View Winchester Houses for Sale in Winchester, Kentucky. Winchester sits 20 miles east of Lexington and has so much to offer residents. From a friendly community to lots of local amenities, Winchester is an excellent place to call home. Whether you're interested in walking along the historic downtown, checking out museums, enjoying outdoor recreation, or partaking of the offerings of Kentucky's Bluegrass Region, Winchester shouldn't be missed. Winchester Houses for Sale come in all shapes and prices, from single-family homes, to sprawling luxury estates, Winchester has the home you're looking for. Contact Rector Hayden Realtors today for more information about Winchester Houses for Sale and living in the Lexington/Central Kentucky area.