321 LOOKOUT POINT DRIVE, Osprey, FL 34229

• 3 beds |
• 4 baths |
• 3,122 sqft

Property Description

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.

Listing Status:

Pending

Date Added:

June 26, 2026

Data Last Updated:

June 28, 2026 at 7:23AM

Listing Office:

COLDWELL BANKER REALTY : 941-383-6411

Listing Agent:

Steve Abbe : 941-400-3969

MLS ID:

A4697345

Interior

• General: High Ceilings
• Appliances: Built-In OvenCooktopDishwasher
• Laundry: Inside
• Flooring: CarpetTileWood
• A/C: Central Air
• Heating: Central

Exterior

• General: BalconyOutdoor GrillOutdoor KitchenSliding Doors
• Pool: In Ground

Construction

• Roofing: Tile
• General: StuccoTwoSlab

Location

• Road/Access: Paved
• HOA Amenities: 656.62Quarterly
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: RSF2LOT 292 SOUTHBAY YACHT & RACQUET CLUB0158020018

Utilities

• Utilities: Electricity Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple