2 N Main St Winchester, KY 40391
Estimated payment $10,082/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
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| 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
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| 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 |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | -- | -- |
Source: ImagineMLS (Bluegrass REALTORS®)
MLS Number: 25017572
APN: 0543209018020
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The information is being provided by LBAR Multiple Listing Service. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 LBAR Multiple Listing Service. All Rights Reserved.
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Ask me questions while you tour the home.