75 Osprey Point Drive, Osprey, FL 34229
$1,649,000 - For Sale
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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
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Equipment:
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Microwave
Range
Range Hood
Refrigerator
Washer
Wine Refrigerator
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
View:
Trees/Woods
Water
Amenities:
Gated
Security
Vehicle Restrictions
Financial Information:
Taxes: $14,635.87
Tax Year: 2025
Association Fee: $5,700.00
Association Fee Frequency: Semi-Annually
Room Dimensions:
Laundry: Inside, Laundry Room
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
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View Virtual Tour
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.
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.
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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
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3255 Tamiami Trail North
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The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of these sources: M.L.S. of Naples, Inc., Bonita Springs-Estero Association of REALTORS®, Southwest Florida MLS (Gulf Coast), My Florida Regional MLS DBA Stellar MLS, Sanibel and Captiva Island Association of Realtors®. Properties listed with brokerage firms other than Featured Home Listings are marked with the BR House Icon and detailed information about them includes the name of the Listing Brokers. The properties displayed may not be all the properties available through the BR Program. The data is updated every 4 hours, but can be influenced by delays from various real estate companies entering data in MLS. Some properties that appear for sale on this website may subsequently have sold or may otherwise no longer be available. All properties are subject to price or other changes without notice. For the most current information, please contact us using this form, or click on the "Request Info or Appointment" button on the search results and detailed property pages.
The source of this real property information is the copyrighted and proprietary database compilation of the © 2026 M.L.S. of Naples, Inc., © 2026 Bonita Springs-Estero Association of REALTORS®, © 2026 Southwest Florida MLS (Gulf Coast), © 2026 My Florida Regional MLS DBA Stellar MLS and © 2026 Featured Home Listings, a Florida Real Estate Brokerage. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it. Information last refreshed: 2026-07-19 00:08:41
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