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177 Properties Available In Osprey
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
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- Square Feet (Biggest)
$1,595,000
Single Family Home
228 SAINT JAMES PARK, Osprey, FL 34229
Experience the unparalleled charm and convenience of this golf course home in The Oaks Club, the country club community ...
Listed by MICHAEL SAUNDERS & COMPANY
$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
$1,195,000
Single Family Home
3921 WAYPOINT AVE, Osprey, FL 34229
CASUAL, COASTAL ELEGANCE in this charming WATERFRONT community – BAYSIDE on LITTLE SARASOTA BAY! The Florida Lifestyle ...
Listed by WHITE SANDS REALTY GROUP FL
$2,395,000
Single Family Home
600 EAGLE WATCH LN, Osprey, FL 34229
Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generou...
Listed by COLDWELL BANKER REALTY
$1,200,000
Single Family Home
142 DORY LN, Osprey, FL 34229
Southbay Yacht & Racquet Club, The waterfront Community with Resort-Style Amenities. Welcome to this beautiful three-bed...
Listed by GOLF & BAY PROPERTIES LLC
$169,900
Manufactured Home
216 PALM AIR DR, Osprey, FL 34229
This home is located in the sought-after 55+ community of The Arbors. It offers a blend of comfort, updates, and a prime...
Listed by KELLER WILLIAMS ON THE WATER S
$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
$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
$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
$1,100,000
Single Family Home
820 PLACID LAKE DR, Osprey, FL 34229
HUGE PRICE IMPROVEMENT ***carpet was professionally cleaned 3/26/25*** Discover this beautiful, expansive 5-bedroom, 4-b...
Listed by LOYD ROBBINS & CO. LLC
$585,000
Single Family Home
221 SORRENTO DR, Osprey, FL 34229
Discover your slice of paradise in the highly sought-after boating community of Sorrento Shores. This meticulously maint...
Listed by COLDWELL BANKER SARASOTA CENT.
$549,500
Single Family Home
574 CRANE PRAIRIE WAY, Osprey, FL 34229
This stunning two-bedroom plus den/office, two-bath home by the esteemed builder Lee Wetherington is a masterpiece of in...
Listed by PREMIER SOTHEBYS INTL REALTY
$2,345,000
Single Family Home
140 N CASEY KEY RD, Osprey, FL 34229
Welcome to your own private oasis on the coveted Casey Key Island—an 8-mile stretch of paradise known for its pristine b...
Listed by KELLER WILLIAMS ON THE WATER
$1,995,000
Single Family Home
525 S SHORE DR, Osprey, FL 34229
This redesigned mid-century styled 3-bedroom Bayfront home has been fully remastered with entertaining in mind. The stun...
Listed by COLDWELL BANKER REALTY
$1,097,000
Single Family Home
3904 WAYPOINT AVE, Osprey, FL 34229
This stunning Taylor Morrison Lazio floor plan residence offers an exceptional blend of luxury and tranquility in a desi...
Listed by PREMIER SOTHEBYS INTL REALTY
$795,000
Single Family Home
424 CEZANNE DR, Osprey, FL 34229
Welcome to your tropical oasis in ideally located, neighbor friendly Sorrento Shores! This spacious two-story, 3-bedroom...
Listed by MICHAEL SAUNDERS & COMPANY
$700,000
Condo
14041 BELLAGIO WAY #315, Osprey, FL 34229
SIGNIFICANT PRICE IMPROVEMENT! IF YOU HAVE BEEN WAITING FOR A FANTASTIC WATERFRONT PROPERTY AND PRICE.. THIS IS THE ONE...
Listed by WILLIAM RAVEIS REAL ESTATE
$299,900
Condo
304 PINE RUN DR, Osprey, FL 34229
HUGE PRICE REDUCTION " LOWEST Price In The Community - Your Opportunity To Add Your Personal Touch! Charming Coastal Ret...
Listed by KELLER WILLIAMS ON THE WATER S
$6,950,000
Single Family Home
144 N CASEY KEY RD, Osprey, FL 34229
Priced reduced! Welcome to this extraordinary waterfront estate on exclusive Casey Key, showcasing panoramic views of Li...
Listed by EXP REALTY LLC
$824,000
Single Family Home
790 SHADOW BAY WAY, Osprey, FL 34229
Brand New Tile Roof March 2025. Experience the ultimate in serene living within the picturesque Woodlands of Rivendell, ...
Listed by PREMIER SOTHEBYS INTL REALTY
$724,900
Single Family Home
644 RIVENDELL BLVD, Osprey, FL 34229
Optional Turnkey! Built in 2001, this home features high tray ceilings and a smart, functional layout. <br> <br>The form...
Listed by MICHAEL SAUNDERS & COMPANY
$769,000
Single Family Home
518 LUMINARY BLVD, Osprey, FL 34229
Discover the perfect blend of comfort and sophistication in this meticulously maintained home located in the highly desi...
Listed by PREMIER SOTHEBYS INTL REALTY
$3,997,000
Single Family Home
275 LOOKOUT POINT DR, Osprey, FL 34229
This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida's Gulf Coast where boats are a...
Listed by PREMIER SOTHEBYS INTL REALTY
$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