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137 Properties Available In Osprey
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
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$249,900
Condo
109 WOODLAND PL, Osprey, FL 34229
Welcome to 109 Woodland Place, a serene retreat nestled within the lush, natural surroundings of the Pine Run community ...
Listed by KELLER WILLIAMS ON THE WATER S
$650,000
Single Family Home
124 VILLA DR #124, Osprey, FL 34229
Nestled along a serene saltwater canal with DIRECT BOATING ACCESS TO THE GULF OF MEXICO and no fixed bridges, this exqui...
Listed by NEXTHOME BEACH TO BAY
$1,085,000
Condo
385 N POINT RD #404, Osprey, FL 34229
Discover this unique condominium in the Oaks Preserve overlooking Little Sarasota Bay, Gulf of Mexico sunsets, the Intra...
Listed by MICHAEL SAUNDERS & COMPANY
$329,900
Condo
128 NAVIGATION CIR #103, Osprey, FL 34229
This charming Florida condo is perfect for anyone seeking a full-time residence or a seasonal getaway. The unit is bein...
Listed by EXIT KING REALTY
$1,795,000
Single Family Home
676 EAGLE WATCH LN, Osprey, FL 34229
Florida living at its finest! You'll find this lovely home tucked away on a cul-de-sac in the luxurious community known ...
Listed by COLDWELL BANKER REALTY
$240,000
Condo
137 WOODLAND PL, Osprey, FL 34229
Unbelievable!!! A West of Trail condo for under $250,000! Come home to this warm, cozy and charming unit and enjoy a cup...
Listed by COMPASS FLORIDA LLC
$375,000
Condo
7102 JESSIE HARBOR DR #7102, Osprey, FL 34229
Spectacular views in all directions at highly desired Blackburn Harbor in Osprey. Tucked back and surrounded by mature a...
Listed by RE/MAX PALM REALTY
$795,000
Single Family Home
710 SHADOW BAY WAY, Osprey, FL 34229
Florida's perfect floor plan. Built in 2002, it features soaring ceilings and a smartly designed layout, perfect for liv...
Listed by MICHAEL SAUNDERS & COMPANY
$2,425,000
Single Family Home
1862 ISLAND WAY, Osprey, FL 34229
South Sarasota waterfront property surrounded by 312 feet of water on three sides feels like living on a private island....
Listed by PREMIER SOTHEBYS INTL REALTY
$1,150,000
Single Family Home
247 KEEL WAY, Osprey, FL 34229
No hurricane problems here! impact windows and storm curtains on the lanai helped to keep this home safe. Also located ...
Listed by PAT WILLIAMS REALTY, LLC
$469,900
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
$1,295,000
Condo
14021 BELLAGIO WAY #201, Osprey, FL 34229
Welcome to Unit #201 in the exclusive Bellagio Harbor Village, where luxury meets the serene beauty of Florida’s Gulf Co...
Listed by COMPASS FLORIDA LLC
$299,000
Condo
225 WOODLAND DR, Osprey, FL 34229
This completely updated GROUND LEVEL 2/2 condo is available in a charming West of Trail community that you’ll be glad yo...
Listed by COMPASS FLORIDA LLC
$2,695,000
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 PREMIER SOTHEBYS INTL REALTY
$699,500
Single Family Home
1109 SCHERER WAY, Osprey, FL 34229
This fabulous residence, featuring a new tile roof installed in November 2024 and hurricane-impact windows and shutters ...
Listed by PREMIER SOTHEBYS INTL REALTY
$2,590
Townhouse
4212 EXPEDITION WAY, Osprey, FL 34229
WELCOME TO SEASON 2025. Furnished-Turnkey, Condo Close to Beaches! In Season rate $3950 month-2 month rental minimum OR ...
Listed by DALTON WADE INC
$1,850,000
Single Family Home
401 WALLS WAY, Osprey, FL 34229
Exquisite Executive Home in The Oaks Clubside, Step into elegance and luxury with this stunning two-story masterpiece. P...
Listed by RE/MAX ALLIANCE GROUP
$765,000
Single Family Home
1076 MALLARD MARSH DR, Osprey, FL 34229
Welcome to the POOL home at the sought after RIVENDELL. This spacious home is located in the acclaimed PINEVIEW SCHOOL ...
Listed by RE/MAX ALLIANCE GROUP
$420,000
Single Family Home
108 PARK DR, Osprey, FL 34229
Welcome to your dream home! This oversized pool home is perfectly situated just minutes from the intercoastal, offering ...
Listed by COLDWELL BANKER REALTY
$940,000
Single Family Home
448 PARK TRACE BLVD, Osprey, FL 34229
**THIS PROPERTY QUALIFIES FOR A 1.5% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** Experience ...
Listed by KELLER WILLIAMS CLASSIC GROUP
$625,000
Single Family Home
111 WEBB ST, Osprey, FL 34229
Postcard home at Village of Osprey. WEST OF THE TRAIL . TWO HOMES FROM THE BAY on a DEAD-END STREET. High and dry home, ...
Listed by RE/MAX ALLIANCE GROUP
$450,000
Townhouse
4284 EXPEDITION WAY, Osprey, FL 34229
Experience the ultimate in coastal living with this beautifully designed 3-bedroom, 2-bathroom second-floor townhouse lo...
Listed by MARK SPAIN REAL ESTATE
$749,900
Single Family Home
123 TINA ISLAND DR, Osprey, FL 34229
Spectacular lot and setting for home priced under county tax appraisal. This is your opportunity to own a waterfront pro...
Listed by COLDWELL BANKER SARASOTA CENT.
$2,500,000
Single Family Home
703 MACEWEN DR, Osprey, FL 34229
Bathed in natural light, with highly sought after southern lanai exposure, is this stunning and meticulously maintained ...
Listed by COLDWELL BANKER REALTY