321 LOOKOUT POINT DRIVE, Osprey, FL, 34229 | $3,100,000

Experience the epitome of waterfront living in the sought-after Southbay neighborhood. This 3 bedroom, 3. 5 bath home is ideally positioned on a peninsula, providing sweeping panoramic water views. The moment you step inside, you will be mesmerized by the breathtaking bay views through a plethora of windows and sliding glass doors that flood the space with natural light. The open, main level is designed for both comfort and style, with vaulted ceilings, unobstructed water views from every room and hardwood floors. The kitchen is uniquely designed, featuring an extended breakfast bar, high end designer cabinets and stainless steel appliances. The great room, with wet bar, has views so perfect, they almost feel like artwork. The new clear view lanai screens provide a gorgeous tropical back drop to the pool and spa. Host friends and loved ones, using the outdoor kitchen and setting area for a fun-filled dinner, and watch the sun set, painting the sky with a golden glow. The first floor master suite consists of a spacious bedroom, a spa-like bathroom, and a separate area utilized as a private study. Upstairs you will find two additional en suite bedrooms. One opens to the new deck, has views over the Dryman Bay out to Casey Key, and is large enough to use as a second master suite. While the views and location of this home are drop-dead gorgeous, practical features also abound. This home has impact windows and doors, a brand new washer and dryer, and recently replaced roof, AC and tankless hot water heater. Southbay Yacht and Racquet Club has a seven-acre deep-water marina accommodating boats up to 55 feet with slips available to homeowners. It has an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children’s pool, tennis, pickleball, shuffleboard, basketball and kayak storage. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events.

Features

  • Rooms: 7
  • Bedrooms: 3
  • Baths: 3 full / 1 half
  • Laundry: Inside
  • Year Built: 1978
  • Garage: 2-car
  • Heating: Central
  • Cooling: Central Air
  • Approx Sq. Feet: 3,122
  • Acreage: 0.34
  • Est. Taxes: $16,002
  • HOA Fee: $657 Quarterly
  • Elem. School: Laurel Nokomis Elementary
  • Middle School: Sarasota Middle
  • High School: Venice Senior High
  • Pool: In Ground
  • Pet Policy: Yes
  • Appliances: Built-In Oven, Cooktop, Dishwasher
  • MLS#: A4697345
  • Days on Market: 1 day
  • Website: https://www.raveis.com
    /eprop/A4697345/321lookoutpointdrive_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 6/28/2026 3:33:13 PM)
Listing courtesy of Coldwell Banker Realty   Phone: 941-383-6411

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

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321 LOOKOUT POINT DRIVE, Osprey, FL, 34229

$3,100,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $2,480,000 $2,480,000 $2,480,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.000% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.251% 6.086% 6.183%
Monthly Tax Payment $1,334 $1,334 $1,334
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $14,473 $14,869 $20,928
Total Monthly Payment $15,932 $16,328 $22,387

* 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.