View Winchester Homes available in Winchester, Kentucky. Winchester sits in Kentucky's Bluegrass Region, surrounded by lush, rolling hills and the beauty known throughout this part of Kentucky. Whether you're looking to spend your time in a museum, walking along the streets of a historic downtown, or enjoying the beauty of the area, Winchester is an excellent choice for a home. With a low cost of living, affordable home prices, lots of local amenities and a stable housing market, Winchester homes are a great investment opportunity for any homebuyer or investor. Winchester homes come in all shapes and prices, from affordable simple starter homes to sprawling, luxury estates. Contact Rector Hayden Realtors for more information about Winchester homes and Central Kentucky Real Estate.