40 Oleson Drive Southbury, CT $ 535,000
40 Oleson Drive
$ 535,000
Open House 8/15 1pm - 3pm
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40 Oleson Drive

Southbury, CT, 06488
$ 535,000
Bedrooms5 Baths1.1 Sq 2,040

Monthly Estimate*

$ 3,378

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Single Family Home for sale in Southbury, CT

for $535,000 with 5 bedrooms and 1 full bath, 1 half bath. This 2,040 square foot home was built in 1963 on a lot size of 2.9.

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. Major updates have already been completed, including a new roof (2023) with a transferable warranty, furnace (2023), well equipment (2023), and newer gutters. A new septic tank and distribution box will be installed in August 2026. The home also features a whole-house Generac generator. For added peace of mind, the home is equipped with a whole house Generac generator. Offering a rare combination of privacy, character, and potential, this Southbury property is ready for its next owner to bring their vision and personal touches. Conveniently located just minutes from Exit 15, shopping, restaurants, Main Street, nearby lakes, and the movie theater.

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Open House

8/15/2026 1:00 PM - 3:00 PM
40 Oleson Drive Southbury, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 535,000

Bedrooms

5

Full Bath

1

Half Bath

1

Property Type

Single Family

Taxes

$ 5,318

Style

Lot Size

2.9

Year Built

1963

Town/City

Southbury

MLS | Web ID

24174641

Features
General
Zoning R-60
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.9
Directions GPS Friendly. Route 67 to Painter Road to Oleson Drive. Oleson Drive is a shared private road/driveway. House is down the driveway on the right. Please drive slowly and do not block shared driveway.
High School Pomperaug
City Southbury
Elementary School Per Board of Ed
Sq Ft Total 2040
DOM 90
Year Built 1963
Exclusions As Per Inclusion/Exclusion Rider
Style Cape Cod Colonial
Year Built Source Public Records
Pool Description Vinyl In Ground Pool
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Interior
Cooling System None
Total Rooms 9
Basement Description Full Unfinished Storage Garage Access Interior Access
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Exterior
Water Source Private Well
Lot Description Level Lot
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* Excluded Features
List By
Liz Newnham

Listing Agent

William Pitt Sotheby's Int'l

Broker

lnewnham@wpsir.com

Email

Affordability Calculator

$3,821
Per Month
88%
12%
0%
Monthly Principal & Interest
$3,378
Monthly Property Taxes
$443
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3042222 Elementary School
3042695 Middle School
Pomperaug High School High School
Pricing History
DatePricePrice ChangeDescription
8/2/2026$535,000 -2.55% Price Down
6/4/2026$549,000 -2.83% Price Down
5/11/2026$565,000 Listed Price

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40 Oleson Drive, Southbury, CT, 06488 is a Single Family Home for sale at $535,000 with 2,040 sqft and a lot size of 2.9. 40 Oleson Drive has 5 bedrooms, 1.1 baths, and was built in 1963. The property's zip code is 06488 which is in Southbury, CT