Date
Details
Price
Change
Source
5/15/2026
Listed
$565,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$565,000 Just Listed
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Property Description
Tucked away at the end of a shared private driveway, this 5BR home sits on 2.9 private wooded acres offering a peaceful setting with room to explore and enjoy the outdoors. A covered front 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, creating a warm and inviting gathering area. The main level includes an eat in kitchen with a large pantry, a dining room, a full bath, three bedrooms, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms along with a half bath offering potential for expansion into a full bath or laundry area. There is ample closet space throughout. The unfinished lower level includes a workshop area, laundry and mechanical space, a storage area that could also serve as a potential wine or root cellar and a two-car tandem garage. Outside, the level property features an inground pool with a new liner (2024), multiple outbuildings, and wood sheds. Recent improvements include a new roof (2023), furnace (2023), well equipment (2023), gutters (2024), and interior paint (2025). A whole house Generac generator provides added peace of mind. This wonderful property, offering privacy and natural surroundings, is ready for its next owner to bring their vision and personal touches.
Full Property Details
Full Property Details for 40 Oleson Dr
General
- Price: $565,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24174641
- Updated: Today (5/15/2026)
- Added to Site: Today
Interior
- Number of Rooms: 9
- Rooms/Areas: Foyer, Workshop
- Interior Features: Auto Garage Door Opener
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 1
- Half Bathrooms: 1
- Full Bath: Main
- Partial Bath: Upper
Bedrooms
- Total Bedrooms: 5
- Primary Bedroom: Primary Bedroom - Bay/Bow Window, Hardwood Floor, 16.6 x 12, Main
- Bedroom 1: Bedroom - Hardwood Floor, 10.7 x 9, Main
- Bedroom 2: Bedroom - Hardwood Floor, 13.7 x 11, Main
- Bedroom 3: Bedroom - Walk-In Closet, Hardwood Floor, 11.3 x 8.5, Upper
- Bedroom 4: Bedroom - Hardwood Floor, 15.2 x 9, Upper
Other Rooms
- Living Room: Living Room - Beams, Book Shelves, Fireplace, Wood Stove, Hardwood Floor, 16 x 15.5, Main
- Eat In Kitchen: Eat-In Kitchen - Bay/Bow Window, Eating Space, Pantry, 14 x 10.8, Main
- Dining Room: Dining Room - Built-Ins, Hardwood Floor, 11.5 x 9, Main
- Laundry: Lower Level
Additional Information
- Pool: Yes
- Pool Description: Vinyl, In Ground Pool
Exterior
- Exterior Features: Shed, Porch, Gutters, Stone Wall
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 4
- Parking: Tandem, Under House Garage, Driveway
Location
- County: New Haven
- Driving 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.
School Information
- Elementary School: Per Board of Ed
- Middle School: Memorial Middle School
- Intermediate School: Regional District 15
- High School: Pomperaug
Heating & Cooling
- Cooling Type: None
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Electric, 50 Gallon Tank, Upright Tank
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Cape Cod, Colonial
- Construction Status: No/Resale
- Exterior Const.: Wood
- Basement Desc.: Full, Unfinished, Storage, Garage Access, Interior Access
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 2,040
- Above Ground: 2,040 Sq. Ft.
- Year Built: 1963
Lot Features
- Lot Size (Acres): 2.9
- Driveway/Sidewalk: Private, Shared, Paved
- Zoning: R-60
- Lot Description: Level Lot
Financial Considerations
- Assessment Amount: $219,740
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Exclusions: As Per Inclusion/Exclusion Rider
- Property ID: 1331688
Listed by William Pitt Sotheby's Int'l, Liz Newnham
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 40 Oleson Dr —
Liz Newnham
William Pitt Sotheby's Int'l
Agent Contact: (203) 994-4123 Office Contact: (203) 796-7700
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 40 Oleson Dr
School District:Regional School District 15
| Name | Grades | Distance |
|---|---|---|
Long Meadow Elementary School 65 North Benson Road, Middlebury, CT 06762 | PK-5 | 2.6 mi |
Memorial Middle School, Middlebury, CT 1 Memorial Drive, Middlebury, CT 06762 | 6-8 | 6.7 mi |
Pomperaug Regional High School 234 Judd Road, Southbury, CT 06488 | 9-12 | 2.2 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 40 Oleson Dr
Tax History
Tax History for 40 Oleson Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,318
3%
$219,740
—
2023
$5,186
5%
$219,740
—
2023
$4,944
-13%
$219,740
11%
2022
$5,656
-2%
$197,500
—
2021
$5,787
—
$197,500
—
2020
$5,787
1%
$197,500
—
2019
$5,747
—
$197,500
—
2018
$5,728
-8%
$197,500
-7%
2017
$6,253
2%
$213,420
—
2016
$6,146
1%
$213,420
—
2015
$6,061
3%
$213,420
—
2014
$5,890
5%
$213,420
—
2011
$5,634
—
$213,420
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 40 Oleson Dr
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40 Oleson Drive, Southbury, CT 06488 (MLS# 24174641) is a Single Family property with 5 bedrooms, 1 full bathroom and 1 partial bathroom. 40 Oleson Drive is currently listed for $565,000 and was received on May 15, 2026. Want to learn more about 40 Oleson Drive? Do you have questions about finding other Single Family real estate for sale in Southbury? You can browse all Southbury real estate or contact a Coldwell Banker agent to request more information.