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75 Osprey Point Drive

Osprey, FL 34229
  • $1,595,000
  • STATUS: Active
  • ON SITE: 64 Days
  • MLS #: A4695145
Price Reduced
UPDATED: 235 min ago
$1,595,000
  • 4
    BEDS
  • 0.76
    ACRES
  • 4
    BATHS
  • 0
    1/2 BATHS
  • 4,001
    SQFT
  • $399
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1983
County:
Area:

School Information

Elementary School:
Middle School:
High School:

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.

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-14T23:44:06.507.
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75 Osprey Point Drive Osprey, FL 34229

  • Price: $1,595,000
  • Status: Active
  • On Site: 64 Days
  • Updated: 235 min ago
  • MLS #: A4695145
4
Beds
4
Baths
0
½ Baths
0.76
Acres
4,001
SQFT
$399
$/SQFT
1983
Built
Neighborhood:
Oaks
County:
Sarasota
Area:
Osprey
Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High
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.
Exterior Features

Architectural Style Traditional Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 2 Direction Faces South Exterior Features Irrigation System Foundation Details Slab Lot Features In CountyNear Golf Course Lot Size Dimensions 260 x 130 Open Parking YN Yes Other Structures Guest House Parking Features Circular DrivewayGarage Faces Side Patio And Porch Features Patio Pool Features In Ground Pool Private Yn Yes Road Frontage Type Private Road Road Surface Type Paved Roof ConcreteTile Spa YN No View Trees/WoodsWater Water Access Yn No Water Extras Yn No Water View Pond Water View Yn Yes Waterfront Features Waterfront Waterfront Yn No

Interior Features

Additional Rooms Breakfast Room SeparateDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateGreat Room Appliances DishwasherDisposalDryerElectric Water HeaterExhaust FanMicrowaveRangeRange HoodRefrigeratorWasherWine Refrigerator Building Area Total 5028 Cooling Central AirZoned Cooling YN Yes Fireplace Features Wood Burning Fireplace Yn Yes Flooring CarpetTile Furnished Unfurnished Heating Heat PumpZoned Heating YN Yes Interior Features Ceiling Fan(s)Crown MoldingHigh CeilingsPrimary Bedroom Main FloorSolid Wood CabinetsVaulted Ceiling(s)Walk-In Closet(s)Window Treatments Laundry Features InsideLaundry Room Levels One Rooms Studio Kitchen Bedroom 3 (Built-in Closet) Bedroom 2 (Built-in Closet) Laundry Foyer Primary Bedroom (Walk-In Closet(s)) Great Room Dining Room Sewer Public Sewer Water Source Public Window Features BlindsDrapesInsulated WindowsRodsWindow Treatments

Property Features

Additional Lease Restrictions See documents Additional Parcels YN Yes Approval Process Submit application Association Amenities GatedSecurityVehicle Restrictions Association Approval Required Yn Yes Association Fee 5700 Association Fee Frequency Semi-Annually Association Fee Includes 24-Hour GuardCommon Area TaxesEscrow Reserves FundFidelity BondManagerPrivate RoadSecurity Association Fee Monthly Amount 950 Association Fee Requirement Required Association Yn Yes Builder Name Bo MacEwen Cdd Yn No Community Features DockWaterfrontDeed RestrictionsGolfIrrigation-Reclaimed Water Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn No Lease Considered YN Yes Lease Restrictions YN Yes Listing Terms CashConventional Max Pet Weight 101 Minimum Lease 1-2 Years New Construction Yn No Number Of Pets 3 Occupant Type Owner Ownership Fee Simple Pet Size Extra Large (101+ Lbs.) Pets Allowed Dogs OKYes Property Sub Type Single Family Residence Security Features Security SystemSecurity System OwnedSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Sw Subdiv Community Name The Oaks Tax Annual Amount 14635.87 Total Annual Fees 11400 Total Monthly Fees 950 Utilities BB/HS Internet AvailableCable Connected Yrs Of Owner Prior To Leasing Re No Zoning RE1


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of COLDWELL BANKER REALTY: 941-383-6411.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-14T23:44:06.507.
 
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