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157 Properties Available In Osprey
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$3,750
Single Family Home
650 CRANE PRAIRIE WAY, Osprey, FL 34229
Now Available – Lease Option or Lease Purchase Opportunity in Willowbend! Flexible lease terms now offered: <br>Lease Op...
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$725,000
Condo
5100 JESSIE HARBOR DR #701, Osprey, FL 34229
Perched on the top floor of Blackburn Harbor Residences, this 3-bedroom, 3-bath end unit is just under 2500 square feet ...
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$699,000
Single Family Home
471 PARK TRACE BLVD, Osprey, FL 34229
SIGNIFICANT PRICE IMPROVEMENT!! Welcome to your dream home! This stunning, custom-built 4 bedroom, 3 bathroom residence...
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$3,800
Condo
5100 JESSIE HARBOR DR #602, Osprey, FL 34229
Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences on the West si...
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$474,900
Condo
7303 JESSIE HARBOR DR #7303, Osprey, FL 34229
PENTHOUSE CONDO IN WATERFRONT COMMUNITY! <br>Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthou...
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$689,000
Single Family Home
819 SHADOW BAY WAY, Osprey, FL 34229
A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of Rivendell. Live so beautifully...
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$5,700,000
Single Family Home
622 BAYSHORE DR, Osprey, FL 34229
ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! <br>Welcome to 622 Bayshore Drive - where coasta...
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$164,900
Manufactured Home
170 EDGEWOOD DR, Osprey, FL 34229
YOUR PERFECT FLORIDA RETREAT AWAITS.... Imagine spending your winter days in a swimming pool or in the warm waters and b...
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$1,250,000
Single Family Home
1484 SEAFARER DR, Osprey, FL 34229
Under contract-accepting backup offers. Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coast's most coveted c...
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$310,000
Condo
4267 EXPEDITION WAY, Osprey, FL 34229
Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minut...
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$550,000
Single Family Home
813 OAK POND DR, Osprey, FL 34229
One or more photo(s) has been virtually staged. WELCOME HOME!! THERE HAS BEEN NO FLOODING OR DAMAGE FROM RECENT STORMS!!...
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$599,000
Single Family Home
4428 CONCHFISH LN, Osprey, FL 34229
Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not co...
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$4,000
Condo
280 HIDDEN BAY DR #303, Osprey, FL 34229
One or more photo(s) has been virtually staged. *** PRICE REDUCED*** Annual Rental. This newly constructed 3rd floor con...
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$1,970,000
Single Family Home
140 SUGAR MILL DR, Osprey, FL 34229
**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Se...
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$175,000
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...
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$949,900
Single Family Home
766 SHADOW BAY WAY, Osprey, FL 34229
Under contract-accepting backup offers. LISTING AGENT WILL CONTINUE TO ACCOMPANY SHOWINGS. Nestled on a quiet street in ...
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$1,279,000
Single Family Home
1527 BUOY LN, Osprey, FL 34229
Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilin...
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$1,150,000
Condo
401 N POINT RD #504, Osprey, FL 34229
FULLY UPDATED ~ WATER VIEWS ~ PRIVATE 2 CAR GARAGE ~ OFFICE/4TH BEDROOM OPTION ~ The eye of an artist and perfected skil...
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$1,450,000
Single Family Home
296 PINE RANCH TRL, Osprey, FL 34229
**THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** ...
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$444,000
Single Family Home
352 GLENWOOD AVE, Osprey, FL 34229
Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions <br> <br>Welcome to this immaculate 3-bedroom, 2-...
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$7,000
Condo
5100 JESSIE HARBOR DR #504, Osprey, FL 34229
Available from December 7, 2025, and Jan/Feb/Mar/Apr 2026. Beautiful 5th Floor condo located in Blackburn Harbor Residen...
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$3,325,000
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...
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$5,000
Condo
14041 BELLAGIO WAY #218, Osprey, FL 34229
Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from M...
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$789,000
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...
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