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147 Properties Available In Osprey
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$597,000
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.
$299,500
Condo
232 EXPLORER DR #15, Osprey, FL 34229
Charming 2 Bedroom 2 Bath corner end unit( which provides extra natural light) condominium with attached 1 car Garage. O...
Listed by COLDWELL BANKER REALTY
$1,900
Townhouse
184 EXPLORER DR, Osprey, FL 34229
Exclusive promotional offer. The unit is available for rent from June 1 until December 15, 2025. THIS IS NOT A LONG- TER...
Listed by DALTON WADE INC
$699,000
Single Family Home
241 WILLOW BEND WAY, Osprey, FL 34229
Stunning Home in Park Trace Estates. Prime Location Near Oscar Scherer Park. Welcome to this beautiful 3-bedroom, 2-bath...
Listed by MICHAEL SAUNDERS & COMPANY
$190,000
Manufactured Home
320 TROPIC DR, Osprey, FL 34229
A GREAT HOME IN A GREAT PARK AT A GREAT PRICE. Welcome to your new home in the Arbors, Sarasota County's most sought-af...
Listed by FINE PROPERTIES
$3,695
Townhouse
60 BISHOPS COURT RD #114, Osprey, FL 34229
This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing ...
Listed by STRINGER MANAGEMENT INC
$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
$2,382,500
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
$1,350,000
Condo
3621 NORTH POINT RD #603, Osprey, FL 34229
Prepare to be captivated by this COMPLETELY UPDATED, meticulously maintained, and thoughtfully appointed 3 bedroom, 3 ba...
Listed by COLDWELL BANKER REALTY
$2,500,000
Single Family Home
340 OSPREY POINT DR, Osprey, FL 34229
Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota's most pres...
Listed by RE/MAX ALLIANCE GROUP
$715,000
Single Family Home
110 PINE AVE, Osprey, FL 34229
Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of...
Listed by BRIGHT REALTY
$350,000
Condo
4236 EXPEDITION WAY #106, Osprey, FL 34229
FABULOUS, MODERN, FURNISHED 3 BEDROOM/2 BATHROOM/1 CAR GARAGE CONDO in desirable Bay Street Village. This second story (...
Listed by RE/MAX ALLIANCE GROUP
$965,000
Single Family Home
13 BAYHEAD LN, Osprey, FL 34229
**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This reside...
Listed by GENEROUS PROPERTY
$365,000
Single Family Home
240 PATTERSON AVE, Osprey, FL 34229
Charming 3-bedroom, 2-bath bungalow with no HOA or deed restrictions—perfect for boaters, RV owners, or anyone seeking f...
Listed by COLDWELL BANKER REALTY
$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.
$295,000
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
$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
$1,500,000
Single Family Home
402 WALLS WAY, Osprey, FL 34229
Welcome to timeless elegance and modern comfort in The Oaks Clubside. <br>This stunning 4-bedroom plus den/office, 3.5-b...
Listed by COLDWELL BANKER REALTY
$749,000
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
$629,000
Single Family Home
51 WEBB ST, Osprey, FL 34229
***PRICE IMPROVEMENT***Location, Location, Location! Situated west of the trail in the heart of Osprey, this stunning 3-...
Listed by FINE PROPERTIES
$1,050,000
Single Family Home
742 SHADOW BAY WAY, Osprey, FL 34229
Welcome to Luxury Living in Rivendell! Nestled on a premium, private lot with serene lake and preserve views, this impec...
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