27-29 South Main Street

For Sale

27 S Main St, Winchester, KY 40391

This Winchester property for sale is located at 27 S Main St. The current listed sale price for 27-29 South Main Street is $314,900. 27-29 South Main Street is situated on a lot that is 0.13 acre in size.

Contacts

broker
Lara Thornbury

Block+Lot

Property Details

  • 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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Getting around

  • 79/100

    Walk Score ®

  • 48/100

    Bike Score ®

Powered by Walk Score ®

Location

  • 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

In-Depth Research Available for this Property

Access more in-depth information about this property — including ownership, tenant details, property characteristics and transaction history, along with local market insights and much more — on CommercialEdge.

Contact Listing Broker
broker
Lara Thornbury

Block+Lot

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