5 Southwest Florida Waterfront Retreats from Naples to Fort Myers Beach

Along the water’s edge on Fort Myers Beach, this 2-bedroom, 2-bath home (with possible 3/3) pairs a coveted mid-island setting with one of the highest elevations on the island. A wide, deep canal sets the tone for days on the water, with quick access to both the Intracoastal and the Gulf of Mexico. Boaters will appreciate the two private docks and lifts, while quieter moments unfold as dolphins and manatees drift past. The neighborhood’s location keeps everyday life easy—close to the Public, restaurants, and shopping, with beach access reached by bike or a short walk. Post Ian, the home is remodel ready to your specifications, with remediated rooms and a floor plan available to spark what comes next.

Along the water’s edge on Terra Ceia Bay, 5003 Commonwealth Road unfolds as a private tropical retreat with a rare double-lot setting and 150 feet of deep-water frontage. Palm trees sway overhead, dolphins pass by, and sunsets become part of the daily rhythm. Lovingly maintained by the same family since 1965, the 3-bedroom, 3-bath residence carries a sense of character and long-held pride of ownership. With nearly 4,400 square feet under roof, the home offers generous indoor and outdoor living spaces suited to easy entertaining, quiet afternoons, and lingering evenings by the bay. Two lots and 150 feet of seawall create room to live in the home as it is, expand, or reimagine the property into a true waterfront estate—shaped around boating, fishing, and unhurried breezes off the water.

Along the lake’s edge in Valencia Bonita, the coveted Chandon model pairs an open-concept plan with the ease of maintenance-free living and an active social calendar. Crown molding, custom built-ins, and plantation shutters add polish throughout, while full hurricane protection and a whole-house generator bring everyday peace of mind. The kitchen is designed for gathering, with stainless steel appliances, an oversized island, and easy flow to the breakfast nook, dining area, and great room, anchored by a custom accent wall with built-in shelving. The primary suite offers two walk-in closets and a spa-inspired bath with dual vanities, a large walk-in tiled shower, a private water closet, and linen storage. Outdoors, an expansive lanai frames serene water views with a pool, spa, outdoor kitchen, and wall-mounted TV. Beyond the manned gate, enjoy a grand clubhouse, resort pool, fitness studios, courts, trails, and a dog park.

Steps from downtown Naples and tucked away on a private street in the Royal Harbor area, this Old Florida multi-level residence balances proximity with privacy. A new metal roof adds peace of mind, while the absence of HOA fees keeps day-to-day living refreshingly straightforward. The double garage supports an easy coastal routine—whether you’re coming and going for dinner in town or simply enjoying a quieter pace at home. On the ground floor, a bonus guest or mother-in-law suite creates welcome flexibility, with a spacious open area, a private bath, and a screened lanai that extends living space into the breeze. With its thoughtful multi-level layout and secluded setting, the home is designed for hosting, retreating, and settling into Naples life at your own rhythm.

Along the Gulf shoreline on Fort Myers Beach, this beachfront penthouse keeps expansive 12th-floor views of the seashore in constant frame. The outlook is always on display, turning everyday moments into something more cinematic—especially at sunset, best enjoyed from the comfort of the living room. With two bedrooms and two baths, the layout is designed for easy coastal living while the elevation delivers a sweeping perspective over the water. Outside your door, a short walk leads to local restaurants and shops, and a trolley stop out front makes it simple to roam farther afield. Head north to sample nearby offerings, or travel south toward Bonita and Naples when the day calls for a change of scene—then return home as the light fades over the Gulf.