5 Waterfront and Private Florida Retreats in Naples and Fort Myers

Set on 1.14 acres in Logan Woods, 5179 Sycamore Drive offers a rare sense of space and privacy with the ease of non-HOA living. A private pool anchors the outdoor setting, creating a relaxed backdrop for everyday life—morning swims, quiet afternoons, and unhurried evenings at home. Inside, the layout is designed for flexibility, with two bedrooms plus an additional space that can adapt as a home office, guest area, or even a potential third bedroom, depending on your needs. The overall effect is simple and livable: room to spread out, options for how you use the interior, and a property that balances privacy with an accessible Naples location. Life here can move at your own pace, indoors and out.

Price: $600,000 (Sold)

With the lake as its backdrop, this second-floor condo in the gated community of Carlton Lakes pairs tranquil water and fountain views with an easy, everyday layout. Vaulted ceilings bring volume to the main living area, while a spacious kitchen opens directly to the gathering space—ideal for entertaining. Two outdoor lanai spaces extend the living experience, and electric hurricane shutters on the rear lanai add peace of mind. Inside, freshly painted walls set a crisp tone, complemented by elegant plantation shutters and upgraded carpet in the bedrooms and den. Top-of-the-line stainless steel appliances finish the kitchen with a polished edge. Community amenities include bocce and tennis courts, a 60-foot lap pool, hot tub, fitness room, clubhouse, and tot lot. Set on a serene cul-de-sac, it’s a leisurely walk to Seed To Table and a short drive to Mercado and Naples’ white-sand beaches.

Set against the Intracoastal Waterway in Largo, this contemporary waterfront estate is designed to keep the horizon close at hand. An open floorplan and five spacious bedrooms create an easy rhythm for daily living, while walls of glass draw in natural light and sweeping water-and-sky views, including vivid sunset panoramas. A 3-stop elevator adds everyday convenience, and the kitchen pairs efficiency with polish, featuring Subzero and Wolf appliances alongside beautiful water views. The primary suite sits on the main floor, elevated above the floodplain for added peace of mind; bedroom two, currently used as an office, is also on the main living level, with additional guest bedrooms upstairs for privacy. Outdoors, a pool deck, private pool, dock, and boat lift shape days around the water, and evenings on the west-facing terrace linger long after the sun slips toward the Gulf.

Price: SOLD

Along the Caloosahatchee River in Fort Myers, this Tuscan-inspired estate pairs artisanal detail with a front-row seat to sweeping western exposure and open-water sunset views. Built by Pinnacle Awards winner Norm Bloxham, it’s positioned on higher ground and remained fully protected with no interior water intrusion during Hurricane Ian. Inside, a grand foyer introduces soaring cathedral ceilings, a statuesque fireplace, and a Juliet balcony with Italian-villa romance. Spacious living areas set the stage for entertaining, while a private home theater and custom-designed fitness space invite easy nights in. The lower-level primary suite features a jetted tub and outdoor atrium; upstairs, a game room and two bedrooms—including an additional master suite with a huge sitting area—open to a large balcony overlooking the water features below. A resort-style pool and spa with a stone-wall waterfall completes the outdoor experience, with quick Gulf access for boaters.

Price: SOLD

Along the water’s edge on over half an acre of direct riverfront, this 2009 residence by luxury builder Norm Bloxham frames sweeping river views and western sunsets with a finely crafted sense of ease. The thoughtful plan includes four bedrooms, five baths (three full and two half), and a private study, set beneath soaring ceilings. A chef’s kitchen with gas cooktop and statement vent hood anchors daily life, while an inviting bar and sitting area open to balcony access. Two river-view balconies strengthen the indoor-outdoor connection, including a private balcony off the primary suite, paired with an oversized walk-in closet and abundant storage throughout. Outside, a resort-style pool and spa, fully equipped outdoor kitchen, and fully fenced hibiscus-lined yard create a lush retreat, complemented by mango, avocado, orange, and guava trees. Minutes from the Fort Myers River District, it keeps culture, markets, and boating close at hand.

Price: SOLD