313 LOOKOUT POINT DRIVE, OSPREY, FL 34229

Description of 313 LOOKOUT POINT DRIVE, OSPREY, FL 34229

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.

Property Details for 313 LOOKOUT POINT DRIVE, OSPREY, FL 34229

Bathrooms Full

4

Bathrooms Half

1

Interior Features

Ceiling Fan(s), Central Vacuum, Crown Molding, Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s), Wet Bar

Appliances

Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Gas Water Heater, Ice Maker, Microwave, Refrigerator, Washer, Wine Refrigerator

Flooring

Carpet, Ceramic Tile, Hardwood

Heating

Central

Cooling

Central Air

Furnished

Partially

Garage Spaces

5

Attached Garage

Yes

Parking Features

Covered, Driveway, Garage Door Opener, Ground Level, Guest

Pool Features

Chlorine Free, Heated, In Ground, Lighting, Salt Water

Pool Private

Yes

Property Condition

Completed

Direction Faces

Northeast

Building Information for 313 LOOKOUT POINT DRIVE, OSPREY, FL 34229

Building Area Total

6896

Building Area Units

Square Feet

Stories Total

2

Association

Yes

Association Fee

$656

Association Fee Frequency

Quarterly

Pets Allowed

Yes

Property Information for 313 LOOKOUT POINT DRIVE, OSPREY, FL 34229

Lot Features

Near Marina, Street Dead-End

Lot Size Square Feet

17,967

Waterfront

Yes

Waterfront Features

Waterfront, Intracoastal Waterway, Marina

View

Water

Construction Materials

Stucco

Roof

Concrete, Tile

Exterior Features

Balcony, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors, Storage

Sewer

Public Sewer

Water Source

Public

New Construction

No

Public Records for 313 LOOKOUT POINT DRIVE, OSPREY, FL 34229

Parcel Number

0158020017

Tax Annual Amount

$20,559

Tax Year

2025

Tax Legal Description

LOT 293 SOUTHBAY YACHT & RACQUET CLUB

Zoning

RSF2

County Or Parish

Sarasota

Schools Near 313 LOOKOUT POINT DRIVE, OSPREY, FL 34229

Elementary School

Laurel Nokomis Elementary

Middle School

Laurel Nokomis Middle

High School

Venice Senior High

School assignments are provided by the listing and should be independently verified.

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