- 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)
$749,900
Single Family Home
123 TINA ISLAND DR, Osprey, FL 34229
Spectacular lot and setting for home priced under county tax appraisal. This is your opportunity to own a waterfront pro...
Listed by COLDWELL BANKER SARASOTA CENT.
$2,500,000
Single Family Home
703 MACEWEN DR, Osprey, FL 34229
Bathed in natural light, with highly sought after southern lanai exposure, is this stunning and meticulously maintained ...
Listed by COLDWELL BANKER REALTY
$729,000
Single Family Home
819 SHADOW BAY WAY, Osprey, FL 34229
This charming 2,145-square-foot pool home is in the premier community of Rivendell. This maintenance-free, tropically la...
Listed by PREMIER SOTHEBYS INTL REALTY
$589,000
Single Family Home
1327 THORNAPPLE DR, Osprey, FL 34229
Under contract-accepting backup offers. This stunning Lee Wetherington-built home in Osprey's Willowbend community beaut...
Listed by PREMIER SOTHEBYS INTL REALTY
$374,000
Single Family Home
115 VILLA DR #115, Osprey, FL 34229
Welcome to your future waterfront retreat in the heart of Osprey, where coastal living meets convenience. This beautiful...
Listed by KELLER WILLIAMS ON THE WATER S
$3,275,000
Single Family Home
135 TINA ISLAND DR, Osprey, FL 34229
If you are ready to retreat to paradise, look no more. This home is amazing. Located in a very desirable area in Sorrent...
Listed by RE/MAX PALM REALTY OF VENICE
$739,000
Condo
232 HIDDEN BAY DR #504, Osprey, FL 34229
Located in the sought-after Hidden Bay community in Osprey, with breathtaking views of Little Sarasota Bay and the Intra...
Listed by PREMIER SOTHEBYS INTL REALTY
$959,000
Single Family Home
21 BAYHEAD LN, Osprey, FL 34229
This incredible newly updated house with many upgrades and amenities is the home you have been waiting for! Ideally loc...
Listed by MICHAEL SAUNDERS & COMPANY
$2,350
Single Family Home
221 GLENWOOD AVE, Osprey, FL 34229
Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our ...
Listed by MAIN STREET RENEWAL LLC
$650,000
Condo
784 SARABAY RD #18, Osprey, FL 34229
Welcome to Your Waterfront Villa in Osprey, Florida! <br>Discover the ultimate seasonal retreat in this beautifully upda...
Listed by COLDWELL BANKER SARASOTA CENT.
$425,000
Condo
4239 EXPEDITION WAY, Osprey, FL 34229
Welcome to Bay Street Village, a highly sought-after gated condominium community in the heart of Osprey. This rarely ava...
Listed by RE/MAX ALLIANCE GROUP
$365,000
Single Family Home
214 PATTERSON AVE, Osprey, FL 34229
Welcome to your dream home in the enchanting village of Osprey! This inviting 3-bedroom, 2-bathroom block home is nestle...
Listed by RE/MAX ALLIANCE GROUP
$675,000
Condo
242 HIDDEN BAY DR #403, Osprey, FL 34229
Enjoy breathtaking 180º views of the Intracoastal Waterway and Little Sarasota Bay from this beautifully updated fourth-...
Listed by KELLER WILLIAMS ISLAND LIFE REAL ESTATE
$290,000
Manufactured Home
203 PALM AIR DR, Osprey, FL 34229
Bright and Spacious 2-Bedroom Manufactured Home with Lake View in a 55+ Co-Op Community! <br>Welcome to 203 Palm Air Dri...
Listed by LOKATION
$950,000
Single Family Home
186 TURQUOISE LN, Osprey, FL 34229
This Lee Wetherington built maintenance free home is nestled in the Emerald Woods section of The Oaks Preserve. Enter th...
Listed by COLDWELL BANKER REALTY
$399,000
Townhouse
1827 HIGHLAND RD, Osprey, FL 34229
This adorable quintessential Florida 2 bedroom, 2 bathroom end unit townhome feels incredibly private, peaceful and mode...
Listed by PREFERRED SHORE LLC
$850,000
Condo
393 N POINT RD #603, Osprey, FL 34229
Enjoy breathtaking views of the Gulf of Mexico, Little Sarasota Bay and the Intercoastal waterway from your living room,...
Listed by COLDWELL BANKER REALTY
$7,000
Single Family Home
543 PINE RANCH EAST RD, Osprey, FL 34229
An Ascendia Property! **Available beginning January 15, 2025, for a 90-night minimum stay or longer. The rental rate in ...
Listed by ASCENDIA REAL ESTATE
$4,495,000
Single Family Home
854 MACEWEN DR, Osprey, FL 34229
One or more photo(s) has been virtually staged. **NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE** Boasts OVER 9,000sf an...
Listed by GENEROUS PROPERTY
$929,000
Single Family Home
320 GAUGIN DR, Osprey, FL 34229
Welcome to Sorrento Shores in Osprey, FL. This Canal Waterfront home is the perfect entertaining poolside home with many...
Listed by KELLER WILLIAMS REALTY GOLD
$565,000
Single Family Home
328 WOODS POINT RD, Osprey, FL 34229
This fully updated, one-story, end-unit villa in Osprey's highly coveted, maintenance-free & pet-friendly Blackburn Poin...
Listed by COMPASS FLORIDA LLC
$673,000
Single Family Home
610 PINE RANCH EAST RD, Osprey, FL 34229
Price Reduced on this Magnificent three bedroom, two bath home with den, heated pool, fenced yard for privacy in Bay Oak...
Listed by COLDWELL BANKER REALTY
$399,900
Condo
294 HIDDEN BAY DR #103, Osprey, FL 34229
First-floor end-unit with hurricane-rated windows and lots of natural light, in the gated community of Hidden Bay that s...
Listed by PREMIER SOTHEBYS INTL REALTY
$1,690,000
Single Family Home
325 OSPREY POINT DR, Osprey, FL 34229
**BEAUTIFULLY UPDATED ESTATE with WATER VIEW and STUNNING ARCHITECTURAL DETAILS** is located in the COVETED, OAKS BAYSID...
Listed by GENEROUS PROPERTY