2 N Main St Winchester, KY 40391
Estimated payment $10,115/month
About This Home
Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.
Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC apartments and 2 renovated ground-floor offices totaling 20 income-producing units. Additional space at 4-10 Main Street offers a blank canvas for tenant improvements and added cash flow. Downtown Winchester is thriving — turn-key, stabilized, and priced to sell. Seize this opportunity!
Property Details
Home Type
- Multi-Family
Lot Details
- 9,583 Sq Ft Lot
Interior Spaces
- 26,124 Sq Ft Home
- 4-Story Property
Bedrooms and Bathrooms
- 37 Bedrooms
Schools
- Justice Elementary School
- Robert Campbell Middle School
- Grc High School
Community Details
- 2 Buildings
- 20 Units
- Downtown Subdivision
Listing and Financial Details
- Assessor Parcel Number 054-3209-018-020
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2024 | -- | $0 | $0 | $0 |
| 2023 | $1,469 | $150,000 | $0 | $0 |
| 2022 | $1,478 | $150,000 | $0 | $0 |
| 2021 | $1,473 | $150,000 | $0 | $0 |
| 2020 | $1,476 | $150,000 | $0 | $0 |
| 2019 | $1,484 | $150,000 | $0 | $0 |
| 2018 | $1,466 | $150,000 | $0 | $0 |
| 2017 | $2,453 | $250,000 | $0 | $0 |
| 2016 | $365 | $250,000 | $0 | $0 |
| 2015 | $2,403 | $250,000 | $0 | $0 |
| 2013 | -- | $250,000 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 04/07/2026 04/07/26 | Price Changed | $1,575,000 | -1.3% | $60 / Sq Ft |
| 02/13/2026 02/13/26 | For Sale | $1,595,000 | 0.0% | $61 / Sq Ft |
| 12/31/2025 12/31/25 | Off Market | $1,595,000 | -- | -- |
| 08/09/2025 08/09/25 | For Sale | $1,595,000 | -- | $61 / Sq Ft |
Source: ImagineMLS (Bluegrass REALTORS®)
MLS Number: 25017572
APN: 0543209018020
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Ask me questions while you tour the home.