$4,590,000

275 Lookout Point DrOsprey, FL 34229

  • 5 beds
  • 5 baths
  • 5,279 sqft
  • 0.38 acres
  • 35 days on market

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 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.

Virtual tour

Facts

Property type
Single Family Residence
Year built
2007
Stories
2
Garage spaces
3
Lot size
0.38 acres
Pool
Yes
Waterfront
Yes
Water view
Intracoastal Waterway
Subdivision
SOUTHBAY YACHT & RACQUET CLUB
Community
Southbay Yacht & Racquet Club
County
Sarasota
HOA fee
$656 / quarterly
CDD
0
Annual taxes
$17,826 (2025)
Flood zone
AE, X
Pets
Yes
New construction
No
MLS #
A4707430

Features

Interior
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)
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
Flooring
Carpet, Ceramic Tile
Heating
Central, Electric, Exhaust Fan, Propane
Cooling
Central Air
Exterior
Balcony, Hurricane Shutters, Lighting
Patio & porch
Rear Porch, Screened
Pool features
Heated, In Ground, Lighting
Parking
Driveway, Ground Level, Guest, Workshop in Garage
Construction
Cement Siding, Stucco
Roof
Concrete, Tile
Lot
Landscaped, Near Marina
View
Water
Community features
Clubhouse, Dog Park, Fitness Center, Golf Carts OK, Handicap Modified, No Truck/RV/Motorcycle Parking, Park, Playground, Pool, Sidewalks, Tennis Court(s), Street Lights
Association amenities
Basketball Court, Clubhouse, Fitness Center, Handicap Modified, Lobby Key Required, Park, Pickleball Court(s), Playground, Pool, Shuffleboard Court, Tennis Court(s), Wheelchair Access
HOA fee includes
Pool
Utilities
BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Fiber Optics, Propane, Sewer Available, Sewer Connected, Underground Utilities, Water Available, Water Connected
Water
Private, Public
Sewer
Public Sewer
Elementary school
Laurel Nokomis Elementary
Middle school
Laurel Nokomis Middle
High school
Venice Senior High

Location

Stellar MLS Listing courtesy of MICHAEL SAUNDERS & COMPANY. MLS # A4707430.

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Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS. Last updated: 2026-11-04 1:00 PM EST.