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$2,595,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,953 Sq. Ft.
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Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

Full Property Details for 49 Osprey Point Dr

General

  • Price: $2,595,000
  • HOA FEE: $475/month
  • HOA FEE FREQ.: Annually
  • Taxes: $14,206 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4671762
  • Updated: 11/13/2025
  • Added to Site: 64 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 5
  • Interior Features: Built-in Features, Ceiling Fan(s), Central Vacuum, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room, Living Room
  • Appliances: Dishwasher, Range, Range Hood, Refrigerator
  • Flooring: Concrete

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Fiber Optic Lighting, In Ground, Salt Water
  • Spa: Yes
  • Spa Description: Heated, In Ground, Other
  • Security/Safety: Gated Community

Exterior

  • Exterior Features: Outdoor Shower, Sliding Doors, Storage
  • Deck/Patio: Covered, Enclosed, Screened
  • Porch/Patio/Deck: Covered, Enclosed, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Workshop in Garage

Location

  • Area: 34229 - Osprey
  • County: Sarasota
  • Development Name: 34229 - Osprey
  • Subdivision: OAKS
  • Driving Directions: From US 41 go South to Osprey Point Drive. West on Osprey point drive, show gate guard your card. 49 Osprey Point is on the right.
  • Direction Faces: North

School Information

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

Community

  • Community Name: 34229 - Osprey
  • Community Features: Bay/Harbor Front, Dock, Fishing, Water Access, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Restaurant, Tennis Court(s)
  • Optional Amenities: Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)
  • Association: Yes
  • Assoc. Name: The Oaks Club
  • Number of Pets: 3

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Public, Water Connected

Structural Information

  • Architectural Info: Contemporary, Custom
  • Architectural Style: Contemporary, Custom
  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Tile
  • Stories/Levels: One
  • Square Feet: 3,953
  • Sq. Ft. Source: Public Records
  • Year Built: 1989

Lot Features

  • Lot Size (Acres): 0.4
  • Lot Size (Sq. Ft.): 17,230
  • Lot Size: 17230
  • Street/Road Desc.: Asphalt

Water Features

  • Water Front: Yes
  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Desc.: Bay/Harbor Front, Lake Front

Green Features

  • Indoor Air Quality: Whole House Vacuum System

Financial Considerations

  • Association Fee: $5,700
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $14,206.23
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 135 OAKS
  • Flood Zone Info: X
  • APN: 142060007
  • Property ID: 142060007

Listed by Michael Saunders & Company

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Listing agent

— 49 Osprey Point Dr —

  • Michael Saunders & Company

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 49 Osprey Point Dr

School District:Sarasota County School District
NameGradesDistance
Laurel Nokomis School
1900 Laurel Road East, Nokomis, FL 34275
PK-86.5 mi
Venice Senior High School
1 Indian Avenue, Venice, FL 34285
9-128.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 49 Osprey Point Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/13/2025
Listed
$2,595,000
224.38%
MLS
5/31/2019
Sold
$800,000
—
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 49 Osprey Point Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$14,206
15%
$1,369,700
19%
2023
$12,389
52%
$1,148,800
86%
2021
$8,167
-31%
$618,500
-45%
2022
$11,844
45%
$1,115,900
87%
2021
$8,167
2%
$595,200
-6%
2019
$7,970
2%
$631,780
2%
2018
$7,814
-3%
$620,000
-1%
2017
$8,021
—
$625,900
2%
2016
$8,046
-2%
$613,500
—
2015
$8,215
—
$610,885
1%
2014
$8,187
—
$606,037
1%
2013
$8,187
—
$597,081
—
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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NMLS#: 1598647

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Listed by Michael Saunders & Company

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49 Osprey Point Drive, Osprey, FL 34229 (MLS# A4671762) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 49 Osprey Point Drive is currently listed for $2,595,000 and was received on November 13, 2025. Want to learn more about 49 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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