313 LOOKOUT POINT DRIVE, Osprey, FL 34229

• 4 beds |
• 5 baths |
• 5,337 sqft

Property Description

Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.

Listing Status:

Active

Date Added:

April 7, 2026

Data Last Updated:

June 28, 2026 at 7:23AM

Listing Office:

MICHAEL SAUNDERS & COMPANY : 941-951-6660

Listing Agent:

Natalie Gutwein : 941-993-2660

MLS ID:

A4688995

Interior

• General: Ceiling Fans(s)Central VaccumCrown MoldingEat-in KitchenHigh CeilingsLiving Room/Dining Room ComboOpen FloorplanPrimary Bedroom Main FloorThermostatWalk-In Closet(s)Wet Bar
• Rooms: AtticBonus RoomDen/Library/OfficeGreat RoomStorage Rooms
• Appliances: Bar FridgeBuilt-In OvenCooktopDishwasherDisposalDryerExhaust FanFreezerGas Water HeaterIce MakerMicrowaveRefrigeratorWasherWine Refrigerator
• Laundry: Laundry ChuteLaundry Room
• Flooring: CarpetCeramic TileWood
• A/C: Central Air
• Heating: Central
• Fireplace: Living RoomFireplace

Exterior

• General: BalconyFire PitFrench DoorsLightingOutdoor GrillRain GuttersSliding DoorsStorageHeatedIn Ground
• Other Structures: CabanaOutdoor KitchenFront PorchPatio
• Pool: Chlorine FreeHeatedIn GroundLightingSalt Water
• Parking: CoveredDrivewayGarage Door OpenerGround LevelGuest

Construction

• Roofing: ConcreteTile
• General: StuccoTwoSlabStem Wall

Location

• Road/Access: Paved
• HOA Amenities: 656.0Quarterly
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: RSF2LOT 293 SOUTHBAY YACHT & RACQUET CLUB0158020017
• View: Water

Utilities

• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple