49 OSPREY POINT DRIVE, Osprey, FL, 34229 | $2,500,000

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.

Features

  • Amenities: Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)
  • Rooms: 5
  • Bedrooms: 4
  • Baths: 3 full / 1 half
  • Laundry: Inside, Laundry Room
  • Style: Contemporary, Custom
  • Year Built: 1989
  • Garage: 2-car Workshop in Garage
  • Heating: Central, Zoned
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 3,953
  • Acreage: 0.4
  • Est. Taxes: $14,206
  • HOA Fee: $5,700 Annually
  • Lot Desc: Landscaped, Oversized Lot
  • Elem. School: Laurel Nokomis Elementary
  • Middle School: Sarasota Middle
  • High School: Venice Senior High
  • Pool: Fiber Optic Lighting, In Ground, Salt Water
  • Pet Policy: Yes
  • Appliances: Dishwasher, Range, Range Hood, Refrigerator
  • MLS#: A4671762
  • Days on Market: 105 days
  • Website: https://www.raveis.com
    /eprop/A4671762/49ospreypointdrive_osprey_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 2/28/2026 11:38:21 AM)

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NMLS Mortgage Loan Originator ID 12303

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49 OSPREY POINT DRIVE, Osprey, FL, 34229

$2,500,000

Team AFA - Darien

Luxury Properties Specialists

William Raveis Real Estate

Phone: 203.256.3264

Al@Raveis.com

Jorge L Rivera

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 203.913.1633

Jorge.Rivera@Raveis.com

NMLS Mortgage Loan Originator ID 12303

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $2,000,000 $2,000,000 $2,000,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.250% 5.750% 5.500%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.046% 5.846% 5.700%
Monthly Tax Payment $1,184 $1,184 $1,184
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $11,044 $11,671 $16,342
Total Monthly Payment $12,353 $12,980 $17,651

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.