EasyStreet

Call to Schedule a Showing

(813) 527-9259

(813) 527-9259

275 Lookout Point Dr, Osprey, FL 34229

$4,750,000

Luxury waterfront home with a large lot and stunning landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Bedrooms

    5

  • Baths

    5

  • Sq. Feet

    5279

  • Year Built

    2007

  • Days On Market

    15

  • $/SqFt

    $900

100 Photos

  • Luxury waterfront home with a large lot and stunning landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Grand estate with a circular driveway and lush landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Waterfront property boasting a large home and beautiful views at 275 Lookout Point Dr, Osprey, FL 34229
  • Expansive waterfront property with a private dock at 275 Lookout Point Dr, Osprey, FL 34229
  • Luxury waterfront home with private pool and dock access at 275 Lookout Point Dr, Osprey, FL 34229
  • Waterfront home with expansive views and private dock at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing balcony offering breathtaking waterfront views at 275 Lookout Point Dr, Osprey, FL 34229
  • Inviting screened pool with spa and stunning water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious patio with seating area overlooking the pool and water at 275 Lookout Point Dr, Osprey, FL 34229
  • Serene balcony boasting sunset views over the water at 275 Lookout Point Dr, Osprey, FL 34229
  • Luxury pool and spa with dolphin statues, surrounded by a spacious patio at 275 Lookout Point Dr, Osprey, FL 34229
  • Wooden dock extending over calm water, offering scenic views at 275 Lookout Point Dr, Osprey, FL 34229
  • Elegant entryway with double doors and lush landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Grand entry with double doors and views into the living room at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious living room with fireplace, piano, and water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Living room features a cozy seating area and large windows at 275 Lookout Point Dr, Osprey, FL 34229
  • Bright dining room with a large table and access to the foyer at 275 Lookout Point Dr, Osprey, FL 34229
  • Formal dining area with a round table and elegant decor at 275 Lookout Point Dr, Osprey, FL 34229
  • Elegant living room with a fireplace, piano and large windows at 275 Lookout Point Dr, Osprey, FL 34229
  • Living room with fireplace, seating area, and large windows at 275 Lookout Point Dr, Osprey, FL 34229
  • Wet bar with granite countertop and wooden cabinetry at 275 Lookout Point Dr, Osprey, FL 34229
More Photos \/
  • Spacious kitchen featuring granite counters and custom cabinetry at 275 Lookout Point Dr, Osprey, FL 34229
  • Gourmet kitchen with granite countertops and stainless steel appliances at 275 Lookout Point Dr, Osprey, FL 34229
  • Island kitchen with granite countertops and wooden cabinets at 275 Lookout Point Dr, Osprey, FL 34229
  • Open kitchen boasts granite countertops and a large island at 275 Lookout Point Dr, Osprey, FL 34229
  • Bright dining room with water views and elegant chandelier at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing living room with water views and comfortable seating at 275 Lookout Point Dr, Osprey, FL 34229
  • Game room with pool table and stunning water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Dark granite wet bar with microwave and cabinetry at 275 Lookout Point Dr, Osprey, FL 34229
  • Game room with pool table and access to balcony at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing media room featuring leather seating and built-in cabinetry at 275 Lookout Point Dr, Osprey, FL 34229
  • Elegant hallway with decorative arches and built-in shelving at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious main bedroom with a large four poster bed and water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Peaceful bedroom sitting area with French doors opening to a patio and pool at 275 Lookout Point Dr, Osprey, FL 34229
  • Luxurious bathroom with double vanities, a large soaking tub, and lots of natural light at 275 Lookout Point Dr, Osprey, FL 34229
  • Spa-like bathroom with a soaking tub and walk-in shower at 275 Lookout Point Dr, Osprey, FL 34229
  • Bathroom shower with large windows overlooking a lush garden at 275 Lookout Point Dr, Osprey, FL 34229
  • Home office with built-in bookshelves and lake views at 275 Lookout Point Dr, Osprey, FL 34229
  • Nautical-themed bathroom with a walk-in shower and a unique sink at 275 Lookout Point Dr, Osprey, FL 34229
  • Comfortable bedroom with a queen bed and a ceiling fan at 275 Lookout Point Dr, Osprey, FL 34229
  • Elegant bathroom with granite vanity, glass sink, and water view at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious bedroom with bay window, water view, and ample closet space at 275 Lookout Point Dr, Osprey, FL 34229
  • Upscale bathroom with a vessel sink and view into bedroom at 275 Lookout Point Dr, Osprey, FL 34229
  • Home office with built-in desk, window seat, and hardwood floors at 275 Lookout Point Dr, Osprey, FL 34229
  • Stylish bathroom with a round mirror and decorative wallpaper at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious waterfront patio with seating and water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Private wooden dock extending into the water at 275 Lookout Point Dr, Osprey, FL 34229
  • Covered patio overlooking pool and waterfront at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing patio with white rocking chairs and water view at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious pool area with patio furniture and water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Resort-style pool and spa with covered patio, offering luxurious outdoor living at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing pool and spa with covered patio, overlooking the waterfront at 275 Lookout Point Dr, Osprey, FL 34229
  • Stunning view of calm water, lush greenery, and a boat passing by at 275 Lookout Point Dr, Osprey, FL 34229
  • Wooden dock extending over calm water, perfect for enjoying the waterfront view at 275 Lookout Point Dr, Osprey, FL 34229
  • Wooden dock with bench, offering a peaceful waterfront view at 275 Lookout Point Dr, Osprey, FL 34229
  • Back of house with private dock, offering waterfront living at 275 Lookout Point Dr, Osprey, FL 34229
  • Aerial view of home, pool, and private dock on waterfront property at 275 Lookout Point Dr, Osprey, FL 34229
  • Aerial view of waterfront home with private dock and lush landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Aerial view showcasing waterfront home, dock, and lush landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Luxury waterfront home at sunset, showcasing beautiful reflection at 275 Lookout Point Dr, Osprey, FL 34229
  • Elegant two-story home with a three-car garage and a large driveway at 275 Lookout Point Dr, Osprey, FL 34229
  • Stunning home with a grand entrance and lush landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Impressive entryway with double doors and decorative glass at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious living area with a stunning sunset view and comfortable seating at 275 Lookout Point Dr, Osprey, FL 34229
  • Game room featuring a pool table and large windows with water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Covered patio with outdoor seating and amazing water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing patio overlooking the pool and water, perfect for sunset views at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious covered patio with comfortable seating and beautiful water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Inviting pool area with a covered patio and outdoor dining space at 275 Lookout Point Dr, Osprey, FL 34229
  • Resort-style pool and patio area with stunning sunset views at 275 Lookout Point Dr, Osprey, FL 34229
  • Resort-style pool with screened enclosure, brick pavers, and sunset views at 275 Lookout Point Dr, Osprey, FL 34229
  • Private dock with stunning sunset views over the calm water at 275 Lookout Point Dr, Osprey, FL 34229
  • Wooden walkway leads to private dock with sunset views at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing waterfront dock with a bench, perfect for fishing at 275 Lookout Point Dr, Osprey, FL 34229
  • Scenic sunset view over calm water and lush greenery at 275 Lookout Point Dr, Osprey, FL 34229
  • Southbay Yacht & Racquet Club entrance with landscaping at 275 Lookout Point Dr, Osprey, FL 34229
  • Southbay Yacht & Racquet Club marina and community view at 275 Lookout Point Dr, Osprey, FL 34229
  • Southbay Yacht & Racquet Club building exterior at 275 Lookout Point Dr, Osprey, FL 34229
  • Spacious clubhouse with comfortable seating and water views at 275 Lookout Point Dr, Osprey, FL 34229
  • Bright and airy multi-purpose room with tables and chairs at 275 Lookout Point Dr, Osprey, FL 34229
  • Well-equipped fitness center with various exercise machines at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing community room with comfortable seating and a large TV at 275 Lookout Point Dr, Osprey, FL 34229
  • Fully equipped community kitchen with stainless steel appliances at 275 Lookout Point Dr, Osprey, FL 34229
  • Bright community room with tables and chairs overlooking the marina at 275 Lookout Point Dr, Osprey, FL 34229
  • Inviting pool area with marina views and ample seating at 275 Lookout Point Dr, Osprey, FL 34229
  • Large community room with multiple tables and chairs at 275 Lookout Point Dr, Osprey, FL 34229
  • Relaxing outdoor seating area with covered patio at 275 Lookout Point Dr, Osprey, FL 34229
  • Aerial view of community pool and marina at 275 Lookout Point Dr, Osprey, FL 34229
  • Community tennis courts and surrounding neighborhood at 275 Lookout Point Dr, Osprey, FL 34229
  • playground with swings and a slide at 275 Lookout Point Dr, Osprey, FL 34229
  • Scenic park with gazebo and walking path at 275 Lookout Point Dr, Osprey, FL 34229
  • Boats docked at a marina with shuffleboard at 275 Lookout Point Dr, Osprey, FL 34229
  • Wooden dock with boats moored alongside at 275 Lookout Point Dr, Osprey, FL 34229
  • Aerial view of a boat in the water at 275 Lookout Point Dr, Osprey, FL 34229
  • Tranquil sunset over canal with boats at 275 Lookout Point Dr, Osprey, FL 34229
  • Nokomis community entrance sign at 275 Lookout Point Dr, Osprey, FL 34229
  • Wooden boardwalk to beach with lifeguard at 275 Lookout Point Dr, Osprey, FL 34229
  • Wooden walkway to the beach at 275 Lookout Point Dr, Osprey, FL 34229
  • Expansive beach with clear water at 275 Lookout Point Dr, Osprey, FL 34229
  • Stunning sunset over the ocean at 275 Lookout Point Dr, Osprey, FL 34229
Less Photos /\

Tour This Home

Fri
10 Jan
Sat
11 Jan
Sun
12 Jan
Mon
13 Jan
Tue
14 Jan
Wed
15 Jan
Thu
16 Jan

Home 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.

  • MLS #: A4632453
  • Address: 275 Lookout Point Dr
  • Levels: Two
  • City: Osprey
  • Zip: 34229
  • County: Sarasota
  • Subdivision: Southbay Yacht & Racquet Club
  • Community Features: Clubhouse,Deed Restrictions,Fitness Center,Golf Carts OK,Park,Playground,Pool,Sidewalks,Tennis Courts
  • Elementary School: Laurel Nokomis Elementary
  • Middle School: Laurel Nokomis Middle
  • High School: Venice Senior High
  • Private Pool: True
  • Pool Features: Gunite,Heated,In Ground,Lighting,Outside Bath Access,Screen Enclosure
  • Spa Features: Heated,In Ground
  • Water View: Bay/Harbor - Full,Intracoastal Waterway
  • Water Frontage: Bay/Harbor,Intracoastal Waterway
  • Water Feet: 0
  • Water Extras: Bridges - No Fixed Bridges,Fishing Pier,No Wake Zone,Sailboat Water
  • Water Access: Bay/Harbor,Canal - Saltwater,Gulf/Ocean,Intracoastal Waterway,Marina
  • 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
  • Fireplace Desc: Gas,Living Room,Outside
  • Floor Covering: Carpet,Marble,Tile,Wood
  • Living Room Features: Built-In Shelving
  • Primary Bathroom Features: Bidet,Dual Sinks,Garden Bath,Rain Shower Head
  • Laundry Features: Built-In Shelving
  • Kitchen Features: Granite Counters,Island,Pantry,Stone Counters
  • Family Room Features: Ceiling Fan(s)
  • Media Room Features: Ceiling Fan(s)
  • Additional Rooms: Bonus Room,Breakfast Room Separate,Den/Library/Office,Family Room,Formal Dining Room Separate,Formal Living Room Separate,Inside Utility
  • Architectural Style: Mediterranean
  • Exterior Features: Balcony,Hurricane Shutters,Irrigation System,Lighting,Outdoor Kitchen,Outdoor Shower,Private Mailbox,Rain Gutters,Sidewalk,Sliding Doors
  • Exterior Contruction: Block,Concrete,Stucco
  • Foundation: Stem Wall
  • Front Exposure: East
  • Roof: Concrete,Tile
  • Building Sqft: 7781

Available now at $4,750,000

Approximate Room Sizes / Descriptions

Living Room16x15FirstTile
Dining Room15x15FirstTile
Primary BathroomFirstTile
LaundryFirstTile
Kitchen12x15FirstTile
Dinette9x11First
Family Room13x19FirstTile
Media RoomSecondCarpet
Primary Bedroom28x15FirstCarpet
Bedroom 212x12FirstCarpet
Bedroom 312x13FirstCarpet
Bedroom 415x11First
Bedroom 513x12Second
  • Attached Garage: True
  • Garage: True
  • Garage Spaces: 3
  • Garage Feature: Driveway,Garage Door Opener,Garage Faces Side,Golf Cart Garage,Oversized,Workshop in Garage
  • Carport: False
  • Carport Spaces: 0
  • Air Conditioning: Central Air,Zoned
  • Heating: Central,Electric,Propane
  • Utilities: BB/HS Internet Available,Cable Connected,Electricity Connected,Underground Utilities,Water Connected
  • Lot Sqft: 16709.00
  • Lot Acres: 0.3800
  • Total Acre: 1/4 to less than 1/2
  • Lot Num: 301
  • HOA Fees: $612 Quarterly
  • HOA Monthly Amount: $204
  • HOA/Community Assoc: Required
  • Senior Community: False
  • Style: Single Family Residence
  • Location: Cleared,FloodZone,In County,Landscaped,Near Marina,Paved
  • Disaster Mitigation: Hurricane Shutters/Windows
  • Maintenance Includes: Common Area Taxes,Pool,Recreational Facilities
  • Building Name Number: JOHN CANNON
  • Pets Allowed: Cats OK,Dogs OK,Yes
  • Pet Restrictions: See Association Documents.
  • Pet Size: Extra Large (101+ Lbs.)
  • : 941-364-4000

Neighborhood

The average asking price of a 5 bedroom Osprey home in this zip code is $2,920,000 (38.5% less than this home).

This home is priced at $900/sqft, which is 22.1% less than similar homes in the 34229 zip code.

Map | Street | Birds Eye

Print Map | Driving Directions

Financial

  • Approx Payment:$23,107*
  • Taxes:$16,732

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (813) 527-9259 and speak with one of our real estate consultants.

Listing Courtesy of PREMIER SOTHEBYS INTL REALTY. For information or to schedule a viewing of this property (MLS# A4632453), call: 813-527-9259

275 Lookout Point Dr, Osprey FL is a single family home of 5279 sqft and is currently priced at $4,750,000 . This single family home has 5 bedrooms. A comparable home for sale at 312 Yacht Harbor Dr in Osprey is listed at $2,695,000. In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos and New Homes in Osprey, FL. Casey Key, Sorrento Shores and Oaks are nearby neighborhoods. MLS A4632453 has been posted on this site since 12/27/2024 (today).

2025 1/10/2025.

Message Agent

Send

Schedule a tour

275 Lookout Point Dr Osprey FL 34229

Choose a day and time

You Requested

We'll be in touch shortly to confirm your tour time and other details. Please let us know how to reach you.

Schedule Tour

CLOSE

Your message has been sent!

The agent will be in touch with you in just a minute.