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$1,649,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 4,001 Sq. Ft.
  • Updated 2 days ago
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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.

Full Property Details for 75 Osprey Point Dr

General

  • Price: $1,649,000
  • HOA FEE: $950/month
  • HOA FEE FREQ.: Semi-Annually
  • Taxes: $14,635 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4695145
  • Updated: 6/11/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 9
  • 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
  • Fireplace: Yes
  • Fireplace(s): Gas
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Gated, Security, Vehicle Restrictions
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground
  • Security/Safety: Security System, Security System Owned, Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System
  • Deck/Patio: Patio
  • Porch/Patio/Deck: Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Circular Driveway, Garage Faces Side

Location

  • Area: 34229 - Osprey
  • County: Sarasota
  • Development Name: 34229 - Osprey
  • Subdivision: OAKS
  • Driving Directions: Rte. 41/Tamiami S to The Oaks Bayside entrance. West through guard gate. Bear left to address on right.
  • Direction Faces: South

School Information

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

Community

  • Community Name: 34229 - Osprey
  • Community Features: Dock, Waterfront, Deed Restrictions, Golf, Irrigation-Reclaimed Water
  • Optional Amenities: Gated, Security, Vehicle Restrictions
  • Association: Yes
  • Assoc. Name: Access Management/Hope Root
  • Assoc. Fees Include: 24-Hour Guard, Common Area Taxes, Escrow Reserves Fund, Fidelity Bond, Manager, Private Road, Security
  • Number of Pets: 3
  • Pet Restrictions: 101lbs.

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Heat Pump, Zoned

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected

Structural Information

  • Architectural Info: Traditional
  • Architectural Style: Traditional
  • Builder: Bo MacEwen
  • Exterior Const.: Block, Stucco
  • Roof: Concrete, Tile
  • Windows: Blinds, Drapes, Insulated Windows, Rods, Window Treatments
  • Stories/Levels: One
  • Square Feet: 4,001
  • Sq. Ft. Source: Public Records
  • Year Built: 1983

Additional Structures

  • Other Structures: Guest House

Lot Features

  • Property View: Trees/Woods, Water
  • Lot Size (Acres): 0.76
  • Lot Size (Sq. Ft.): 32,983
  • Lot Size: 32983
  • Lot Dimensions: 260 x 130
  • Frontage: Private Road
  • Street/Road Desc.: Paved

Water Features

  • Water View: Yes
  • Water Front Desc.: Waterfront

Financial Considerations

  • Association Fee: $5,700
  • Assoc Fee Freq.: Semi-Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $14,635.87
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOTS 140 & 141 OAKS
  • Flood Zone Info: X
  • APN: 142050014
  • Property ID: 142050014
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 75 Osprey Point Dr —

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NMLS#: 1598647

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NMLS#: 1598647

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Schools serving 75 Osprey Point Dr

School District:Sarasota County School District
NameGradesDistance
Laurel Nokomis School
1900 Laurel Road East, Nokomis, FL 34275
PK-86.6 mi
Venice Senior High School
1 Indian Avenue, Venice, FL 34285
9-128.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 75 Osprey Point Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/11/2026
Listed
$1,649,000
153.69%
MLS
2/19/2021
Sold
$650,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 75 Osprey Point Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,636
3%
$1,172,127
-5%
2024
$14,229
18%
$1,237,700
28%
2023
$12,038
7%
$968,700
8%
2022
$11,222
82%
$896,700
82%
2021
$6,178
—
$491,384
1%
2021
$6,178
-18%
$484,600
-19%
2019
$7,547
2%
$597,847
2%
2018
$7,398
-1%
$586,700
1%
2017
$7,445
-5%
$580,100
3%
2016
$7,853
-14%
$564,000
-8%
2015
$9,141
5%
$610,445
10%
2014
$8,737
18%
$554,950
10%
2013
$7,398
—
$504,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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75 Osprey Point Drive, Osprey, FL 34229 (MLS# A4695145) is a Single Family property with 4 bedrooms and 4 full bathrooms. 75 Osprey Point Drive is currently listed for $1,649,000 and was received on June 11, 2026. This property is listed by Abbe Ross Team from our Longboat Key Office.Want to learn more about 75 Osprey Point Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

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