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    27-29 S Main St Winchester, KY 40391

    For Sale
    $314,900

    COMMERCIAL - Winchester, KY

    Property size:
    3,132 SF
    Lot size:
    0.09 Acres
    Days on Market:
    62
    Last Refresh:
    Dec 13 at 9:06 pm

    Property Features for 27-29 S Main St

    General Information

    Special listing conditions
    Standard
    Property type
    Commercial Sale
    Property subtype
    Other
    TransactionType
    Standard
    Standard status
    Active
    APN
    054-3217-017-00
    Size
    3,132 SF
    Lot size
    0.09 Acres

    Building Details

    Year built
    1880
    Floors in Building
    2
    Building materials
    Brick

    Block + Lot Real Estate 3090099

    Listing agent Lara Thornbury (859) 309-0099

    Listing date Oct 13, 2025

    Copyright © 2025 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

    Overview

    Renovated Mixed-Use Building, Winchester, KY

    This mixed-use property is located across from the Court House on Main Street. The downstairs area has been completely renovated, featuring a new storefront, new HVAC system, exposed brick walls, and new flooring. The upstairs apartment boasts a staircase, hardwood floors, and abundant natural light. Demolition work is complete upstairs, a new back deck has been added, walls are up, plaster work is completed, and the new back windows are in. The property includes a large back parking lot with alley access and is located in an Opportunity Zone. It is suitable for living upstairs and operating a business downstairs. The building size is 3132 square feet and the lot size is 0.09 acres.
    Property Profile Insight Report Location Intelligence

    Current Use by Public Records

    Storefront properties

    Suggested Use

    Realty agency Law Firm Restaurant Spa & Massage Dental Office Hair Salon Nail Salon Clothing Store Building Supply Gym & Fitness

    Zoning and permitted uses should be independently verified with local authorities.

    Location Insight

    • Map
    • Local Demand
    City
    Winchester
    County
    Clark
    State
    Kentucky
    Longitude
    -84.176786
    Latitude
    37.992712

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    FAQs

    What type of property is this?
    Mixed-use property - Mixed-use property with renovated storefront and residential space.
    Where is this mixed-use property located?
    The property is located at 27-29 S Main St Winchester, KY.
    What is the asking price?
    The asking price for this property is $314,900.
    What are key features of this property?
    This property features: - Prime Location: Directly across from the Court House on Main Street.; - Live/Work Opportunity: Perfect building to live upstairs and operate your business downstairs.; - Renovated Downstairs: Completely renovated storefront with **new HVAC, exposed brick, and new flooring.**
    (859) 309-0099
    Request Owner's contact information
    27-29 S Main St Winchester, KY 40391
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    Winchester, KY 40391
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    Realmo Value Estimation

    Realmo estimates a property’s market value using a proprietary methodology that incorporates public data and user-submitted information. This cumulative value is generated by integrating a variety of conventional and innovative methods. 

    Disclaimer

    These figures are not official appraisals and should not be used as a substitute for a valuation performed by a licensed appraiser.

    Actual market value may differ due to factors not captured in the data. Estimates are offered for informational purposes only, and users should conduct independent research before making financial or investment decisions.

    By using this feature, you acknowledge that Realmo is not responsible for actions taken based on these estimates.

    AI approach

    Realmo AI Method estimates property value using machine learning models trained on millions of comparable listings, transactions, and market signals. It analyzes property features, location intelligence data, and current market dynamics to predict the most probable market value in real time.

    Cap approach

    Capitalization Method calculates value based on estimated net operating income (NOI) and applying a market-based capitalization rate (cap rate), we estimate what a typical investor might be willing to pay for it.

    Comparable approach

    Comparable estimate is based on recent sales of similar nearby properties, adjusted for factors like size, condition, and location.

    Relative

    Relative property class coefficient uses factors that account for typical price differences between various asset types (e.g., retail vs. industrial) to provide a more accurate market-aligned estimate.

    Geo

    Comparable Sales Method, enhanced by Geo coefficients — location-based adjustment factors that reflect differences in price levels across neighborhoods, cities, or regions ensuring a more accurate, market-sensitive valuation.

    Alternative use

    Estimate considers the property’s potential value if used for a different purpose-based on zoning, demand, and market feasibility.

    More about this property
    27-29 S Main St Winchester, KY 40391
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