Holly Winkle

For Holly Winkle, real estate is a way of life. After relocating to Sarasota, Florida, from Chicago, Holly became a full-time Realtor in 2003 and a obtained her Brokers license in 2013. She believes that real estate is about creating a positive experience for buyers and sellers through personal, attentive service. Her warm, empathetic approach has garnered her a stellar reputation founded on abundant communication, genuine relationships, and success.

Consistently ranked a top agent in volume and transactions, Holly has repeatedly proven that she has the knowledge and skill to help both buyers and sellers confidently complete their real estate transactions. The high level of trust Holly’s clients have in her has transformed them into repeat client families — which have now become generational — confidently providing steady referrals. Her established system guides her clients through the real estate process step by step, and her personal touch fosters long-term relationships with her clients.

Holly focuses on the luxury housing market in Sarasota and its neighboring islands as well as east-county communities, including Lakewood Ranch. Through a collaborative approach that coordinates with trusted service providers, fellow brokers and agents, and the clients themselves, Holly creates a fun, stress-free buying and selling experience for everyone.

When she is not working with clients, Holly’s family is her primary focus and source of happiness. She also enjoys dining out at Sarasota’s many exceptional restaurants, playing tennis, boating, and traveling. Holly regularly donates to St. Jude, One Child Matters, and several animal charities, and she aspires to start her own nonprofit to assist mothers suffering from terminal illness.