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    Winchester, KY
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    Winchester, KY Office Buildings for Sale

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    Brandenburg, KY Lexington, KY N Middletown, KY
    Freestanding Office Building For Sale
    $750,000
    16,857 SF

    Freestanding Office Building For Sale

    321 Venable Road, Winchester, KY 40391

    Single-story office building on 10 acres near Winchester Road.

    • Ideal location for corporate headquarters or operations center.
    • Freestanding +/-16,857 SF single‑story corporate office building.
    • Located on a 10‑acre parcel, allowing for future development.
    • Features an elevator, wet/dry sprinkler system, and back‑up generator.
    • Located near Winchester Road (US 60) on Venable Road.
    Updated: Mar 6
    View details
    Winchester Multifamily and Office Investment
    $1,575,000
    26,124 SF

    Winchester Multifamily and Office Investment

    2 N Main Street, Winchester, KY 40391

    Historical landmark with 18 apartments and 2 offices.

    • Significant CAPEX investments in 2022 & 2024, including facade transformation and full restoration.
    • Strong income potential: Current $168,000 annual rent with a $4,000/month upside, exceeding the 1% rule.
    • 20 income‑producing units: 18 LIHTC apartments and 2 renovated ground‑floor offices.
    • Located in the Kerr Building, the largest downtown historical landmark, with structural repairs and new roofing.
    • Turn‑key and stabilized property in a thriving downtown Winchester location.
    Updated: Aug 9, 2025
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    Based on your search, we've compiled 12 Potential Opportunities for your consideration. Besides 2 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 2 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Class B Office Building
    Contact for pricing

    Class B Office Building

    Class B office building with abundant parking in Lexington, KY.

    151 N Eagle Creek Drive, Lexington, KY 40509
    View details
    Eastern Fayette County Office Building
    Contact for pricing
    38,367 SF

    Eastern Fayette County Office Building

    Four-story office building in Eastern Fayette County near Hamburg Place.

    2285 Executive Drive, Lexington, KY 40505
    View details
    Hamburg Place Office Leasing Opportunity
    Contact for pricing
    27,516 SF

    Hamburg Place Office Leasing Opportunity

    Office space for lease in Lexington's Hamburg Place.

    2517 Sir Barton Way, Lexington, KY 40509
    View details
    Office Conversion Data Center Opportunity
    $18,086,600
    180,866 SF

    Office Conversion Data Center Opportunity

    180,866 SF Class A building suitable for data center.

    101 Yorkshire Blvd., Lexington, KY 40509
    View details

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Commercial Land in Prime Location
    $105,000
    1.59 Acres

    Commercial Land in Prime Location

    1.5 acre commercial lot with high exposure and bypass access.

    1 Tighlman Way, Mt Sterling, KY 40353
    View details
    Commercial Land in Mt Sterling
    $105,000
    1.59 Acres

    Commercial Land in Mt Sterling

    1.5 acre commercial lot with high exposure and bypass access.

    1 Tighlman Way, Mt Sterling, KY 40353
    View details
    Richmond, KY Commercial Land
    $3,200,000
    16.00 Acres

    Richmond, KY Commercial Land

    16 acres of B-3 commercial land on Robert Martin Bypass.

    999 Dr Robert R Martin Bypass, Richmond, KY 40475
    View details
    Richmond, KY Commercial Corner Lot
    $699,000
    3.48 Acres

    Richmond, KY Commercial Corner Lot

    3.48+/- acre corner lot suitable for retail or office development.

    1963 Irvine Road, Richmond, KY 40475
    View details

    Off-Market Properties in Winchester, KY

    Consider similar Off-Market properties in Winchester, KY. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    1129 Lexington Ave

    1129 Lexington Ave

    OFFICE BUILDING • 2,310 SF
    Value Estimation by Request
    1129 Lexington Ave, Winchester, KY 40391-1134
    View details
    175 Hospital Dr

    175 Hospital Dr

    PROFESSIONAL BUILDING • 45,000 SF
    Value Estimation by Request
    175 Hospital Dr, Winchester, KY 40391-9591
    View details

    Winchester, KY Office Buildings Investment Opportunities Market Analysis

    Explore 4 office buildings for sale in Winchester, KY on our real estate platform. These investment opportunities span a total of 42,981 square feet of properties for sale, with an estimated market value of $2,325,000.

    Sale prices for office properties in Winchester, KY start at $750,000, averaging $1,162,500, and reaching up to $1,575,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Top Commercial Asset Segments

    Office Units 8
    Office buildings 4
    Medical Office Space 1

    Demographics Overview

    Population 37K
    Population Growth (5Y) +3.5%
    Median Household Income $67,910
    College Educated 15.1%

    High-Yield Neighborhoods for Strategic Investment

    Identify Winchester submarkets with the highest inventory density on the market and evaluate the median listing prices of real estate assets

    Neighborhood Average Price
    40391 $1.2M

    Taxes & Financing

    Tax Rate (average for all types) 0.91%
    Property Tax per SF $10.57 per sq ft
    Average Loan-to-Value 65.0%

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