275 LOOKOUT POINT DRIVE, OSPREY, FL 34229
What's special
Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.
- 30 days
- 1,519
- 101
Originating MLS: Sarasota - ManateeTravel times
Living Room
Kitchen
Primary Bedroom
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: 5
- Bathrooms: 5
- Full bathrooms: 5
Rooms
- Room types: Bonus Room, Den/Library/Office, Family Room
Primary bedroom
- Features: Built-In Shelving, Dual Closets
- Level: First
- Area: 420 Square Feet
- Dimensions: 28x15
Bedroom 2
- Features: Walk-In Closet(s)
- Level: First
- Area: 144 Square Feet
- Dimensions: 12x12
Bedroom 3
- Features: Ceiling Fan(s), Walk-In Closet(s)
- Level: First
- Area: 156 Square Feet
- Dimensions: 12x13
Bedroom 4
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
- Area: 165 Square Feet
- Dimensions: 15x11
Bedroom 5
- Features: Ceiling Fan(s), Walk-In Closet(s)
- Level: Second
- Area: 156 Square Feet
- Dimensions: 13x12
Primary bathroom
- Features: Bidet, Dual Sinks, Garden Bath, Rain Shower Head, Walk-In Closet(s)
- Level: First
Great room
- Features: Ceiling Fan(s)
- Level: First
- Area: 247 Square Feet
- Dimensions: 13x19
Kitchen
- Features: Granite Counters, Kitchen Island, Pantry, Stone Counters
- Level: First
- Area: 180 Square Feet
- Dimensions: 12x15
Laundry
- Features: Built-In Shelving
- Level: First
Living room
- Features: Built-In Shelving
- Level: First
- Area: 240 Square Feet
- Dimensions: 16x15
Media room
- Features: Ceiling Fan(s)
- Level: Second
Heating
- Central, Electric, Exhaust Fan, Propane
Cooling
- Central Air
Appliances
- Included: Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Laundry: Inside, Laundry Room
Features
- Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s)
- Flooring: Carpet, Ceramic Tile
- Doors: French Doors, Sliding Doors
- Windows: Hurricane Shutters, Hurricane Shutters/Windows
- Has fireplace: Yes
- Fireplace features: Living Room
Interior area
- Total structure area: 7,781
- Total interior livable area: 5,279 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Driveway, Ground Level, Guest, Workshop in Garage
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Rear Porch, Screened
- Exterior features: Balcony, Lighting
- Has private pool: Yes
- Pool features: Heated, In Ground, Lighting
- Has spa: Yes
- Spa features: Heated, In Ground
- Has view: Yes
- View description: Water, Intracoastal Waterway
- Has water view: Yes
- Water view: Water,Intracoastal Waterway
- Waterfront features: Intracoastal Waterway, Intracoastal Waterway Access, Marina Access, No Wake Zone
Lot
- Size: 0.38 Acres
- Features: Landscaped, Near Marina
- Residential vegetation: Trees/Landscaped
Details
- Parcel number: 0158070010
- Zoning: RSF2
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Cement Siding, Stucco
- Foundation: Slab, Stem Wall
- Roof: Concrete,Tile
Condition
- Completed
- New construction: No
- Year built: 2007
Details
- Builder name: John Cannon
Utilities & green energy
- Sewer: Public Sewer
- Water: Private, Public
- Utilities for property: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Fiber Optics, Propane, Sewer Available, Sewer Connected, Street Lights, Underground Utilities, Water Available, Water Connected
Community & HOA
Community
- Features: Dock, Fishing, Intracoastal Waterway, Marina, Clubhouse, Dog Park, Fitness Center, Golf Carts OK, Handicap Modified, No Truck/RV/Motorcycle Parking, Park, Playground, Pool, Sidewalks, Tennis Court(s)
- Pet fee: $0 monthly
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
HOA
- Has HOA: Yes
- Amenities included: Basketball Court, Clubhouse, Fitness Center, Handicap Modified, Lobby Key Required, Park, Pickleball Court(s), Playground, Pool, Shuffleboard Court, Tennis Court(s), Wheelchair Access
- Services included: Community Pool
- HOA fee: $219 monthly
- HOA name: Southbay Yacht & Racquet Club - Rachelle Freed
- HOA phone: 941-966-4237
Location
- Region: Osprey
Financial & listing details
- Price per square foot: $869/sqft
- Tax assessed value: $3,362,100
- Annual tax amount: $17,826
- Date on market: 10/1/2026
- Cumulative days on market: 30 days
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 10/1/2026 | Listed for sale | $4,590,000+30.2%$869/sqft |
Source:  Stellar MLS #A4707430 Report a problem | ||
| 6/6/2025 | Sold | $3,525,000-11.8%$668/sqft |
Source: Stellar MLS #A4632453 Report a problem | ||
| 5/1/2025 | Pending sale | $3,997,000$757/sqft |
Source: Stellar MLS #A4632453 Report a problem | ||
| 4/17/2025 | Price change | $3,997,000-6%$757/sqft |
Source: Stellar MLS #A4632453 Report a problem | ||
| 3/6/2025 | Price change | $4,250,000-5%$805/sqft |
Source: Stellar MLS #A4632453 Report a problem | ||
| 2/5/2025 | Price change | $4,475,000-5.8%$848/sqft |
Source: Stellar MLS #A4632453 Report a problem | ||
| 12/27/2024 | Listed for sale | $4,750,000+265.4%$900/sqft |
Source: Stellar MLS #A4632453 Report a problem | ||
| 10/9/2003 | Sold | $1,300,000$246/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $17,826 +6.5% | $1,479,275 +2.9% |
| 2024 | $16,732 +2.6% | $1,437,585 +3% |
| 2023 | $16,311 +1.9% | $1,395,714 +3% |
| 2022 | $16,011 +0.2% | $1,355,062 +3% |
| 2021 | $15,981 -0.8% | $1,315,594 +1.4% |
| 2020 | $16,104 +2.9% | $1,297,430 +2.3% |
| 2019 | $15,652 | $1,268,260 +1.9% |
| 2018 | $15,652 +1.8% | $1,244,612 +2.1% |
| 2017 | $15,373 -1.4% | $1,219,013 -28.2% |
| 2016 | $15,592 | $1,697,600 +4.4% |
| 2015 | $15,592 +4.2% | $1,625,500 +45.6% |
| 2014 | $14,962 0% | $1,116,170 |
| 2013 | $14,967 +3.3% | $1,116,170 +2.2% |
| 2012 | $14,486 +4.8% | $1,092,006 +3% |
| 2011 | $13,819 -10.5% | $1,060,200 -7.7% |
| 2010 | $15,434 -20.5% | $1,149,000 -15.4% |
| 2009 | $19,416 | $1,358,200 -10.7% |
| 2008 | $19,416 +76.6% | $1,520,200 +77.8% |
| 2007 | $10,995 | $854,800 -37.1% |
| 2006 | -- | $1,358,700 +31% |
| 2005 | -- | $1,037,300 +12.2% |
| 2004 | $13,884 +35.1% | $924,600 +35.4% |
| 2003 | $10,280 +37.1% | $682,838 +35.3% |
| 2002 | $7,498 +7.4% | $504,627 +1.6% |
| 2001 | $6,980 +2.3% | $496,680 +3% |
| 2000 | $6,821 | $482,214 |
Monthly payment
Estimated market value
Not available
Estimated sales range
Not available
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Climate risks
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