101 Osprey Point Drive, OSPREY, FL

$5,000,000

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4

Beds

6

Baths

5,087

Square feet

0.93

Acres

About 101 Osprey Point Drive

A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a white onyx floor with marble inserts. Spaces include an oversized living room with dual fireplaces, a crystal chandelier, and multiple sets of French doors opening to the lakefront patio. The dining room, anchored by another fireplace and framed by custom casings and built-in shelving, is ideal for grand entertaining. A domed ceiling sitting room with French doors to the patio adds an intimate space for cocktails or conversation, while the custom bar and wine room, with etched glass cabinetry, stone counters, and display shelving, enhances the home’s appeal for gatherings. The kitchen, completely remodeled in 2019, is a showcase of craftsmanship with UltraKraft® cabinetry, custom soffit lighting, Corian countertops, and a center island with breakfast bar. Luxury appliances include a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A butler’s pantry provides additional storage, while the sunny breakfast nook overlooks lush gardens. Family and gathering rooms carry the same sense of scale, with dramatic fireplaces, intricate moldings, and detailed ceiling treatments that flow seamlessly for everyday living or large-scale entertaining. The primary suite is a true retreat with a spacious sitting area, custom closets, and a well-appointed bathroom that was newly remodeled in 2025 with spa-inspired finishes. Three guest suites, each with updated full baths (2021 and 2025), provide privacy and comfort. One is a suite with a bathroom near the laundry room, which offers flexibility for live-in staff or extra accommodation. Outdoors, the home embraces its setting with an open pool, expansive deck, and cabana surrounded by manicured hedges and mature landscaping. The views are equally compelling, with mature gardens and community reflecting pond in the front and sweeping lake vistas in the back. Additional highlights include a three-car garage, refinished hardwood floors (2020), and a new Daikin 5-ton AC system installed in 2022. Ownership at The Oaks Club brings an unmatched lifestyle, with two championship golf courses, tennis and pickleball courts, croquet, a fitness center and spa, three on-site restaurants, and a community dock on Little Sarasota Bay. Elegant yet inviting, 101 Osprey Point Drive stands as a rare opportunity to enjoy lakefront living with resort-style amenities in one of Sarasota’s most established private enclaves.

Features of 101 Osprey Point Drive

MLS® # A4664424
Price $5,000,000
Bedrooms 4
Bathrooms 6.00
Full Baths 5
Half Baths 1
Square Footage 5,087
Acres 0.93
Year Built 1985
Type Residential
Sub-Type Single Family Residence
Style Custom, Traditional
Status Active
Property Taxes 12,940.00
Total Annual Fees 11400.00
Pet Allowed Yes
Pet Size Limit Extra Large (101+ Lbs.)
Minimum Lease 1-2 Years

Community Information

Address 101 Osprey Point Drive
Area Osprey
Subdivision THE OAKS
City OSPREY
County Sarasota
State FL
Zip Code 34229-9248

Amenities

Amenities Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(s)
Parking Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
# of Garages 3
View Water
Is Waterfront Yes
Waterfront Lake Front
Has Pool Yes

Interior

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
Heating Central, Electric, Zoned
Cooling Central Air, Zoned
Fireplace Yes
Fireplaces Family Room, Living Room, Other Room, Master Bedroom, Wood Burning

Exterior

Exterior Features French Doors, Hurricane Shutters, Irrigation System, Lighting, Private Mailbox
Lot Description Cul-De-Sac, In County, Landscaped
Roof Tile
Foundation Slab

School Information

Elementary Laurel Nokomis Elementary
Middle Sarasota Middle
High Venice Senior High

Additional Information

Date Listed September 17th, 2025
Days on Market 17
Zoning RSF1
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeDOUGLAS ELLIMAN

Listing Map

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