75 Osprey Point Drive, Osprey, FL 34229
For Sale $1,649,000
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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.
Ceiling Fans(s)
Crown Molding
High Ceilings
Primary Bedroom Main Floor
Solid Wood Cabinets
Vaulted Ceiling(s)
Walk-In Closet(s)
Window Treatments
Gated
Security
Vehicle Restrictions
Taxes: $14,635.87
Tax Year: 2025
Association Fee: $5,700.00
Association Fee Frequency: Semi-Annually
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Microwave
Range
Range Hood
Refrigerator
Washer
Wine Refrigerator
Trees/Woods
Water
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
Building Description: Traditional
MLS Area: 34229 - Osprey
Total Square Footage: 5,028
Price per Square Feet: $412.15
Water: Public
Construction: Block, Stucco
Date Listed: 2026-06-11 00:00:00
Pool: Y
Pool Description: In Ground
Furnished: Unfurnished
Windows: Blinds, Drapes, Insulated Windows, Rods, Window Treatments
Parking: Circular Driveway, Garage Faces Side
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Carpet, Tile
Roof: Concrete, Tile
Heating: Heat Pump, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Security System, Security System Owned, Smoke Detector(S)
Laundry: Inside, Laundry Room
Pets: Dogs Ok, Yes
Sewer: Public Sewer
Lot Desc.: In County, Near Golf Course, Private
Parcel ID: 0142050014
Amenities: Gated, Security, Vehicle Restrictions
Listing Courtesy Of: Coldwell Banker Realty
steveabbe@pga.com
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.
Property Details
Price: $1,649,000
Sq Ft: 4,001
($412 per
sqft)
Bedrooms: 4
Bathrooms: 4
City: Osprey
County: Sarasota
Type: Single Family
Development: The Oaks Club
Subdivision: Oaks
Acres: 0.7600
Virtual Tour/Floorplan: View
Year Built: 1983
Listing Number: A4695145
Status Code: A-Active
Taxes: $14,635.87
Tax Year: 2025
Garage:
2
/
Y
Furnishings: Unfurnished
Pets Allowed: Dogs OK, Yes
Total Recurring Fees: $950
Total Recurring Fee Frequency: 0.00
Interior Features:
Ceiling Fans(s)
Crown Molding
High Ceilings
Primary Bedroom Main Floor
Solid Wood Cabinets
Vaulted Ceiling(s)
Walk-In Closet(s)
Window Treatments
Amenities:
Gated
Security
Vehicle Restrictions
Financial Information:
Taxes: $14,635.87
Tax Year: 2025
Association Fee: $5,700.00
Association Fee Frequency: Semi-Annually
Equipment:
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Microwave
Range
Range Hood
Refrigerator
Washer
Wine Refrigerator
View:
Trees/Woods
Water
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
Additional Information:
Building Description: Traditional
MLS Area: 34229 - Osprey
Total Square Footage: 5,028
Price per Square Feet: $412.15
Water: Public
Construction: Block, Stucco
Date Listed: 2026-06-11 00:00:00
Pool: Y
Pool Description: In Ground
Furnished: Unfurnished
Windows: Blinds, Drapes, Insulated Windows, Rods, Window Treatments
Parking: Circular Driveway, Garage Faces Side
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Carpet, Tile
Roof: Concrete, Tile
Heating: Heat Pump, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Security System, Security System Owned, Smoke Detector(S)
Laundry: Inside, Laundry Room
Pets: Dogs Ok, Yes
Sewer: Public Sewer
Lot Desc.: In County, Near Golf Course, Private
Parcel ID: 0142050014
Amenities: Gated, Security, Vehicle Restrictions
Map of 75 Osprey Point Drive, Osprey, FL 34229
Listing Courtesy Of: Coldwell Banker Realty
steveabbe@pga.com