275 LOOKOUT POINT DRIVE

Property Details

Description

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.

Facts & Costs

Property type

Single Family Residence

Year built

2007

Lot size

0.38 acres

Stories

2

Garage

3 spaces

Price per sq ft

$869

Days on market

1

Private pool

Yes

Waterfront

Yes

Community

Southbay Yacht & Racquet Club

Subdivision

SOUTHBAY YACHT & RACQUET CLUB

County

Sarasota

Builder

John Cannon

Flood zone

AE, X

Monthly & yearly costs

HOA fee

$656 / quarterly

Property taxes

$17,826 / year (2025)

As reported by the listing agent. Verify with the HOA and county.

Construction & systems

Heating

Central, Electric, Exhaust Fan, Propane

Cooling

Central Air

Flooring

Carpet, Ceramic Tile

Roof

Concrete, Tile

Construction

Cement Siding, Stucco

Parking

Driveway, Ground Level, Guest, Workshop in Garage

View

Water

Payment Estimate

$24,914 / month

Principal & interest

$23,210

Property taxes

$1,486

HOA

$219

Home insurance

enter below

Estimate only, not a loan offer. Rate is a starting value; taxes and HOA are as reported by the listing agent. Florida insurance (including flood) varies widely. Ask George for a lender referral.

Location

Features & Amenities

• Built-In Oven
• Cooktop
• Dishwasher
• Disposal
• Dryer
• Microwave
• Refrigerator
• Washer
• 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)
• Balcony
• Hurricane Shutters
• Lighting
• Heated
• In Ground
• Intracoastal Waterway