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147 Properties Available
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$725,000
Single Family Home
463 PARK TRACE BLVD, Osprey, FL 34229
On an oversized lot with a breathtaking lake view, this open floor plan turnkey-furnished residence is designed for mode...
Listed by PREMIER SOTHEBYS INTL REALTY
$169,000
Condo
107 WOODLAND PL #107, Osprey, FL 34229
This ground level condominium comes with a deeded carport and two storage closets. Enjoy a deck off the kitchen and a sc...
Listed by COLDWELL BANKER REALTY
$2,450
Condo
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
$7,500
Single Family Home
1216 FLYING BRIDGE LN, Osprey, FL 34229
DO YOU WANT COMFORT AND LUXURY WHILE YOU LOOK AROUND WATERFRONT ? JUMP ON THIS LUXURY TURNKEY RENTAL. A ROOM FOR EVERY ...
Listed by COLDWELL BANKER REALTY
$4,000
Condo
14041 BELLAGIO WAY #214, Osprey, FL 34229
One or more photo(s) has been virtually staged. ANNUAL or Short Term (3 Months Minimum) CONDO/VILLA AVAILABLE FOR LEASE ...
Listed by FINE PROPERTIES
$3,750,000
Single Family Home
1042 N CASEY KEY RD, Osprey, FL 34229
EXCEPTIONAL WATERFRONT RESIDENCE on the exclusive island of North Casey Key is a rare opportunity to own a piece of coas...
Listed by COLDWELL BANKER REALTY
$979,000
Single Family Home
238 LOOKOUT POINT DR, Osprey, FL 34229
Nestled in the heart of Southbay Yacht & Racquet Club, this exquisitely renovated and impeccably maintained residence of...
Listed by COLDWELL BANKER REALTY
$692,000
Single Family Home
104 PARK TRACE BLVD, Osprey, FL 34229
Welcome to your dream home in beautiful Osprey, Florida inside PARK TRACE! This expansive 2557 sqft residence boasts 4 b...
Listed by KW COASTAL LIVING III
$669,000
Single Family Home
750 ANNA HOPE LN, Osprey, FL 34229
Impeccable style and effortless grace define this Rivendell home, which stands as a testament to refined living. Nestled...
Listed by COLDWELL BANKER REALTY
$597,000
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
$7,000
Condo
5100 JESSIE HARBOR DR #504, Osprey, FL 34229
This beautiful 5th Floor condo located in Blackburn Harbor Residences is now available for Season 2026! There are breath...
Listed by JENNETTE PROPERTIES INC
$3,900,000
Single Family Home
112 OSPREY POINT DR, Osprey, FL 34229
Premier Waterfront Opportunity in The Oaks Bayside <br>This grand estate home, perfectly positioned on a rarely availabl...
Listed by KARA MONEY LLC
$6,000
Condo
14041 BELLAGIO WAY #218, Osprey, FL 34229
If you're looking for a place that offers a rent to own opportunity, now is your chance! Welcome to your coastal sanctua...
Listed by COLDWELL BANKER REALTY
$853,000
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
$269,000
Condo
754 PINE RUN DR #754, Osprey, FL 34229
Rarely available ground-floor 2-bedroom, 2-bath model with a standout location and layout that offers a truly one-of-a-k...
Listed by CALL IT CLOSED INTL REALTY
$2,400
Condo
4214 FRONTIER LN #102, 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
$950,000
Single Family Home
172 SEA ANCHOR DR, Osprey, FL 34229
One or more photo(s) has been virtually staged. Welcome to your dream home! This 3-bedroom, 3-Bath residence offers the ...
Listed by GOLF & BAY PROPERTIES LLC
$650,000
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
$569,000
Single Family Home
104 SHORELAND DR, Osprey, FL 34229
Welcome to your coastal retreat! Currently set up as a furnished rental, This recently remodeled 4 bedroom 2 bathroom ho...
Listed by OAKSTRAND REALTY
$549,000
Single Family Home
1363 NEW FOREST LN, Osprey, FL 34229
Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodland...
Listed by RE/MAX PLATINUM
$815,000
Single Family Home
901 REFLECTION WAY, Osprey, FL 34229
LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-...
Listed by GENEROUS PROPERTY
$1,295,000
Condo
385 N POINT RD #903, Osprey, FL 34229
From the moment the private elevator doors open, the panorama of the view has you at ‘hello,” with a northwest-facing ex...
Listed by COLDWELL BANKER REALTY
$1,000,000
Single Family Home
1085 MALLARD MARSH DR, Osprey, FL 34229
Step into this beautifully renovated Rivendell home and discover a stunning pool and lanai area, thoughtfully <br>design...
Listed by MICHAEL SAUNDERS & COMPANY
$510,000
Single Family Home
519 BAYVIEW AVE, Osprey, FL 34229
Live the Sarasota Coastal Lifestyle in Bay Acres – Boating Community! Nestled in the desirable waterfront neighborhood o...
Listed by COLDWELL BANKER REALTY