View Winchester Real Estate available in Winchester, Oregon. Sitting in Oregon Wine Country, Winchester offers affordable real estate with easy access to Roseburg, which is only four miles south. A serene small town where homes sit on large lots, Winchester is an excellent choice for Oregon Real Estate in the Umpqua Valley. Winchester residents benefit from a low cost of living, low crime rates, high graduation rates, and if you can't find what you're looking for in Winchester, Roseburg is only minutes away. If you're interested in Southern Oregon Real Estate or living in Winchester, contact Berkshire Hathaway HomeServices Real Estate Professionals for more information about Winchester Real Estate for Sale in Oregon.