$2,399,000
49 Osprey Point Drive
Osprey, FL 34229
About this home
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.
Estimated monthly payment
$14,889/mo
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history187 days on market
- Status: ActiveNov 13, 2025
- Listed$2,595,000Nov 13, 2025
- Price reduced$2,399,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 187
- Subdivision
- Oaks
- County
- Sarasota
- Year built
- 1989
- Living area
- 3,953 sq ft
- Price/sq ft
- $607
- Building area
- 5,227 sq ft (Public Records)
- Lot size
- 17,230 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $14,206 (2024)
- Parcel #
- 0142060007
- Zoning
- RSF1
- MLS #
- A4671762
Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Half bathrooms
- 1
- Flooring
- Concrete
- Appliances
- Dishwasher, Range, Range Hood, Refrigerator
- Interior features
- Built-in Features, Ceiling Fans(s), Central Vaccum, Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- North
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Zoned
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Workshop in Garage
HOA & Financial
- HOA fee
- $5,700 / Annually
- Monthly HOA
- $475/mo
- Total monthly fees
- $475/mo
- Total annual fees
- $5,700
- HOA name
- The Oaks Club
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1-2 Years
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- See HOA docs
- Approval process
- See HOA docs
Exterior & Construction
- Exterior features
- Outdoor Shower, Sliding Doors, Storage
- Construction materials
- Block, Concrete, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Connected, Electricity Connected, Public, Water Connected
Community
- Pets allowed
- Yes
Schools
School data from listing agent. Verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | |
| Great Room | First | |
| Primary Bedroom | First | |
| Bedroom 2 | First | |
| Bedroom 3 | First |
Listing Details
- Listing date
- 2025-11-11
- On market date
- 2025-11-13
- Original list price
- $2,595,000
- Occupant type
- Owner
- MLS area
- 34229 - Osprey
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2025-11-13
- Tax legal description
- LOT 135 OAKS
Location
- Flood zone
- X
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of May 19, 2026 at 12:33 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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