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20 Properties Available In Osprey
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- Newest Listings
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$550,000
Single Family Home
120 VILLA DR #120, Osprey, FL 34229
Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the i...
Listed by COLDWELL BANKER SARASOTA CENT.
$4,200
Single Family Home
510 LATITUDE LN, Osprey, FL 34229
Custom, Lee Wetherington home with a private heated pool in the sought after, maintenance free community of Willow Bend....
Listed by BRIGHT REALTY
$2,195
Condo
291 HIDDEN BAY DR #201, Osprey, FL 34229
Spacious 2nd-floor end-unit with one car garage (22x11) provides nearly 1,600 sq. ft. and stunning lake and courtyard vi...
Listed by LINDSAY LEASING LLC
$4,250
Condo
280 HIDDEN BAY DR #303, Osprey, FL 34229
One or more photo(s) has been virtually staged. Annual Rental. This newly constructed 3rd floor condo is available for i...
Listed by GULF COAST REALTY & MANAGEMENT
$188,000
Condo
137 WOODLAND PL, Osprey, FL 34229
Unbelievable!!! A 2-bedroom/2-bathroom, West of Trail condo for under $200,000! Come home to this warm, cozy and charmin...
Listed by COMPASS FLORIDA LLC
$684,900
Single Family Home
866 OAK BRIAR LN, Osprey, FL 34229
Welcome to the highly desirable Park Trace Estates where residents enjoy low HOA fees! This beautiful pool home is mov...
Listed by COLDWELL BANKER REALTY
$2,299
Condo
4248 EXPEDITION WAY #4248, Osprey, FL 34229
Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards you...
Listed by RYNTAL
$2,350
Townhouse
4209 EXPEDITION WAY #102, Osprey, FL 34229
This lovely 3 bedroom, 2 ½ bath townhome. This unfurnished unit has (2) Separate Single car garages-Storage and Parking...
Listed by EXIT KING REALTY
$549,000
Single Family Home
1313 THORNAPPLE DR, Osprey, FL 34229
Stunning finishes welcome you to this enchanting Lee Wetherington-built residence in Willowbend. Incredibly light and br...
Listed by PREMIER SOTHEBYS INTL REALTY
$820,000
Condo
260 HIDDEN BAY DR #305, Osprey, FL 34229
Move-in Ready | Turnkey Furnished | Gulf & Intracoastal Views + Glorious Sunsets <br>3 Bed | 2.5 Bath | Den w/ Custom Qu...
Listed by FIRST LIGHT REAL ESTATE
$625,000
Condo
242 HIDDEN BAY DR #603, Osprey, FL 34229
One of Sarasota's Best-Kept Secrets! Top-Floor Bayfront Retreat in Hidden Bay. 2 Bed | 2 Bath + Den | Enclosed Lanai | 2...
Listed by REAL ESTATE REFINED
$2,200
Townhouse
184 EXPLORER DR, Osprey, FL 34229
The unit is available for rent from August 1 ,2025.The minimum rental period is 2months. The monthly rent is $2200. The ...
Listed by DALTON WADE INC
$1,990,000
Single Family Home
600 EAGLE WATCH LN, Osprey, FL 34229
Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generou...
Listed by COLDWELL BANKER REALTY
$2,695,000
Single Family Home
49 OSPREY POINT DR, Osprey, FL 34229
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently upda...
Listed by MICHAEL SAUNDERS & COMPANY
$279,000
Condo
304 PINE RUN DR, Osprey, FL 34229
Your Opportunity To Add Your Personal Touch! Charming Coastal Retreat in the Heart of Osprey Welcome to 304 Pine Run Dr....
Listed by KELLER WILLIAMS ON THE WATER S
$324,900
Condo
294 HIDDEN BAY DR #203, Osprey, FL 34229
Escape from the hustle and bustle of the real world to the charms of Hidden Bay. Located on 12 beautiful acres on Little...
Listed by MICHAEL SAUNDERS & COMPANY
$409,900
Single Family Home
2251 JESSIE HARBOR DR #2101, Osprey, FL 34229
**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT A...
Listed by GENEROUS PROPERTY
$261,900
Condo
758 PINE RUN DR #758, Osprey, FL 34229
This home was professionally inspected by a Contractor following Hurricanes Helene and Milton, and I'm pleased to report...
Listed by REALNET FLORIDA REAL ESTATE
$1,570,000
Single Family Home
360 N POINT RD, Osprey, FL 34229
**DON'T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure ...
Listed by GENEROUS PROPERTY
$185,000
Manufactured Home
191 PALM AIR DR, Osprey, FL 34229
Come home to this tastefully-furnished, well-maintained spacious home in a top-of-the-line, perfectly located Co-Op park...
Listed by FINE PROPERTIES