Winchester, KY Apartment buildings for sale

Historical Landmark Multifamily and Office

$1,595,000

26,124 SF

Historical Landmark Multifamily and Office

2 N Main St, Winchester, KY 40391

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

Significant CAPEX investments in 2022 & 2024, including facade transformation and full restoration.
Currently grossing $168,000 annual rent with a $4,000/month upside, exceeding the 1% rule.
Features 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.
Includes additional space at 4‑10 Main Street, offering potential for tenant improvements and increased cash flow.

Updated: Feb 13

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Winchester Multi-Family Development Opportunity

Pending

$800,000

4.87 Acres

Winchester Multi-Family Development Opportunity

1108 W Lexington Ave, Winchester, KY 40391

Large multi-family development opportunity in Winchester, across from Legacy Grove Park.

Approved plans for a 66‑unit townhome development (with potential for 4 more).
Prime location directly across from Legacy Grove Park.
Large 4.87‑acre property with two additional parcels included.
Zoned PD (Planned Development) with potential for commercial rezoning.
Sewer infrastructure materials already purchased.

Updated: Sep 27, 2025

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Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities

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1,104 SF

Updated Condo in Hamburg Neighborhood

Updated condo with new roof, gutters, and fresh paint.

2905 Affirmed Ct, Lexington, KY 40509

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$1,700,000

Lexington Townhome Portfolio For Sale

Nine townhomes in Lexington with strong renter demand.

3521 Squires Woods Way, Lexington, KY 40515

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Converted Warehouse with Income Potential

$825,000

5,100 SF

Converted Warehouse with Income Potential

Income-producing mixed-use property with residential loft and office rentals.

105 E St, Richmond, KY 40475

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$650,000

9,763 SF

Downtown Richmond Mixed-Use Building

Mixed-use commercial building with retail and residential units.

204-206 S 3Rd St, Richmond, KY 40475

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Winchester, KY Apartment Buildings Investment Opportunities Market Analysis

Explore 2 apartment buildings for sale in Winchester, KY on our real estate platform. These investment opportunities span a total of 221,720 square feet of properties for sale, with an estimated market value of $2,395,000.

Sale prices for two-family homes in Winchester, KY start at $800,000, averaging $1,197,500, and reaching up to $1,595,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Winchester, KY Apartment Buildings for Sale

Historical Landmark Multifamily and Office

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

Winchester Multi-Family Development Opportunity

Large multi-family development opportunity in Winchester, across from Legacy Grove Park.