Former The Old South Inn FSBO in Downtown Winchester, KY

Property Description

This 5-bedroom historic property For Sale By Owner in downtown Winchester, KY is a rare and iconic landmark offering endless potential for residential, commercial, or mixed-use purposes.
Formerly known as The Old South Inn, this well-recognized property has served the community for decades, including many years as professional medical offices, and now presents a unique opportunity to reimagine a piece of Winchester history in a prime downtown location.
The main level is ideally suited for professional offices, boutique businesses, studios, or a live-work setup, while the upper level features two full apartments, creating excellent income-producing potential or private living space.
One of the most exceptional features of this property is the availability of approximately 25 on-site parking spaces, along with a detached three-car garage, a true rarity in downtown Winchester.
The property also includes a beautiful open lawn and expansive greenspace, perfect for entertaining, outdoor gatherings, gardening, or enjoying a peaceful retreat in the heart of the city.
Zoned for both residential and commercial use, this versatile property allows for multiple configurations, including operating a business downstairs with rental units above, converting the entire structure into a stunning historic residence, or creating a unique mixed-use investment.
With thoughtful updates, the building can easily transition back into a home while preserving its historic charm and character.
Rich in history and full of opportunity, this 5-bedroom house for sale in Winchester, KY FSBO is a one-of-a-kind offering ready for its next chapter.

Details & Amenities

• Heating:

• Cooling:

• Auxiliary SQ FT: 200

Listing History

Property Location

218 South Maple Street, Winchester, KY 40391, USA, City - Clark County