Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks.
Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting.
A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout.
The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer.
Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community.
Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key.
Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar.
Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.
Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting.
A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout.
The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer.
Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community.
Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key.
Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar.
Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.
Property Details
Price:
$1,649,000
MLS #:
A4695145
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKS
Neighborhood:
34229osprey
Listed Date:
Jun 11, 2026
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:
Sarasota Middle
High School:
Venice Senior High
Interior
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Bathrooms
4 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Carpet, Tile
Heating
Heat Pump, Zoned
Interior Features
Ceiling Fan(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Architectural Style
Traditional
Association Amenities
Gated, Security, Vehicle Restrictions
Attached Garage YN
1
Community Features
Dock, Waterfront, Deed Restrictions, Golf, Irrigation-Reclaimed Water
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
South
Exterior Features
Irrigation System
Garage Spaces
2
Lot Features
In County, Near Golf Course
Open Parking YN
1
Other Structures
Guest House
Parking Features
Circular Driveway, Garage Faces Side
Patio And Porch Features
Patio
Roof
Concrete, Tile
Security Features
Security System, Security System Owned, Smoke Detector(s)
View
Trees/Woods, Water
Waterfront Features
Waterfront
Window Features
Blinds, Drapes, Insulated Windows, Rods, Window Treatments
Financial
HOA Fee
$5,700
HOA Fee Frequency
Semi-Annually
HOA Includes
24-Hour Guard, Common Area Taxes, Escrow Reserves Fund, Fidelity Bond, Manager, Private Road, Security
HOA Name
Access Management/Hope Root
HOA Phone
813-607-2220
Tax Year
2025
Taxes
$14,636
Map
Community
- Address75 POINT DRIVE OSPREY FL
- SubdivisionOAKS
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN POINT MARINA VILLAGE
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- HIDDEN BAY; LAKE VISTA
- LAKE VISTA
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY PARK 2
- PALMER
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SORRENTO VILLAS 2
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WEBBS W D ADD
- WILLOWBEND
- WILLOWBEND PH 1
- WILLOWBEND PH 2
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of Jun 20, 2026
85
Single Family Listed
157
Avg DOM
465
Avg $ / SqFt
$1,432,294
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 $1,649,000 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 $412. The average price per square foot for Single Family listings in OSPREY is $465. The average listing price for Single Family in OSPREY is $1,432,294. To schedule a showing of MLS#a4695145 at 75 POINT DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of COLDWELL BANKER REALTY. 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