$3,100,000
321 Lookout Point Drive
Osprey, FL 34229
Listing updated: June 26, 2026 at 5:01 PM ET
Listing courtesy of Coldwell Banker Realty · Steve Abbe · MLS #A4697345 · Active · 941-383-6411Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Local Insight
At $993/sqft for a 1978 home, you're paying premium prices for the Southbay location and amenities rather than for the age of the structure—so factor in that this will likely need significant updates soon, especially given the AE flood zone designation which will keep insurance costs elevated. The private pool and yacht club access are genuine draws if waterfront lifestyle matters to you, but the 0.34-acre lot is tight, so you're really buying the community and location here, not land flexibility.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveJun 26, 2026
- Listed$3,100,000Jun 26, 2026
- Price increased$3,100,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Southbay Yacht & Racquet Club
- County
- Sarasota
- Year built
- 1978
- Living area
- 3,122 sq ft
- Price/sq ft
- $993
- Building area
- 4,469 sq ft (Public Records)
- Lot size
- 14,888 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- AE* (12115C0236G)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $16,002 (2025)
- Parcel #
- 0158020018
- Zoning
- RSF2
- MLS #
- A4697345
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 3
- Half bathrooms
- 1
- Flooring
- Carpet, Tile, Wood
- Appliances
- Built-In Oven, Cooktop, Dishwasher
- Interior features
- High Ceilings
- Laundry
- Inside
- Stories / Levels
- Two
- Direction faces
- Northeast
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $657 / Quarterly
- Monthly HOA
- $219/mo
- Total monthly fees
- $219/mo
- Total annual fees
- $2,626
- HOA name
- Southbay Yacht and Racquet Club/Judy Brown
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1-2 Years
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- See docs
- Approval process
- See docs
Exterior & Construction
- Exterior features
- Balcony, Outdoor Grill, Outdoor Kitchen, Sliding Doors
- Construction materials
- Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Electricity Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Great Room | First | 34x20 |
| Dining Room | First | 21x13 |
| Kitchen | First | 19x12 |
| Primary Bedroom | First | 19x13 |
| Bedroom 2 | Second | 14x13 |
| Bedroom 3 | Second | 16x13 |
| Balcony/Porch/Lanai | First | 48x29 |
Listing Details
- Listing date
- 2026-06-26
- On market date
- 2026-06-26
- Original list price
- $3,100,000
- Occupant type
- Vacant
- MLS area
- 34229 - Osprey
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-06-26
- Tax legal description
- LOT 292 SOUTHBAY YACHT & RACQUET CLUB
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
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Based on information submitted to the MLS GRID as of June 26, 2026 at 5:01 PM ET. 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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