Skip to Content Skip to Navigation Skip to Dashboard

275 Lookout Point Drive, OSPREY, FL – $3,997,000

  • 5 Beds
  • 5 Baths
  • 5,279 Sqft
  • .38 Acres
  • 5 Beds
  • 5 Baths
  • 5,279 Sqft
  • .38 Acres

275 Lookout Point Drive

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.

Upcoming Open Houses

  • Apr27th
  • Sunday1-4PM

Essential Information

  • MLS® #A4632453
  • Price$3,997,000
  • Bedrooms5
  • Bathrooms5.00
  • Full Baths5
  • Square Footage5,279
  • Acres0.38
  • Year Built2007
  • TypeResidential
  • Sub-TypeSingle Family Residence
  • StyleMediterranean
  • StatusActive

Community Information

  • Address275 Lookout Point Drive
  • AreaOsprey
  • SubdivisionSOUTHBAY YACHT & RACQUET CLUB
  • CityOSPREY
  • CountySarasota
  • StateFL
  • Zip Code34229

Amenities

  • # of Garages3
  • ViewWater
  • Is WaterfrontYes
  • Has PoolYes

Amenities

Basketball Court, Clubhouse, Elevator(s), Fitness Center, Park, Pickleball Court(s), Playground, Pool, Recreation Facilities, Tennis Court(s)

Parking

Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage, Oversized, Workshop in Garage

Waterfront

Bay/Harbor, Intracoastal Waterway

Interior

  • HeatingCentral, Electric, Propane
  • CoolingCentral Air, Zoned
  • FireplaceYes
  • FireplacesGas, Living Room, Outside

Interior Features

Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, In Wall Pest System, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments

Appliances

Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Dryer, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer

Exterior

  • RoofConcrete, Tile
  • FoundationStem Wall

Exterior Features

Balcony, Hurricane Shutters, Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors

Lot Description

Cleared, FloodZone, In County, Landscaped, Near Marina, Paved

School Information

  • ElementaryLaurel Nokomis Elementary
  • MiddleLaurel Nokomis Middle
  • HighVenice Senior High

Additional Information

  • Date ListedDecember 27th, 2024
  • Days on Market118
  • ZoningRSF2
  • Taxes$16,732
  • HOA Fees$612
  • HOA Fee FrequencyQuarterly

Listing Details

  • OfficePREMIER SOTHEBYS INTL REALTY
Please provide a valid email address.

Price Change History for 275 Lookout Point Drive, OSPREY, FL (MLS® #A4632453)

Date Details Change
Price Reduced from $4,250,000 to $3,997,000 $253,000 (5.95%)
Price Reduced from $4,475,000 to $4,250,000 $225,000 (5.03%)
Price Reduced from $4,750,000 to $4,475,000 $275,000 (5.79%)

Similar Nearby Listings

3201 Casey Key Road - $3,995,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,273 SQFT
View details More Photos Save

Gulf-front Serenity On Casey Key. On The Desirable Shores Of Casey Key, This Quintessential Beachfront Retreat, Osmyrrah, Is A Sanctuary Of Tranquility, Designed For Relaxed, Or...

5 North Casey Key Road - $3,675,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 2,380 SQFT
View details More Photos Save

Price Improvement! Iconic Gulf-front Mid-century Modern Gated Residence On Casey Key Embodies The True Essence Of Casual Coastal Living, Offering An Unparalleled Retreat For The...

2340 Bayshore Road - $3,500,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,750 SQFT
View details More Photos Save

Be Prepared To Be Captivated By This Custom 2023 Spanish Courtyard Home. Every Detail Of This 4 Bedroom 5 ½ Bathroom Smart Home, With Two Oversized Garages Has Been Thoughtfully...

443 Picasso Drive - $3,500,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,543 SQFT
View details More Photos Save

This Exceptional Island Living Boasts All The Convenience Of A Mainland Location. Prepare To Be Amazed By This Newly Renovated Waterfront Property Overlooking The Breathtaking B...

1523 Bayshore Road - $3,500,000

Residential, Single Family Residence
  • 5 Beds
  • 4 Baths
  • 4,616 SQFT
View details More Photos Save

One Or More Photo(s) Has Been Virtually Staged. This Custom-built, One-owner, Four-bedroom, 4,600 Square Foot Home Is Located Above The Base Flood Elevation On A Wide One-acre P...

854 Macewen Drive - $4,195,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
View details More Photos Save

One Or More Photo(s) Has Been Virtually Staged. **seller Will Pay 100% Of The Mandatory Social Membership – Worth $80,000 – If Closing By June 2nd, 2025** Newly Renovated, Spaci...

PREMIER SOTHEBYS INTL REALTY.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on April 24th, 2025 at 6:04pm EDT.