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For sale
    • Price cut: $16K (6/4)
    $549,000

    40 Oleson Drive, Southbury, CT 06488

    5beds
    2,040sqft
    : 
    $3,606/mo
    Get pre-qualified
    Single Family Residence
    Built in 1963
    2.9 Acres Lot
    $545,000 Zestimate®
    $269/sqft
    $-- HOA

    What's special

    Wood stoveCovered porchTwo car tandem garageAbundant parkingHardwood flooringShared private drivewayDining room
    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.
    80 days
    |
    2,101
    |
    175
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Liz Newnham (203)994-4123,

    William Pitt Sotheby's Int'l 203-796-7700

    Source: Smart MLS,MLS#: 24174641MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 2
      • Full bathrooms: 1
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Workshop
      Primary bedroom
      • Features: Bay/Bow Window, Hardwood Floor
      • Level: Main
      • Area: 199.2 Square Feet
      • Dimensions: 12 x 16.6
      Bedroom
      • Features: Hardwood Floor
      • Level: Main
      • Area: 150.7 Square Feet
      • Dimensions: 11 x 13.7
      Bedroom
      • Features: Hardwood Floor
      • Level: Main
      • Area: 96.3 Square Feet
      • Dimensions: 9 x 10.7
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 136.8 Square Feet
      • Dimensions: 9 x 15.2
      Bedroom
      • Features: Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 96.05 Square Feet
      • Dimensions: 8.5 x 11.3
      Bathroom
      • Level: Main
      Bathroom
      • Level: Upper
      Dining room
      • Features: Built-in Features, Hardwood Floor
      • Level: Main
      • Area: 103.5 Square Feet
      • Dimensions: 9 x 11.5
      Kitchen
      • Features: Bay/Bow Window, Eating Space, Pantry
      • Level: Main
      • Area: 151.2 Square Feet
      • Dimensions: 10.8 x 14
      Living room
      • Features: Beamed Ceilings, Bookcases, Fireplace, Wood Stove, Hardwood Floor
      • Level: Main
      • Area: 248 Square Feet
      • Dimensions: 15.5 x 16
      Sun room
      • Features: Beamed Ceilings, Sliders, Wall/Wall Carpet
      • Level: Main
      • Area: 128.02 Square Feet
      • Dimensions: 7.4 x 17.3
      Heating
      • Forced Air, Oil
      Cooling
      • None
      Appliances
      • Included: Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater
      • Laundry: Lower Level
      Features
      • Entrance Foyer
      • Basement: Full,Unfinished,Storage Space,Garage Access,Interior Entry
      • Attic: Pull Down Stairs
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 2,040
      • Total interior livable area: 2,040 sqft
      • Finished area above ground: 2,040

      Property

      Parking
      • Total spaces: 4
      • Parking features: Tandem, Attached, Driveway, Garage Door Opener, Private, Shared Driveway, Paved
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Porch
      • Exterior features: Rain Gutters, Stone Wall
      • Has private pool: Yes
      • Pool features: Vinyl, In Ground
      Lot
      • Size: 2.9 Acres
      • Features: Level
      Details
      • Additional structures: Shed(s)
      • Parcel number: 1331688
      • Zoning: R-60

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod,Colonial
      • Property subtype: Single Family Residence
      Materials
      • Wood Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1963

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Basketball Court, Golf, Health Club, Lake, Library, Medical Facilities, Park, Tennis Court(s)
      HOA
      • Has HOA: No
      Location
      • Region: Southbury

      Financial & listing details

      • Price per square foot: $269/sqft
      • Tax assessed value: $219,740
      • Annual tax amount: $5,318
      • Date on market: 5/11/2026
      • Exclusions: As Per Inclusion/Exclusion Rider

        Estimated market value

        $545,000

        $518,000 - $572,000

        $3,418/mo

        Price history

        DateEventPrice
        6/4/2026Price change$549,000-2.8%$269/sqft
        Source: Smart MLS #24174641 Report a problem
        5/15/2026Listed for sale$565,000$277/sqft
        Source: Smart MLS #24174641 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,318 +2.5%$219,740
        2024$5,186 +4.9%$219,740
        2023$4,944 -12.6%$219,740 +11.3%
        2022$5,656 -2.3%$197,500
        2021$5,787 +0.8%$197,500
        2020$5,743 -0.1%$197,500
        2019$5,747 +0.3%$197,500
        2018$5,728 -8.4%$197,500 -7.5%
        2017$6,253 +3.2%$213,420
        2015$6,061 +2.9%$213,420
        2014$5,890 +4.5%$213,420
        2013$5,634 +4.1%$213,420 -16.4%
        2012$5,413 -0.9%$255,330
        2011$5,464 -0.5%$255,330
        2010$5,490 +2.9%$255,330
        2009$5,336 -0.9%$255,330
        2008$5,387 +38.2%$255,330 +66.4%
        2007$3,898 +1.2%$153,480
        2006$3,852 +5%$153,480
        2005$3,668 +13.8%$153,480
        2003$3,223 +5.2%$153,480 +22.8%
        2001$3,063 $125,000
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 06488

        Getting around

        0 / 100
        Car-Dependent
        5 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: Pomperaug

        Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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