101 Osprey Point Drive, Osprey, FL 34229
For Sale $5,000,000
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Listing Agent: Joel Schemmel
Agent Phone:
941-587-4894
Agent Email:
Joel.Schemmel@elliman.com
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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.
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
Clubhouse
Fitness Center
Gated
Handicap Modified
Pool
Recreation Facilities
Security
Tennis Court(s)
Taxes: $12.00
Tax Year: 2025
HOA Fee 1: $5,700.00
HOA Frequency 1: Semi-Annually
Condo Fee Frequency: Semi-Annually
French Doors
Hurricane Shutters
Lighting
Private Mailbox
Bar Fridge
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Electric Water Heater
Microwave
Range Hood
Refrigerator
Washer
Water Filtration System
Water Softener
Wine Refrigerator
Water
Lake Front
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
MLS Area: 34229 - Osprey
Water: Public, Well
Lot Desc.: Cul-De-Sac, In County, Landscaped, Paved
Construction: Block, Stucco
Date Listed: 2025-09-17 20:05:20
Pool: Yes
Pool Type: Gunite, In Ground
Private Spa: Yes
Windows: Blinds, Drapes, Window Treatments
Parking: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
Garage Spaces: 3
Flooring: Brick, Ceramic Tile, Parquet
Roof: Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Public Sewer
Amenities: Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(S)
Listing Courtesy Of: Douglas Elliman
Joel.Schemmel@elliman.com
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.
Property Details
Price: $5,000,000
Sq Ft: 5,087
($983 per sqft)
Bedrooms: 4
Bathrooms: 5
Partial Baths: 1
City: Osprey
County: Sarasota
Type: Single Family Reside
Development: The Oaks
Acres: 0.93
Virtual Tour/Floorplan: View
Year Built: 1985
Listing Number: A4664424
Status Code: A-Active
Taxes: $12.00
Tax Year: 2025
Garage:
3
Pets Allowed: Yes
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
Amenities:
Clubhouse
Fitness Center
Gated
Handicap Modified
Pool
Recreation Facilities
Security
Tennis Court(s)
Financial Information:
Taxes: $12.00
Tax Year: 2025
HOA Fee 1: $5,700.00
HOA Frequency 1: Semi-Annually
Condo Fee Frequency: Semi-Annually
Exterior Features:
French Doors
Hurricane Shutters
Lighting
Private Mailbox
Equipment:
Bar Fridge
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Electric Water Heater
Microwave
Range Hood
Refrigerator
Washer
Water Filtration System
Water Softener
Wine Refrigerator
View:
Water
Waterfront Description:
Lake Front
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
Additional Information:
MLS Area: 34229 - Osprey
Water: Public, Well
Lot Desc.: Cul-De-Sac, In County, Landscaped, Paved
Construction: Block, Stucco
Date Listed: 2025-09-17 20:05:20
Pool: Yes
Pool Type: Gunite, In Ground
Private Spa: Yes
Windows: Blinds, Drapes, Window Treatments
Parking: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
Garage Spaces: 3
Flooring: Brick, Ceramic Tile, Parquet
Roof: Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Public Sewer
Amenities: Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(S)
Map of 101 Osprey Point Drive, Osprey, FL 34229
Listing Courtesy Of: Douglas Elliman
Joel.Schemmel@elliman.com