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157 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)

$325,000
Condo
116 NAVIGATION CIR #106, Osprey, FL 34229
Location, Lifestyle, and Peace of Mind — All in One! <br> <br>Welcome home to this beautifully appointed 3-bedroom, 2-ba...
Listed by COLDWELL BANKER REALTY


$234,000
Manufactured Home
238 PALM AIR DR, Osprey, FL 34229
AN ARBORS BEAUTY in one of Florida's most-sought-after 55+ parks. You won't believe how BIG and BEAUTIFUL this home is ...
Listed by FINE PROPERTIES


$785,500
Single Family Home
523 HABITAT BLVD, Osprey, FL 34229
In the Lee Wetherington-built community of Willowbend is a stunning home. This enchanting residence borders a sparkling ...
Listed by PREMIER SOTHEBY'S INTERNATIONAL REALTY


$710,000
Condo
250 HIDDEN BAY DR #302, Osprey, FL 34229
WHAT A VIEW! Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offerin...
Listed by COLDWELL BANKER REALTY


$800,000
Single Family Home
851 PLACID LAKE DR, Osprey, FL 34229
One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has Fresh Interior Paint, ...
Listed by OPENDOOR BROKERAGE LLC


$897,000
Single Family Home
678 CRANE PRAIRIE WAY, Osprey, FL 34229
It's always about the view and the new tile roof in June 2025 plus the Tesla whole-house solar system comprising 26 roof...
Listed by PREMIER SOTHEBY'S INTERNATIONAL REALTY


$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...
Listed by COLDWELL BANKER REALTY


$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...
Listed by HORIZON REALTY INTERNATIONAL


$998,000
Single Family Home
766 SHADOW BAY WAY, Osprey, FL 34229
Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home featur...
Listed by COLDWELL BANKER SARASOTA CENT.


$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.** ...
Listed by ASHTON LAKES REALTY INC


$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


$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.


$2,495,000
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


$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


$2,695
Single Family Home
607 OAK RIVER CT, Osprey, FL 34229
Don't miss out on this 3 bed/2bath with 2 car garage. Immaculate home. Light and bright. <br>Great floor plan includes a...
Listed by PMI SOUTHWEST FLORIDA


$2,999,000
Single Family Home
478 ORISKANY CT, Osprey, FL 34229
Welcome to your dream home, a sanctuary of elegance and comfort nestled on an exclusive, private street with only nine r...
Listed by COLDWELL BANKER REALTY


$4,200
Condo
Osprey, FL 34229
NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCY <br>Modern Elegance at Edgewater | Stunning Condo with Bay Views ...
Listed by BERKSHIRE HATHAWAY HOMESERVICE


$925,000
Condo
385 N POINT RD #404, Osprey, FL 34229
**STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of higher floors!** This LARGE, COR...
Listed by GENEROUS PROPERTY


$2,550,000
Single Family Home
852 MACEWEN DR, Osprey, FL 34229
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country ...
Listed by GENEROUS PROPERTY


$1,499,500
Condo
385 N POINT RD #701, Osprey, FL 34229
**INCOMPARABLE VIEW! 7th FLOOR, CORNER CONDO UNIT WITH UNOBSTRUCTED SOUTH AND WEST PANORAMA. This Spacious unit of near...
Listed by GENEROUS PROPERTY


$649,995
Single Family Home
594 PINE RANCH EAST RD, Osprey, FL 34229
Discover this beautifully maintained 3-bedroom, 2-bathroom home nestled in a peaceful, private community just steps from...
Listed by DALTON WADE INC


$1,550,000
Single Family Home
462 E MACEWEN DR, Osprey, FL 34229
This completely remodeled home in The Oaks Clubside, set on nearly an acre of mature, meticulously landscaped grounds, i...
Listed by COLDWELL BANKER REALTY


$3,750
Single Family Home
650 CRANE PRAIRIE WAY, Osprey, FL 34229
Now Available – Lease Option or Lease Purchase Opportunity in Willowbend! <br> Lease Option: Lease now with the option—b...
Listed by KELLER WILLIAMS ON THE WATER


$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 ...
Listed by WILLIAM RAVEIS REAL ESTATE
