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Home Homes for Sale Southbury, CT 40 Oleson Drive

40 Oleson Drive, Southbury, CT 06488

Single Family For Sale

$549,000
$269/sqft
40 Oleson Drive, Southbury, CT
Active
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5
Bedrooms
2
Bathrooms
2,040
Sq Ft
2.9
Acres
1963
Year Built

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.

Listed by Liz Newnham (203) 994-4123 with William Pitt Sotheby's Int'l (203) 796-7700

Listing Snapshot

Price $549,000 Days on Our Site 36 days
Property Tax $5,318/yr Style Cape Cod,Colonial
Year Built 1963 Total Sq Ft 2,040
Lot Size 2.9 acres HOA Fees N/A
Bedrooms 5 Full Bathrooms 1
Total Rooms 9 Half Baths 1

Key Features

Interior
  • Auto Garage Door Opener
Appliances
  • Oven/Range
  • Range Hood
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • Shed
  • Porch
  • Gutters
  • Stone Wall
  • Vinyl
  • In Ground Pool
Nearby
  • Basketball Court
  • Golf Course
  • Health Club
  • Lake
  • Library
  • Medical Facilities
  • Park
  • Tennis Courts

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Tandem, Under House Garage, Driveway

Systems & Utilities

Heat Hot Air
Fuel Oil
Cooling None
Hot Water Electric, 50 Gallon Tank, Upright Tank
Water Private Well
Sewer Septic

Schools

Elem Per Board of Ed
Middle Memorial Middle School
High Pomperaug

Mortgage Calculator

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Est. Monthly Payment
Principal & Interest
Est. Property Tax $443/mo
Est. Home Insurance

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Jun 4, 2026 Price Reduced $549,000
May 11, 2026 Listed $565,000

Frequently Asked Questions

How much does 40 Oleson Drive in Southbury, CT cost?
This property is listed at $549,000, which works out to $269 per square foot.
How many bedrooms does 40 Oleson Drive have?
This home has 5 bedrooms and 2 bathrooms.
What is the square footage of 40 Oleson Drive?
The home is 2,040 square feet, situated on 2.9 acres.
When was 40 Oleson Drive in Southbury built?
This property was built in 1963.
Is 40 Oleson Drive, Southbury, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 40 Oleson Drive, Southbury in?
This home is served by the Southbury public school system, with Per Board of Ed as the elementary school and Pomperaug as the high school.
How do I schedule a tour of 40 Oleson Drive, Southbury, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Liz Newnham · (203) 994-4123

William Pitt Sotheby's Int'l · (203) 796-7700

MLS# 24174641 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Jun 14, 2026 10:40 PM UTC