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$1,775,000
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Property Description
**STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks' Clubhouse, boasts an impressive 253FT frontage along the highly sought-after Osprey Point Drive in the Bayside neighborhood often regarded as the "Park Avenue" of The Oaks Golf & Country Club. A gorgeous new 4ft x 4ft "Celini Agento Italian" tile accentuates the fresh color scheme throughout this well-appointed home complete with impressive fireplace, 14-inch crown moldings, wainscoting, palladium windows and much more! The nearby, private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. The Oaks-Bayside is a truly distinguished, 24hr guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America's Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the AERIAL VIDEO**
Full Property Details
Full Property Details for 75 Osprey Point Dr
General
- Price: $1,775,000
- HOA FEE: $950/month
- HOA FEE FREQ.: Semi-Annually
- Taxes: $14,228 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4672439
- Updated: 1/8/2026
- Added to Site: 58 day(s) ago
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 9
- Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Skylight(s), Solid Wood Cabinets, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Electric, Living Room
- Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Microwave, Range, Refrigerator, Washer
- Furnishings: Negotiable
- Flooring: Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 4
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Basketball Court, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Pickleball Court(s), Playground, Pool, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
- Pool: Yes
- Private Pool: Yes
- Pool Description: Chlorine Free, Gunite, Heated, In Ground, Other, Self Cleaning
- Security/Safety: Fire Alarm, Gated Community, Medical Alarm, Security System, Security System Owned, Smoke Detector(s)
Exterior
- Exterior Features: French Doors, Hurricane Shutters, Irrigation System, Lighting, Rain Gutters
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Oversized
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: OAKS
- Driving Directions: US41 TO WEST ONTO OSPREY POINT DR. (D/L / REALTOR CREDENTIALS REQUIRED AT GATE). PROCEED THROUGH ENTRY GATE AND ARRIVE AT PROPERTY ON RIGHT.
- Direction Faces: South
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Laurel Nokomis Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- Community Features: Bay/Harbor Front, Dock, Intracoastal Waterway, Waterfront, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, No Truck/RV/Motorcycle Parking, Playground, Pool, Restaurant, Tennis Court(s)
- Optional Amenities: Basketball Court, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Pickleball Court(s), P
- Association: Yes
- Assoc. Name: ACCESS MANAGEMENT / HOPE ROOT
- Assoc. Fees Include: 24-Hour Guard, Common Area Taxes, Community Pool, Manager, Private Road, Recreational Facilities, Security
- Number of Pets: 3
- Pet Restrictions: REFER TO DOCS
Heating & Cooling
- Cooling Type: Zoned
- Heating Type: Central, Electric, Zoned
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Underground Utilities, Water Connected
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Concrete, Stucco
- Roof: Built-Up, Membrane, Tile
- Stories/Levels: One
- Square Feet: 4,001
- Sq. Ft. Source: Public Records
- Year Built: 1983
Additional Structures
- Other Structures: Guest House
Lot Features
- Property View: Park/Greenbelt, Water
- Lot Size (Acres): 0.76
- Lot Size (Sq. Ft.): 32,983
- Lot Size: 32983
- Frontage: Street Paved, Private Road
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Masonry
Water Features
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake
- Water Front Desc.: Bay/Harbor Front, Waterfront
Financial Considerations
- Association Fee: $5,700
- Assoc Fee Freq.: Semi-Annually
- Assoc Fee Desc.: Required
- Tax Amount: $14,228.54
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOTS 140 & 141 OAKS
- Flood Zone Info: X
- APN: 142050014
- Property ID: 142050014
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Schools
Schools serving 75 Osprey Point Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 6.6 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 8.6 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 75 Osprey Point Dr
Date
Details
Price
Change
Source
1/08/2026
Price Reduced
$1,775,000
-10.13%
MLS
11/19/2025
Listed
$1,975,000
203.85%
MLS
2/19/2021
Sold
$650,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 75 Osprey Point Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$13,581
-5%
$1,193,700
-4%
2024
$14,229
18%
$1,237,700
28%
2023
$12,038
7%
$968,700
8%
2022
$11,222
82%
$896,700
82%
2021
$6,178
—
$491,384
1%
2021
$6,178
-18%
$484,600
-19%
2019
$7,547
2%
$597,847
2%
2018
$7,398
-1%
$586,700
1%
2017
$7,445
-5%
$580,100
3%
2016
$7,853
-14%
$564,000
-8%
2015
$9,141
5%
$610,445
10%
2014
$8,737
18%
$554,950
10%
2013
$7,398
—
$504,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 75 Osprey Point Dr
75 Osprey Point Drive, Osprey, FL 34229 (MLS# A4672439) is a Single Family property with 4 bedrooms and 4 full bathrooms. 75 Osprey Point Drive is currently listed for $1,775,000 and was received on November 19, 2025. Want to learn more about 75 Osprey Point Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

