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Sold for $465,000
  • $465,000

    541 Benson Road, Middlebury, CT 06762

    3beds
    1,600sqft
    Multi Family
    Built in 1942
    -- sqft lot
    $466,700 Zestimate®
    $291/sqft
    $2,720 Estimated rent

    Home value

    $466,700

    $420,000 - $518,000

    $2,720/mo

    Zestimate® history
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    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!

    Zillow last checked:

    Listing updated:

    Listed by:

    Joseph Martino joe@joemartinore.com,

    Joseph Martino Real Estate 203-671-2384

    Bought with:

    Scott Hellriegel, RES.0815820

    Berkshire Hathaway NE Prop.

    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: $291/sqft
    • Tax assessed value: $309,000
    • Annual tax amount: $10,049
    • Date on market: 8/14/2026

    Price history

    DateEventPrice
    6/17/2026Sold$465,000-11.4%$291/sqft
    Source: Smart MLS #24161555 Report a problem
    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

    Neighborhood: 06762

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