5 Premier Florida Homes and Waterfront Retreats in Winter Park and Beyond

On a quiet, tree-lined street in Winter Park, 151 Oakwood Way reads as a true in-city showpiece. Crafted by LunDev Custom Homes, the residence is introduced with a sense of privacy and calm, yet remains firmly in the heart of the city—an address that balances everyday ease with a more tucked-away feel. The setting suggests morning walks beneath a canopy of mature trees and evenings that unwind away from through-traffic, while still keeping Winter Park’s rhythms close at hand. With its “rare” positioning and thoughtful presence on Oakwood Way, it’s a home that feels considered from the outset, offering a refined backdrop for day-to-day living and a setting that invites you to settle in and stay awhile.

Along the water’s edge in Jacksonville’s Epping Forest, this end-unit condominium at Knightsbridge Riverfront Villas has been completely renovated with a one-of-a-kind custom floorplan and meticulous craftsmanship. Wide-plank 100% White Oak Select natural wood floors run through most rooms, complemented by new Marvin windows and doors and finely executed moldings, trim, and interior doors. Breathtaking views stretch across the St. Johns River, the gardens, and the marina at Epping Forest Yacht and Country Club, with spectacular sunsets as a daily backdrop. The three-bedroom, four-bath layout includes an owners suite with oversized custom closets and separate his-and-hers baths, while generous storage supports an easy transition without leaving treasures behind. Four parking spaces and two storage rooms sit in the lower-level garage, and 24-hour security is provided at the manned community entrance.

Along the water’s edge on Massalina Bayou, the Barron & Redding Law Office pairs a rare waterfront setting with an unmatched Panama City address adjacent to the Bay County Courthouse. The two-story masonry building is finished in brick veneer and wrapped in expansive windows, while extensive wood moldings carry a quiet sense of tradition throughout. Inside, the layout is purpose-built and generous: 18 private offices, two conference rooms, a dedicated law library, open administrative space, a reception area, and a large breakroom for daily ease. Built in 1986 and renovated in 2019 following Hurricane Michael, the property was upgraded with storm-rated windows and doors, a new roof, HVAC, and flooring. Outside, mature oak landscaping frames approximately 550 linear feet of waterfront, deep-water dockage, and a large pier looking out to St. Andrew Bay and the Gulf of America.

Along the water’s edge in Rockledge, this custom-built 2023 residence sits within Adelaide’s exclusive guard-gated enclave, pairing modern design with a sense of privacy from the moment you arrive. Set farther back on the lot—yet positioned closer to the lake—the home is oriented to make the setting part of daily life, with sunset views that read as deliberate rather than incidental. Ten-foot doors draw you outward while framing the lake as a constant backdrop, opening into a soaring, open-concept interior that feels expansive and calm. The result is a layout designed for easy flow and unhurried evenings, where light, water, and sky set the rhythm of the day and the architecture simply follows.

Along the Banana River on over half an acre, this rare Lansing Island estate frames daily life with a quiet sense of waterfront ease. Set behind the gates of an exclusive enclave in Indian Harbour Beach, the residence is defined by a material palette that speaks to careful craftsmanship rather than excess. Marble and wood floors create a refined rhythm from room to room, complemented by travertine details and coral stone castings that add texture and warmth. Solid-core doors underscore the home’s substantial build, lending privacy and a satisfying heft to everyday moments. Here, luxury reads as enduring and tactile—cool stone underfoot, rich wood tones, and riverfront surroundings that invite a slower pace from morning to evening.