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    Winchester, KY Office Properties & Spaces for Sale

    10 results
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    Winchester Commercial Building with Apartments
    $825,000
    6,110 SF

    Winchester Commercial Building with Apartments

    218 S Maple Street, Winchester, KY 40391

    Two-story building with office, apartments, and ample parking.

    • Two‑story building featuring a main floor office space and two apartments on the second floor
    • Large asphalt parking lot with space for over 25 vehicles
    • Detached 3‑bay garage for parking and storage
    • Zoned heating and cooling with heat pump system
    • Unfinished basement for storage and mechanical system access
    Updated: Mar 2
    View details
    Mixed-Use Property in Winchester, KY
    $515,000
    5,094 SF

    Mixed-Use Property in Winchester, KY

    808 Bypass Road, Winchester, KY 40391

    Versatile commercial property with residential income potential near 64S.

    • Turnkey commercial space ideal for restaurant, cafe, or retail.
    • Separate rental unit with private entrance for additional income or live/work setup.
    • High‑visibility location with street frontage and on‑site parking.
    • Less than 1/2 mile from 64S.
    • Outdoor dining area.
    Updated: May 30, 2025
    View details
    Historic Building in Downtown Winchester
    $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
    Winchester Office Building with Flex Space
    $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
    Mixed-Use Property with Residential Income
    $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
    Downtown Winchester Commercial Building For Sale
    $250,000
    4,300 SF

    Downtown Winchester Commercial Building For Sale

    Renovated commercial building with live/work space potential in Winchester, KY.

    18 N Main Street, Winchester, KY 40391
    View details
    Freestanding Office Building For Sale
    $750,000
    16,857 SF

    Freestanding Office Building For Sale

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

    321 Venable Road, Winchester, KY 40391
    View details
    Historical Landmark Multifamily and Office
    $1,595,000
    26,124 SF

    Historical Landmark Multifamily and Office

    Turn-key, stabilized investment property in thriving downtown Winchester.

    2 N Main Street, Winchester, KY 40391
    View details
    Prime Land on Bypass Road
    $775,000
    2.60 Acres

    Prime Land on Bypass Road

    Land for retail, office, storage, and mixed-use development.

    529 Bullion Boulevard 3B, Winchester, KY 40391
    View details
    Winchester Land for Sale
    $775,000

    Winchester Land for Sale

    Land for sale in Winchester, Kentucky, near major retailers.

    529 Bullion Blvd, Winchester, KY 40391
    View details
    Based on your search, we've compiled 21 Potential Opportunities for your consideration. Besides 10 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 3 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

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

    Lexington Commercial Space For Sale
    Contact for pricing
    4,050 SF

    Lexington Commercial Space For Sale

    First floor medical/office suite near I-75/I-64 and Baptist Health Hamburg.

    2424 Sir Barton Way unit: 125, Lexington, KY 40509
    View details
    Versatile Mixed-Use Commercial Property
    $362,000
    4,500 SF

    Versatile Mixed-Use Commercial Property

    4,500+ sq ft property suitable for warehouse, retail, or office.

    201 Main Street, N Middletown, KY 40357
    View details
    Established Office Suite For Sale
    $189,000
    1,000 SF

    Established Office Suite For Sale

    1,000 SF office suite in Lexington, KY for sale.

    1795 Alysheba Way, Lexington, KY 40509
    View details
    Class A Office Condo
    Contact for pricing

    Class A Office Condo

    Turn-key office condo in Lexington's Hamburg area.

    2704 Old Rosebud Rd, 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.

    Winchester Land For Sale
    $400,000
    2.19 Acres

    Winchester Land For Sale

    2.19 acre commercial land near Winchester Bypass with development potential.

    145 Codella Drive, Winchester, KY 40391
    View details
    Prime Land Near Winchester Bypass
    $650,000
    3.00 Acres

    Prime Land Near Winchester Bypass

    Land available near Winchester Bypass amidst new commercial development.

    205 Codella Drive, Winchester, KY 40391
    View details
    Land Near Winchester Bypass
    $650,000

    Land Near Winchester Bypass

    Land for sale near new development and major retailers.

    205 Codella Dr, Winchester, KY 40391
    View details
    Land Near Winchester Bypass
    $400,000

    Land Near Winchester Bypass

    Land for sale near new development and major retailers.

    145 Codella Dr, Winchester, KY 40391
    View details

    Explore 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.

    10 Court St

    10 Court St

    Office Units • 1,800 SF
    Value Estimation by Request
    10 Court St, Winchester, KY 40391
    View details
    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 Properties & Spaces Investment Opportunities Market Analysis

    Explore 13 office properties & spaces for sale in Winchester, KY, showcased through 10 active listings on our real estate platform. These investment opportunities span a total of 101,364 square feet of properties for sale, with an estimated market value of $7,529,000.

    Sale prices for office spaces in Winchester, KY start at $250,000, averaging $941,125, and reaching up to $1,750,000 — 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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