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    39 S Main Street Winchester, KY 40391

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    Claim this Listing
    For Sale
    $429,000

    COMMERCIAL - Winchester, KY

    Property size:
    3,538 SF
    Lot size:
    0.01 Acres
    Price / SF:
    $121/SF
    Added:
    Jul 9, 2025
    Days on Market:
    297
    Last Refresh:
    May 1 at 12:06 pm

    Property Features for 39 S Main Street

    General Information

    Property type
    Commercial Sale
    Property subtype
    Other
    Parking
    10
    Standard status
    Active
    APN
    054-3217-014-00
    Size
    3,538 SF
    Lot size
    0.01 Acres

    We can help!

    Listing Contact
    Lara Thornbury
    Lara Thornbury

    Listing agent Lara Thornbury License #SL3587398

    Listing office Block + Lot Real Estate 133 W Short St, Lexington, KY

    Listing date Jul 9, 2025

    MLS# 25014867

    Copyright © 2026 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

    Historic Building in Downtown Winchester

    This wonderfully renovated historic building is located across from the Court House in Downtown Winchester. The well-appointed restaurant space features a full hood system, concrete bar, beautiful hardwood floors, and a tin ceiling. Parking is available in the back. The property also includes an apartment with a private deck. This setup offers a great opportunity for a live/work arrangement, with the potential to live upstairs and operate a restaurant downstairs. Downtown Winchester is experiencing a period of growth, attracting shops, restaurants, and new apartment developments. Its proximity to Lexington, combined with its own attractions, makes it a destination for both residents and tourists. The building retains historic charm, with a significant portion dating back to the original construction, enhanced by a recent renovation to maximize functionality. The property is conducive to a live/work layout and/or short-term rentals. The property size is 3538 square feet and the lot size is 0.01 acres.
    Property Profile Insight Report Location Intelligence

    Current Use by Public Records

    Conventional restaurants

    Suggested Use

    Real Estate Agency Law Firm Restaurant Spa & Massage Center Dental Office Hair Salon Nail Salon Building Supply Gym & Fitness Center Pharmacy

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

    Location Insight

    • Map
    • Local Demand
    City
    Winchester
    County
    Clark
    State
    Kentucky
    Longitude
    -84.176882
    Latitude
    37.992525

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    FAQs

    What type of property is this?
    Conventional restaurant - Renovated commercial building with restaurant and apartment in Winchester.
    Where is this conventional restaurant located?
    The property is located at 39 S Main Street Winchester, KY.
    What is the asking price?
    The asking price for this property is $429,000.
    What are key features of this property?
    This property features: Renovated historic building in Downtown Winchester.; Restaurant space with full hood system and commercial kitchen.; Live/work layout potential with apartment upstairs.
    (859) 771-2552
    We can help!
    Listing Contact
    Lara Thornbury
    Lara Thornbury
    Real Estate License ID: SL3587398
    Learn More
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    Realmo Value Estimations

    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.

    Realmo CapRate Calculation

    Realmo calculates the Capitalization Rate (Cap Rate) to help estimate a property's potential return on investment. The Cap Rate is a fundamental metric in commercial real estate that measures the relationship between a property's net operating income and its market value.

    How We Calculate Cap Rate

    Cap Rate Formula:
    Cap Rate (%) = (Net Operating Income / Property Value) × 100

    Net Operating Income (NOI) Formula:
    NOI = Area × Lease Rate × (1 - Vacancy Rate) × (1 - Operating Expense Ratio)

    Components

    Net Operating Income (NOI) represents the annual income a property generates after operating expenses:

    • Area: Building square footage from property records
    • Lease Rate: Annual $/sqft based on market data for the property type and geographic location
    • Vacancy Rate: Percentage of unoccupied space based on market data for the property type and location
    • Operating Expense Ratio: Operating costs as a percentage of income, varies by property type

    Property Value is derived from:

    • Recent sale price (if available)
    • Statistical models using comparable sales
    • AI-powered valuation estimates

    Example Calculation

    For a 100,000 sqft Office Building:

    • Lease Rate: $25.00/sqft/year (market data for Office in this area)
    • Vacancy Rate: 8% (market data for Office in this area)
    • Operating Expense Ratio: 35% (typical for Office properties)
    • Property Value: $15,000,000

    Step 1: Calculate NOI

    NOI = 100,000 × $25.00 × (1 - 0.08) × (1 - 0.35)
    NOI = 100,000 × $25.00 × 0.92 × 0.65
    NOI = $1,495,000/year

    Step 2: Calculate Cap Rate

    Cap Rate = ($1,495,000 / $15,000,000) × 100
    Cap Rate = 9.97%

    Property Type Considerations

    Net Operating Income calculations vary by property type due to different operating expense ratios:

    • Office: Higher expenses (30-40%) for HVAC, utilities, maintenance
    • Retail: Moderate expenses (25-35%) for common area maintenance
    • Industrial/Warehouse: Lower expenses (15-25%) for minimal tenant services
    • Multifamily: Moderate expenses (35-45%) including property management
    • Self-Storage: Lower expenses (25-35%) due to minimal maintenance

    Market lease rates and vacancy rates are specific to each property type and geographic location, reflecting local market conditions.

    Disclaimer

    These calculations are estimates for informational purposes only and should not be used as a substitute for professional financial analysis or appraisal.

    • Cap Rate calculations depend on market data that may change over time
    • Actual operating expenses, lease rates, and vacancy rates may differ from market averages
    • Individual property conditions, lease terms, and tenant quality significantly impact actual NOI
    • Property value estimates are approximations and not official appraisals
    • Cap rates vary widely by market, property condition, and investment risk profile

    Professional Guidance Recommended: Before making any investment or financial decisions, consult with licensed appraisers, commercial real estate brokers, and financial advisors who can evaluate your specific property and circumstances.
    By using this feature, you acknowledge that Realmo is not responsible for investment decisions or actions taken based on these estimates.

    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.

    Stat Estimate

    This method estimates value based on actual market adjusted recent (~5 years) sales of comparable properties around by location and property type.

    • Ranges - area data calculated by industry standard IQR Outlier Removal Method
    • Range-from: 75% of all similar sales ($/sqft) are above this value
    • Range-to: 75% of all similar sales ($/sqft) are below this value
    AI Estimate

    This method estimates value based on AI market estimation of comparable properties around by location and property type.

    • Ranges - area data calculated by industry standard IQR Outlier Removal Method
    • Range-from: 75% of all estimations ($/sqft) are above this value
    • Range-to: 75% of all estimations ($/sqft) are below this value
    Alternative use

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

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    39 S Main Street, Winchester, KY 40391

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