About South Osprey
Market Summary
Avg. List Price
Current Listings
Avg. Active Days on Market
Currently no active listings available that meet the criteria for market statistics calculations.
What Locals Say
Sites to see
Civic engagement
Fashion trending
Travelers are here
Trendy eats
Nature
Luxury culture
Dog lovers
Homey & Leisurely
Live music
market snapshot
We’ve gathered the latest market data to help you better understand what’s happening in South Osprey.
active listings
Currently no active listings available that meet the criteria for market statistics calculations.
Recently Sold
Recently Sold Avg.
Avg. Days on Market
Recently Sold
Avg. Price/Area
Properties in South Osprey
All
Sold
New - 2,079 Hours
Open House
View listing to see more images.
••••••
5 bd
5 ba
275 LOOKOUT POINT DRIVE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Tamara Currey
Sold
New - 3,187 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
117 VILLA DRIVE #117, OSPREY, FL 34229
Listing Courtesy Of: RE/MAX PLATINUM REALTY, 941-929-9090, Bill Garrison
Sold
New - 278 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
111 WOODLAND PLACE, OSPREY, FL 34229
Listing Courtesy Of: FLAT FEE MLS REALTY, 813-642-6030, Stephen Hachey
Sold
New - 4,097 Hours
Open House
Price Drop
(2d)
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••••••
2 bd
3 ba
264 WOODS POINT ROAD, OSPREY, FL 34229
Listing Courtesy Of: KELLER WILLIAMS ON THE WATER S, 941-803-7522, Mark Midyett
Sold
New - 1,285 Hours
Open House
Price Drop
(2d)
View listing to see more images.
••••••
3 bd
2 ba
1237 FLYING BRIDGE LANE, OSPREY, FL 34229
Listing Courtesy Of: PAT WILLIAMS REALTY, LLC, Pat Williams
Sold
New - 2,626 Hours
Open House
View listing to see more images.
••••••
4 bd
4 ba
312 YACHT HARBOR DRIVE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 1,161 Hours
Open House
Price Drop
(Just Now)
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••••••
4 bd
3 ba
146 WILLOW BEND WAY, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Darlene Gamble
Sold
New - 447 Hours
Open House
View listing to see more images.
••••••
4 bd
3 ba
201 EAGLENOOK WAY, OSPREY, FL 34229
Listing Courtesy Of: WILLIAM RAVEIS REAL ESTATE, 941-894-1255, Dawn Bear
Sold
New - 1,284 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
3904 WAYPOINT AVENUE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Tamara Currey
Sold
New - 8,366 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #203, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 1,835 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
280 HIDDEN BAY DRIVE #201, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 8,365 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #302, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 8,365 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
280 HIDDEN BAY DRIVE #204, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 3,543 Hours
Open House
Price Drop
(1d)
View listing to see more images.
••••••
2 bd
2 ba
328 WOODS POINT ROAD, OSPREY, FL 34229
Listing Courtesy Of: COMPASS FLORIDA LLC, Priscilla Adams
Sold
New - 2,506 Hours
Open House
Price Drop
(2d)
View listing to see more images.
••••••
2 bd
2 ba
225 WOODLAND DRIVE, OSPREY, FL 34229
Listing Courtesy Of: COMPASS FLORIDA LLC, Priscilla Adams
Sold
New - 59 Hours
Open House
•••••
109 BURNEY ROAD, OSPREY, FL 34229
Listing Courtesy Of: MANGROVE REALTY ASSOCIATES, 941-957-0080, Lori Madden
Sold
New - 1,458 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
304 PINE RUN DRIVE, OSPREY, FL 34229
Listing Courtesy Of: KELLER WILLIAMS ON THE WATER S, 941-803-7522, Derek Edwards
Sold
New - 2,271 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
109 WOODLAND PLACE, OSPREY, FL 34229
Listing Courtesy Of: KELLER WILLIAMS ON THE WATER S, 941-803-7522, Derek Edwards
Sold
New - 3,593 Hours
Open House
Price Drop
(2d)
View listing to see more images.
••••••
2 bd
2 ba
294 HIDDEN BAY DRIVE #103, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 9,564 Hours
Open House
View listing to see more images.
••••••
2 bd
1 ba
38 OLD VENICE ROAD, OSPREY, FL 34229
Listing Courtesy Of: CHARLES RUTENBERG REALTY INC, 866-580-6402, Christopher Lowe
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Active
Sold
New - 2,079 Hours
Open House
View listing to see more images.
••••••
5 bd
5 ba
275 LOOKOUT POINT DRIVE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Tamara Currey
Sold
New - 3,187 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
117 VILLA DRIVE #117, OSPREY, FL 34229
Listing Courtesy Of: RE/MAX PLATINUM REALTY, 941-929-9090, Bill Garrison
Sold
New - 278 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
111 WOODLAND PLACE, OSPREY, FL 34229
Listing Courtesy Of: FLAT FEE MLS REALTY, 813-642-6030, Stephen Hachey
Sold
New - 4,097 Hours
Open House
Price Drop
(2d)
View listing to see more images.
••••••
2 bd
3 ba
264 WOODS POINT ROAD, OSPREY, FL 34229
Listing Courtesy Of: KELLER WILLIAMS ON THE WATER S, 941-803-7522, Mark Midyett
Sold
New - 1,285 Hours
Open House
Price Drop
(2d)
View listing to see more images.
••••••
3 bd
2 ba
1237 FLYING BRIDGE LANE, OSPREY, FL 34229
Listing Courtesy Of: PAT WILLIAMS REALTY, LLC, Pat Williams
Sold
New - 2,626 Hours
Open House
View listing to see more images.
••••••
4 bd
4 ba
312 YACHT HARBOR DRIVE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 1,161 Hours
Open House
Price Drop
(Just Now)
View listing to see more images.
••••••
4 bd
3 ba
146 WILLOW BEND WAY, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Darlene Gamble
Sold
New - 447 Hours
Open House
View listing to see more images.
••••••
4 bd
3 ba
201 EAGLENOOK WAY, OSPREY, FL 34229
Listing Courtesy Of: WILLIAM RAVEIS REAL ESTATE, 941-894-1255, Dawn Bear
Sold
New - 1,284 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
3904 WAYPOINT AVENUE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Tamara Currey
Sold
New - 8,366 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #203, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 1,835 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
280 HIDDEN BAY DRIVE #201, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 8,365 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #302, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 8,365 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
280 HIDDEN BAY DRIVE #204, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 3,543 Hours
Open House
Price Drop
(1d)
View listing to see more images.
••••••
2 bd
2 ba
328 WOODS POINT ROAD, OSPREY, FL 34229
Listing Courtesy Of: COMPASS FLORIDA LLC, Priscilla Adams
Sold
New - 59 Hours
Open House
•••••
109 BURNEY ROAD, OSPREY, FL 34229
Listing Courtesy Of: MANGROVE REALTY ASSOCIATES, 941-957-0080, Lori Madden
Sold
New - 1,458 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
304 PINE RUN DRIVE, OSPREY, FL 34229
Listing Courtesy Of: KELLER WILLIAMS ON THE WATER S, 941-803-7522, Derek Edwards
Sold
New - 2,271 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
109 WOODLAND PLACE, OSPREY, FL 34229
Listing Courtesy Of: KELLER WILLIAMS ON THE WATER S, 941-803-7522, Derek Edwards
Sold
New - 3,593 Hours
Open House
Price Drop
(2d)
View listing to see more images.
••••••
2 bd
2 ba
294 HIDDEN BAY DRIVE #103, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 155 Hours
Open House
View listing to see more images.
••••••
4 bd
3 ba
826 OAK BRIAR LANE, OSPREY, FL 34229
Listing Courtesy Of: PREFERRED SHORE LLC, 941-999-1179, Peter Lasalle
Sold
New - 6,785 Hours
Open House
View listing to see more images.
••••••
216 OSPREY POINT DRIVE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Judie Berger
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Pending
Sold
New - 2,506 Hours
Open House
Price Drop
(2d)
View listing to see more images.
••••••
2 bd
2 ba
225 WOODLAND DRIVE, OSPREY, FL 34229
Listing Courtesy Of: COMPASS FLORIDA LLC, Priscilla Adams
Sold
New - 9,564 Hours
Open House
View listing to see more images.
••••••
2 bd
1 ba
38 OLD VENICE ROAD, OSPREY, FL 34229
Listing Courtesy Of: CHARLES RUTENBERG REALTY INC, 866-580-6402, Christopher Lowe
Sold
New - 7,785 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
5100 JESSIE HARBOR DRIVE #504, OSPREY, FL 34229
Listing Courtesy Of: PREFERRED SHORE, 941-999-1179, Rory McDonald
Sold
New - 1,259 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
1152 BEACHCOMBER COURT #15, OSPREY, FL 34229
Listing Courtesy Of: BRIGHT REALTY, 941-552-6036, Jennifer Bright
Sold
New - 7,043 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
14041 BELLAGIO WAY #313, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-412-3323, Megan E. George, PA
Sold
New - 1,242 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
76 EXPLORER DRIVE #104, OSPREY, FL 34229
Listing Courtesy Of: COLDWELL BANKER REALTY, 941-349-4411, Pan Steele
Sold
New - 3,422 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
236 HIDDEN BAY DRIVE #504, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 6,345 Hours
Open House
•
3 bd
3 ba
280 HIDDEN BAY DRIVE #301, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 6,076 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
329 BAY VISTA AVENUE, OSPREY, FL 34229
Listing Courtesy Of: HORIZON REALTY INTERNATIONAL, 941-238-0953, Colette Jay
Sold
New - 1,930 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #303, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 1,240 Hours
Open House
View listing to see more images.
••••••
14 OLD VENICE ROAD, OSPREY, FL 34229
Listing Courtesy Of: COLDWELL BANKER SARASOTA CENT., 941-487-5600, Glenn Davis
Sold
New - 1,582 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
312 TROPIC DRIVE, OSPREY, FL 34229
Listing Courtesy Of: COMPASS FLORIDA LLC, Ania McGinty
Sold
New - 2,461 Hours
Open House
View listing to see more images.
••••••
4 bd
3 ba
1862 ISLAND WAY, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Nancy Endara
Sold
New - 18,034 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #403, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 15,733 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
280 HIDDEN BAY DRIVE #401, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 3,112 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
4239 EXPEDITION WAY, OSPREY, FL 34229
Listing Courtesy Of: RE/MAX ALLIANCE GROUP, 941-954-5454, Joe Cleary
Sold
New - 947 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
128 SEA ANCHOR DRIVE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-412-3323, Lisa Napolitano
Sold
New - 18,542 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #402, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
New - 2,462 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
247 KEEL WAY, OSPREY, FL 34229
Listing Courtesy Of: PAT WILLIAMS REALTY, LLC, Pat Williams
Sold
New - 16,356 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
280 HIDDEN BAY DRIVE #502, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
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Upcoming Open Houses
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Recently Sold
Sold
- Mar 12, 2025
New - 1,446 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
738 HARMS DRIVE, OSPREY, FL 34229
Listing Courtesy Of: MCGREGOR INTERNATIONAL REAL ESTATE CO, 941-363-1210, Warren McGregor
Sold
- Feb 21, 2025
New - 3,129 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
242 HIDDEN BAY DRIVE #403, OSPREY, FL 34229
Listing Courtesy Of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE, 941-254-6467, Tina Renta
Sold
- Feb 18, 2025
New - 2,698 Hours
Open House
View listing to see more images.
••••••
4 bd
3 ba
108 PARK DRIVE, OSPREY, FL 34229
Listing Courtesy Of: COLDWELL BANKER REALTY, 941-493-1000, Michele Monteiro
Sold
- Feb 17, 2025
New - 7,289 Hours
Open House
View listing to see more images.
••••••
570 BLACKBURN POINT ROAD #C2, OSPREY, FL 34229
Listing Courtesy Of: BRIGHT REALTY, 941-552-6036, David Babel
Sold
- Feb 14, 2025
New - 1,558 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
146 YACHT HARBOR DRIVE, OSPREY, FL 34229
Listing Courtesy Of: COLDWELL BANKER REALTY, 941-388-3966, Susanne Losso
Sold
- Feb 14, 2025
New - 1,842 Hours
Open House
View listing to see more images.
••••••
2 bd
3 ba
716 SARABAY ROAD, OSPREY, FL 34229
Listing Courtesy Of: COLDWELL BANKER SARASOTA CENT., 941-487-5600, Peggy Lewis
Sold
- Feb 12, 2025
New - 1,454 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
419 YACHT HARBOR DRIVE, OSPREY, FL 34229
Listing Courtesy Of: PREMIER SOTHEBYS INTL REALTY, 941-364-4000, Thomas Netzel
Sold
- Feb 7, 2025
New - 2,161 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
128 NAVIGATION CIRCLE #103, OSPREY, FL 34229
Listing Courtesy Of: EXIT KING REALTY, 941-497-6060, Tim Weller
Sold
- Feb 3, 2025
New - 1,166 Hours
Open House
•
2 bd
2 ba
480 FAITH AVENUE, OSPREY, FL 34229
Listing Courtesy Of: MICHAEL SAUNDERS & COMPANY, 941-349-3444, Robin Leonardi
Sold
- Jan 17, 2025
New - 2,505 Hours
Open House
View listing to see more images.
••••••
3 bd
4 ba
14021 BELLAGIO WAY #201, OSPREY, FL 34229
Listing Courtesy Of: COMPASS FLORIDA LLC, Brian Wood
Sold
- Jan 15, 2025
New - 4,424 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
193 WILLOW BEND WAY, OSPREY, FL 34229
Listing Courtesy Of: FLORIDA HOME TEAM LLC, 941-486-0012, Bill Cantrell
Sold
- Jan 10, 2025
New - 4,744 Hours
Open House
View listing to see more images.
••••••
3 bd
4 ba
14021 BELLAGIO WAY #204, OSPREY, FL 34229
Listing Courtesy Of: ALLISON JAMES ESTATES & HOMES, 941-500-4922, Kym Biggar III
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Nearby Schools
Public
Private
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Grade
Student-Teacher Ratio:
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Student-Teacher Ratio:
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Transit & Commute
Estimated commute times from South Osprey
Car-Dependent
Walkable
Very Walkable
Nearby Neighborhoods
Cordes
Calusa Lakes
20
Current Listings
Silver Oak
Huntington Pointe Dr
3
Current Listings
Oaks Preserve
15
Current Listings
Mission Estates
3
Current Listings
Turquoise
2
Current Listings
Esplanade/Legacy Estates on Palmer Ranch
5
Current Listings
Lake Village
2
Current Listings
Bellacina By Casey Key
10
Current Listings
Bay Oaks Estates
2
Current Listings
Bishopscourt
4
Current Listings
Willowbend
5
Current Listings
Oaks
16
Current Listings
Sorrento East
32
Current Listings
Sorrento Cay
5
Current Listings
North Casey Key
7
Current Listings
Spanish Point
1
Current Listings
Osprey Park
1
Current Listings
Sorrento South
9
Current Listings
Springhill
2
Current Listings
Bay Street Park
3
Current Listings
Sorrento Shores
8
Current Listings
Rivendell
8
Current Listings