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$2,399,000

49 OSPREY POINT DRIVE, OSPREY, FL 34229

Active335 days on market

Beds

4

Baths

4

Sq Ft

3,953 sq ft

Year Built

1989

Lot Size

0.40 acres

Garage

2

About This Property

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.

Property Overview

Property TypeResidential
Sub TypeSingle Family Residence
MLS #A4671762
StatusActive
Year Built1989
Stories1
Total Rooms5
ConstructionBlock, Concrete, Stucco
RoofTile
FoundationSlab
FacesNorth
SubdivisionOAKS
CountySarasota
OwnershipFee Simple

Interior Features

InteriorBuilt-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)
FlooringConcrete
AppliancesDishwasher, Range, Range Hood, Refrigerator
LaundryInside, Laundry Room
CoolingCentral Air, Zoned
HeatingCentral, Zoned
FireplaceYes ()
SecurityGated Community

Exterior & Lot

ExteriorOutdoor Shower, Sliding Doors, Storage
Lot Size0.40 acres (17,230 sq ft)
Lot FeaturesLandscaped, Oversized Lot
Road SurfaceAsphalt

Pool & Spa

Private PoolYes
Pool FeaturesFiber Optic Lighting, In Ground, Salt Water
SpaHeated, In Ground, Other

Waterfront

WaterfrontYes
FeaturesBay/Harbor Front, Lake Front

Utilities

WaterPublic
SewerPublic Sewer
UtilitiesCable Connected, Electricity Connected, Public, Water Connected

Parking

GarageYes (2 spaces)

HOA & Community

HOAYes
HOA Fee$5,700 / Annually
Senior CommunityNo

Financial Details

List Price$2,399,000
Original Price$2,595,000
Annual Taxes$14,206 (2024)
ZoningRSF1
Parcel #0142060007

Schools

ElementaryLaurel Nokomis Elementary
MiddleSarasota Middle
HighVenice Senior High

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.

Location

49 OSPREY POINT DRIVE, OSPREY, FL 34229

Listing Information

OfficeMICHAEL SAUNDERS & COMPANY
ListedNovember 13, 2025

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Home Price

$2,399,000

20% ($479,800)
6.75%

Loan Term

Principal & Interest$12,448
Property Tax (est.)$2,199
Insurance (est.)$150
Total Monthly$14,797
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Nearby Schools

Financing a Luxury Home

Specialized financing for this $2,399,000 property in OSPREY. Luxury purchases typically require jumbo or portfolio lending.

💎

Jumbo Loan

$239,900 Down

For homes exceeding conforming loan limits. Typically requires 10-20% down, strong credit, and reserves.

🎖️

VA Jumbo

$0 Down

VA-eligible borrowers can go above conforming limits with zero down in many cases.

🏦

Portfolio Loan

$359,850 Down

Held by the lender, not sold. Flexible terms for high-net-worth buyers with non-traditional income.

🔑

Bridge Loan

$479,800 Down

Short-term financing to buy before selling. Ideal for move-up buyers in competitive markets.

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Listing information is deemed reliable but not guaranteed. All measurements and data should be independently verified. This information is provided by the Stellar MLS. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed. 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. Data last updated: October 14, 2026.

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