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175 Properties Available In Osprey
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
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- Square Feet (Biggest)
$1,750
Single Family Home
1835 HIGHLAND RD, Osprey, FL 34229
Charming 2 bedroom 2 bathroom villa in GREAT location just across the street from Oscar Scherer Park in Osprey! Nice and...
Listed by JENNETTE PROPERTIES, INC.
$2,200
Condo
129 WOODLAND PL #129, Osprey, FL 34229
One or more photo(s) has been virtually staged. AVAILABLE FURNISHED FOR $3,300. Step into the serene lifestyle at 129 Wo...
Listed by KELLER WILLIAMS ON THE WATER S
$310,000
Single Family Home
208 VILLA DR #208, Osprey, FL 34229
Welcome Home!To this beautiful fully remodeled Villa in Osprey Village. Enjoy the sunrise and a coffee in your lanai and...
Listed by WWW.HOMEZU.COM
$2,900,000
Single Family Home
236 SAINT JAMES PARK, Osprey, FL 34229
Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home ...
Listed by MICHAEL SAUNDERS & COMPANY
$5,300,000
Single Family Home
101 OSPREY POINT DR, Osprey, FL 34229
One or more photo(s) has been virtually staged. Indulge in the epitome of sophistication and timeless elegance with this...
Listed by COLDWELL BANKER REALTY
$1,695,000
Single Family Home
402 WALLS WAY, Osprey, FL 34229
This captivating 4 bedroom (plus den/office), 3.5 bathroom home is ready to welcome you into its charm and warmth. Built...
Listed by COLDWELL BANKER REALTY
$890,000
Condo
14021 BELLAGIO WAY #410, Osprey, FL 34229
Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of...
Listed by UKEEPCOMMISSION REAL ESTATE
$769,900
Single Family Home
826 OAK BRIAR LN, Osprey, FL 34229
Welcome to this Impressive 4-bedroom, 3-bath pool home located in the highly desirable Park Trace Estates in Osprey, Flo...
Listed by PREFERRED SHORE LLC
$7,200
Townhouse
101 WOODLAND PL, Osprey, FL 34229
Now AVAILABLE FOR LEASE WINTER SEASON 2026 at PINE RUN Condominiums in Osprey, Florida! 3BR/2.5BA Location! Location! We...
Listed by WAGNER REALTY
$659,000
Single Family Home
51 WEBB ST, Osprey, FL 34229
Location, Location, Location! Situated west of the trail in the heart of Osprey, this stunning 3-bedroom, 2-bathroom plu...
Listed by FINE PROPERTIES
$799,999
Condo
242 HIDDEN BAY DR #302, Osprey, FL 34229
Spectacular water views. This two-bedroom condominium with den/office offers breathtaking views and amazing sunsets over...
Listed by PREMIER SOTHEBYS INTL REALTY
$4,650
Single Family Home
1438 LANDVIEW LN, Osprey, FL 34229
Welcome to this bright and spacious 4 Bed, 3 Bath home with an office and a private pool located within the highly sough...
Listed by KELLER WILLIAMS ON THE WATER S
$1,100,000
Single Family Home
742 SHADOW BAY WAY, Osprey, FL 34229
ARTHUR RUTENBERG HOME . . . FORMER MODEL . . . NEW ROOF . . . NEW INTERIOR AND EXTERIOR PAINT . . . HURRICANE DOUBLE-LAY...
Listed by RE/MAX ALLIANCE GROUP
$780,250
Condo
280 HIDDEN BAY DR #202, Osprey, FL 34229
READY FOR IMMEDIATE OCCUPANCY! <br>Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota Bay <br> ...
Listed by KELLER WILLIAMS ISLAND LIFE REAL ESTATE
$2,900
Condo
260 HIDDEN BAY DR #202, Osprey, FL 34229
Edgewater at Hidden Bay Annual Rental available now. This pristine 3-bedroom, 2.5-bath condo features a spacious lanai, ...
Listed by LINDSAY LEASING LLC
$2,300
Condo
4223 FRONTIER LN, Osprey, FL 34229
This 1,135-square-foot condo features 2 bedrooms, 2 bathrooms, and a 1-car garage and will be available for an annual le...
Listed by PELICAN REALTY CORP
$4,750,000
Single Family Home
1049 N CASEY KEY RD, Osprey, FL 34229
Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, ...
Listed by PREMIER SOTHEBYS INTL REALTY
$2,800
Condo
758 SARABAY RD #5, Osprey, FL 34229
ANNUAL UNFURNISED CONDO/VILLA WITH BOAT DOCK AVAILABLE FOR LEASE IN HERON BAY! Heron Bay is a secluded waterfront commu...
Listed by PREMIER SOTHEBY'S INTERNATIONAL
$315,000
Condo
4226 FRONTIER LN #103, Osprey, FL 34229
BEING SOLD FULLY FURNISHED AND FULLY EQUIPPED - TURNKEY !! Please check the 3D matter port tour. Start enjoying the Flor...
Listed by EXIT KING REALTY
$11,750,000
Single Family Home
1216 N CASEY KEY RD, Osprey, FL 34229
This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured ...
Listed by PREMIER SOTHEBYS INTL REALTY
$774,900
Single Family Home
866 PLACID LAKE DR, Osprey, FL 34229
Immerse yourself in the blissful lifestyle located in the Woodlands of Rivendell, where this beautifully appointed home ...
Listed by KELLER WILLIAMS ON THE WATER S
$3,099
Single Family Home
591 OAK BAY DR, Osprey, FL 34229
Mint-condition, immaculate pool home nestled within an exclusive Osprey, FL community. This pristine 3-bedroom, 3.5-bath...
Listed by REAL PROPERTY MANAGEMENT
$2,795,000
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
$1,200,000
Single Family Home
201 EAGLENOOK WAY, Osprey, FL 34229
Nestled in the exclusive Pine Ranch community of Osprey, Florida, this 4-bedroom, 3-bath estate offers a rare opportunit...
Listed by WILLIAM RAVEIS REAL ESTATE