$5,000,000
101 Osprey Point Drive Osprey, FL 34229
For Sale MLS# A4664424
4 beds 6 baths 5,087 sq ft Single Family
Details for 101 Osprey Point Drive
MLS# A4664424
Description for 101 Osprey Point Drive, Osprey, FL, 34229
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.
Listing Information
Property Type: Residential, Single Family Residence
Status: Active
Bedrooms: 4
Bathrooms: 6
Lot Size: 0.93 Acres
Square Feet: 5,087 sq ft
Year Built: 1985
Garage: Yes
Stories: 1 Story
Construction: Block,Stucco
Subdivision: The Oaks
Foundation: Slab
County: Sarasota
School Information
Elementary: Laurel Nokomis Elementary
Middle: Sarasota Middle
High: Venice Senior High
Room Information
Main Floor
Living Room:
Dining Room: 25x15
Primary Bathroom:
Primary Bedroom: 22x25
Bedroom 3: 13x13
Bedroom 2: 12x15
Library: 26x20
Bedroom 4: 10x12
Kitchen: 23x16
Family Room: 20x20
Bathrooms
Full Baths: 5
1/2 Baths: 1
Additonal Room Information
Laundry: Laundry Room, Inside
Interior Features
Appliances: Water Purifier, Bar Fridge, Built-In Oven, Electric Water Heater, Water Softener, Range Hood, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine Refrigerator
Flooring: Brick,Ceramic Tile,Parquet
Doors/Windows: Window Treatments, Drapes, Blinds
Fireplaces: Primary Bedroom, Living Room, Family Room, Wood Burning, Other
Additional Interior Features: Walk-In Closet(s), Built-in Features, Window Treatments, High Ceilings, Separate/Formal Dining Room, Wet Bar, Eat-In Kitchen, Ceiling Fan(s), Main Level Primary, Chair Rail, Separate/Formal Living Room, Solid Surface Counters, Stone Counters, Crown Molding
Utilities
Water: Well, Public
Sewer: Public Sewer
Other Utilities: Cable Available,Electricity Connected,High Speed Internet Available,Propane,Municipal Utilities,Phone Available,Sewer Connected,Water Connected
Cooling: Ceiling Fan(s), Central Air, Zoned
Heating: Zoned, Electric, Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 3
Parking Description: Off Street, Garage, Garage Door Opener, Circular Driveway, driveway, Garage Faces Side
Roof: Tile
Pool: Community, In Ground, Association, Gunite
Lot View: Lake,Water
Additional Exterior/Lot Features: French Patio Doors, Storm/Security Shutters, Sprinkler/Irrigation, Lighting, Front Porch, Rear Porch, Landscaped, Cul-de-Sac, Buyer Approval Required, Outside City Limits
Waterfront Details
Water Front Features: Lake Front
Community Features
Community Features: Clubhouse, Fitness, Golf, Pool, Tennis Court(s), Street Lights, Gated
Security Features: Gated with Guard, Gated Community, Smoke Detector(s), Security System Owned
Association Amenities: Security, Gated, Clubhouse, Fitness Center, Tennis Court(s), Pool, Recreation Facilities
HOA Dues Include: Security, Association Management, Road Maintenance, Pool(s)
Homeowners Association: Yes
HOA Dues: $5,700 / Semi-Annually
Driving Directions
US 41 to west into Oaks Bayside - Osprey Point Drive. Follow to 101 on the right.
Financial Considerations
Terms: Cash,Conventional
Tax/Property ID: 0142050008
Tax Amount: 12940.05
Tax Year: 2025
A broker reciprocity listing courtesy: DOUGLAS ELLIMAN
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Sales History & Tax Summary for 101 Osprey Point Drive
Sales History
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Tax Summary
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Schools
Schools nearby 101 Osprey Point Drive
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The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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