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For sale
    • Price cut: $100K (2/18)
    $599,900

    10 Old Waterbury Road, Middlebury, CT 06762

    5beds
    2,345sqft
    : 
    Multi Family
    Built in 1930
    -- sqft lot
    $-- Zestimate®
    $256/sqft
    $-- HOA

    What's special

    Short no-thru streetIn-ground pool
    4 UNITS IN MIDDLEBURY-NOT ONLY "NEXT TO IMPOSSIBLE" TO FIND, BUT UNBELIEVABLY PRICED AT $599900! THIS "ONCE IN A LIFETIME" OPPORTUNITY CAN BE YOURS! LIVE IN ONE, AND COLLECT RENT FROM THE OTHER THREE UNITS, OR, ADD THIS ONE TO YOUR INVESTMENT PORTFOLIO AND "WATCH IT GROW"! One parcel (.41 ACRE), ON "PARKLIKE" GROUNDS WITH THE ATMOSPHERE OF NATURE ON A SHORT, NO-THRU STREET, consists of a detached, 1 bedroom single family, approximately (620 s.f.), 3 units SIDE BY SIDE, w/1 car garage under and in-ground pool. AN ADDITIONAL 2 car detached garage, AND HUGE DRIVEWAY FOR plenty of off street parking. Public water and sewer. Separate utilities paid by tenants. Single family has oil heat and 3 family is electric heat. Historically LOW VACANCY. Prime location-easy access to RT 8 and I-84. Minutes to Middlebury Greenway trails, Hop Brook State Park with lake, swimming, picnicking, biking, hiking & MORE! "TOP RATED" Middlebury schools. WALKING DISTANCE to Post University, & NVCC. Close to fine dining and shopping. Please refer to agent comments.
    104 days
    |
    1,441
    |
    46
    |

    Zillow last checked: 7 hours ago

    Listing updated: February 28, 2026 at 03:40pm

    Listed by:

    Judith Caputo (203)755-4015,

    Advantage Realty Group, Inc. 203-755-4015

    Source: Smart MLS,MLS#: 24143678MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 4
      Heating
      • Baseboard, Electric, Oil
      Cooling
      • Window Unit(s)
      Appliances
      • Included: Water Heater
      Features
      • Basement: Full,Unfinished
      • Attic: None
      • Has fireplace: No
      Interior area
      • Total structure area: 2,345
      • Total interior livable area: 2,345 sqft
      • Finished area above ground: 2,345

      Property

      Parking
      • Total spaces: 3
      • Parking features: Attached, Detached
      • Attached garage spaces: 3
      Features
      • Patio & porch: Porch, Deck
      • Exterior features: Sidewalk, Rain Gutters, Garden, Lighting
      • Has private pool: Yes
      • Pool features: In Ground
      Lot
      • Size: 0.41 Acres
      • Features: Few Trees, Sloped
      Details
      • Parcel number: 1194297
      • Zoning: R40

      Construction

      Type & style
      • Home type: MultiFamily
      • Architectural style: Units are Side-by-Side
      • Property subtype: Multi Family
      • Attached to another structure: Yes
      Materials
      • Vinyl Siding
      • Foundation: Concrete Perimeter, Stone
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1930

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Community
      • Features: Near Public Transport, Health Club, Lake, Park, Public Rec Facilities, Shopping/Mall
      HOA
      • Has HOA: No
      Location
      • Region: Middlebury

      Financial & listing details

      • Price per square foot: $256/sqft
      • Tax assessed value: $236,000
      • Annual tax amount: $7,675
      • Date on market: 12/5/2025
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        Price history
        DateEventPrice
        2/18/2026Price change$599,900-14.3%$256/sqft
        Source: Smart MLS #24143678 Report a problem
        12/5/2025Listed for sale$699,900+40%$298/sqft
        Source: Smart MLS #24143678 Report a problem
        2/1/2023Listing removed--
        Source: Smart MLS #170538468 Report a problem
        11/30/2022Listed for sale$499,900-26.5%$213/sqft
        Source: Smart MLS #170538468 Report a problem
        1/1/2022Listing removed--
        Source: Smart MLS #170449626 Report a problem
        11/3/2021Listed for sale$679,900+655.4%$290/sqft
        Source: Smart MLS #170449626 Report a problem
        8/19/2018Listing removed$1,050
        Source: Hadir Realty Group, LLC #170094933 Report a problem
        6/26/2018Price change$1,050-12.5%
        Source: Hadir Realty Group, LLC #170094933 Report a problem
        6/13/2018Listed for rent$1,200$1/sqft
        Source: Hadir Realty Group, LLC #170094933 Report a problem
        1/29/1993Sold$90,000-50%$38/sqft
        Source: Public Record Report a problem
        4/4/1988Sold$180,000$77/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2025$7,675 -0.2%$236,000
        2024$7,694 +1.1%$236,000
        2023$7,613 +3.2%$236,000
        2022$7,377 +11.7%$236,000 +24.4%
        2021$6,607 -0.8%$189,700
        2020$6,658 +5.1%$189,700
        2019$6,336 +2.7%$189,700
        2018$6,167 +3.2%$189,700
        2017$5,974 -1%$189,700 -2.5%
        2016$6,035 $194,600

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $4,012/mo
        Principal & interest
        $2947
        Property taxes
        $1065
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          Climate risks

          Neighborhood: 06762

          Getting around

          38 / 100
          Car-Dependent
          25 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating

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