Brookside Naples Real Estate - Homes and Properties for Sale Florida: Brookside centrally located to downtown and 5th Ave, offers a unique setting of single-family homes situated on navigable canals surrounded by tropical foliage. Brookside was built in the early 1960 with low density living on waterfront lots, a tropical haven for boaters and fishing enthusiasts alike. Just a few minutes by boat with just one bridge you’re at Naples Bay and from there right into the Gulf of Mexico where you can enjoy some of the most beautiful sunsets in the world. Brookside is just a short drive from the famous Naples Pier, Tin City, 5th Avenue Shopping District, Naples Beach and more! Neighborhood Schools includes Shadowlawn Elementary, East Naples Middle School, and Gulfview Middle School.