**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**
Property Details
Price:
$1,775,000
MLS #:
A4672439
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKS
Neighborhood:
34229osprey
Listed Date:
Nov 19, 2025
Finished Sq Ft:
4,001
Total Sq Ft:
5,028
Lot Size:
32,983 sqft / 0.76 acres (approx)
Year Built:
1983
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Laurel Nokomis Middle
High School:
Venice Senior High
Interior
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Microwave, Range, Refrigerator, Washer
Bathrooms
4 Full Bathrooms
Cooling
Zoned
Flooring
Ceramic Tile
Heating
Central, Electric, Zoned
Laundry Features
Inside, Laundry Room
Exterior
Architectural Style
Traditional
Association Amenities
Basketball Court, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Pickleball Court(s), Playground, Pool, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
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)
Construction Materials
Concrete, Stucco
Exterior Features
French Doors, Hurricane Shutters, Irrigation System, Lighting, Rain Gutters
Other Structures
Guest House
Parking Features
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Oversized
Roof
Built-Up, Membrane, Tile
Security Features
Fire Alarm, Gated Community, Medical Alarm, Security System, Security System Owned, Smoke Detector(s)
Financial
HOA Fee
$5,800
HOA Frequency
Semi-Annually
HOA Includes
24-Hour Guard, Common Area Taxes, Community Pool, Manager, Private Road, Recreational Facilities, Security
HOA Name
ACCESS MANAGEMENT / HOPE ROOT
Tax Year
2024
Taxes
$14,229
Map
Community
- Address75 POINT DRIVE OSPREY FL
- SubdivisionOAKS
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BAYPOINTE VISTA 2
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN HARBOR WATERFRONT VILLAS PHASE 2
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- MERIDIAN AT THE OAKS
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-A
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OGBURNS T B ADD
- OSPREY EXECUTIVE PARK
- OSPREY HARBOR VILLAGE
- OSPREY PARK 2
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 1 OF BAY STREET
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL THE WOODLANDS
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WILLOWBEND PH 1
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WILLOWBEND PHASE 3
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of Mar 12, 2026
116
Single Family Listed
118
Avg DOM
465
Avg $ / SqFt
$1,451,200
Avg List Price
Property Summary
- Located in the OAKS subdivision, 75 POINT DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $1,775,000 and features 4 beds, 4 baths, and has approximately 4,001 square feet of living space, and was originally constructed in 1983. The current price per square foot is $444. The average price per square foot for Single Family listings in OSPREY is $465. The average listing price for Single Family in OSPREY is $1,451,200. To schedule a showing of MLS#a4672439 at 75 POINT DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of GENEROUS PROPERTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 75 POINT DRIVE
OSPREY, FL