5 Florida Waterfront Estates and Penthouses from St. Petersburg to Naples

Along the water’s edge in Pasadena Isles, this newly completed modern European-style estate by Everstone Development pairs elevated two-story design with direct frontage on the Intracoastal Waterway (Boca Ciega Bay). Inside, an expansive open-concept layout is wrapped in 80 feet of dramatic floor-to-ceiling glass, drawing the horizon into daily life and framing views of the sparkling pool and serene waterway beyond. With five bedrooms and four full bathrooms plus two half bathrooms, the home balances generous scale with an easy, coastal rhythm. Outdoors, a 40-foot covered lanai extends the living space for year-round alfresco dining and entertaining, set against sunset skies. Mornings begin to the gentle sounds of the water; afternoons invite boating and water sports; evenings settle into golden light from the backyard oasis, just a five-minute drive from the beach.

Along the water’s edge on Madeira Beach’s limited-access Crystal Island, this open-water estate pairs privacy with a distinctly modern sense of arrival. Set at the end of a private cul-de-sac, the property enjoys 200 feet of open bay frontage—an everyday backdrop that shifts with the light and tide. Completely reimagined in 2013 with all-new construction, the residence was updated from the essentials out, including a new roof, electric, and plumbing, along with travertine floors and hurricane-grade windows and doors for added peace of mind. Inside, a grand two-story entry sets an airy tone, complemented by a glass elevator that underscores the home’s contemporary polish. Life here unfolds with a quiet, waterfront rhythm—secluded, effortless, and connected to the bay.

Within the exclusive, gated community of Boca Grande Isles, this western-facing waterfront homesite offers 96 feet of direct frontage and approximately 0.30 acres for a carefully considered island retreat. Seamless access to the Intracoastal Waterway and the Gulf—without obstructing bridges—sets an easy rhythm for days on the water. A concrete seawall and picturesque wooden dock bring you immediately to the shoreline, while recent landscaping adds privacy and a sense of natural calm. For those ready to shape what comes next, conceptual house plans by renowned architectural firm Stofft Cooney are available for both one- and two-story designs, supported by a current survey and comprehensive site study. With electricity, sewer, and water already in place—and extensive site preparation completed—the focus can stay on design and lifestyle, moments from Boca Grande’s historic village, beaches, and boating community.

Size: 0.3 acre

Along the waterfront in Bayfront Place, this completely reimagined 3-bedroom penthouse pairs a refined modern coastal aesthetic with expansive living spaces and abundant natural light. Water and city views unfold from three private balconies, extending the open-concept great room into multiple indoor/outdoor settings designed to maximize the bay backdrop. At the center, a gourmet kitchen with a substantial island connects seamlessly to the dining area, creating an easy rhythm for everyday living and entertaining. A split-bedroom layout adds privacy and comfort for both owners and guests. Beyond the front door, Bayfront’s resort-style amenities include two pools, two spas, a fitness center, tennis, pickleball, grilling areas, and lush outdoor gathering spaces, plus on-site waterfront dining, boutique shopping, and a lively cabana bar—an effortless downtown Naples routine, moments from Fifth Avenue South and the Gulf’s white-sand beaches.

Along Estero Boulevard on Fort Myers Beach, this Gulfside parcel offers a rare, build-ready setting in the middle of the island’s everyday energy. The site sits next to Neptune and DiamondHead Resorts and is positioned just one mile from Margaritaville and Time Square, placing beach life, dining, shops, and beach parks within walking distance. Previously, the property operated as a mixed-use development with 15 units—13 residential vacation rental condo units plus two commercial office condo units—making its history as flexible as its location. The offering includes the entire parcel of land, creating a clear canvas for a new luxury development in a corridor defined by resort activity and an easy, on-foot rhythm. Days here would begin and end with the beach close at hand.

Size: 0.4 acre