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Under contract
  • $525,000

    541 Benson Road, Middlebury, CT 06762

    3beds
    1,600sqft
    : 
    Multi Family
    Built in 1942
    -- sqft lot
    $-- Zestimate®
    $328/sqft
    $-- HOA

    What's special

    Separate soaking tubBrand-new spa-like bathroomCentral airHigh-end finishesPrivate primary suite retreatClassic new england stonewallsOak cabinets
    Rare Two-Home Compound in Middlebury - Ideal for Investment or Owner-Occupant! An extraordinary opportunity for investors or owner-occupants looking to offset their mortgage! This unique property at 541 Benson Road features TWO distinct, detached dwellings on a private .8-acre lot, offering a total of 3 bedrooms, 3 full baths, and 4 garage bays. Unit 1: The Main Residence (2BR/2BA) This beautifully appointed home features an open-concept layout with gleaming hardwood floors and high-end finishes. Chef's Kitchen: U-shaped layout with oak cabinets, granite countertops, stainless steel appliances (gas stove), and a large pantry. Main Level: Includes a spacious bedroom and a brand-new spa-like bathroom with a custom tiled walk-in shower and separate soaking tub. Upper Level: A private primary suite retreat finished in warm natural pine, featuring abundant closet space, a full ensuite bath, and a charming built-in reading nook/office area. Central Air, pellet stove for efficient heating, and a massive 3-car attached garage for ample storage or workshop space. Unit 2: Detached Carriage House (1BR/1BA) A completely separate, legal-style dwelling perfect for rental income, multi-generational living, or a professional home office. Living Space: Features a functional galley kitchen with gas cooking, a bright living area, and a private bedroom. Amenities: Full bathroom with a tiled shower and its own dedicated 1-car garage/workshop located directly be Exterior & Location The property sits on a lush .8-acre "private oasis" framed by classic New England stonewalls and a brick patio. Whether you are looking for a high-end rental property or a way to live in one home while the other pays your taxes, this versatile compound is a rare find in Middlebury. Total Garage Bays: 4 | Total Acreage: 0.80 | Separate Utilities Schedule your private tour today to explore the unmatched flexibility of this two-family setup!
    40 days
    |
    852
    |
    43
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Joseph Martino joe@joemartinore.com,

    Joseph Martino Real Estate 203-671-2384

    Source: Smart MLS,MLS#: 24161555MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 3
      Heating
      • Baseboard, Bottle Gas, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Water Heater
      Features
      • Basement: Full
      • Attic: Finished,Walk-up
      • Has fireplace: No
      Interior area
      • Total structure area: 1,600
      • Total interior livable area: 1,600 sqft
      • Finished area above ground: 1,600

      Property

      Parking
      • Total spaces: 3
      • Parking features: Attached
      • Attached garage spaces: 3
      Lot
      • Size: 0.8 Acres
      • Features: Sloped
      Details
      • Parcel number: 1192162
      • Zoning: L200

      Construction

      Type & style
      • Home type: MultiFamily
      • Architectural style: Other
      • Property subtype: Multi Family
      Materials
      • Vinyl Siding, Cedar
      • Foundation: Concrete Perimeter, Masonry
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1942

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Middlebury

      Financial & listing details

      • Price per square foot: $328/sqft
      • Tax assessed value: $309,000
      • Annual tax amount: $10,049
      • Date on market: 3/23/2026
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        $3,509/mo

        Price history

        DateEventPrice
        4/17/2026Pending sale$525,000$328/sqft
        Source: Smart MLS #24161555 Report a problem
        3/23/2026Listed for sale$525,000+5.2%$328/sqft
        Source: Smart MLS #24161555 Report a problem
        1/29/2026Listing removed$499,000$312/sqft
        Source: Smart MLS #24128030 Report a problem
        12/26/2025Price change$499,000-14%$312/sqft
        Source: Smart MLS #24128030 Report a problem
        9/19/2025Listed for sale$579,900+96.6%$362/sqft
        Source: Smart MLS #24128030 Report a problem
        3/24/2021Listing removed--
        Source: Owner Report a problem
        11/24/2016Listing removed$295,000$184/sqft
        Source: Owner Report a problem
        8/26/2016Listed for sale$295,000+20.4%$184/sqft
        Source: Owner Report a problem
        2/16/2007Sold$245,000$153/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,049 -0.2%$309,000
        2024$10,073 +1.1%$309,000
        2023$9,968 +3.2%$309,000
        2022$9,659 +18.7%$309,000 +32.3%
        2021$8,136 -0.8%$233,600
        2020$8,199 +5.1%$233,600
        2019$7,802 +2.7%$233,600
        2018$7,594 +3.2%$233,600
        2017$7,356 +1.4%$233,600 -3%
        2015$7,253 +2.7%$240,800
        2014$7,065 +1.7%$240,800
        2013$6,949 +2.8%$240,800
        2012$6,759 +3.3%$240,800 -12.4%
        2011$6,540 +43.8%$274,900 +42.8%
        2009$4,549 +1.8%$192,500
        2008$4,468 +6%$192,500
        2007$4,216 +18%$192,500 +64.6%
        2005$3,573 -0.9%$116,950
        2004$3,604 +8.2%$116,950 0%
        2003$3,332 +17.8%$117,000 +32.6%
        2000$2,828 $88,250

        Find assessor info on the county website

        Monthly payment

        Est. payment
        $3,524/mo
        Principal & interest
        $2592
        Property taxes
        $932
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          Climate risks

          Neighborhood: 06762

          Getting around

          9 / 100
          Car-Dependent
          19 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating

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