
- Register
- Sign In
- Agent Email[email protected]
- Agent Phone+1(305) 766-7993
157 Properties Available In Osprey
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$199,000
Manufactured Home
238 PALM AIR DR, Osprey, FL 34229
AN ARBORS BEAUTY in one of Florida's most-sought-after 55+ parks. You won't believe how BIG and BEAUTIFUL this home is ...
Listed by


$760,000
Single Family Home
851 PLACID LAKE DR, Osprey, FL 34229
One or more photo(s) has been virtually staged. Your dream home is waiting for you! Enjoy a bright interior decorated wi...
Listed by


$479,900
Condo
780 SARABAY RD #16, Osprey, FL 34229
Boater's Paradise! Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 a...
Listed by


$1,200,000
Condo
401 NORTH POINT RD #404, Osprey, FL 34229
Step into a residence that redefines elegance and sophistication. This stunning 2,778 sq ft condo has been completely re...
Listed by


$2,850,000
Single Family Home
225 HARBOR HOUSE DR, Osprey, FL 34229
Considered one of the finest community owned marinas on Florida's west coast, Southbay Yacht & Racquet Club is a premier...
Listed by


$939,000
Single Family Home
392 PARK TRACE BLVD, Osprey, FL 34229
Set on a premier lakefront lot in Osprey, 392 Park Trace offers serene water views, incredible privacy, and a lifestyle ...
Listed by


$225,000
Condo
244 WOODLAND DR #244, Osprey, FL 34229
Tranquil Coastal Living in Pine Run <br>244 Woodland Dr, Osprey, FL 34229 <br> <br>Tucked beneath a canopy of mature oak...
Listed by


$1,100,000
Condo
385 N POINT RD #903, Osprey, FL 34229
One or more photo(s) has been virtually staged. From the moment the private elevator doors open, the panorama of the vie...
Listed by


$2,350,000
Condo
393 NORTH POINT RD #1002, Osprey, FL 34229
Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks ...
Listed by


$3,000
Single Family Home
554 PINE RANCH EAST RD, Osprey, FL 34229
ANNUAL/ GENTLY FURNISHED 4 BED/2.5 BATH. The home is gently furnished which will work perfectly for the family who has s...
Listed by


$495,000
Single Family Home
32 BAY AVE, Osprey, FL 34229
Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to...
Listed by


$2,150,000
Single Family Home
85 SUGAR MILL DR, Osprey, FL 34229
**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Lit...
Listed by


$189,900
Condo
238 WOODLAND DR #238, Osprey, FL 34229
Live like you're on vacation every day in this beautiful one bedroom, one and a half bath, FIRST FLOOR condo in the popu...
Listed by


$3,550
Single Family Home
603 PINE RANCH EAST RD, Osprey, FL 34229
*AVAILABLE NOVEMBER 15, 2025 — PREVIEW BY APPOINTMENT ONLY* <br>Currently occupied — showings available by appointment o...
Listed by


$7,100,000
Single Family Home
121 N CASEY KEY RD, Osprey, FL 34229
Newly Remodeled Gulf-Front Mediterranean Villa on Casey Key <br>Framed by the pristine natural beauty of North Casey Key...
Listed by


$2,299,000
Single Family Home
312 YACHT HARBOR DR, Osprey, FL 34229
One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast o...
Listed by


$875,000
Condo
242 HIDDEN BAY DR #401, Osprey, FL 34229
END UNIT with RARE THREE CAR GARAGE, IMPACT WINDOWS AND SLIDERS, and sweeping panoramic views. This beautifully appointe...
Listed by


$2,139
Single Family Home
Osprey, FL 34229
Take a look at this beautiful home, Clean and Move-In Ready, split plan featuring 3 bedrooms, 2 bathrooms, 1 car garage ...
Listed by


$1,175,000
Single Family Home
219 KEEL WAY, Osprey, FL 34229
**IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** o...
Listed by


$925,000
Single Family Home
38 W BAY ST, Osprey, FL 34229
Live like you're on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam...
Listed by


$349,000
Single Family Home
115 GREEN ST, Osprey, FL 34229
Under contract-accepting backup offers. This charming home located in the heart of Osprey checks ALL the boxes. With ove...
Listed by


$545,000
Single Family Home
742 HARMS DR, Osprey, FL 34229
Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and sur...
Listed by


$925,000
Single Family Home
3957 WAYPOINT AVE, Osprey, FL 34229
A beautiful story book home of Coastal living with mainland conveniences is ready for your discovery. Come see Bayside o...
Listed by


$4,800
Single Family Home
456 YACHT HARBOR DR, Osprey, FL 34229
This newly renovated home in Southbay Yacht and Racquet Club provides resort-style living with an array of amenities inc...
Listed by
