Meet Our Team

Toby Anastasio is the owner and broker of Winding Creek Properties, a Florida real estate brokerage firm. He is also the broker for a Georgia based real estate firm, Twin Oaks Realty.

Toby was born and raised in Melbourne, Florida. He grew up working a generational cattle, orange grove, and hay farm operation. After graduating, Toby pursued a career as an electrician, working for companies like EG&G and Boeing, and managing the high voltage operation for the Kennedy Space Center. In 1996, he and his beloved wife Pamela opened their business Richard’s Paint and Decorating Centers. These two retail paint and decorating centers served Brevard County for 12 years. Through the operating of these retail stores, Toby came to appreciate how important relationships in business are. He takes this appreciation into his dealings each day with his real estate clients, most of them becoming lifelong friends.

Toby has been an avid outdoorsman his entire life and has a passion for the land that makes the Southeast unique. This passion for the land is what drew him to become a real estate professional over the last 18 years. As a six-generation native Floridian, Toby understands what makes Florida so special: from the rolling hills of North Florida to the rich agricultural landscapes and pristine waterscapes. Toby’s passion and depth of knowledge continues to be an asset to his clients. He has a unique expertise of brokering the purchase and sale of large-scale agriculture farms and investment properties. He has a thorough knowledge and specialty in Blueberry operations.

Faith and Family are the foremost of Toby’s core values. He has a great love for God that shows in his honest and transparent dealings with his clients. You will find him spending most of his days outdoors on his farm in rural North Florida with the loves of his life: his beautiful wife of 45 years, Pamela, their 3 children, 6 wonderful grandchildren, and his Labrador, Maizey.