeo last checked: 10 minutes ago
- Listing updated: November 5, 2026 at 8:39 pm
- Listing Provided by: Liz Newnham | William Pitt Sotheby's Int'l
- Source: SMART MLS-CT | MLS#: 24207493

Property Details
Status
Active Under Contract
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1963
HOA Fees
-
Finished Area
2,040 sqft
Lot Size
2.9 acres lot
Basement Area
- sqft
MLS Name
SMART MLS
MLS Number
24207493
MLS Status
Under Contract - Continue to Show
Days on Market
51

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Location
HOA Management
0
HOA Fees
$-/
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 2
Interior
Sewer
Septic
Heating
Oil
Exterior Features
Shed, Porch, Barn, Gutters, Stone Wall
Cooling
None
Interior Features
Auto Garage Door Opener
Appliances
Oven/range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
Construction
Year Built
Year Built: 1963
Home type
Single Family Residence
Architectural Style
Cape Cod, Other
Foundation Details
Concrete
Roof
Asphalt Shingle
Utilities & Energy
Parking Features
Tandem, Under House Garage, Driveway
Water Source
Private Well
Basement
Full, Unfinished, Storage, Garage Access, Interior Access, Concrete Floor
Laundry Features
Lower Level
Pool Features
Vinyl, In Ground Pool
Other Features
Subdivision Name
N/a
Lot Features
Secluded, Treed, Level Lot
Price History
| Date | Event | Price |
|---|---|---|
11/05/2026 Source: | Contingent (Active Under Contract) | $499,900 $245/sqft |
10/14/2026 Source: | Price Decreased | $499,900 -5.68% $245/sqft |
09/16/2026 Source: | Price Decreased | $530,000 -0.93% $260/sqft |
08/02/2026 Source: | Off Market | $535,000 -2.55% $262/sqft |
07/07/2026 Source: | Listed for Sale | $549,000 $269/sqft |
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Based on information provided to and compiled by the SMART MLS, Inc. through Nov 07, 2026, 04:45AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.
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