321 LOOKOUT POINT DRIVE OSPREY FL 34229 MLS #A4697345

321 LOOKOUT POINT DRIVE
OSPREY, FL, 34229
$3,100,000
3 Beds
3.5 Baths
3,122 SqFt
0.34 Acres
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MLS #A4697345 image #0
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.

Property Details

Price:
$3,100,000
MLS #:
A4697345
Status:
Pending
Beds:
3
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
SOUTHBAY YACHT & RACQUET CLUB
Neighborhood:
34229osprey
Listed Date:
Jun 26, 2026
Finished Sq Ft:
3,122
Total Sq Ft:
4,469
Lot Size:
14,888 sqft / 0.34 acres (approx)
Year Built:
1978
Pool34229 – Osprey34229ospreySouthbay Yacht & Racquet ClubLaurel Nokomis ElementarySarasota MiddleVenice Senior HighSee Docs1-2 YearsPets Allowed

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Schools

Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High

Interior

Appliances
Built-In Oven, Cooktop, Dishwasher
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile, Hardwood
Heating
Central
Interior Features
High Ceilings
Laundry Features
Inside
Levels
Two

Exterior

Attached Garage YN
1
Construction Materials
Stucco
Covered Spaces
2
Direction Faces
Northeast
Exterior Features
Balcony, Outdoor Grill, Outdoor Kitchen, Sliding Doors
Garage Spaces
2
Roof
Tile

Financial

HOA Fee
$657
HOA Fee Frequency
Quarterly
HOA Name
Southbay Yacht and Racquet Club/Judy Brown
HOA Phone
941-966-4237
Tax Year
2025
Taxes
$16,002

Map

Community

Market Summary

Current real estate data for Single Family in OSPREY as of Jul 02, 2026
87
Single Family Listed
151
Avg DOM
453
Avg $ / SqFt
$1,300,814
Avg List Price

Property Summary

    Located in the SOUTHBAY YACHT & RACQUET CLUB subdivision, 321 LOOKOUT POINT DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $3,100,000 and features 3 beds, 4 baths, and has approximately 3,122 square feet of living space, and was originally constructed in 1978. The current price per square foot is $993. The average price per square foot for Single Family listings in OSPREY is $453. The average listing price for Single Family in OSPREY is $1,300,814. To schedule a showing of MLS#a4697345 at 321 LOOKOUT POINT DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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