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175 Properties Available In Osprey
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$599,000
Single Family Home
104 SHORELAND DR, Osprey, FL 34229
Welcome to your coastal retreat! Currently set up as a furnished rental, This recently remodeled 4 bedroom 2 bathroom ho...
Listed by OAKSTRAND REALTY
$549,000
Single Family Home
1363 NEW FOREST LN, Osprey, FL 34229
Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodland...
Listed by RE/MAX PLATINUM REALTY
$815,000
Single Family Home
901 REFLECTION WAY, Osprey, FL 34229
LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-...
Listed by GENEROUS PROPERTY
$1,295,000
Condo
385 N POINT RD #903, Osprey, FL 34229
From the moment the private elevator doors open, the panorama of the view has you at ‘hello,” with a northwest-facing ex...
Listed by COLDWELL BANKER REALTY
$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
$4,200
Single Family Home
534 OAK BAY DR, Osprey, FL 34229
New to the rental market, very nice light and bright 4 bedroom pool home with private secluded lot in the quaint communi...
Listed by REALTY BY DESIGN LLC
$525,000
Single Family Home
519 BAYVIEW AVE, Osprey, FL 34229
Bay Acres, Boating community. The home features hurricane shutters, RV parking pad 42 feet x16 feet, boat docks availabl...
Listed by COLDWELL BANKER REALTY
$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.
$2,200
Condo
137 NAVIGATION CIR #137, Osprey, FL 34229
Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards you...
Listed by RYNTAL
$4,900
Condo
14021 BELLAGIO WAY #410, Osprey, FL 34229
Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of...
Listed by UKEEPCOMMISSION REAL ESTATE
$3,250
Single Family Home
531 LATITUDE LN, Osprey, FL 34229
Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake vi...
Listed by PREMIER SOTHEBY'S INTERNATIONAL
$329,000
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
$2,200
Townhouse
184 EXPLORER DR, Osprey, FL 34229
FULLY FURNISHED Property available for $2200 from April 15, 2025 till December 15 ,2025. Tenant pays electricity and int...
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
$249,900
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
$5,500
Single Family Home
228 LOOKOUT POINT DR, Osprey, FL 34229
SouthBay Yacht & Raquet Club one of the most desirable communities in Osprey! This beautiful well maintained home welcom...
Listed by MONARCH PROPERTY GROUP LLC
$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
$729,000
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
$370,000
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
$4,800
Single Family Home
956 SCHERER WAY, Osprey, FL 34229
This luxuriously FULLY furnished 4 Bedroom Pool home is available starting April 15, 2025! It backs right onto the trop...
Listed by KELLER WILLIAMS ON THE WATER S
$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
$370,000
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