313 LOOKOUT POINT DRIVE, OSPREY, FL 34229
What's special
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.
- 190 days
- 1,132
- 58
Originating MLS: Sarasota - ManateeTravel times
Living Room
Kitchen
Dining Room
Zillow last checked:
Listing updated:
Natalie Gutwein 941-993-2660,
MICHAEL SAUNDERS & COMPANY 941-951-6660,
Madison Brown 941-773-7660,
MICHAEL SAUNDERS & COMPANY
Originating MLS: Sarasota - Manatee
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Attic, Bonus Room, Den/Library/Office, Great Room, Storage Rooms
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 319 Square Feet
- Dimensions: 22x14.5
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 167.7 Square Feet
- Dimensions: 13x12.9
Bedroom 3
- Features: Built-in Closet
- Level: Second
- Area: 196 Square Feet
- Dimensions: 14x14
Bedroom 4
- Features: Built-in Closet
- Level: Second
- Area: 196 Square Feet
- Dimensions: 14x14
Primary bathroom
- Level: First
- Area: 236.9 Square Feet
- Dimensions: 23x10.3
Bathroom 2
- Level: First
- Area: 65.6 Square Feet
- Dimensions: 8x8.2
Bathroom 3
- Level: Second
- Area: 53.2 Square Feet
- Dimensions: 9.5x5.6
Bathroom 4
- Level: Second
- Area: 64.9 Square Feet
- Dimensions: 11.8x5.5
Dining room
- Level: First
- Area: 299 Square Feet
- Dimensions: 23x13
Family room
- Level: Second
- Area: 257.4 Square Feet
- Dimensions: 18x14.3
Florida room
- Level: First
Kitchen
- Level: First
- Area: 234 Square Feet
- Dimensions: 18x13
Laundry
- Level: First
Living room
- Level: First
- Area: 399 Square Feet
- Dimensions: 21x19
Office
- Level: First
- Area: 170.8 Square Feet
- Dimensions: 14x12.2
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Gas Water Heater, Ice Maker, Microwave, Refrigerator, Washer, Wine Refrigerator
- Laundry: Laundry Chute, Laundry Room
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
- Flooring: Carpet, Ceramic Tile, Hardwood
- Doors: French Doors, Outdoor Grill, Sliding Doors
- Has fireplace: Yes
- Fireplace features: Living Room
Interior area
- Total structure area: 6,896
- Total interior livable area: 5,337 sqft
Property
Parking
- Total spaces: 6
- Parking features: Covered, Driveway, Garage Door Opener, Ground Level, Guest
- Attached garage spaces: 5
- Carport spaces: 1
- Covered spaces: 6
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 32x27
Features
- Levels: Two
- Stories: 2
- Patio & porch: Front Porch, Patio
- Exterior features: Balcony, Fire Pit, Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Storage
- Has private pool: Yes
- Pool features: Chlorine Free, Heated, In Ground, Lighting, Salt Water
- Has spa: Yes
- Spa features: Heated, In Ground
- Has view: Yes
- View description: Water, Intracoastal Waterway, Marina
- Has water view: Yes
- Water view: Water,Intracoastal Waterway,Marina
- Waterfront features: Waterfront, Intracoastal Waterway, Marina, Intracoastal Waterway Access, No Wake Zone
Lot
- Size: 0.41 Acres
- Features: Near Marina, Street Dead-End
Details
- Additional structures: Cabana, Outdoor Kitchen
- Parcel number: 0158020017
- Zoning: RSF2
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Stucco
- Foundation: Slab, Stem Wall
- Roof: Concrete,Tile
Condition
- Completed
- New construction: No
- Year built: 2016
Details
- Builder name: John Cannon
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Street Lights
Community & HOA
Community
- Features: Boat Slip, Dock, Fishing, Intracoastal Waterway, Marina, Water Access, Waterfront
- Pet fee: $0 monthly
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
HOA
- Has HOA: Yes
- HOA fee: $219 monthly
- HOA name: Southbay Yacht & Racquet Club
Location
- Region: Osprey
Financial & listing details
- Price per square foot: $993/sqft
- Tax assessed value: $3,201,200
- Annual tax amount: $20,559
- Date on market: 4/7/2026
- Cumulative days on market: 190 days
- Ownership: Fee Simple
- Total actual rent: 0
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 10/6/2026 | Listed for sale | $5,299,999-11.7%$993/sqft |
Source:  Stellar MLS #A4688995 Report a problem | ||
| 4/7/2026 | Listed for sale | $5,999,999+252.9%$1,124/sqft |
Source: Stellar MLS #A4688995 Report a problem | ||
| 1/18/2005 | Sold | $1,700,000+59.3%$319/sqft |
Source: Public Record Report a problem | ||
| 12/16/2002 | Sold | $1,067,000+47.2%$200/sqft |
Source: Public Record Report a problem | ||
| 10/20/1999 | Sold | $725,000$136/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $20,559 +5.8% | $1,722,463 +2.9% |
| 2024 | $19,430 +2.5% | $1,673,919 +3% |
| 2023 | $18,950 +1.8% | $1,625,164 +3% |
| 2022 | $18,611 0% | $1,577,829 +3% |
| 2021 | $18,617 -0.8% | $1,531,873 +1.4% |
| 2020 | $18,765 +2.9% | $1,510,723 +2.3% |
| 2019 | $18,243 | $1,476,758 +1.9% |
| 2018 | $18,243 +1.8% | $1,449,223 +2.1% |
| 2017 | $17,922 +97.5% | $1,419,415 +146.1% |
| 2016 | $9,075 | $576,800 -36.7% |
| 2015 | $9,075 +0.3% | $910,500 +34% |
| 2014 | $9,043 0% | $679,318 |
| 2013 | $9,043 +2.8% | $679,318 +1.7% |
| 2012 | $8,797 +4.2% | $667,963 +2.4% |
| 2011 | $8,439 -7.9% | $652,100 -5.1% |
| 2010 | $9,160 -31.2% | $687,000 -14.1% |
| 2009 | $13,308 | $799,900 -25% |
| 2008 | $13,308 -17.5% | $1,066,900 -16.1% |
| 2007 | $16,121 | $1,271,300 -4.5% |
| 2006 | -- | $1,330,700 +31% |
| 2005 | -- | $1,015,900 +14.8% |
| 2004 | $13,300 +15.2% | $884,900 +19.4% |
| 2003 | $11,545 +23% | $741,100 +17.4% |
| 2002 | $9,386 +4.5% | $631,500 +2.9% |
| 2001 | $8,980 +4.1% | $614,000 +4.9% |
| 2000 | $8,626 | $585,100 |
Monthly payment
Estimated market value
Not available
Estimated sales range
Not available
Not available
Climate risks
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