Skip to Content Skip to Navigation Skip to Dashboard

49 Osprey Point Drive, OSPREY, FL – $2,595,000

  • 4 Beds
  • 4 Baths
  • 3,953 Sqft
  • .4 Acres
  • 4 Beds
  • 4 Baths
  • 3,953 Sqft
  • .4 Acres

49 Osprey Point Drive

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.

Essential Information

  • MLS® #A4671762
  • Price$2,595,000
  • Bedrooms4
  • Bathrooms4.00
  • Full Baths3
  • Half Baths1
  • Square Footage3,953
  • Acres0.40
  • Year Built1989
  • TypeResidential
  • Sub-TypeSingle Family Residence
  • StyleContemporary, Custom
  • StatusActive

Community Information

  • Address49 Osprey Point Drive
  • AreaOsprey
  • SubdivisionOAKS
  • CityOSPREY
  • CountySarasota
  • StateFL
  • Zip Code34229-9246

Amenities

  • ParkingWorkshop in Garage
  • # of Garages2
  • Is WaterfrontYes
  • WaterfrontBay/Harbor Front, Lake Front
  • Has PoolYes

Amenities

Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)

Interior

  • HeatingCentral, Zoned
  • CoolingCentral Air, Zoned
  • FireplaceYes
  • FireplacesFamily Room, Living Room
  • # of Stories1

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)

Appliances

Dishwasher, Range, Range Hood, Refrigerator

Exterior

  • Lot DescriptionLandscaped, Oversized Lot
  • RoofTile
  • FoundationSlab

Exterior Features

Outdoor Shower, Sliding Doors, Storage

School Information

  • ElementaryLaurel Nokomis Elementary
  • MiddleSarasota Middle
  • HighVenice Senior High

Additional Information

  • Date ListedNovember 13th, 2025
  • Days on Market24
  • ZoningRSF1
  • Taxes$14,206
  • HOA Fees$5,700
  • HOA Fee FrequencyAnnually

Listing Details

  • OfficeMICHAEL SAUNDERS & COMPANY
Please provide a valid email address.

Similar Nearby Listings

85 Sugar Mill Drive - $2,150,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 4,191 SQFT
View details More Photos Save

**stunningly Designed And Updated -- Architectural Estate In The Coveted Oaks Bayside Country Club Neighborhood** On Little Sarasota Bay Waters Features 3 Beds Plus Den/office, ...

393 N Point Road 1002 - $2,350,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 3,738 SQFT
View details More Photos Save

Experience Unmatched Luxury In This Meridian Penthouse! Welcome To The Epitome Of Luxury Living At Meridian At The Oaks Preserve. This Stunning 3 Bedroom, 2.5 Bath Penthouse Off...

852 Macewen Drive - $2,550,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,519 SQFT
View details More Photos Save

**charming And Private, Golf Course Estate** Is Located Behind The Secure Gates Of The Highly Sought After Oaks Country Club Community And Offers A Lovely, Golf Course View Of T...

889 Macewen Drive - $2,300,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,235 SQFT
View details More Photos Save

**incredible Transformation Of This Move-in Ready, Golf Course Estate** From The Reimagined Entryway And Through The Stunning Iron Double Front Door, You Will Be Captivated By ...

600 Eagle Watch Lane - $2,195,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,681 SQFT
View details More Photos Save

One Or More Photo(s) Has Been Virtually Staged. **brilliantly Updated, Move-in Ready, Golf Course Estate In The Highly Sought-after Oaks Country Club Community** Offers An Ideal...

140 N Casey Key Road - $2,350,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,473 SQFT
View details More Photos Save

Step Into A World Where The Horizon Meets The Sea And Every Sunset Paints A Masterpiece. This Exceptional Cedar-sided Residence On Exclusive Casey Key Offers The Perfect Blend O...

MICHAEL SAUNDERS & COMPANY.

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 consumer 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.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on December 8th, 2025 at 2:43am EST.