View Winchester Homes for Sale in Winchester, Kentucky. Winchester sits 20 miles east of Lexington in the Bluegrass Region of Kentucky. Surrounded by beautiful rolling hills, Winchester exudes a charm not found in other Kentucky cities. With a historic downtown and lots of activities for every interest, Winchester shouldn't be missed on the Central Kentucky Real Estate Market. Winchester Homes for Sale are available for all budgets, with many affordable options with modern fixtures and bonuses on the market. Winchester homes for sale also come in luxury options, with sprawling estates available. Winchester residents have access to amenities, outdoor recreation and activities. Contact Rector Hayden Realtors today for more information about Winchester Homes for Sale and living in Central Kentucky.