About This Home

This 5-bedroom, 2-bathroom single family at 40 Oleson Drive in Southbury, CT is listed for $499,900 ($245 per sqft). Built in 1963, the home offers 2,040 sqft of living space on a 2.90 acres lot.

Key Features

  • Built in 1963
  • 2.90 acre lot
  • 4 parking spaces
  • Fireplace

Property Details

1 full, 1 half
2-car garage
1963

Amenities

Fireplace
Listing 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). New well pump/tank/cap (2024). New pool liner (2024). A whole-house Generac generator provides peace of mind. The property may offer subdivision potential, subject to municipal approvals. Buyers should perform their own due diligence regarding any development possibilities. Surrounded by nature, this home is ready for its next owner to make it their own.

Monthly Cost Estimate

$2,674/mo

20% down · 6.5% · 30 years

Principal$362
Interest$2,166
Insurance$146

Estimates only. Actual payments may vary.

Location

40 Oleson Drive

Southbury, CT 06488

Features & Amenities

Interior Features

Auto Garage Door Opener

Exterior Features

Shed,Porch,Barn,Gutters,Stone Wall

Property Details

Outdoor Features

Porch

Appliances

Oven/RangeRange HoodRefrigeratorDishwasherWasherDryer

Questions & Answers

This 5-bedroom, 2-bathroom single family at 40 Oleson Drive is listed at $499,900 ($245/sqft). The estimated monthly payment is $2,674 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1963, 2.90 acre lot, 4 parking spaces, Fireplace. Interior Features: Auto Garage Door Opener. Exterior Features: Shed,Porch,Barn,Gutters,Stone Wall.

This property is listed by Liz Newnham.

LN

Liz Newnham

Agent at William Pitt Sotheby's International Realty

Listed by William Pitt Sotheby's International Realty · Broker phone: 2037967700 · View on Broker Site · Broker website

MLS# 24207493· Source: SmartMLS, Inc.· 46 days on PropertySimple

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

40 Oleson Drive, Southbury, CT 06488

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