About Tommy

Tommy Medawar is a dedicated real estate broker with deep roots in Chicago’s property market. With a family background spanning 40+ years in real estate investment, construction, property management, and brokerage, he brings insider knowledge and hands-on experience to every deal. Prior to becoming a full-time broker, Tommy spent seven years as a top-producing IT sales professional, managing over $40 million in annual sales and earning national recognition. During that time, he personally invested in over a dozen properties, developing expertise in negotiation, construction, and property evaluation. Now, as a broker specializing in small-market multifamily and single-family residential real estate, Tommy focuses on Chicago’s most dynamic neighborhoods—Old Town, Lincoln Park, Lakeview, Wrigleyville, Bucktown, Wicker Park, and Logan Square. His firsthand experience as an investor and his proven track record in sales make him a trusted advisor for buyers and sellers alike. While not working, Tommy enjoys golfing, hiking, traveling, and spending time outdoors.