Add Listing
    For Sale
    • For Sale
    • For Lease
    • Recently Sold
    • Property Lookup
    • Brokers
    AI Search
    The Largest CRE Database in the US with Over 1 Million Listings

    265 S Highland Street Winchester, KY 40391

    View on Map
    For Sale
    $505,000

    MULTI_FAMILY - Winchester, KY

    Property size:
    5,058 SF
    Lot size:
    0.14 Acres
    Added:
    Mar 12, 2026
    Days on Market:
    21
    Last Refresh:
    Apr 1 at 5:06 am

    Property Features for 265 S Highland Street

    General Information

    Property type
    Residential Multi Family
    Property subtype
    Other
    Bedrooms
    8
    Bathrooms
    4
    Rooms
    Bathroom 4, Bedroom 6, Bathroom 3, Bedroom 2, Laundry Room, Bedroom 8, Bathroom 2, Bedroom 5, Bedroom 1, Bedroom 3, Bedroom 7, Bedroom 4, Bathroom 1
    Parking features
    Offsite
    Standard status
    Active
    APN
    054-4004-023-00
    Size
    5,058 SF
    Lot size
    0.14 Acres

    Utilities

    Heating system
    Electric (Heating)
    Cooling system
    Central Air

    Building Details

    Year built
    1940
    Floors in Building
    2
    Number of units
    4
    Roof type
    Shingle

    We can help!

    Listing Contact
    J Corey Griffo

    Listing agent J Corey Griffo License #70549

    Listing office RE/MAX Elite Lexington 203 Ruccio Way, Lexington, KY

    Listing date Mar 12, 2026

    MLS# 26004961

    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

    Updated Quadplex in Downtown Winchester

    This spacious quadplex in downtown Winchester presents an investment opportunity. The property has been updated throughout and is move-in ready. Each of the four units includes two bedrooms, one bathroom, a full kitchen, and a private laundry area. The total area of the property is approximately 5058 square feet and it sits on a 0.14-acre lot. The property features a total of 8 bedrooms and 4 bathrooms. Utilities are separately metered, allowing tenants to manage their own services. The location is convenient to downtown shopping, dining, and local amenities. The units are clean and well-maintained, making the property suitable for investors seeking an income-producing property.
    Property Profile Insight Report Location Intelligence

    Current Use by Public Records

    Quadplexes

    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
    -84.177947
    Latitude
    37.987145

    Nearby Similar for Sale

    • $215,000
      2,808 SF

      Winchester Commercial Units For Sale

      Two commercial units in Winchester, ideal for business or investment.
      103 Talbott Avenue unit: 2,3, Winchester, KY 40391
      View Details
    • $319,500
      3,637 SF

      Multifamily Investment Opportunity in Winchester

      Two income-producing buildings on one lot, great investment opportunity.
      144 Holly Avenue, Winchester, KY 40391
      View Details
    • $379,000
      1,536 SF

      Turnkey Bar in Historic Winchester

      Established bar with equipment and inventory included in sale.
      137 East Broadway Street, Winchester, KY 40391
      View Details
    • $825,000
      6,110 SF

      Winchester Commercial Building with Apartments

      Two-story building with office, apartments, and ample parking.
      218 S Maple Street, Winchester, KY 40391
      View Details
    • $614,900
      2,906 SF

      Freestanding Retail Building on Bypass

      Highly visible retail building in a busy commercial corridor.
      838 Bypass Road, Winchester, KY 40391
      View Details
    • $515,000
      5,094 SF

      Mixed-Use Property in Winchester, KY

      Versatile commercial property with residential income potential near 64S.
      808 Bypass Road, Winchester, KY 40391
      View Details
    • $429,000
      3,538 SF

      Historic Building in Downtown Winchester

      Renovated commercial building with restaurant and apartment in Winchester.
      39 S Main Street, Winchester, KY 40391
      View Details
    • $1,799,900
      20,252 SF

      Turnkey Industrial Facility, Winchester, KY

      20,252 sqft industrial warehouse with highway access and racking system.
      599 BLT Way, Winchester, KY 40391
      View Details
    • $600,000
      5,046 SF

      Renovated 4-Plex in Downtown Winchester

      Restored 4-unit building with modern updates in prime location.
      101 S Burns Avenue unit: 1,2,3,4, Winchester, KY 40391
      View Details
    • $780,000
      3,080 SF

      Profitable Car Wash and Oil Change

      Established car wash and oil change business for sale in Winchester.
      126 Shoppers Drive, Winchester, KY 40391
      View Details
    • $1,650,000
      10,136 SF

      Winchester Office Building with Flex Space

      10,136 SF office building with conversion potential and pole barn.
      273 Shoppers Drive, Winchester, KY 40391
      View Details
    • $515,000
      1,440 SF

      Mixed-Use Property with Residential Income

      Versatile commercial space with separate income-producing residential home.
      35-37 Hays Street, Winchester, KY 40391
      View Details

    FAQs

    What type of property is this?
    Quadplex - Turn-key quadplex with strong rental potential near downtown amenities.
    Where is this quadplex located?
    The property is located at 265 S Highland Street Winchester, KY.
    What is the asking price?
    The asking price for this property is $505,000.
    What are key features of this property?
    This property features: Turn‑key quadplex, updated throughout and ready for tenants.; Strong rental potential in a convenient downtown Winchester location.; Each unit has 2 bedrooms, 1 bathroom, full kitchen, and private laundry.
    (502) 804-7067
    We can help!
    Listing Contact
    J Corey Griffo
    Real Estate License ID: 70549
    Learn More
    Request Owner's contact information
    Message sent successfully
    Error
    If you are the owner or broker of this property and would like to edit or remove this listing please send a message to web site administrator.
    Message sent successfully
    Error
    Email to Your Friends
    Link copied to clipboard
    Separate multiple addresses with a comma
    Message sent successfully
    Error

    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
    Thanks! Your message was sent.
    Error! Your message wasn't sent.
    Please enter your name
    Please enter email
    Please enter the email in the correct format
    Please enter phone
    Please enter the number in the correct format
    Please enter message
    Thank You

    You are Unsubscribed From Notifications

    Google sign-in failed. Please try again or use another login method.
    Sign Up Successful!
    You now have access to more from Realmo!