275 Lookout Point Drive, Osprey, FL 34229
For Sale $4,590,000
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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.
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Thermostat
Walk-In Closet(s)
Basketball Court
Clubhouse
Fitness Center
Handicap Modified
Lobby Key Required
Park
Pickleball Court(s)
Playground
Pool
Shuffleboard Court
Tennis Court(s)
Wheelchair Access
Taxes: $17,826.00
Tax Year: 2025
Association Fee: $656.00
Association Fee Frequency: Quarterly
Balcony
Hurricane Shutters
Lighting
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Microwave
Refrigerator
Washer
Water
Intracoastal Waterway
No Wake Zone
View: Intracoastal Waterway
Elementary School: Laurel Nokomis Elementary
Middle School: Laurel Nokomis Middle
Junior High: Laurel Nokomis Middle
High School: Venice Senior High
MLS Area: 34229 - Osprey
Total Square Footage: 7,781
Price per Square Feet: $869.48
Total Floors: 2
Water: Private, Public
Construction: Cement Siding, Stucco
Date Listed: 2026-10-01 00:00:00
Pool: Y
Pool Description: Heated, In Ground, Lighting
Private Spa: Y
Furnished: Unfurnished
Parking: Driveway, Ground Level, Guest, Workshop In Garage
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Carpet, Ceramic Tile
Roof: Concrete, Tile
Heating: Central, Electric, Exhaust Fan, Propane
Cooling: Central Air
Fireplace: Y
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Public Sewer
Lot Desc.: Landscaped, Near Marina
Parcel ID: 0158070010
Amenities: Basketball Court, Clubhouse, Fitness Center, Handicap Modified, Lobby Key Required, Park, Pickleball Court(S), Playground, Pool, Shuffleboard Court, Tennis Court(S), Wheelchair Access
Listing Courtesy Of: Michael Saunders & Company
nataliegutwein@michaelsaunders.com
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.
Property Details
Price: $4,590,000
Sq Ft: 5,279
($869 per
sqft)
Bedrooms: 5
Bathrooms: 5
City: Osprey
County: Sarasota
Type: Single Family
Development: Southbay Yacht And Racquet Club
Subdivision: Southbay Yacht & Racquet Club
Acres: 0.3800
Virtual Tour/Floorplan: View
Year Built: 2007
Listing Number: A4707430
Status Code: A-Active
Taxes: $17,826.00
Tax Year: 2025
Garage:
3
/
Y
Furnishings: Unfurnished
Pets Allowed: Yes
Total Recurring Fees: $219
Total Recurring Fee Frequency: 0.00
Interior Features:
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Thermostat
Walk-In Closet(s)
Amenities:
Basketball Court
Clubhouse
Fitness Center
Handicap Modified
Lobby Key Required
Park
Pickleball Court(s)
Playground
Pool
Shuffleboard Court
Tennis Court(s)
Wheelchair Access
Financial Information:
Taxes: $17,826.00
Tax Year: 2025
Association Fee: $656.00
Association Fee Frequency: Quarterly
Exterior Features:
Balcony
Hurricane Shutters
Lighting
Equipment:
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Microwave
Refrigerator
Washer
View:
Water
Waterfront Description:
Intracoastal Waterway
No Wake Zone
View: Intracoastal Waterway
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Laurel Nokomis Middle
Junior High: Laurel Nokomis Middle
High School: Venice Senior High
Additional Information:
MLS Area: 34229 - Osprey
Total Square Footage: 7,781
Price per Square Feet: $869.48
Total Floors: 2
Water: Private, Public
Construction: Cement Siding, Stucco
Date Listed: 2026-10-01 00:00:00
Pool: Y
Pool Description: Heated, In Ground, Lighting
Private Spa: Y
Furnished: Unfurnished
Parking: Driveway, Ground Level, Guest, Workshop In Garage
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Carpet, Ceramic Tile
Roof: Concrete, Tile
Heating: Central, Electric, Exhaust Fan, Propane
Cooling: Central Air
Fireplace: Y
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Public Sewer
Lot Desc.: Landscaped, Near Marina
Parcel ID: 0158070010
Amenities: Basketball Court, Clubhouse, Fitness Center, Handicap Modified, Lobby Key Required, Park, Pickleball Court(S), Playground, Pool, Shuffleboard Court, Tennis Court(S), Wheelchair Access
Map of 275 Lookout Point Drive, Osprey, FL 34229
Listing Courtesy Of: Michael Saunders & Company
nataliegutwein@michaelsaunders.com