Upside Real Estate

In 1985, Judy Black opened her first real estate office in Windermere, Florida, calling it Main Street, REALTORS. Known for luxury home marketing, a service-first mindset, and elevated professionalism, the company grew to 4 traditional offices and 120 talented professionals, selling close to properties over 28 years. In 2019, Judy and company opened UPSIDE Real Estate by reimagining the modern real estate office for accomplished real estate agents looking to join forces and break the mold. UPSIDE may be introducing a fresh taken on our profession, but it was born from a familiar mission – to open doors and change the lives of the neighbors we serve.