2 homes in 1! Major renovations in 2004 2017 and 2023! In the heart of Naples "Olde Florida" meets a Hemingway-esque tropical setting. This enchanting 5-bedroom, 4-bath residence, spans a lush oak filled 1.29 acres with its own island on Rock Creek. A rare combination of privacy, with close in town convenience. The 2 stories feature 3 bedrooms and 3 baths upstairs. The open concept kitchen and living room with vaulted ceilings and 27-foot high cupola add wow, beautiful heart pine floors to tie it all together. Large master suite offers a private deck & new custom bath. First floor has a new, separate mother-in-law suite w/2 bedrooms, 1 full bath, kitchen & laundry. Perfect for guests or potential income generation. An amazing pool w/spa and 3 decks offer space for relaxation and entertainment. Surrounded by Oak trees and nature, this home has privacy and peace, yet just minutes from Old Naples attractions, 5th Ave, 3rd St, Tin City, Marinas, The Greenway, Pier & world-class beaches. Car & toy people will love the 5-car garages. The property's real charm lies in its personal oasis. A scenic walk through lush tropical flora leads to a creekside firepit. A perfect home & space to raise your family.