New Listing - 06/26/2026

$3,100,000 ($992.95 per sqft)

Pending

Est. Mortgage $14,869/mo *

Quick Pre-Approval

321 LOOKOUT POINT DRIVE, Osprey, FL, 34229

321 LOOKOUT POINT DRIVE, Osprey, FL, 34229

7 rooms

3 beds

3 Full / 1 Half baths

1978

3,122 sqft

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.


Status:

Pending

Type:

Single-family residential

Furnished Remarks:

Unfurnished

Laundry Remarks:

Inside

Subdivision:

SOUTHBAY YACHT & RACQUET CLUB

Garage:

2-car

Heating:

Central

Cooling:

Central Air

Levels:

2

Common Charge:

$657 Quarterly

Acreage:

0.34

Est. Taxes:

$16,002

HOA Fee

$657

Construction

Stucco

Utilities

Electricity Connected

Elementary School:

Laurel Nokomis Elementary

Middle School:

Sarasota Middle

High School:

Venice Senior High

Days on Market:

1

Pet Policy:

Yes

Appliances:

Built-In Oven, Cooktop, Dishwasher

Pool:

In Ground

Min Lease Term:

1-2 Years

MLS #:

A4697345


Community Info

School Info

Walk Score

Yelp



Listing courtesy of Coldwell Banker Realty 941-383-6411