Active Under Contract
Price CutPrice Drop: $30.1K (11/05)
Single family home for sale at 40 Oleson Dr, Southbury, CT 06488 | MLS# 24207493 | Listing updated on 2026-11-05
Photo 1 of Single family home for sale at 40 Oleson Dr, Southbury, CT 06488 | MLS# 24207493 | Listing updated on 2026-11-05
Photo 2 of Single family home for sale at 40 Oleson Dr, Southbury, CT 06488 | MLS# 24207493 | Listing updated on 2026-11-05
Photo 3 of Single family home for sale at 40 Oleson Dr, Southbury, CT 06488 | MLS# 24207493 | Listing updated on 2026-11-05
Photo 4 of Single family home for sale at 40 Oleson Dr, Southbury, CT 06488 | MLS# 24207493 | Listing updated on 2026-11-05
31+
Beds Icon

Street View

$499,900

Monthly Est:$2,488

  • Beds Icon5 Beds
  • Beds Icon
    2 Baths
  • Beds Icon2,040sqft

40 Oleson Dr, Southbury, CT 06488

$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 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    New Haven County

  • City

    Southbury

  • 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

DateEventPrice

11/05/2026

Source: mls_logoSMART MLS-CT #24207493

Contingent (Active Under Contract)

$499,900

$245/sqft

10/14/2026

Source: mls_logoSMART MLS-CT #24207493

Price Decreased

$499,900 -5.68%

$245/sqft

09/16/2026

Source: mls_logoSMART MLS-CT #24207493

Price Decreased

$530,000 -0.93%

$260/sqft

08/02/2026

Source: mls_logoSMART MLS-CT #24174641

Off Market

$535,000 -2.55%

$262/sqft

07/07/2026

Source: mls_logoSMART MLS-CT #24174641

Listed for Sale

$549,000

$269/sqft

Show more

Nearby Homes

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.

Advertising Broker: Derek Greene | The Greene Realty Group

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