View Winston Real Estate for Sale in Oregon. These listing are for Winston properties up to $500,000, and cover the most up-to-date listings for Winston real estate for sale. Winston is a small town in Southern Oregon, just south of Roseburg. A small community, Winston is an excellent choice for those looking for a relaxed and comfortable living experience. Winston residents have access to lots of local amenities, a sunny year-round climate, low crime rates and a stable housing market. Winston has a number of properties available on the market, from open land to custom homes and simple single-family properties. If you're interested in Southern Oregon or Winston, contact Berkshire Hathaway HomeServices Real Estate Professionals for more information about Winston Real Estate for Sale in Oregon.