275 Lookout Point Dr, Osprey, Florida

  • MLS #: A4632453
  • Price: $3,997,000
  • Beds: 5
  • Baths: 5
  • Square Feet: 5279
1 of 100
  • City: OSPREY
  • Zip Code: 34229
  • Subdivision: SOUTHBAY YACHT & RACQUET CLUB
  • Garage: 3
  • Year Built: 2007
  • HOA Fee: $612
  • Payments Due: Quarterly
  • Status: Sold
  • Sold Date: Jun 06, 2025
  • Water Front: Bay/Harbor, Intracoastal Waterway
  • Water View: Bay/Harbor - Full, Intracoastal Waterway
  • Water Access: Bay/Harbor, Canal - Saltwater, Gulf/Ocean, Intracoastal Waterway, Marina
  • Water Extras: Bridges - No Fixed Bridges, Fishing Pier, No Wake Zone, Sailboat Water
  • Lot Size: 1/4 to less than 1/2

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Property Description

This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida's Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property. The custom John Cannon home features a grand double door entry that opens to breathtaking wide open bay views. Inside, the home showcases high-end finishes and upgrades, including impressive, vaulted ceilings reaching up to 21 feet. You'll find abundant crown molding, elaborate tray ceilings, and exquisite wall finishes adorned with artfully painted faux designs and plantation shutters throughout. The home is designed for entertaining, with a full bar and wine room for guests, as well as an upper-level wet bar. The chef's kitchen is a culinary dream, featuring a spacious granite island, a gas cooktop with a pot filler, and views overlooking the pool, patio and bay. An upper-level bonus room offers versatile space for play, music, movies or exercise, all while enjoying some of the best views in the house. The main level primary suite is a serene retreat with a sitting area, two large closets and a luxurious bath that includes a garden shower, large tub, dual sinks, and a separate toilet and bidet. The expansive outdoor living spaces, including main level and upper terraces, are ideal for enjoying sunsets and observing local wildlife such as ospreys, dolphins, manatees and a parade of boats. Private dock for sunset viewing and fishing. Ideally between Sarasota and Venice, this residence is just minutes from the pristine sands of Siesta Key and Nokomis Beach. Convenience abounds with nearby shopping, dining the Legacy Trail, private and commercial airports, and top-rated schools, including the renowned Pine View School. This exquisite home embodies the essence of Florida living. Southbay Yacht & Racquet Club lives up to its name with a newly renovated community clubhouse, geothermal pool, gym overlooking the marina, banquet rooms, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboards, basketball, kayak storage area, a waterfront park, 20 acres of common grounds and miles of trails. Ideally in between culturally rich Sarasota and charming Venice, minutes to beaches, Legacy Trail, No. 1 rated Pine View School, shopping, waterfront restaurants and Oscar Scherer State Park. Walk to your boat or take your golf cart around the neighborhood. For those who seek an exceptional waterfront life, nothing compares.

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    • Miscellaneous Info

    • Subdivision: Southbay Yacht & Racquet Club
    • Annual Taxes: $16,732
    • HOA Fee: $612
    • HOA Payments Due: Quarterly
    • Water Front: Bay/Harbor, Intracoastal Waterway
    • Water View: Bay/Harbor - Full, Intracoastal Waterway
    • Water Access: Bay/Harbor, Canal - Saltwater, Gulf/Ocean, Intracoastal Waterway, Marina
    • Water Extras: Bridges - No Fixed Bridges, Fishing Pier, No Wake Zone, Sailboat Water
    • Lot Size: 1/4 to less than 1/2
    • Schools

    • Elementary: Laurel Nokomis Elementary
    • High School: Venice Senior High
    • Home Features

    • Appliances: Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Dryer, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
    • Flooring: Carpet, Marble, Tile, Wood
    • Fireplace: Gas, Living Room, Outside
    • Air Conditioning: Central Air, Zoned
    • Exterior: Balcony, Hurricane Shutters, Lighting, Outdoor Kitchen, Outdoor Shower, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors
    • Garage Features: Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage, Oversized, Workshop in Garage
    • Pool Size: 27 x 13

    Listing data source: MFRMLS - IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS.

    Thanks to PREMIER SOTHEBYS INTL REALTY for this listing.

    Last Updated: 12-14-2025