$5,000,000

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.… Read More 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. Read Less

Courtesy of DOUGLAS ELLIMAN 941-867-6199

Listing Snapshot

Days Online

Last Updated

Sep 17, 2025

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

5,087

Lot Size

0.93 Acres

Year Built

1985

MLS Number

A4664424

30 Days Snapshot Of 34229

$1.02M

+29%

(avg) sold price

-50%

homes sold

184

+148%

(avg) days on market

Snapshot

Area Map

Additional Details

Garage

Attached Garage Yn: t, Garage Spaces: 3, Garage Dimensions: 22x35

Building

Living Area Meters: 472.60, Room Count: 10, Architectural Style: "Custom", "Traditional", Building Area Total: 6841, Building Area Units: Square Feet, Construction Materials: "Block", "Stucco", Direction Faces: West, Levels: "One", Living Area: 5087, Year Built: 1985

Fees

Total Annual Fees: $11,400, Total Monthly Fees: $950

Water Features

Water View: Lake, Lake Frontage: 150 Feet, Total Water Frontage: 150 Feet, Water Front Features: "Lake Front"

Home Owner's Association

Association Email: [email protected], Association Fee Requirement: Required, Association Approval Required YN: 1, Monthly HOA Amount: $950, Association Fee Frequency: Semi-Annually, Association Fee Includes: "Guard - 24 Hour", "Pool", "Management", "Private Road", "Security", Association Fee: $5700, Association Name: Asset Management/ Hope Root, Association Phone: 813-607-2220

Lot

Lot Size Square Meters: 3771, Total Acreage: 1/2 to less than 1, Features: "Cul-De-Sac", "In County", "Landscaped", "Paved", 0.93 acres, 40593 square feet, View: "Water"

Miscellaneous

Number Times per Year: 1

Pets Policy

Pet Size: Extra Large (101+ Lbs.), Pets Allowed: "Yes"

Pool

Pool Dimensions: 36x20, Pool Features: "Gunite", "In Ground", Spa Features: "In Ground"

Property Access

Road Surface: "Asphalt", "Paved"

Appliances & Equipment

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", Other Equipment: "Irrigation Equipment"

Community

Community Features: "Buyer Approval Required", "Clubhouse", "Deed Restrictions", "Fitness Center", "Gated Community - Guard", "Golf", "Pool", "Special Community Restrictions", "Tennis Court(s)", "Street Lights"

Cooling

Cooling: "Central Air", "Zoned"

Exterior Features

Exterior Features: "French Doors", "Hurricane Shutters", "Lighting", "Private Mailbox"

Fireplaces

Fireplace Features: "Family Room", "Living Room", "Other", "Primary Bedroom", "Wood Burning"

Floors

Flooring: "Brick", "Ceramic Tile", "Parquet"

Foundation

Foundation Details: "Slab"

Heating

Heating: "Central", "Electric", "Zoned"

Interior Features

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

Laundry

Laundry Features: "Inside", "Laundry Room"

Parking

Parking Features: "Circular Driveway", "Driveway", "Garage Door Opener", "Garage Faces Side", "Off Street"

Property

Patio and Porch Features: "Front Porch", "Rear Porch", Vegetation: "Mature Landscaping", "Trees/Landscaped", Zoning: RSF1

Roof

Roof: "Tile"

Sewer

Sewer: "Public Sewer"

Utilities

Utilities: "BB/HS Internet Available", "Cable Available", "Electricity Connected", "Phone Available", "Propane", "Public", "Sewer Connected", "Sprinkler Well", "Water Connected", Water Source: "Public", "Well"

Windows

Window Features: "Blinds", "Drapes", "Window Treatments"

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