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Fran Schwartz
REALTOR®
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75 Osprey Point Drive, Osprey, FL 34229

$1,649,000
  • 75 Osprey Point Drive, Osprey, FL 34229 Main Photo

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New to the Market Active
BEDS4 BATHS4 full SQUARE FEET4,001 MLS#A4695145
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONOAKS

Property Description

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.

75 Osprey Point Drive | MLS# A4695145

This single family home located at 75 Osprey Point Drive, Osprey, FL 34229 is currently listed for sale with an asking price of $1,649,000. This property was built in 1983 and has 4 bedrooms and 4 full baths with 4001 sq. ft. Osprey Point Drive is located in the OAKS subdivision. Search OAKS real estate on fschwartz.floridaexecutiverealty.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air, Zoned
Garage: 2 car attached
Heating: Heat Pump, Zoned
Home Style: Traditional
Lot Size: 0.76 Acres
Roof Type: Concrete, Tile
Stories: 1.0
Taxes: $14,635
Year Built: 1983

Amenities

Ceiling Fans(s)
Crown Molding
High Ceilings
Primary Bedroom Main Floor
Solid Wood Cabinets
Vaulted Ceiling(s)
Walk-In Closet(s)
Window Treatments

Feature Descriptions

Additional Rooms: Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Great Room
Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Association Amenities: Gated, Security, Vehicle Restrictions
Builder: Bo MacEwen
Community Features: Deed Restrictions, Golf, Irrigation-Reclaimed Water
Directions: Rte. 41/Tamiami S to The Oaks Bayside entrance. West through guard gate. Bear left to address on right.
Exterior: Block, Stucco
Fireplace: Gas
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Carpet, Tile
Foundation: Slab
HOA Fee: 5700/ Semi-Annually
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: In County, Near Golf Course, Private
Lot Dimensions: 0.76
Number of Pets: 3
Other Equipment: Irrigation Equipment
Other Structures: Guest House
Ownership: Fee Simple
Parking: Circular Driveway, Garage Faces Side
Parking Notes: Circular Driveway, Garage Faces Side
Patio/Porch: Patio
Pets Allowed: Dogs OK, Yes
Pets Size: Extra Large (101+ Lbs.)
Pets Weight (Max): 101
Pool: In Ground
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Security System, Security System Owned, Smoke Detector(s)
Sewer: Public Sewer
Showing Instructions: Appointment Only, Contact Call Center, Listing Agent Must Accompany, ShowingTime
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: BB/HS Internet Available, Cable Connected
Vegetation: Bamboo, Mature Landscaping, Oak Trees, Trees/Landscaped, Wooded
Water: Public
Water Access Y/N: No
Water View: Pond
Windows: Blinds, Drapes, Insulated Windows, Rods, Window Treatments
Zoning: RE1

Room Sizes

Foyer: 12x18
Great Room: 22x45
Dining Room: 29x40
Studio: 12x20
Kitchen: 9x15
Primary Bedroom: 14x16
Bedroom 2: 13x16
Bedroom 3: 11x11
Laundry: 13x8

Local Schools

High School: Venice Senior High
Middle School: Sarasota Middle
Elementary School: Laurel Nokomis Elementary

Listed By / Shown By

Listed By

Agency Name: COLDWELL BANKER REALTY
Agency Contact: 941-383-6411

Shown By

Agent Name: Fran Schwartz
Agent Phone: (813) 324-2440
Agency Title: Florida Executive Realty

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Estimated Payment

$ 5,370.50 per month $3,669.96 Principal & Interest $1,219.58 Property Tax $480.96 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/11/2026. The listing information on this page last changed on 06/11/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 06/11/2026 12:01:40 AM EST) or Stellar MLS (last updated Wed 06/10/2026 11:44:19 PM EST). Real estate listings held by brokerage firms other than Florida Executive Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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