101 OSPREY POINT DR new Save Request In-Person Tour Request Virtual Tour
Osprey,FL 34229
Key Details
Property Type Single Family Home
Sub Type Single Family Residence
Listing Status Active
Purchase Type For Sale
Square Footage 5,087 sqft
Price per Sqft $982
Subdivision The Oaks
MLS Listing ID A4664424
Bedrooms 4
Full Baths 5
Half Baths 1
HOA Fees $475/Semi-Annually
HOA Y/N Yes
Annual Recurring Fee 11400.0
Year Built 1985
Annual Tax Amount $12,940
Lot Size 0.930 Acres
Acres 0.93
Property Sub-Type Single Family Residence
Source Stellar MLS
Property Description
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.
Location
State FL
County Sarasota
Community The Oaks
Area 34229 - Osprey
Zoning RSF1
Rooms
Other Rooms Breakfast Room Separate,Den/Library/Office,Family Room,Formal Dining Room Separate,Formal Living Room Separate
Interior
Interior Features Built-in Features,Ceiling Fans(s),Chair Rail,Crown Molding,Eat-in Kitchen,High Ceilings,Primary Bedroom Main Floor,Solid Surface Counters,Stone Counters,Thermostat,Walk-In Closet(s),Wet Bar,Window Treatments
Heating Central,Electric,Zoned
Cooling Central Air,Zoned
Flooring Brick,Ceramic Tile,Parquet
Fireplaces Type Family Room,Living Room,Other,Primary Bedroom,Wood Burning
Fireplace true
Appliance Bar Fridge,Built-In Oven,Cooktop,Dishwasher,Disposal,Dryer,Electric Water Heater,Microwave,Range Hood,Refrigerator,Washer,Water Filtration System,Water Softener,Wine Refrigerator
Laundry Inside,Laundry Room
Exterior
Exterior Feature French Doors,Hurricane Shutters,Lighting,Private Mailbox
Parking Features Circular Driveway,Driveway,Garage Door Opener,Garage Faces Side,Off Street
Garage Spaces 3.0
Pool Gunite,In Ground
Community Features Buyer Approval Required,Clubhouse,Deed Restrictions,Fitness Center,Gated Community - Guard,Golf,Pool,Special Community Restrictions,Tennis Court(s),Street Lights
Utilities Available BB/HS Internet Available,Cable Available,Electricity Connected,Phone Available,Propane,Public,Sewer Connected,Sprinkler Well,Water Connected
Amenities Available Clubhouse,Fitness Center,Gated,Handicap Modified,Pool,Recreation Facilities,Security,Tennis Court(s)
Waterfront Description Lake Front
View Y/N Yes
View Water
Roof Type Tile
Porch Front Porch,Rear Porch
Attached Garage true
Garage true
Private Pool Yes
Building
Lot Description Cul-De-Sac,In County,Landscaped,Paved
Entry Level One
Foundation Slab
Lot Size Range 1/2 to less than 1
Sewer Public Sewer
Water Public,Well
Architectural Style Custom,Traditional
Structure Type Block,Stucco
New Construction false
Schools
Elementary Schools Laurel Nokomis Elementary
Middle Schools Sarasota Middle
High Schools Venice Senior High
Others
Pets Allowed Yes
HOA Fee Include Guard - 24 Hour,Pool,Management,Private Road,Security
Senior Community No
Pet Size Extra Large (101+ Lbs.)
Ownership Fee Simple
Monthly Total Fees $950
Acceptable Financing Cash,Conventional
Membership Fee Required Required
Listing Terms Cash,Conventional
Special Listing Condition None
Virtual Tour https://listings.threesixtyviews.net/videos/019953f8-eec5-710f-bd80-86bf091497ce