2 N Main St Winchester, KY 40391
Estimated payment $9,811/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 |
|---|---|---|---|---|
| 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
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.
- 17 W Lexington Ave
- 39 S Highland St
- 101 E Lexington Ave
- 24 N Burns Ave
- 146 W Lexington Ave
- 133 S Highland St
- 101 S Burns Ave Unit 1,2,3,4
- 102 W Hickman St
- 217 S Highland St
- 221 S Highland St
- 218 E Washington St
- 214 S Burns Ave
- 220 E Washington St
- 233 E Washington St
- 122 Calloway St
- 149 Winn Ave
- 220 Jackson St
- 228 Jackson St
- 17 Euclid Ave
- 297 S Main St
- 27 E Washington St
- 16 Central Ave Unit A
- 510 College St
- 117 Linden Ave Unit B
- 300 C G Stephenson Dr
- 260 Oxford Dr
- 900 Westwood Dr
- 4971 Old Boonesboro Rd
- 4033 Bacopa Place
- 2085 Falling Leaves Ln
- 840 Hays Blvd
- 3293 Sweet Clover Ln
- 139 Peacock Rd
- 1212 Iron Lace Ct
- 6600 Man o War Blvd
- 3096 Roundway Down Ln
- 1409 Pleasant Ridge Dr
- 2785 Polo Club Blvd
- 2920 Polo Club Blvd
- 2920 Polo Club Blvd
Ask me questions while you tour the home.