101 OSPREY POINT DRIVE

Property Details

Description

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

Facts & Costs

Property type

Single Family Residence

Year built

1985

Lot size

0.93 acres

Garage

3 spaces

Half baths

1

Price per sq ft

$942

Days on market

127

Private pool

Yes

Waterfront

Yes

Community

Oaks

Subdivision

OAKS

County

Sarasota

Flood zone

AE X

Monthly & yearly costs

HOA fee

$5,700 / semi-annually

Property taxes

$12,940 / year (2025)

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

Construction & systems

Heating

Central, Electric, Zoned

Cooling

Central Air, Zoned

Flooring

Brick, Ceramic Tile, Parquet

Roof

Tile

Construction

Block, Stucco

Parking

Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street

View

Water

Payment Estimate

$26,249 / month

Principal & interest

$24,221

Property taxes

$1,078

HOA

$950

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

• Bar Fridge
• Built-In Oven
• Cooktop
• Dishwasher
• Disposal
• Dryer
• Electric Water Heater
• Microwave
• Range Hood
• Refrigerator
• Washer
• Water Filtration System
• Water Softener
• Wine Refrigerator
• Built-in Features
• Ceiling Fans(s)
• Chair Rail
• Crown Molding
• Eat-in Kitchen
• High Ceilings
• Primary Bedroom Main Floor
• Solid Surface Counters
• Stone Counters
• Thermostat
• Walk-In Closet(s)
• Wet Bar
• Window Treatments
• Hurricane Shutters
• Lighting
• Private Mailbox
• Gunite
• In Ground
• Lake Front