27-29 South Main Street

27 S Main St, Winchester, KY 40391

  • For Sale $314,900
  • Property Type Retail
  • Property Size 3,132 SF
  • Lot Size 0.13 Acre
  • Date Updated Jul 7, 2025

This is one of the oldest buildings in Downtown Winchester! The main floor has been renovated with large scale windows that look into an open floor plan. There is exposed brick, new lighting and flooring. This main floor also has new HVAC. There's a large parking lot in the back. The upstairs has been demoed and is ready for the finishing touches. Beautiful iron mantels, hardwood floors, new skylights and wonderful woodwork are just a part of what makes this building so unique! It's also in the Opportunity Zone! There are several grant opportunities for this building. Find out more information at downtownwinchesterky.org. The owner is the agent.

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Location

Getting Around

  • Walk Score ®

    79/100 Very Walkable
  • Bike Score ®

    48/100 Somewhat Bikeable
Powered by Walk Score ®
  • City Winchester, KY
  • Zip Code 40391
  • Market Lexington

Points of Interest

  • Speedway

    0.12 miles

  • Shell

    1.58 miles

  • Gasoline Alley

    1.78 miles

  • BP Gas Station

    1.84 miles

  • Maka Mia Pizza on Main

    0.05 miles

  • Pit Masters BBQ

    0.06 miles

  • Amy’s Asian Kitchen

    0.07 miles

  • The Engine House Deli + Pub

    0.09 miles

  • Loma's

    0.10 miles

  • Dairy Queen

    0.16 miles

  • Giovanni's Pizza

    1.55 miles

  • Don Senor

    1.64 miles

  • Little Caesars

    1.68 miles

  • Domino's

    1.76 miles

  • Walmart Supercenter

    1.89 miles

  • Gordmans

    2.21 miles

  • Kroger

    2.24 miles

Frequently Asked Questions

How much does 27-29 South Main Street cost?

The space currently listed for sale at 27-29 South Main Street asks for $314,900.

What is the total square footage of 27-29 South Main Street?

27-29 South Main Street totals 3,132 square feet.

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