313 Lookout Point Drive, OSPREY, FL

$5,999,999

Previous Next

4

Beds

5

Baths

5,337

Square feet

0.41

Acres

About 313 Lookout Point Drive

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.

Features of 313 Lookout Point Drive

MLS® # A4688995
Price $5,999,999
Bedrooms 4
Bathrooms 5.00
Full Baths 4
Half Baths 1
Square Footage 5,337
Acres 0.41
Year Built 2016
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 313 Lookout Point Drive
Area Osprey
Subdivision SOUTHBAY YACHT & RACQUET CLUB
City OSPREY
County Sarasota
State FL
Zip Code 34229-9798

Amenities

Parking Covered, Driveway, Garage Door Opener, Ground Level, Guest
# of Garages 5
View Water
Is Waterfront Yes
Waterfront Waterfront, Intracoastal Waterway, Marina
Has Pool Yes

Interior

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
Heating Central
Cooling Central Air
Fireplace Yes
Fireplaces Living Room
# of Stories 2

Exterior

Exterior Features Balcony, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors, Storage
Lot Description Near Marina, Street Dead-End
Roof Concrete, Tile
Foundation Slab, Stem Wall

School Information

Elementary Laurel Nokomis Elementary
Middle Laurel Nokomis Middle
High Venice Senior High

Additional Information

Date Listed April 7th, 2026
Days on Market 3
Zoning RSF2
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeMICHAEL SAUNDERS & COMPANY

Listing Map

Request a Showing

Provide a valid email address.
When would you like to view this property?