101 Osprey Point Dr, Osprey, FL 34229

About this home

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.

Monthly costs

HOA

$950/mo

Asset Management/ Hope Root

Includes

24-Hour Guard, Community Pool, Manager, Private Road, Security

Est. monthly fees

$950/mo

Estimated total including HOA and other monthly association fees

Key facts

Type

Single Family Residence

Size

5,087 sqft

Bedrooms

4

Bathrooms

5.5

Avg. price per sqft

$942

Days on market

87

Year built

1985

Lot size

0.93 acres

Parking

3-car garage

HOA

$950/mo

Annual taxes

$12,940

Flood zone

X

Heating

Central, Electric, Zoned

Cooling

Central Air, Zoned

Pets

Yes

Waterfront

Yes

Furnished

Unfurnished

Subdivision

OAKS

Financing

Cash, Conventional

Levels

One

County

Sarasota

MLS number

A4694716

Status

Active

Property address

101 Osprey Point Dr, Osprey, FL 34229

Features and extras

• 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 Fan(s)
• Chair Rail
• Crown Molding
• Eating Space In Kitchen
• High Ceilings
• Primary Bedroom Main Floor
• Solid Surface Counters
• Stone Counters
• Thermostat
• Walk-In Closet(s)
• Wet Bar
• Window Treatments
• French Doors
• Hurricane Shutters
• Irrigation System
• Lighting
• Private Mailbox
• Buyer Approval Required
• Clubhouse
• Deed Restrictions
• Fitness Center
• Gated Community - Guard
• Golf
• Pool
• Special Community Restrictions
• Tennis Court(s)
• Circular Driveway
• Driveway
• Garage Door Opener
• Garage Faces Side
• Off Street
• Gunite
• In Ground
• Gated
• Handicap Modified
• Recreation Facilities
• Security
• Inside
• Laundry Room
• Brick/Stone
• Ceramic Tile
• Parquet

Property details

Schools

District

Sarasota County School District

Elementary

Laurel Nokomis Elementary

Middle

SARASOTA MIDDLE SCHOOL

High

VENICE SENIOR HIGH SCHOOL

School grades from FLDOE public records. District polygons and school points from NCES EDGE. Assignment is not a legal attendance guarantee. Composite scores, when present, are derived from public records and are not official FLDOE grades.

Where is this home?

Common questions