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For sale
  • $395,000

    720 Main Street, Winchester, CT 06098

    3beds
    1,909sqft
    : 
    Multi Family
    Built in 1900
    -- sqft lot
    $370,500 Zestimate®
    $207/sqft
    $-- HOA

    What's special

    Existing kitchen areaOpen seating areaRecent updatesNew roofOn-demand hot water systemHigh-visibility two-story building
    Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe, retail, or service business! The second floor offers a spacious 3-bedroom apartment with many recent updates, a new roof, windows, a deck, a kitchen, and an on-demand hot water system. The unit was renovated down to the studs. Separate gas and electric meters make it ideal for owner-occupier or investment use. On-street parking only, but surrounded by other downtown businesses with strong walkability and visibility. Excellent location near Highland Lake, Route 44, and all downtown amenities. Great opportunity to live and work in the same building or generate dual rental income. Bring your vision and make this Main Street property shine again! Also listed as a commercial property- MLS# 24138743
    135 days
    |
    795
    |
    16
    |

    Zillow last checked: 7 hours ago

    Listing updated: February 13, 2026 at 06:14pm

    Listed by:

    Ryan Marconi (860)960-6946,

    The Washington Agency 860-482-7044

    Source: Smart MLS,MLS#: 24138050MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 1
      • 1/2 bathrooms: 1
      Heating
      • Baseboard, Forced Air, Natural Gas
      Cooling
      • None
      Appliances
      • Included: Gas Water Heater, Water Heater, Tankless Water Heater
      Features
      • Basement: None
      • Attic: None
      • Has fireplace: No
      Interior area
      • Total structure area: 1,909
      • Total interior livable area: 1,909 sqft
      • Finished area above ground: 1,909

      Property

      Features
      • Patio & porch: Deck
      Lot
      • Size: 3,049.2 Square Feet
      • Features: Level
      Details
      • Parcel number: 927576
      • Zoning: CB-3

      Construction

      Type & style
      • Home type: MultiFamily
      • Architectural style: Units on different Floors,Other
      • Property subtype: Multi Family
      Materials
      • Vinyl Siding
      • Foundation: Slab
      • Roof: Asphalt,Flat
      Condition
      • New construction: No
      • Year built: 1900

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Winsted

      Financial & listing details

      • Price per square foot: $207/sqft
      • Tax assessed value: $47,810
      • Annual tax amount: $1,395
      • Date on market: 11/12/2025
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        Estimated market value

        $370,500

        $352,000 - $389,000

        $1,561/mo

        Price history

        Price history
        DateEventPrice
        11/12/2025Listed for sale$395,000+243.5%$207/sqft
        Source: Smart MLS #24138050 Report a problem
        6/6/2024Sold$115,000+155.6%$60/sqft
        Source: Public Record Report a problem
        11/1/2016Sold$45,000$24/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2025$1,395 +10.5%$47,810
        2024$1,262 $47,810
        2023$1,262 +9.9%$47,810 +39.7%
        2022$1,148 $34,230
        2021$1,148 $34,230
        2020$1,148 $34,230
        2019$1,148 $34,230
        2018$1,148 -38.1%$34,230 -38.1%
        2017$1,855 -11.4%$55,300 -11.4%
        2016$2,094 +2.5%$62,440
        2015$2,042 $62,440

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $2,563/mo
        Principal & interest
        $1977
        Property taxes
        $586
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          Climate risks

          Neighborhood: 06098

          Getting around

          63 / 100
          Somewhat Walkable
          17 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating

          Local experts in 06098

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