Imagine owning a slice of Florida’s most coveted coastline, where sprawling waterfront estates redefine luxury living. From the historic charm of Captiva Island’s Teddy Roosevelt-linked boathouse to the expansive, gated grounds of Snell Isle, these six extraordinary properties offer unparalleled privacy, direct Gulf access, and resort-style amenities. Nestled in prime locations like St. Petersburg and Manasota Key, they blend architectural grandeur with the potential for bespoke legacy estates. Each home or lot promises a rare waterfront lifestyle, steeped in exclusivity and cultural significance, waiting to be discovered.
15735 Captiva Drive | $11,900,000


Valerie Tutor

Valerie Tutor
Set against the shimmering waters of the Gulf and the serene Bay, this extraordinary estate on Captiva Island offers a rare waterfront lifestyle defined by natural beauty and timeless elegance. Spanning from beach to bay, the property captures mesmerizing sunrises and sunsets, with every detail reflecting meticulous renovations. The main residence blends sophistication with comfort, boasting airy spaces, shell stone floors, soaring ceilings, and panoramic views that inspire awe. Seamless indoor-outdoor living unfolds through pocketing sliders, connecting expansive entertaining areas to a stunning pool and spa framed by lush surroundings. A historic boathouse, once a retreat for Teddy Roosevelt in 1917 and listed on the Historic Register, now serves as a charming guest cottage with updated charm and captivating bay views. This estate embodies the ultimate island legacy, harmonizing history, luxury, and the captivating allure of waterfront living.
- Price:
- $11,900,000
- Size:
- 6,313 sq ft
- Contact:
- Valerie Tutor, Kingfisher Real Estate Inc., 239.834.8141
Rare Double Waterfront Homesite | $10,000,000


Tom O’Neill

Tom O’Neill
Perched in the prestigious Snell Isle neighborhood, 140 Brightwaters and 105 Estado Way combine to form a rare 0.77-acre waterfront homesite, ideal for crafting a legacy estate. With 75 feet of direct bay and harbor frontage, this elevated property offers protected boating water, a private dock, and a boatlift supporting up to 13,000 pounds, accommodating yachts as large as 60 feet. Unobstructed access to the open Gulf enhances the allure for avid boaters. The expansive lot size invites a grand residence with generous setbacks, resort-style amenities, and dual entrances on Brightwaters Boulevard and Estado Way, limited only by imagination. Scenic bay views frame the setting, while the proximity to downtown St. Petersburg—mere minutes away—brings cultural attractions, fine dining, and convenient access to highways and airports. This is a natural canvas for a multi-generational retreat to cherish for decades.
Size: 0.42 & 0.35
- Price:
- $10,000,000
- Contact:
- Tom O’Neill, Charles Rutenberg Realty, Inc, 727.244.4141
319 12th Ave NE | $2,700,000


Tom O’Neill

Tom O’Neill
Welcome to this stunning newer home (2018) in the heart of St. Petersburg’s Historic Old Northeast. This five bedroom beauty is beckoning you and your family to all it has that will enhance your life, along with its proximity to downtown St. Petersburg, with its cultural jewels, parks, restaurants, and inviting waterfront. As you enter this amazing home, the gleaming wood floors lead you to the dining room, spacious kitchen, and family room. There is also a large office on this level. As you wander upstairs, you will find four large bedrooms, perfect for family and/or guests. There is a private living room, and this leads you to your considerable primary suite. The primary bath has a spa-like feel to it, with its free-standing soaking tub, double vanity, and a large walk-in shower. This leads into a commodious walk-in closet. It’s just a comfortable stroll to our vibrant downtown. Our glistening waterfront that stretches for miles is just a short walk from your front door. We have three airports, all within 30 minutes of your home. Public and private schools are close by, and are highly thought of. These are just a few highlights of this amazing home, and our flourishing city. Make the call to come see it! You won’t be disappointed.
- Price:
- $2,700,000
- Size:
- 3,652 sq ft
- Contact:
- Tom O’Neill, Charles Rutenberg Realty, Inc, 727.244.4141
ResortStyle Waterfront Estate On Lemon Bay | $11,900,000


Brian Giacomello

Brian Giacomello
Rising above nearly 3 private acres along Lemon Bay, this Mediterranean-inspired estate offers 12,789 square feet of resort-style living on Florida’s Gulf Coast. Enter through grand gates to a sweeping driveway, framed by mature oaks, serene ponds, cascading waterfalls, and curated sculptures. The expansive grounds feature manicured lawns, a putting green, bocce and volleyball courts, and abundant outdoor recreation spaces. Inside, a dramatic two-story foyer with double glass doors and stained-glass transoms welcomes you, leading to interiors adorned with coffered ceilings, marble floors, and eight fireplaces. With six ensuite bedrooms, 9.5 baths, a chef’s kitchen boasting dual islands, and rooftop terraces for sunset Gulf views, every detail exudes sophistication. Outdoor amenities include a 30×50 saltwater pool, full kitchen, shaded terraces, and a private dock with Gulf beach access. A tiled garage for up to 30 vehicles completes this extraordinary mountain-elevated retreat.
- Price:
- $11,900,000
- Size:
- 12,789 sq ft
- Contact:
- Brian Giacomello, William Raveis, 239.281.5269
773 N Manasota Key Road | $5,485,000


Cheryl Hayek

Cheryl Hayek
Set against the serene backdrop of Manasota Key, 773 North Manasota Key Road offers an unparalleled Gulf-to-Bay lifestyle. Each day begins with the gentle sunrise over Lemon Bay, where boats drift quietly and birds take flight in the soft morning light. By afternoon, the Gulf of Mexico beckons, inviting barefoot strolls along your private beachfront, with endless horizons to soothe the soul. As evening falls, vibrant sunsets over the Gulf transform into a cherished daily ritual. Architecturally timeless, this residence prioritizes proportion and flow, with every line and space crafted to frame breathtaking water views. Seamless indoor-outdoor transitions balance private retreats with inviting gathering areas, creating a home that feels both grounding and expansive. Rare on a barrier island, this property embodies calm authenticity, offering a true sense of belonging amidst two captivating bodies of water.
- Price:
- $5,485,000
- Size:
- 5,248 sq ft
- Contact:
- Cheryl Hayek, Coldwell Banker Sunstar Realty, 732.539.5777
Gecko House | $1,890,000


Traci Creighton

Traci Creighton
Positioned along the serene shores of Manasota Key, Gecko House emerges as a captivating waterfront retreat with deeded beach and bay access. This fully updated quadplex offers a resort-like ambiance, complete with a heated pool, private dock, and kayak launch, inviting a lifestyle of leisure and exploration. Surrounded by mature coastal landscaping, graceful bamboo, and towering oak trees, the property exudes a secluded tropical charm, creating a peaceful escape from the everyday. The top-floor residence, spanning 1,419 square feet, features two expansive bedrooms, two full bathrooms, a modern open kitchen, and in-unit laundry. A large, sunlit balcony provides the perfect spot for evening relaxation, overlooking the tranquil surroundings. With meticulous maintenance and a design focused on comfort, Gecko House promises an unparalleled blend of privacy and natural beauty on the Key.
- Price:
- $1,890,000
- Size:
- 3,174 sq ft
- Contact:
- Traci Creighton, Keller Williams Island Life Real Estate, 941.451.9419



















