101 Osprey Point Drive, Osprey, FL 34229
Local realty services provided by:Bingham Realty ERA Powered
Listed by:joel schemmel
Office:douglas elliman
MLS#:A4664424
Source:MFRMLS
Price summary
- Price:$5,000,000
- Price per sq. ft.:$730.89
- Monthly HOA dues:$950
About this home
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.
Contact an agent
Home facts
- Year built:1985
- Listing ID #:A4664424
- Added:11 day(s) ago
- Updated:September 29, 2025 at 12:12 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:6
- Full bathrooms:5
- Half bathrooms:1
- Living area:5,087 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Central, Electric, Zoned
Structure and exterior
- Roof:Tile
- Year built:1985
- Building area:5,087 sq. ft.
- Lot area:0.93 Acres
Schools
- High school:Venice Senior High
- Middle school:Sarasota Middle
- Elementary school:Laurel Nokomis Elementary
Utilities
- Water:Public, Water Connected, Well
- Sewer:Public, Public Sewer, Sewer Connected
Finances and disclosures
- Price:$5,000,000
- Price per sq. ft.:$730.89
- Tax amount:$12,940 (2025)
The information being provided by My Florida Regional MLS DBA Stellar MLS. is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS.. Bingham Realty ERA Powered is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Bingham Realty ERA Powered, a broker participant of My Florida Regional MLS DBA Stellar MLS.. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.
The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by My Florida Regional MLS DBA Stellar MLS. and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.
Properties in listings may have been sold or may no longer be available.
Copyright 2025 My Florida Regional MLS DBA Stellar MLS.. All rights reserved.New listings near 101 Osprey Point Drive
- New
$1,950,000Active4 beds 5 baths3,857 sq. ft.627 N Macewen Drive, OSPREY, FL 34229
MLS# A4666440Listed by: GENEROUS PROPERTY - New
$685,000Active5 beds 3 baths2,746 sq. ft.571 Pine Ranch East Road, OSPREY, FL 34229
MLS# A4665938Listed by: MICHAEL SAUNDERS & COMPANY - New
$236,000Active2 beds 2 baths1,480 sq. ft.158 Edgewood Drive, OSPREY, FL 34229
MLS# N6140697Listed by: NEXTHOME IN THE SUN - New
$995,000Active4 beds 4 baths2,980 sq. ft.1602 Southbay Drive, OSPREY, FL 34229
MLS# A4665288Listed by: COMPASS FLORIDA LLC - New
$2,850,000Active6 beds 4 baths4,546 sq. ft.225 Harbor House Drive, OSPREY, FL 34229
MLS# TB8430963Listed by: HOMECOIN.COM - New
$549,000Active3 beds 2 baths2,133 sq. ft.708 Anna Hope Lane, OSPREY, FL 34229
MLS# TB8430902Listed by: PINEYWOODS REALTY LLC - New
$850,000Active3 beds 2 baths1,894 sq. ft.123 Windward Drive, OSPREY, FL 34229
MLS# A4656319Listed by: WILLIAM RAVEIS REAL ESTATE - New
$545,000Active4 beds 3 baths2,688 sq. ft.447 Oak Point Road, OSPREY, FL 34229
MLS# A4664810Listed by: COMPASS FLORIDA LLC 
$675,000Pending3 beds 2 baths2,346 sq. ft.563 Pine Ranch East Road, OSPREY, FL 34229
MLS# N6140562Listed by: PREMIER SOTHEBYS INTL REALTY
Protect your home and budget with an American Home Shield© home warranty. Learn more© 2023 - 2025 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.