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2 N Main Street, Winchester, KY 40391

Winchester
Local realty services provided by:CENTURY 21 Simpson & Associates
2 N Main Street,Winchester, KY 40391
$1,575,000
  • 37 Beds
  • 20 Baths
  • 26,124 sq. ft.
  • Multi-family
  • Active
Listed by: blanca cheung
Office: tsubaki group, llc.
MLS#:25017572
Source:KY_LBAR

Price summary

  • Price:$1,575,000
  • Price per sq. ft.:$60.29

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!

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Home facts

  • Year built:9999
  • Listing ID #:25017572
  • Added:224 day(s) ago
  • Updated:April 07, 2026 at 12:43 AM

Rooms and interior

  • Bedrooms:37
  • Total bathrooms:20
  • Full bathrooms:19
  • Half bathrooms:1
  • Living area:26,124 sq. ft.

Structure and exterior

  • Year built:9999
  • Building area:26,124 sq. ft.
  • Lot area:0.22 Acres

Schools

  • High school:GRC
  • Middle school:Robert Campbell
  • Elementary school:Justice

Finances and disclosures

  • Price:$1,575,000
  • Price per sq. ft.:$60.29
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