View Winchester Houses available in Winchester, Kentucky. Kentucky's Bluegrass Region is ripe with beauty, and Winchester sits in the middle of it, surrounded by lush, rolling hills. Winchester is a historic town with lots of small-town charm. Residents benefit from a low cost of living here, with many affordable houses in a very stable housing market. Winchester sits in an area that's blessed with good year-round weather, and local amenities can be found throughout the city. Winchester Houses are available for all budgets, and homebuyers and investors alike will find Winchester a true investment opportunity location. Contact Rector Hayden Realtors today for more information about Winchester Houses and Central Kentucky Real Estate for Sale.