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For sale
  • $399,900

    108 High Street, Middletown, CT 06457

    6beds
    2,584sqft
    : 
    $2,847/mo
    Get pre-qualified
    Multi Family
    Built in 1900
    -- sqft lot
    $-- Zestimate®
    $155/sqft
    $-- HOA

    What's special

    Charming period details throughoutConvenient walkout basementCorner lotBeautiful built-in cabinetryThree bedroomsWood flooringSpacious unit
    Welcome to this character-filled, turn-of-the-century two-family Colonial in the heart of Middletown, ideally located directly across from Wesleyan University and within walking distance of downtown, restaurants, shops, and public transportation. Each spacious unit offers three bedrooms, a generous living room with a fireplace, beautiful built-in cabinetry, wood flooring, and French doors opening to a sunroom. Large, open kitchens with walk-in pantries provide ample space and functionality, while charming period details throughout reflect the home's original character. The first-floor unit is vacant and move-in ready, while the second-floor unit is currently tenant-occupied, offering immediate rental income. A new roof adds significant value, while the interiors still provide opportunities for updates and personal touches. Situated on a corner lot with two separate driveways accessed from different streets, plus a convenient walkout basement. An excellent opportunity for an owner-occupant or investor!
    7 days
    691
    56

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Michelle Mazzotta (860)305-5908,

    eXp Realty 866-828-3951

    Source: Smart MLS,MLS#: 24202328MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 2
      • Full bathrooms: 2
      Heating
      • Hot Water, Oil
      Cooling
      • None
      Appliances
      • Included: Electric Water Heater, Water Heater
      • Laundry: In Unit
      Features
      • Basement: Full,Unfinished,Concrete
      • Attic: Crawl Space,Storage,Access Via Hatch
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 2,584
      • Total interior livable area: 2,584 sqft
      • Finished area above ground: 2,584

      Property

      Parking
      • Total spaces: 4
      • Parking features: Off Street, Driveway, Paved
      • Has uncovered spaces: Yes
      Lot
      • Size: 4,791 Square Feet
      • Features: Corner Lot, Level
      Details
      • Parcel number: 1013153
      • Zoning: DVD

      Construction

      Type & style
      • Home type: MultiFamily
      • Architectural style: Units on different Floors
      • Property subtype: Multi Family
      Materials
      • Aluminum Siding
      • Foundation: Brick/Mortar
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1900

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Middletown

      Financial & listing details

      • Price per square foot: $155/sqft
      • Tax assessed value: $132,990
      • Annual tax amount: $5,426
      • Date on market: 8/28/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/28/2026Listed for sale$399,900+33.3%$155/sqft
        Source: Smart MLS #24202328 Report a problem
        4/19/2024Listing removed--
        Source: Smart MLS #24001431 Report a problem
        3/28/2024Listed for rent$1,750$1/sqft
        Source: Smart MLS #24001431 Report a problem
        2/22/2024Sold$300,000-4.8%$116/sqft
        Source: Smart MLS #170613183 Report a problem
        1/25/2024Listed for sale$315,000$122/sqft
        Source: Smart MLS #170613183 Report a problem
        1/3/2024Contingent$315,000$122/sqft
        Source: Smart MLS #170613183 Report a problem
        12/6/2023Listed for sale$315,000+120.6%$122/sqft
        Source: Smart MLS #170613183 Report a problem
        6/19/2017Sold$142,800-10.7%$55/sqft
        Source: Smart MLS #G10201997 Report a problem
        4/24/2017Pending sale$159,900$62/sqft
        Source: Hagel & Assoc. Real Estate #G10201997 Report a problem
        3/6/2017Listed for sale$159,900$62/sqft
        Source: Hagel & Assoc. Real Estate #G10201997 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,173 +5.7%$132,990
        2024$4,894 +4.8%$132,990
        2023$4,668 +14.6%$132,990 +43.7%
        2022$4,073 $92,570
        2021$4,073 -0.5%$92,570
        2020$4,092 -0.4%$92,570
        2019$4,110 +1.6%$92,570
        2018$4,045 -16.1%$92,570 -18.6%
        2017$4,822 +7.1%$113,720
        2015$4,503 -1%$113,720
        2014$4,549 -13.7%$113,720 -27%
        2013$5,269 +3.4%$155,880
        2012$5,097 +3.5%$155,880
        2011$4,926 -0.9%$155,880
        2010$4,973 +4.6%$155,880
        2009$4,754 +19.6%$155,880
        2008$3,975 -5.6%$155,880 +41.4%
        2007$4,212 +1.3%$110,270
        2006$4,157 +5.6%$110,270
        2005$3,937 +8.8%$110,270
        2003$3,617 $110,270
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 06457

        Getting around

        72 / 100
        Very Walkable
        39 / 100
        Somewhat Bikeable

        Nearby schools

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

        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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