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For sale
  • $395,000

    720 Main Street, Winchester, CT 06098

    3beds
    1,909sqft
    : 
    Multi Family
    Built in 1900
    -- sqft lot
    $384,300 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
    108 days
    |
    784
    |
    40
    |

    Zillow last checked: 8 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

    $384,300

    $365,000 - $404,000

    $1,523/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
    $2,475/mo
    Principal & interest
    $1889
    Property taxes
    $586

      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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