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275 Lookout Point Drive, Osprey, FL 34229

Osprey
Local realty services provided by:CENTURY 21 North East
275 Lookout Point Drive,Osprey, FL 34229
$4,590,000
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  • 5 Beds
  • 5 Baths
  • 5,279 sq. ft.
  • Single family
  • Active
Listed by: natalie gutwein, madison brown
Office: michael saunders & company
MLS#:A4707430
Source:MFRMLS

Price summary

  • Price:$4,590,000
  • Price per sq. ft.:$589.9
  • Monthly HOA dues:$218.67

About this home

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...

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Home facts

  • Year built:2007
  • Subdivision & Development:SOUTHBAY YACHT & RACQUET CLUB
  • Listing ID #:A4707430
  • Added:27 day(s) ago
  • Updated:October 29, 2026 at 04:32 AM

Rooms and interior

  • Bedrooms:5
  • Total bathrooms:5
  • Full bathrooms:5
  • Flooring:Carpet, Ceramic Tile
  • Dining Description:Eat In Kitchen, Living Room/Dining Room Combo
  • Kitchen Description:Built-In Oven, Cooktop, Dishwasher, Disposal, Eat-in Kitchen, Kitchen/Family Room Combo, Microwave, Refrigerator
  • Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Living area:5,279 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Central, Electric, Exhaust Fan, Propane
  • Central air:Yes

Structure and exterior

  • Roof:Concrete, Tile
  • Year built:2007
  • Building area:5,279 sq. ft.
  • Lot area:0.38 Acres
  • Lot Features:Landscaped, Near Marina
  • Construction Materials:Cement Siding, Stucco
  • Exterior Features:Balcony, Lighting, Rear Porch, Screened
  • Foundation Description:Slab, Stem Wall
  • Levels:2 Story

Schools

  • High school:Venice Senior High
  • Middle school:Laurel Nokomis Middle
  • Elementary school:Laurel Nokomis Elementary

Utilities

  • Water:Public, Water Available, Water Connected
  • Sewer:Public Sewer, Sewer Available, Sewer Connected

Finances and disclosures

  • Price:$4,590,000
  • Price per sq. ft.:$589.9
  • Tax amount:$17,826 (2025)

Features and amenities

  • Appliances:Built-in Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
  • Laundry features:Dryer, Inside, Laundry Room, Washer
  • Amenities:BB/HS Internet Available, Basketball Court, Built-In Features, Cable Available, Cable Connected, Ceiling Fans(s), Clubhouse, Crown Molding, Eat-in Kitchen, Electricity Available, Fiber Optics, Fitness Center, Handicap Modified, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Lobby Key Required, Park, Pickleball Court(s), Playground, Pool, Primary Bedroom Main Floor, Shuffleboard Court, Tennis Court(s), Thermostat, Underground Utilities, Walk-In Closet(s), Wheelchair Access
  • Pool features:Heated, In Ground, Pool, Private Pool

Parking

  • Parking description:Attached Garage, Driveway, Ground Level, Guest, Workshop in Garage
  • Garage:Yes
  • Garage spaces:3
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