321 LOOKOUT POINT DRIVE
OSPREY, FL 34229
Listing courtesy of COLDWELL BANKER REALTY · MLS# A4697345

Property Details
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.
Facts & Costs
- Property type
- Single Family Residence
- Year built
- 1978
- Lot size
- 0.34 acres
- Stories
- 2
- Garage
- 2 spaces
- Half baths
- 1
- Price per sq ft
- $993
- Days on market
- 96
- Private pool
- Yes
- Waterfront
- No
- Community
- Southbay Yacht & Racquet Club
- Subdivision
- SOUTHBAY YACHT & RACQUET CLUB
- County
- Sarasota
- Flood zone
- AE*
Monthly & yearly costs
- HOA fee
- $657 / quarterly
- Property taxes
- $16,002 / year (2025)
As reported by the listing agent. Verify with the HOA and county.
Construction & systems
- Heating
- Central
- Cooling
- Central Air
- Flooring
- Carpet, Tile, Wood
- Roof
- Tile
- Construction
- Stucco
Payment Estimate
$17,228 / month
- Principal & interest
- $15,675
- Property taxes
- $1,333
- HOA
- $219
- Home insurance
- enter below
Estimate only, not a loan offer. Rate is a starting value; taxes and HOA are as reported by the listing agent. Florida insurance (including flood) varies widely. Ask George for a lender referral.
Location
Features & Amenities
- Built-In Oven
- Cooktop
- Dishwasher
- High Ceilings
- Balcony
- Outdoor Grill
- Outdoor Kitchen
- In Ground
Information deemed reliable but not guaranteed.
Listings courtesy of Stellar MLS as distributed by MLS GRID
Based on information submitted to the MLS GRID as of Sep 30, 2026, 6:45 PM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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