$4,790,000
101 Osprey Point Drive Osprey, FL 34229
For Sale MLS# A4694716
4 beds 6 baths 5,087 sq ft Single Family
Details for 101 Osprey Point Drive
MLS# A4694716
Description for 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.
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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