101 Osprey Point Drive, Osprey, FL 34229
$4,790,000 - For Sale
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Property Details
Price: $4,790,000
Sq Ft: 5,087
($942 per sqft)
Bedrooms: 4
Bathrooms: 5
Partial Baths: 1
City:Osprey
County:Sarasota
Type:Single Family
Development:The Oaks Club
Subdivision:Oaks
Acres:0.9300
Virtual Tour/Floorplan:View
Year Built:1985
Listing Number:A4694716
Status Code:A-Active
Taxes:$12,940.05
Tax Year: 2025
Garage: 3
/ Y
Furnishings: Unfurnished
Pets Allowed: Yes
Total Recurring Fees: $950
Total Recurring Fee Frequency: 0.00
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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
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
Exterior Features:
Hurricane Shutters
Lighting
Private Mailbox
View:
Water
Waterfront Description:
Lake Front
View: Lake
Amenities:
Clubhouse
Fitness Center
Gated
Handicap Modified
Pool
Recreation Facilities
Security
Tennis Court(s)
Financial Information:
Taxes: $12,940.05
Tax Year: 2025
Association Fee: $5,700.00
Association Fee Frequency: Semi-Annually
Room Dimensions:
Laundry: Inside, Laundry Room
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
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View Virtual Tour
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.
Building Description: Custom, Traditional
MLS Area: 34229 - Osprey
Total Square Footage: 6,841
Price per Square Feet: $941.62
Water: Public, Well
Construction: Block, Stucco
Date Listed: 2026-05-26 00:00:00
Pool: Y
Pool Description: Gunite, In Ground
Private Spa: Y
Furnished: Unfurnished
Windows: Blinds, Drapes, Window Treatments
Parking: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Brick, Ceramic Tile, Parquet
Roof: Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community, Security System Owned, Smoke Detector(S)
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Public Sewer
Lot Desc.: Cul-De-Sac, In County, Landscaped, Paved
Parcel ID: 0142050008
Amenities: Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(S)
Listing Courtesy Of: Douglas Elliman
joel.schemmel@elliman.com
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.
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Additional Information:
Building Description: Custom, Traditional
MLS Area: 34229 - Osprey
Total Square Footage: 6,841
Price per Square Feet: $941.62
Water: Public, Well
Construction: Block, Stucco
Date Listed: 2026-05-26 00:00:00
Pool: Y
Pool Description: Gunite, In Ground
Private Spa: Y
Furnished: Unfurnished
Windows: Blinds, Drapes, Window Treatments
Parking: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Brick, Ceramic Tile, Parquet
Roof: Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community, Security System Owned, Smoke Detector(S)
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Public Sewer
Lot Desc.: Cul-De-Sac, In County, Landscaped, Paved
Parcel ID: 0142050008
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
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John R. Wood Properties
3255 Tamiami Trail North
Naples, FL 34103
Contact Tracy Lebaron
(239) 821-5162
The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of these sources: M.L.S. of Naples, Inc., Bonita Springs-Estero Association of REALTORS®, Southwest Florida MLS (Gulf Coast), My Florida Regional MLS DBA Stellar MLS, Sanibel and Captiva Island Association of Realtors®. Properties listed with brokerage firms other than Featured Home Listings are marked with the BR House Icon and detailed information about them includes the name of the Listing Brokers. The properties displayed may not be all the properties available through the BR Program. The data is updated every 4 hours, but can be influenced by delays from various real estate companies entering data in MLS. Some properties that appear for sale on this website may subsequently have sold or may otherwise no longer be available. All properties are subject to price or other changes without notice. For the most current information, please contact us using this form, or click on the "Request Info or Appointment" button on the search results and detailed property pages.
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