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    Winchester, KY Office Spaces for Sale

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    Two-Story Medical Office and Apartments
    Updated: Mar 2
    Two-Story Medical Office and Apartments

    218 S Maple Street, Winchester, KY 40391

    $750,000
    6,110 sqft · 0.70 AC lot
    Two‑story building suitable for commercial and residential use.
    Main floor configured as a 'ready to go' office space.
    Two large apartments on the second floor with separate outside entry.
    Detached 3‑bay garage and large asphalt parking lot (25+ vehicles).
    Zoned heating and cooling with heat pump system.
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    This listing looks promising.

    Here's a quick look at some key insights for

    218 S Maple Street, Winchester, KY 40391

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    • Est. Cap Rate

      8.6%
      Above avg (5.9%)

    • Est. NOI

      $65K
      Annual

    • Price @ 7% Cap

      $925K
      Above asking
    View Property Analytics
    Renovated Medical Office Building
    Updated: Jun 30
    Renovated Medical Office Building

    308 W Lexington Avenue, Winchester, KY 40391

    $825,000
    3,570 sqft · 0.57 AC lot
    Recently renovated office space for a medical practice, built in 1967
    Main level features bright reception, large office, file room, kitchen area, and 5 exam rooms
    Back of building includes 2 suites that can be leased separately or incorporated into the main space
    Unfinished basement area could be up‑fitted for additional office space
    Generous parking lot with access to a back alley way
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    Downtown Retail and Live-Work Building
    Downtown Retail and Live-Work Building

    18 N Main Street, Winchester, KY 40391

    $199,900
    4,300 sqft · 0.12 AC lot

    Renovated downtown building with updated main-level systems, storefront, and interior space adaptable for live-work or additional business.

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    Freestanding Office Building For Sale
    Freestanding Office Building For Sale

    321 Venable Road, Winchester, KY 40391

    $750,000
    16,857 sqft · 10.00 AC lot

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

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    Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center
    Prime Land on Bypass Road
    Prime Land on Bypass Road

    529 Bullion Boulevard 3B, Winchester, KY 40391

    $775,000
    2.60 AC lot

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

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    Free Standing Office Building
    Free Standing Office Building

    920 bypass Road, Winchester, KY 40391

    $799,000
    7,200 sqft · 0.53 AC lot

    7,200 SF office building on 0.53 acres.

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    Historic Opera House For Sale
    Historic Opera House For Sale

    101 S Main, Winchester, KY 40391

    $1,750,000
    20,548 sqft · 0.23 AC lot

    Fully-restored Opera House in Downtown Winchester with multiple uses.

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    Winchester Land Near Bypass Road
    Winchester Land Near Bypass Road

    529 Bullion Boulevard, Winchester, KY 40391

    $575,000
    2.60 AC lot

    Land available in Winchester, Kentucky, near retail centers.

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    Prime Land in Winchester, KY
    Prime Land in Winchester, KY

    609 Bullion Boulevard, Winchester, KY 40391

    $550,000
    3.00 AC lot

    Ideally located land suitable for retail, office, storage, mixed-use development.

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    Winchester Land for Sale
    Winchester Land for Sale

    529 Bullion Blvd, Winchester, KY 40391

    $575,000
    1.00 AC lot

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

    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.

    Opportunities in Nearby Cities

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

    Basement Office Suite with Conference Room
    Basement Office Suite with Conference Room

    1795 Alysheba Way Ste 2202, Lexington, KY 40509

    $189,000
    1,000 sqft

    Basement office condominium with hardwood floors, 9-foot ceilings, and dedicated reception, kitchen, and conference space.

    View details
    Established Office Suite For Sale
    Established Office Suite For Sale

    1795 Alysheba Way, Lexington, KY 40509

    $189,000
    1,000 sqft

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

    View details
    Hamburg Pavilion Office Suites
    Hamburg Pavilion Office Suites

    2452 Sir Barton Way, Lexington, KY 40509

    Contact for pricing
    2,549 sqft

    Two office suites in a premier shopping and business destination.

    View details
    Versatile Mixed-Use Commercial Property
    Versatile Mixed-Use Commercial Property

    201 Main Street, N Middletown, KY 40357

    $362,000
    4,500 sqft · 0.99 AC lot

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

    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.

    Richmond, KY Commercial Land
    Richmond, KY Commercial Land

    2725 Lexington Road, Richmond, KY 40475

    $400,000
    2.00 AC lot

    Two acres of commercial land with I-75 access.

    View details
    Commercial Land in Prime Location
    Commercial Land in Prime Location

    1 Tighlman Way, Mt Sterling, KY 40353

    $105,000
    1.59 AC lot

    1.5 acre commercial lot with high exposure and bypass access.

    View details
    Commercial Land in Mt Sterling
    Commercial Land in Mt Sterling

    1 Tighlman Way, Mt Sterling, KY 40353

    $105,000
    1.59 AC lot

    1.5 acre commercial lot with high exposure and bypass access.

    View details
    Mixed-Use Industrial Building
    Mixed-Use Industrial Building

    125 S Queen. Street, Mt Sterling, KY 40353

    $254,000
    3,000 sqft · 1.50 AC lot

    A 3,000+/- sq. ft. building on a 1.5-acre lot with parking and flexible office and warehouse space.

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    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
    Office Units

    10 Court St, Winchester, KY 40391

    Value Estimation by Request
    1,800 sqft
    View details
    1129 Lexington Ave
    OFFICE BUILDING

    1129 Lexington Ave, Winchester, KY 40391-1134

    Value Estimation by Request
    2,310 sqft · 0.17 AC lot
    View details
    175 Hospital Dr
    PROFESSIONAL BUILDING

    175 Hospital Dr, Winchester, KY 40391-9591

    Value Estimation by Request
    45,000 sqft · 30.26 AC lot
    View details

    Winchester, KY Office Spaces Market Trends and Statistics

    Explore 13 office spaces for sale in Winchester, KY, showcased through 10 active listings on our real estate platform. These investment opportunities span a total of 58,585 square feet of properties for sale, with an estimated market value of $5,073,900.

    Sale prices for office spaces in Winchester, KY start at $199,900, averaging $845,650, 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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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Office Units 10
    Office buildings 3
    Medical Office Space 2

    Demographics Overview

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

    High-Yield Neighborhoods for Investment

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

    Neighborhood Average Price
    40391 $801.3K

    Taxes & Financing

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

    Listings Trend

    New vs delisted commercial listings in Clark County

    New Delisted

    Total CRE Inventory on Market (SF)

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