Privacy, scale, and life organized around water and open air. From a gated Gulf-to-Bay compound on Manasota Key to 270 feet of Sarasota Bay frontage on Longboat Key, boating and panoramic views take center stage. Siesta Key contributes a near one-acre Gulf-front homesite within the guarded Sanderling Club, while Sanibel delivers an elevated, resort-minded beachfront residence. Even inland, South Tampa’s nearly two-acre parcel underscores the appeal of legacy land.
Ultimate Waterfront Legacy Estate | $9,900,000


Michelle Hupp

Michelle Hupp
Along the gated north end of Manasota Key, this Gulf-to-Bay estate unfolds across approximately 1.1 acres, balancing architectural elegance with true waterfront privacy. Built by KIMCO and designed by Suncoast, the concrete main residence is complemented by a separate guest house on the Bay with Intracoastal views. Days move easily between private beach access, expansive terraces, a resort-style pool, and an entertaining pavilion with a full outdoor kitchen, while a bayfront dock with lift extends the living experience onto the water. Inside, curated finishes and marble inlays frame sweeping Gulf-to-bay vistas. The great room rises beneath a soaring 35-foot Cypress ceiling, anchored by Baccarat chandeliers and a two-story wall of glass overlooking the Gulf. In the chef’s kitchen, dual islands pair with custom cabinetry, Sub-Zero refrigeration, and Wolf appliances for effortless hosting.
- Price:
- $9,900,000
- Size:
- 7,515 sq ft
- Contact:
- Michelle Hupp, Keller Williams Island Life Real Estate, 941.773.5464
Bayfront Bliss Coastal Luxury With Unmatched Sarasota Bay Views | $9,400,000


Kathleen Callender

Kathleen Callender
Along Sarasota Bay on Longboat Key, this sophisticated coastal modern residence claims 270 feet of waterfront and opens with a serene, far-reaching panorama stretching from the Ringling Museum to Downtown Sarasota. Bay views carry through every room, keeping the water in constant conversation with daily life. For boaters, the dock is thoughtfully equipped with two jet ski lifts and a 13,000-pound boat lift, making spontaneous afternoons on the bay feel effortless. Inside, five ensuite bedrooms and five baths are complemented by a dedicated office. Guests can settle into a private second-floor retreat with its own kitchenette, family room, and game area. An elevator serves every level, including the three-car garage, bringing ease to a multi-story layout. Close to the Longboat Key Club’s golf, restaurants, and beach amenities, the pace here stays unmistakably island-minded.
- Price:
- $9,400,000
- Size:
- 5,982 sq ft
- Contact:
- Kathleen Callender, Florida Capital Realty, 941.321.3115
4623 W San Jose St | $8,499,000


Listing agents: Toni Everett & Allan Mezrah

Listing agents: Toni Everett & Allan Mezrah
Set on one of the largest privately held parcels in South Tampa, this estate unfolds across nearly two full acres, offering a rare sense of privacy, presence, and long-term flexibility. Deeded for a single-family residence with an existing guest house, the property reads as a true compound—intimate in daily living, yet expansive in how it can be used and enjoyed. The main residence is described as featuring 5–6 bedrooms, creating room for quiet retreats, generous hosting, or spaces that adapt to work and leisure over time. With its scale and seclusion in Tampa, the setting feels deliberately removed, while still rooted in a well-established neighborhood fabric—an address designed for those who value both discretion and possibility.
- Price:
- $8,499,000
- Size:
- 7,894 sq ft
- Contact:
- Toni Everett & Allan Mezrah, The Toni Everett Co., 813.839.5000 , 813.918.2954
An Extraordinary Gulf-Front Estate Opportunity | $8,000,000


Listing agents: Kris Niehaus & Jack Dell’amico

Listing agents: Kris Niehaus & Jack Dell’amico
Along the water’s edge on the Gulf of Mexico, 7740 Sanderling Road offers nearly one acre of pristine beachfront on Siesta Key—an increasingly rare setting for a legacy, Gulf-front estate. With expansive frontage and generous dimensions, the homesite provides an exceptional canvas for a custom residence, with sweeping panoramic Gulf views, spectacular year-round sunsets, and direct access to one of the world’s most celebrated beaches. Set within the prestigious Sanderling Club—Siesta Key’s only private, gated Gulf-front community with 24-hour manned security—the property pairs privacy with a thoughtfully preserved coastal environment. Residents enjoy a private beachfront clubhouse overlooking the Gulf, tennis and pickleball courts, a marina with boating access to Sarasota Bay, Heron Lagoon, scenic nature canopy, and beautifully maintained grounds—an inviting backdrop for a life shaped by sea air and open horizons.
Size: 0.89 acres
- Price:
- $8,000,000
- Contact:
- Kris Niehaus & Jack Dell’amico, Coldwell Banker Realty, 941.376.4950 , 941.281.5225
Private Beach Access • Gulf Front • Elevated Construction | $7,250,000


Greg Demaras

Greg Demaras
Along the Gulf-front on Sanibel Island, this elevated residence is defined by panoramic water views and the rare ease of direct beach access. Refined coastal architecture frames a private retreat designed for effortless indoor-outdoor living, where the horizon becomes part of the daily rhythm. Outside, a resort-style pool extends the at-home experience beyond the walls, balancing relaxation with the quiet energy of the shoreline. The setting captures the natural beauty and exclusivity that have long shaped Southwest Florida’s premier island lifestyle—salt air, open sky, and the simple luxury of stepping from home to sand. Here, days naturally move between water, sun, and shaded downtime, with the Gulf always close at hand.
- Price:
- $7,250,000
- Size:
- 3,604 sq ft
- Contact:
- Greg Demaras, Pfeifer Realty Group LLC, 917.837.7009


















