101 OSPREY POINT DRIVE, OSPREY, FL 34229

Description of 101 OSPREY POINT DRIVE, OSPREY, FL 34229

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.

Property Details for 101 OSPREY POINT DRIVE, OSPREY, FL 34229

Bathrooms Full

5

Bathrooms Half

1

Interior Features

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

Appliances

Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine Refrigerator

Flooring

Brick/Stone, Ceramic Tile, Parquet

Heating

Central, Electric, Zoned

Cooling

Central Air, Zoned

Furnished

Unfurnished

Architectural Style

Custom, Traditional

Garage Spaces

3

Attached Garage

Yes

Parking Features

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

Pool Features

Gunite, In Ground

Pool Private

Yes

Direction Faces

West

Building Information for 101 OSPREY POINT DRIVE, OSPREY, FL 34229

Building Area Total

6841

Building Area Units

Square Feet

Association

Yes

Association Fee

$5,700

Association Fee Frequency

Semi-Annually

Association Amenities

Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(s)

Pets Allowed

Yes

Security Features

Gated Community, Security System Owned, Smoke Detector(s)

Property Information for 101 OSPREY POINT DRIVE, OSPREY, FL 34229

Lot Features

Cul-De-Sac, In County, Landscaped

Lot Size Square Feet

40,593

Waterfront

Yes

Waterfront Features

Lake Front

View

Water

Construction Materials

Block, Stucco

Roof

Tile

Exterior Features

French Doors, Hurricane Shutters, Irrigation System, Lighting, Private Mailbox

Sewer

Public Sewer

Water Source

Public, Well

New Construction

No

Public Records for 101 OSPREY POINT DRIVE, OSPREY, FL 34229

Parcel Number

0142050008

Tax Annual Amount

$12,940

Tax Year

2025

Tax Legal Description

LOTS 147 & 148, LESS N 30 FT OF LOT 148, TOGETHER WITH BEG AT SE COR OF LOT 148 TH N-6-10-38-W 96.8 FT TH N-87-22-15-E 2 FT TH S-6-10- 38-E 191.63 FT TH S-53-22-30-W 167.57 FT TH NWLY ALG CURVE TO RIGHT 31.71 FT TH N-54-13-02-E 181.65 FT TH N-6-10-38-W 62.54 FT TO POB, OAKS, BEING SAME LANDS AS DESC IN ORI 2022112936

Zoning

RSF1

County Or Parish

Sarasota

Schools Near 101 OSPREY POINT DRIVE, OSPREY, FL 34229

Elementary School

Laurel Nokomis Elementary

Middle School

Sarasota Middle

High School

Venice Senior High

School assignments are provided by the listing and should be independently verified.

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