- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
144 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)
$199,900
Manufactured Home
312 TROPIC DR, Osprey, FL 34229
Welcome to your dream home in a vibrant 55+ community! This charming residence offers 2 spacious bedrooms and 2 full bat...
Listed by COMPASS FLORIDA LLC
$698,888
Condo
758 SARABAY RD #5, Osprey, FL 34229
Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf of Mexico. He...
Listed by PREMIER SOTHEBYS INTL REALTY
$837,000
Single Family Home
790 SHADOW BAY WAY, Osprey, FL 34229
Experience the ultimate in serene living within the picturesque Woodlands of Rivendell, where this stunning residence se...
Listed by PREMIER SOTHEBYS INTL REALTY
$465,000
Single Family Home
418 SARABAY RD, Osprey, FL 34229
One or more photo(s) has been virtually staged. Welcome to 418 Sarabay Rd, a lovely old-Florida home "West of Trail" in ...
Listed by DALTON WADE INC
$585,000
Single Family Home
1219 CHALET CT, Osprey, FL 34229
This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm ...
Listed by PREMIER SOTHEBYS INTL REALTY
$299,000
Townhouse
752 PINE RUN DR, Osprey, FL 34229
Discover the hidden gem of Pine Run community located within 1 mile of the Gulf of Mexico yet nestled inside a tropical ...
Listed by NEXTHOME SUNCOAST
$4,750,000
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
$795,000
Single Family Home
710 SHADOW BAY WAY, Osprey, FL 34229
Florida's perfect floor plan. Built in 2002, it features soaring ceilings and a smartly designed layout, perfect for liv...
Listed by MICHAEL SAUNDERS & COMPANY
$669,000
Single Family Home
1109 SCHERER WAY, Osprey, FL 34229
This fabulous residence, featuring a new tile roof installed in November 2024 and hurricane-impact windows and shutters ...
Listed by PREMIER SOTHEBYS INTL REALTY
$529,000
Single Family Home
117 VILLA DR #117, Osprey, FL 34229
Saltwater Canal with Deeded Dock - The Gulf of Mexico is your new backyard with this best priced waterfront villa in Os...
Listed by RE/MAX PLATINUM REALTY
$775,000
Single Family Home
524 OAK BAY DR, Osprey, FL 34229
++No Hurricane damage or water intrusion from resent storms. ++ Charming Pool Home with Luxurious Upgrades in Bay Oaks E...
Listed by COLDWELL BANKER REALTY
$935,000
Condo
236 HIDDEN BAY DR #504, Osprey, FL 34229
One or more photo(s) has been virtually staged. Waterfront resort-style living in a gated community with breathtaking pa...
Listed by PREMIER SOTHEBYS INTL REALTY
$951,000
Single Family Home
650 CRANE PRAIRIE WAY, Osprey, FL 34229
**Discover Your Dream Home at 650 Crane Prairie Way, Osprey, FL 34229** <br> <br>Welcome to your tranquil retreat in the...
Listed by KELLER WILLIAMS ON THE WATER
$745,000
Condo
236 HIDDEN BAY DR #301, Osprey, FL 34229
This beauty is a 3-3-3, 3 bedrooms, with 3 en suite full baths, End Unit with a 3 CAR GARAGE. Come home to your own hid...
Listed by COLDWELL BANKER REALTY
$224,900
Manufactured Home
262 SUN AIR CIR, Osprey, FL 34229
Nestled within the serene and sought-after Arbors Mobile Home Park in Osprey, this captivating and meticulously maintain...
Listed by KELLER WILLIAMS ON THE WATER S
$885,000
Single Family Home
1426 LANDVIEW LN, Osprey, FL 34229
Southbay's Lowest-Priced Home – Act Fast! Step into a lifestyle, not just a home, in Southbay's vibrant community! Enjo...
Listed by COLDWELL BANKER SARASOTA CENT.
$529,000
Condo
5100 JESSIE HARBOR DR #504, Osprey, FL 34229
$50k reduction and Opportunity knocks and seller's want it sold. Cheapest waterfront condo on Blackburn point. <br>NO DA...
Listed by PREFERRED SHORE
$7,395,000
Single Family Home
144 N CASEY KEY RD, Osprey, FL 34229
Welcome to this extraordinary waterfront estate on exclusive Casey Key, showcasing panoramic views of Little Sarasota Ba...
Listed by LIVING VOGUE LLC
$2,650,000
Single Family Home
370 SUGAR MILL DR, Osprey, FL 34229
**TIMELESS ELEGANCE! METICULOUSLY MAINTAINED, ARCHITECTURAL GEM FEATURES MANY RECENT UPDATES/UPGRADES** Built by BARON C...
Listed by GENEROUS PROPERTY
$999,500
Single Family Home
146 YACHT HARBOR DR, Osprey, FL 34229
This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on ...
Listed by COLDWELL BANKER REALTY
$2,150,000
Single Family Home
85 SUGAR MILL DR, Osprey, FL 34229
**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Lit...
Listed by GENEROUS PROPERTY
$1,795,000
Single Family Home
269 PINE RANCH TRL, Osprey, FL 34229
One or more photo(s) has been virtually staged. This magnificent modern manse, with 4 bedrooms and 3.5 baths, literally ...
Listed by COLDWELL BANKER REALTY
$1,185,000
Single Family Home
219 KEEL WAY, Osprey, FL 34229
**IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** o...
Listed by GENEROUS PROPERTY
$789,000
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