101 OSPREY POINT DR

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.

MLS ID#

MFRA4694716

Price

$4,790,000

Status

Active

Bedrooms

4

Bathrooms

6

Full Baths

5

Half Baths

1

Square Footage

5,087 sqft

Acres

0.9300

Year Built

1985

Type

Residential

Subtype

Single Family Residence

Style

Custom, Traditional

Address

101 OSPREY POINT DR

Subdivision

The Oaks

City

Osprey

County

Sarasota

State

FL

Zip Code

34229

Senior Community

No

Amenities

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

Parking

N/A

View

No

Waterfront

Yes

Pool

Yes

Interior Features

Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Stone Counters, Crown Molding, Window Treatments, Walk-In Closet(s), Solid Surface Counters, Wet Bar, Built-in Features, Primary Bedroom Main Floor, Thermostat, Chair Rail

Heating

Central, Electric, Zoned

Cooling

Central Air, Zoned

Flooring

Ceramic Tile, Brick, Parquet

Fireplace

Wood Burning, Living Room, Family Room, Other, Primary Bedroom

Stories

N/A

Appliances

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

Exterior Features

Lighting, French Doors, Hurricane Shutters, Private Mailbox

Construction

Block, Stucco

Foundation

Slab

Roof

Tile

Fencing

N/A

Lot Features

Paved, In County, Cul-De-Sac, Landscaped

Elementary

Laurel Nokomis Elementary

Middle

Sarasota Middle

High

Venice Senior High

Date Listed

May 26, 2026

Days on Market

7

Zoning

RSF1

Direction Faces

West

New Construction

No