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    The Largest CRE Database in the US with Over 1 Million Listings

    27-29 S Main St Winchester, KY 40391

    Sponsored
    For Sale
    $299,000

    COMMERCIAL - Winchester, KY

    Property size:
    3,132 SF
    Lot size:
    0.09 Acres
    Days on Market:
    24
    Last Refresh:
    Jan 28 at 5:06 am

    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

    We can help!

    Listing Contact
    Lara Thornbury

    Block + Lot Real Estate 3090099

    Listing agent Lara Thornbury (859) 309-0099

    Listing date Jan 5, 2026

    MLS# 24016294

    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.

    Learn more

    Property Insight Report

    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 natural light. The demolition work is complete upstairs, and 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. The building is suitable for living upstairs and operating a business downstairs. The property size is 3132 square feet, situated on a lot of 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 - Renovated mixed-use building with storefront, apartment, and parking.
    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 $299,000.
    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) 771-2552
    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 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.

    More about this property
    27-29 S Main St Winchester, KY 40391
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    We can help!
    Listing Contact
    Lara Thornbury
    Real Estate License ID: SL3587398
    (859) 771-2552
    Learn more
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