OSPREY, FL 34229 101 OSPREY POINT DRIVE

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Presented By: DOUGLAS ELLIMAN with 941-867-6199. - Lena White
  • MLS# A4664424
  • 09/17/2025
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Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 4
  • Full/Half Baths • 5 / 1
  • SQFT • 5,087
  • Garage • 3

Home Details

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.
Presented By: DOUGLAS ELLIMAN with 941-867-6199. - Lena White

Interior Features for 101 OSPREY POINT DRIVE

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths1
Total Baths6

Other Interior Features

LivingAreaSourcepublic records
Air Conditioning Y/NYes
Fireplace Featuresfamily room, living room, other room, master bedroom, wood burning
Fireplace Y/NYes
Flooringbrick/stone, ceramic tile, parquet
Heating Y/NYes
Interior Amenitiesbuilt-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, w
Laundry Featuresinside, laundry room
Window Featuresblinds, drapes, window treatments

General for 101 OSPREY POINT DRIVE

Additional Parcels Y/NNo
Additional Roomsbreakfast room separate, den/library/office, family room, formal dining room separate, formal living room separate
Appliancesbar fridge, built-in oven, cooktop, dishwasher, disposal, dryer, electric water heater, microwave, range hood, refrigerator, washer, water filtration system, water softener, wine refrigerator
Architectural Stylecustom, traditional
Assoc Fee Paid Persemi-annually
Association Amenitiesclubhouse, fitness center, gated, handicap modified, pool, recreation facilities, security, tennis court(s)
Association Fee Includes24-hour guard, community pool, manager, private road, security
Association Nameasset management/ hope root
Attached Garage Yes
Building Area Unitssquare feet
Carport Y/NNo
Cityosprey
Community Featuresbuyer approval required, clubhouse, deed restrictions, fitness center, gated community - guard, golf, pool, special community restrictions, tennis court(s)
Construction Materialsblock, stucco
Coolingcentral air, zoned
Countysarasota
Directionsus 41 to west into oaks bayside - osprey point drive. follow to 101 on the right.
Elementary Schoollaurel nokomis elementary
Facing Directionwest
Flood Zone Codeae x
Flood Zone Code XY
Full Baths5
Garage Spaces3
Garage Y/NYes
HOAYes
HOA Fee$5700
Heatingcentral, electric, zoned
High Schoolvenice senior high
Land Lease Y/NNo
Lease Considered Y/NYes
Legal Descriptionlots 147 & 148, less n 30 ft of lot 148, together with beg at se cor of lot 148 th n-6-10-38-w 96.8 ft th n-87-22-15-e 2 ft th s-6-10- 38-e 191.63 ft th s-53-22-30-w 167.57 ft th nwly alg curve to righ
Levelsone
Listing Termscash, conventional
Living Area Unitssquare feet
Lot Size Square Feet40593
Lot Size Unitssquare feet
MLS Area34229 - osprey
Middle/Junior High Schoolsarasota middle
Minimum Lease1-2 years
ModificationTimestamp2025-09-18t11:16:01.747z
Monthly HOA Amount950
New ConstructionNo
Occupancy Typeowner
Ownershipfee simple
Patio/Porch Featuresfront porch, rear porch
Pet Size Limitextra large (101+ lbs.)
Pets Allowedyes
Pool Featuresgunite, in ground
Property Subtypesingle family residence
Property Typeresidential
Rooftile
STELLAR_InLawSuiteYNNo
Security Featuresgated community, security system owned, smoke detector(s)
Senior Community Y/NNo
Sewerpublic sewer
Spa Featuresin ground
Standard Statusactive
Statusactive
Subdivision Namethe oaks
Tax Annual Amount12940.05
Tax Lot147
Tax Year2025
Total Rooms10
Utilitiesbb/hs internet available, cable available, electricity connected, phone available, propane, public, sewer connected, sprinkler well, street lights, water connected
Viewwater
Virtual TourClick here
Water Access Y/NNo
Water Viewlake
Water View Y/NYes
Waterfront Featureslake front
Year Built1985
Zoningrsf1

Exterior for 101 OSPREY POINT DRIVE

Building Area Total6841
Covered Spaces3
Exterior Amenitiesfrench doors, hurricane shutters, irrigation system, lighting, private mailbox
Foundation Detailsslab
Lot Featurescul-de-sac, in county, landscaped
Lot Size Acres0.93
Lot Size Area40593
Parking Featurescircular driveway, driveway, garage door opener, garage faces side, off street
Private PoolYes
Road Frontage Typestreet paved
Road Surface Typepaved, asphalt
SpaYes
Vegetationmature landscaping, trees/landscaped
Water Sourcepublic, well
Waterfront Y/NYes

Additional Details

Price History

Schools

Middle School Sarasota Middle
High School Venice Senior High
Elementary School Laurel Nokomis Elementary

Steven Pugh

Broker Associate | Team Leader
Price $5,000,000
MLS#A4664424
List Date 09/17/2025
Property Type Single Family
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