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
See this Listing
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
- Address321 LOOKOUT POINT DRIVE OSPREY FL
- SubdivisionSOUTHBAY YACHT & RACQUET CLUB
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN HARBOR WATERFRONT VILLAS PHASE 2
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY HARBOR CLUB
- OSPREY PARK 2
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 1 OF BAY STREET
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL THE WOODLANDS
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WILLOWBEND PH 1
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WILLOWBEND PHASE 3
- WINDSOR LODGE AT THE OAKS
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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Courtesy of COLDWELL BANKER REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 321 LOOKOUT POINT DRIVE
OSPREY, FL

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