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238 Lookout Point Drive, OSPREY, FL $895,000
- 3 Beds
- 3 Baths
- 2,676 SQFT
- 13 DOM
This Is An Outstanding Southbay Residence And A Fantastic Opportunity To Live In One Of The Best Boating Communities On The Southwest Coast Of Florida. This Home Has Been Updated With A Gourmet Custom Kitchen, Perfect For Entertaining Guests And ...
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102 Windward Drive, OSPREY, FL $800,000
- 3 Beds
- 3 Baths
- 2,134 SQFT
- 15 DOM
Located In The Desirable Southbay Yacht & Racquet Club, This 3-bedroom, 2.5-bath Pool Home With Mature Landscaping Offers A Functional Layout And Excellent Community Amenities. The Home Features A Double-door Front Entry, A Spacious Great Room Wit...
180 Lookout Point Drive, OSPREY, FL $2,299,900
- 5 Beds
- 4 Baths
- 3,236 SQFT
- 19 DOM
One Or More Photo(s) Has Been Virtually Staged. One Or More Photo(s) Has Been Virtually Staged. Welcome To 180 Lookout Point Drive In The Sought-after Southbay Yacht & Racquet Club With Deep Water Marina And Available Boat Slips, The Opportunity T...
431 Yacht Harbor Drive, OSPREY, FL $4,300,000
- 3 Beds
- 3 Baths
- 3,006 SQFT
- 20 DOM
Under Contract-accepting Backup Offers. Ahhh…you Have Finally Found “the One”! This Home Is A One Of A Kind Property With One Of The Best Water Front Lots In Southbay! Features Of This Spectacular Home Include Not Only A Lagoon Style Pool With W...
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172 Sea Anchor Drive, OSPREY, FL $936,000
- 3 Beds
- 3 Baths
- 2,283 SQFT
- 22 DOM
At Last- The Home You've Been Looking For! This Updated 3-bedroom 3 Bath Retreat Is Tucked Inside A Lively Marina Community Where Every Day Feels Like Vacation. This Home Features Modern Updates Throughout, Saltwater Pool, Den, In Home Gym, New Ti...
1486 Landview Lane, OSPREY, FL $995,000
- 3 Beds
- 2 Baths
- 1,869 SQFT
- 23 DOM
Welcome To Your Boater's Paradise! This Well-maintained South Bay Home Is Your Key To Enjoy One Of The Best Neighborhoods In The Area. This Three-bedroom Pool Home Has The Perfect Layout With The Primary Bedroom And En Suite On One Side Of The Ho...
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225 Harbor House Drive, OSPREY, FL $2,690,000
- 6 Beds
- 4 Baths
- 4,546 SQFT
- 47 DOM
Considered One Of The Finest Community Owned Marinas On Florida’s West Coast, Southbay Yacht & Racquet Club Is A Premier Waterfront Community Featuring A Seven Acre Deep Water Boat Basin And A Lifestyle Centered Around The Water. This Exceptional ...
312 Yacht Harbor Drive, OSPREY, FL $2,299,000
- 4 Beds
- 4 Baths
- 2,572 SQFT
- 62 DOM
One Or More Photo(s) Has Been Virtually Staged. Considered One Of The Finest Community-owned Marinas On The West Coast Of Florida, Southbay Yacht & Racquet Club Features A Seven-acre, Deep-water Boat Basin That Will Accommodate Kayaks, Jet Skis, S...
219 Keel Way, OSPREY, FL $1,175,000
- 3 Beds
- 3 Baths
- 2,735 SQFT
- 63 DOM
**impressive, Meticulously Maintained, Single-story, Cul De Sac Estate In The Highly Sought-after Southbay Community** Offers 3 Beds, 2 Full And 1 Half Baths Plus Study/den – And Is Nearly 100% Solar-powered (details Available)! This Custom And Up...
1602 Southbay Drive, OSPREY, FL $995,000
- 4 Beds
- 4 Baths
- 2,980 SQFT
- 69 DOM
Welcome To Your Slice Of Florida Paradise! Nestled On A Spacious Corner Lot In The Highly Sought-after Southbay Yacht & Racquet Club, This Elegant Residence Captures The Essence Of The Coastal Lifestyle. As You Arrive, The Mature Tropical Lands...
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123 Windward Drive, OSPREY, FL $850,000
- 3 Beds
- 2 Baths
- 1,894 SQFT
- 71 DOM
This Immaculate And Meticulously Maintained 3-bedroom, 2-bath Home In The Sought-after Southbay Yacht & Racquet Community Is Move-in Ready And Packed With Beautiful Updates. The Open-concept Kitchen Has Been Tastefully Remodeled With Stainless Ste...
Southbay Yacht & Racquet Club Community Amenities
And don’t think you have to enjoy the recreation alone…Southbay offers residents a social lifestyle revolving around an elaborate clubhouse with private ballroom, community pool, and meeting and card rooms. Whether your speed is adventurous like the Power and Sail Club or a Sunday morning cup of coffee with friends, Southbay offers many enjoyable ways to spend your time.
The clubhouse is accessible between 6 am and 11 pm using the magnetic key card issued to each resident. Owners can rent the second floor ballroom for private affairs which overlooks the marina. The ballroom is equipped with a catering kitchen. The well equipped weight room is the perfect place to tone up or challenge yourself. Afterwards you can steam yourself into total relaxation at the clubhouse sauna. Lookout Point Park is located directly on the Intracoastal Waterway and is the perfect place for residents to enjoy a sunset or get in a little bit of fishing. It is connected to the community by 5 miles of sidewalks and bike paths. The community offers two Sport Clay tennis courts and two asphalt tennis courts. The courts are lighted and can be used until 10 pm. The community pool and expansive pool deck has a million dollar view of the entire marina. It is the perfect place to socialize or just cool off in the pool.
BROWSE OSPREY COMMUNITIES
Southbay Yacht & Racquet Club Image Gallery
Location and Directions
Located at 1400 Southbay Drive in Osprey, Florida 34229
Starting in Osprey, Florida, at the intersection of Blackburn Point Rd and S. Tamiami Trail, proceed South on S. Tamiami Trail. Turn right at Southbay Drive into the community.
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on December 5th, 2025 at 5:58am EST.