This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
$2,910,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
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.
Full Property Details
Full Property Details for 321 Lookout Point Dr
General
- Sold For: $2,910,000
- HOA FEE: $219/month
- HOA FEE FREQ.: Quarterly
- Taxes: $16,001 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4697345
- Added to Site: 108 day(s) ago
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 7
- Interior Features: High Ceilings
- Appliances: Built-In Oven, Cooktop, Dishwasher
- Furnishings: Unfurnished
- Flooring: Carpet, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: In Ground
Exterior
- Exterior Features: Balcony, Outdoor Grill, Outdoor Kitchen, Sliding Doors
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
- Driving Directions: Rte. 41/South Tamiami Trail to Blackburn Point Rd. West on Blackburn. Make a right on Southbay Drive. Make a left on Harbor Huse Drive. Make a right on Lookout Point Dr. to address.
- Direction Faces: Northeast
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Sarasota Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- Association: Yes
- Assoc. Name: Southbay Yacht and Racquet Club/Judy Brown
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Electricity Connected
Structural Information
- Exterior Const.: Stucco
- Roof: Tile
- Stories/Levels: Two
- Square Feet: 3,122
- Sq. Ft. Source: Public Records
- Living Area: 3,122 Sq. Ft.
- Year Built: 1978
Lot Features
- Lot Size (Acres): 0.34
- Lot Size (Sq. Ft.): 14,888
- Lot Size: 14888
- Street/Road Desc.: Paved
Financial Considerations
- Association Fee: $657
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $16,001.71
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 292 SOUTHBAY YACHT & RACQUET CLUB
- Flood Zone Info: AE*
- APN: 158020018
- Property ID: 158020018
Get Pre-Approved Today
Schools
Schools serving 321 Lookout Point Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 4.7 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 6.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 321 Lookout Point Dr
Date
Details
Price
Change
Source
10/07/2026
Sold
$2,910,000
-6.13%
MLS
6/26/2026
Listed
$3,100,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
321 Lookout Point Drive, Osprey, FL 34229 (MLS# A4697345) is a Single Family property that was sold at $2,910,000 on October 07, 2026. This property was listed by Abbe Ross Team from our Longboat Key Office.Want to learn more about 321 Lookout Point Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

