Listings in 34229 - Sarasota County, Florida
Displaying 1 – 200 of 317 Real estate listings
627 N MACEWEN DRIVE
OSPREY, FL | Closed
Listed: Sep, 26, 2025
Price: $1,950,000
Living Area: 3,857 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 26, 2025
Price: $1,950,000
Living Area: 3,857 Sq. Ft.
413 GLENWOOD AVENUE
OSPREY, FL | Closed
Listed: Oct, 03, 2025
Price: $2,139
Living Area: 1,462 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 03, 2025
Price: $2,139
Living Area: 1,462 Sq. Ft.
141 N CASEY KEY ROAD
OSPREY, FL | Active
Listed: Oct, 31, 2025
Price: $3,200,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 31, 2025
Price: $3,200,000
Living Area: 0 Sq. Ft.
115 GREEN STREET
OSPREY, FL | Closed
Listed: Sep, 17, 2025
Price: $349,000
Living Area: 1,503 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 17, 2025
Price: $349,000
Living Area: 1,503 Sq. Ft.
766 SHADOW BAY WAY
OSPREY, FL | Closed
Listed: May, 14, 2025
Price: $949,900
Living Area: 3,438 Sq. Ft.
OSPREY, FL | Closed
Listed: May, 14, 2025
Price: $949,900
Living Area: 3,438 Sq. Ft.
236 SAINT JAMES PARK
OSPREY, FL | Active
Listed: Mar, 27, 2025
Price: $2,700,000
Living Area: 6,246 Sq. Ft.
OSPREY, FL | Active
Listed: Mar, 27, 2025
Price: $2,700,000
Living Area: 6,246 Sq. Ft.
201 WOODLAND DRIVE 201
OSPREY, FL | Closed
Listed: Oct, 01, 2024
Price: $200,000
Living Area: 1,316 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 01, 2024
Price: $200,000
Living Area: 1,316 Sq. Ft.
1313 THORNAPPLE DRIVE
OSPREY, FL | Closed
Listed: Oct, 28, 2025
Price: $539,000
Living Area: 2,082 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 28, 2025
Price: $539,000
Living Area: 2,082 Sq. Ft.
18 N CASEY KEY ROAD
OSPREY, FL | Active
Listed: Oct, 18, 2025
Price: $2,350,000
Living Area: 1,977 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 18, 2025
Price: $2,350,000
Living Area: 1,977 Sq. Ft.
909 MACEWEN DRIVE
OSPREY, FL | Active
Listed: Sep, 13, 2024
Price: $1,695,000
Living Area: 4,241 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 13, 2024
Price: $1,695,000
Living Area: 4,241 Sq. Ft.
385 N POINT ROAD 704
OSPREY, FL | Active
Listed: Nov, 10, 2025
Price: $1,500,000
Living Area: 2,778 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 10, 2025
Price: $1,500,000
Living Area: 2,778 Sq. Ft.
111 WOODLAND PLACE
OSPREY, FL | Closed
Listed: Aug, 28, 2025
Price: $239,000
Living Area: 1,316 Sq. Ft.
OSPREY, FL | Closed
Listed: Aug, 28, 2025
Price: $239,000
Living Area: 1,316 Sq. Ft.
293 TURQUOISE LANE
OSPREY, FL | Active
Listed: Jan, 09, 2024
Price: $5,750
Living Area: 2,271 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 09, 2024
Price: $5,750
Living Area: 2,271 Sq. Ft.
758 PINE RUN DRIVE 758
OSPREY, FL | Active
Listed: Nov, 25, 2025
Price: $1,950
Living Area: 1,184 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 25, 2025
Price: $1,950
Living Area: 1,184 Sq. Ft.
291 HIDDEN BAY DRIVE 101
OSPREY, FL | Pending
Listed: Nov, 06, 2025
Price: $400,000
Living Area: 1,599 Sq. Ft.
OSPREY, FL | Pending
Listed: Nov, 06, 2025
Price: $400,000
Living Area: 1,599 Sq. Ft.
1216 N CASEY KEY ROAD
OSPREY, FL | Active
Listed: Mar, 03, 2025
Price: $10,750,000
Living Area: 8,050 Sq. Ft.
OSPREY, FL | Active
Listed: Mar, 03, 2025
Price: $10,750,000
Living Area: 8,050 Sq. Ft.
112 Osprey Point Drive
OTHER, FL | Closed
Listed: May, 04, 2025
Price: $3,315,000
Living Area: 8,635 Sq. Ft.
OTHER, FL | Closed
Listed: May, 04, 2025
Price: $3,315,000
Living Area: 8,635 Sq. Ft.
360 N POINT ROAD
OSPREY, FL | Active
Listed: Jul, 24, 2024
Price: $1,570,000
Living Area: 2,913 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 24, 2024
Price: $1,570,000
Living Area: 2,913 Sq. Ft.
385 N POINT ROAD 402
OSPREY, FL | Active
Listed: Jan, 25, 2025
Price: $660,000
Living Area: 2,055 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 25, 2025
Price: $660,000
Living Area: 2,055 Sq. Ft.
293 TURQUOISE LANE
OSPREY, FL | Active
Listed: Jan, 10, 2025
Price: $910,000
Living Area: 2,271 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 10, 2025
Price: $910,000
Living Area: 2,271 Sq. Ft.
761 PINE RUN DRIVE 761
OSPREY, FL | Closed
Listed: Dec, 01, 2025
Price: $279,000
Living Area: 1,379 Sq. Ft.
OSPREY, FL | Closed
Listed: Dec, 01, 2025
Price: $279,000
Living Area: 1,379 Sq. Ft.
362 MACEWEN DRIVE
OSPREY, FL | Active
Listed: Jan, 12, 2026
Price: $2,249,000
Living Area: 4,117 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 12, 2026
Price: $2,249,000
Living Area: 4,117 Sq. Ft.
854 MACEWEN DRIVE
OSPREY, FL | Active
Listed: Oct, 19, 2025
Price: $3,890,000
Living Area: 9,081 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 19, 2025
Price: $3,890,000
Living Area: 9,081 Sq. Ft.
700 FAITH AVENUE
OSPREY, FL | Active
Listed: Nov, 08, 2025
Price: $1,250,000
Living Area: 2,474 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 08, 2025
Price: $1,250,000
Living Area: 2,474 Sq. Ft.
85 SUGAR MILL DRIVE
OSPREY, FL | Active
Listed: Oct, 09, 2025
Price: $2,150,000
Living Area: 4,191 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 09, 2025
Price: $2,150,000
Living Area: 4,191 Sq. Ft.
75 OSPREY POINT DRIVE
OSPREY, FL | Active
Listed: Nov, 19, 2025
Price: $1,775,000
Living Area: 4,001 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 19, 2025
Price: $1,775,000
Living Area: 4,001 Sq. Ft.
453 E MACEWEN DRIVE
OSPREY, FL | Closed
Listed: Oct, 23, 2025
Price: $1,899,000
Living Area: 4,191 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 23, 2025
Price: $1,899,000
Living Area: 4,191 Sq. Ft.
471 PARK TRACE BOULEVARD
OSPREY, FL | Pending
Listed: Jul, 11, 2025
Price: $699,000
Living Area: 2,267 Sq. Ft.
OSPREY, FL | Pending
Listed: Jul, 11, 2025
Price: $699,000
Living Area: 2,267 Sq. Ft.
105 TURQUOISE LANE
OSPREY, FL | Pending
Listed: Aug, 15, 2025
Price: $995,000
Living Area: 2,606 Sq. Ft.
OSPREY, FL | Pending
Listed: Aug, 15, 2025
Price: $995,000
Living Area: 2,606 Sq. Ft.
137 OSPREY POINT DRIVE
OSPREY, FL | Active
Listed: Oct, 24, 2025
Price: $1,345,000
Living Area: 3,303 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 24, 2025
Price: $1,345,000
Living Area: 3,303 Sq. Ft.
216 GLENWOOD AVENUE
OSPREY, FL | Pending
Listed: Nov, 26, 2025
Price: $250,000
Living Area: 732 Sq. Ft.
OSPREY, FL | Pending
Listed: Nov, 26, 2025
Price: $250,000
Living Area: 732 Sq. Ft.
104 PARK TRACE BOULEVARD
OSPREY, FL | Active
Listed: Dec, 03, 2025
Price: $650,000
Living Area: 2,557 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 03, 2025
Price: $650,000
Living Area: 2,557 Sq. Ft.
178 WILLOW BEND WAY
OSPREY, FL | Closed
Listed: Nov, 21, 2025
Price: $640,000
Living Area: 1,889 Sq. Ft.
OSPREY, FL | Closed
Listed: Nov, 21, 2025
Price: $640,000
Living Area: 1,889 Sq. Ft.
163 PENNSYLVANIA AVENUE
OSPREY, FL | Closed
Listed: Oct, 23, 2025
Price: $2,400
Living Area: 1,346 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 23, 2025
Price: $2,400
Living Area: 1,346 Sq. Ft.
455 N SHORE DRIVE
OSPREY, FL | Active
Listed: Aug, 18, 2025
Price: $549,000
Living Area: 1,229 Sq. Ft.
OSPREY, FL | Active
Listed: Aug, 18, 2025
Price: $549,000
Living Area: 1,229 Sq. Ft.
479 SOUTH CREEK DRIVE
OSPREY, FL | Active
Listed: Oct, 17, 2025
Price: $2,795,000
Living Area: 4,261 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 17, 2025
Price: $2,795,000
Living Area: 4,261 Sq. Ft.
280 HIDDEN BAY DRIVE 202
OSPREY, FL | Active
Listed: Sep, 03, 2025
Price: $4,200
Living Area: 1,937 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 03, 2025
Price: $4,200
Living Area: 1,937 Sq. Ft.
147 OSPREY POINT DRIVE
OSPREY, FL | Active
Listed: Oct, 01, 2025
Price: $750,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 01, 2025
Price: $750,000
Living Area: 0 Sq. Ft.
116 NAVIGATION CIRCLE 106
OSPREY, FL | Active
Listed: Jul, 08, 2025
Price: $325,000
Living Area: 1,430 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 08, 2025
Price: $325,000
Living Area: 1,430 Sq. Ft.
480 BLACKBURN POINT ROAD 4
OSPREY, FL | Closed
Listed: Sep, 15, 2025
Price: $225,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 15, 2025
Price: $225,000
Living Area: 0 Sq. Ft.
705 FORDINGBRIDGE WAY
OSPREY, FL | Closed
Listed: Sep, 22, 2025
Price: $3,200
Living Area: 2,176 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 22, 2025
Price: $3,200
Living Area: 2,176 Sq. Ft.
521 HABITAT BOULEVARD
OSPREY, FL | Active
Listed: Aug, 14, 2025
Price: $6,500
Living Area: 2,266 Sq. Ft.
OSPREY, FL | Active
Listed: Aug, 14, 2025
Price: $6,500
Living Area: 2,266 Sq. Ft.
3976 DESTINATION DRIVE A411
OSPREY, FL | Active
Listed: Jun, 30, 2025
Price: $90,000
Living Area: 2,314 Sq. Ft.
OSPREY, FL | Active
Listed: Jun, 30, 2025
Price: $90,000
Living Area: 2,314 Sq. Ft.
436 S TAMIAMI TRAIL C4
OSPREY, FL | Active
Listed: Apr, 04, 2025
Price: $374,900
Living Area: 1,272 Sq. Ft.
OSPREY, FL | Active
Listed: Apr, 04, 2025
Price: $374,900
Living Area: 1,272 Sq. Ft.
60 BISHOPS COURT ROAD 114
OSPREY, FL | Active
Listed: Apr, 09, 2025
Price: $2,995
Living Area: 1,890 Sq. Ft.
OSPREY, FL | Active
Listed: Apr, 09, 2025
Price: $2,995
Living Area: 1,890 Sq. Ft.
325 OSPREY POINT DRIVE
OSPREY, FL | Closed
Listed: Oct, 31, 2025
Price: $1,690,000
Living Area: 3,905 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 31, 2025
Price: $1,690,000
Living Area: 3,905 Sq. Ft.
14041 BELLAGIO WAY 316
OSPREY, FL | Active
Listed: Sep, 10, 2024
Price: $7,000
Living Area: 2,058 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 10, 2024
Price: $7,000
Living Area: 2,058 Sq. Ft.
304 PINE RUN DRIVE 304
OSPREY, FL | Closed
Listed: Sep, 07, 2025
Price: $2,000
Living Area: 1,729 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 07, 2025
Price: $2,000
Living Area: 1,729 Sq. Ft.
570 BLACKBURN POINT ROAD 11
OSPREY, FL | Active
Listed: Jul, 14, 2025
Price: $42,500
Living Area: 0 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 14, 2025
Price: $42,500
Living Area: 0 Sq. Ft.
232 HIDDEN BAY DRIVE 504
OSPREY, FL | Active
Listed: Dec, 03, 2025
Price: $3,300
Living Area: 2,000 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 03, 2025
Price: $3,300
Living Area: 2,000 Sq. Ft.
1755 HIGHLAND ROAD
OSPREY, FL | Active
Listed: Jan, 13, 2026
Price: $2,195
Living Area: 1,334 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 13, 2026
Price: $2,195
Living Area: 1,334 Sq. Ft.
433 E MACEWEN DRIVE
OSPREY, FL | Active
Listed: Dec, 30, 2025
Price: $2,250,000
Living Area: 4,012 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 30, 2025
Price: $2,250,000
Living Area: 4,012 Sq. Ft.
17 BAYHEAD LANE
OSPREY, FL | Active
Listed: Jan, 12, 2026
Price: $1,300,000
Living Area: 2,850 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 12, 2026
Price: $1,300,000
Living Area: 2,850 Sq. Ft.
85 NAVIGATION CIRCLE
OSPREY, FL | Closed
Listed: Dec, 11, 2025
Price: $339,000
Living Area: 1,430 Sq. Ft.
OSPREY, FL | Closed
Listed: Dec, 11, 2025
Price: $339,000
Living Area: 1,430 Sq. Ft.
603 PINE RANCH EAST ROAD
OSPREY, FL | Closed
Listed: Oct, 06, 2025
Price: $3,550
Living Area: 2,225 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 06, 2025
Price: $3,550
Living Area: 2,225 Sq. Ft.
1355 SOUTHBAY DRIVE
OSPREY, FL | Active
Listed: Jan, 15, 2026
Price: $4,500
Living Area: 2,367 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 15, 2026
Price: $4,500
Living Area: 2,367 Sq. Ft.
401 N POINT ROAD 304
OSPREY, FL | Active
Listed: Jul, 25, 2025
Price: $850,000
Living Area: 2,778 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 25, 2025
Price: $850,000
Living Area: 2,778 Sq. Ft.
172 EXPLORER DRIVE
OSPREY, FL | Pending
Listed: Dec, 21, 2025
Price: $350,000
Living Area: 1,449 Sq. Ft.
OSPREY, FL | Pending
Listed: Dec, 21, 2025
Price: $350,000
Living Area: 1,449 Sq. Ft.
232 EXPLORER DRIVE 15
OSPREY, FL | Closed
Listed: Apr, 11, 2025
Price: $299,500
Living Area: 1,135 Sq. Ft.
OSPREY, FL | Closed
Listed: Apr, 11, 2025
Price: $299,500
Living Area: 1,135 Sq. Ft.
26 SIESTA CIRCLE W
OSPREY, FL | Pending
Listed: Nov, 25, 2025
Price: $129,500
Living Area: 600 Sq. Ft.
OSPREY, FL | Pending
Listed: Nov, 25, 2025
Price: $129,500
Living Area: 600 Sq. Ft.
260 HIDDEN BAY DRIVE 405
OSPREY, FL | Active
Listed: Jan, 16, 2026
Price: $899,000
Living Area: 2,168 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 16, 2026
Price: $899,000
Living Area: 2,168 Sq. Ft.
570 BLACKBURN POINT ROAD LNG42
OSPREY, FL | Active
Listed: Jan, 08, 2026
Price: $41,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 08, 2026
Price: $41,000
Living Area: 0 Sq. Ft.
234 PATTERSON AVENUE
OSPREY, FL | Active
Listed: Feb, 05, 2026
Price: $2,100
Living Area: 1,173 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 05, 2026
Price: $2,100
Living Area: 1,173 Sq. Ft.
1308 THORNAPPLE DRIVE
OSPREY, FL | Active
Listed: Nov, 14, 2025
Price: $4,250
Living Area: 2,188 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 14, 2025
Price: $4,250
Living Area: 2,188 Sq. Ft.
6100 JESSIE HARBOR DRIVE 202
OSPREY, FL | Active
Listed: Oct, 30, 2025
Price: $970,000
Living Area: 3,771 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 30, 2025
Price: $970,000
Living Area: 3,771 Sq. Ft.
291 HIDDEN BAY DRIVE 102
OSPREY, FL | Active
Listed: Feb, 02, 2026
Price: $399,000
Living Area: 1,479 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 02, 2026
Price: $399,000
Living Area: 1,479 Sq. Ft.
472 PARK TRACE BOULEVARD
OSPREY, FL | Active
Listed: Jan, 30, 2026
Price: $645,000
Living Area: 2,217 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 30, 2026
Price: $645,000
Living Area: 2,217 Sq. Ft.
280 HIDDEN BAY DRIVE 201
OSPREY, FL | Active
Listed: Jan, 26, 2026
Price: $3,895
Living Area: 2,168 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 26, 2026
Price: $3,895
Living Area: 2,168 Sq. Ft.
3976 DESTINATION DRIVE 102
OSPREY, FL | Active
Listed: Feb, 02, 2026
Price: $30,000
Living Area: 1,050 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 02, 2026
Price: $30,000
Living Area: 1,050 Sq. Ft.
571 PINE RANCH EAST ROAD
OSPREY, FL | Active
Listed: Sep, 19, 2025
Price: $665,000
Living Area: 2,746 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 19, 2025
Price: $665,000
Living Area: 2,746 Sq. Ft.
139 WOODLAND PLACE 139
OSPREY, FL | Closed
Listed: Dec, 07, 2025
Price: $244,907
Living Area: 865 Sq. Ft.
OSPREY, FL | Closed
Listed: Dec, 07, 2025
Price: $244,907
Living Area: 865 Sq. Ft.
76 OSPREY POINT DRIVE
OSPREY, FL | Active
Listed: Nov, 24, 2025
Price: $1,650,000
Living Area: 4,364 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 24, 2025
Price: $1,650,000
Living Area: 4,364 Sq. Ft.
152 NAVIGATION CIRCLE 107
OSPREY, FL | Active
Listed: Nov, 11, 2021
Price: $4,500
Living Area: 1,528 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 11, 2021
Price: $4,500
Living Area: 1,528 Sq. Ft.
570 BLACKBURN POINT ROAD 26
OSPREY, FL | Active
Listed: Feb, 12, 2026
Price: $36,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 12, 2026
Price: $36,000
Living Area: 0 Sq. Ft.
14021 BELLAGIO WAY 309
OSPREY, FL | Active
Listed: Feb, 06, 2026
Price: $899,995
Living Area: 2,199 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 06, 2026
Price: $899,995
Living Area: 2,199 Sq. Ft.
662 FERNWALK LANE
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $2,850,000
Living Area: 4,359 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $2,850,000
Living Area: 4,359 Sq. Ft.
200 WOODLAND DRIVE
OSPREY, FL | Active
Listed: Feb, 02, 2026
Price: $175,000
Living Area: 865 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 02, 2026
Price: $175,000
Living Area: 865 Sq. Ft.
570 CRANE PRAIRIE WAY
OSPREY, FL | Pending
Listed: Feb, 07, 2026
Price: $499,900
Living Area: 2,298 Sq. Ft.
OSPREY, FL | Pending
Listed: Feb, 07, 2026
Price: $499,900
Living Area: 2,298 Sq. Ft.
401 N POINT ROAD 1001
OSPREY, FL | Active
Listed: Feb, 01, 2026
Price: $1,995,000
Living Area: 3,029 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 01, 2026
Price: $1,995,000
Living Area: 3,029 Sq. Ft.
1363 NEW FOREST LANE
OSPREY, FL | Closed
Listed: Apr, 24, 2025
Price: $499,000
Living Area: 1,738 Sq. Ft.
OSPREY, FL | Closed
Listed: Apr, 24, 2025
Price: $499,000
Living Area: 1,738 Sq. Ft.
600 EAGLE WATCH LANE
OSPREY, FL | Active
Listed: Oct, 21, 2025
Price: $2,195,000
Living Area: 3,681 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 21, 2025
Price: $2,195,000
Living Area: 3,681 Sq. Ft.
124 TURQUOISE LANE
OSPREY, FL | Active
Listed: Feb, 11, 2026
Price: $5,900
Living Area: 2,306 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 11, 2026
Price: $5,900
Living Area: 2,306 Sq. Ft.
260 HIDDEN BAY DRIVE 305
OSPREY, FL | Closed
Listed: Apr, 28, 2025
Price: $789,000
Living Area: 2,168 Sq. Ft.
OSPREY, FL | Closed
Listed: Apr, 28, 2025
Price: $789,000
Living Area: 2,168 Sq. Ft.
1303 THORNAPPLE DRIVE
OSPREY, FL | Active
Listed: Dec, 15, 2025
Price: $699,000
Living Area: 1,929 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 15, 2025
Price: $699,000
Living Area: 1,929 Sq. Ft.
896 MACEWEN DRIVE
OSPREY, FL | Active
Listed: Jan, 22, 2026
Price: $2,450,000
Living Area: 4,858 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 22, 2026
Price: $2,450,000
Living Area: 4,858 Sq. Ft.
1036 OAK MEADOW LN
OSPREY, FL | Active
Listed: Oct, 16, 2025
Price: $559,000
Living Area: 2,186 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 16, 2025
Price: $559,000
Living Area: 2,186 Sq. Ft.
1602 SOUTHBAY DRIVE
OSPREY, FL | Active
Listed: Aug, 25, 2025
Price: $974,900
Living Area: 2,980 Sq. Ft.
OSPREY, FL | Active
Listed: Aug, 25, 2025
Price: $974,900
Living Area: 2,980 Sq. Ft.
102 WINDWARD DRIVE
OSPREY, FL | Active
Listed: Nov, 19, 2025
Price: $750,000
Living Area: 2,134 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 19, 2025
Price: $750,000
Living Area: 2,134 Sq. Ft.
238 PALM AIR DRIVE
OSPREY, FL | Active
Listed: Jul, 13, 2025
Price: $185,000
Living Area: 1,152 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 13, 2025
Price: $185,000
Living Area: 1,152 Sq. Ft.
140 N CASEY KEY ROAD
OSPREY, FL | Active
Listed: Aug, 28, 2025
Price: $2,100,000
Living Area: 2,473 Sq. Ft.
OSPREY, FL | Active
Listed: Aug, 28, 2025
Price: $2,100,000
Living Area: 2,473 Sq. Ft.
767 FORDINGBRIDGE WAY
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $625,000
Living Area: 2,162 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $625,000
Living Area: 2,162 Sq. Ft.
6100 JESSIE HARBOR DRIVE 203
OSPREY, FL | Active
Listed: Feb, 14, 2026
Price: $769,000
Living Area: 2,630 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 14, 2026
Price: $769,000
Living Area: 2,630 Sq. Ft.
280 HIDDEN BAY DRIVE 202
OSPREY, FL | Active
Listed: Mar, 03, 2025
Price: $780,250
Living Area: 1,937 Sq. Ft.
OSPREY, FL | Active
Listed: Mar, 03, 2025
Price: $780,250
Living Area: 1,937 Sq. Ft.
216 WOODLAND DRIVE 216
OSPREY, FL | Closed
Listed: Jul, 28, 2025
Price: $230,000
Living Area: 1,325 Sq. Ft.
OSPREY, FL | Closed
Listed: Jul, 28, 2025
Price: $230,000
Living Area: 1,325 Sq. Ft.
207 WOODLAND DRIVE 207
OSPREY, FL | Closed
Listed: May, 06, 2024
Price: $269,999
Living Area: 1,325 Sq. Ft.
OSPREY, FL | Closed
Listed: May, 06, 2024
Price: $269,999
Living Area: 1,325 Sq. Ft.
570 BLACKBURN POINT ROAD 25
OSPREY, FL | Closed
Listed: Sep, 05, 2025
Price: $850
Living Area: 5 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 05, 2025
Price: $850
Living Area: 5 Sq. Ft.
1728 S CREEK DRIVE
OSPREY, FL | Closed
Listed: Jul, 25, 2025
Price: $774,900
Living Area: 2,320 Sq. Ft.
OSPREY, FL | Closed
Listed: Jul, 25, 2025
Price: $774,900
Living Area: 2,320 Sq. Ft.
228 SAINT JAMES PARK
OSPREY, FL | Closed
Listed: Oct, 01, 2025
Price: $1,495,000
Living Area: 2,425 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 01, 2025
Price: $1,495,000
Living Area: 2,425 Sq. Ft.
264 WOODS POINT ROAD
OSPREY, FL | Closed
Listed: Sep, 27, 2024
Price: $485,000
Living Area: 2,837 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 27, 2024
Price: $485,000
Living Area: 2,837 Sq. Ft.
51 MAC EWEN DRIVE 1
OSPREY, FL | Active
Listed: Nov, 24, 2023
Price: $2,500
Living Area: 623 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 24, 2023
Price: $2,500
Living Area: 623 Sq. Ft.
594 PINE RANCH EAST ROAD
OSPREY, FL | Closed
Listed: Jul, 15, 2025
Price: $649,995
Living Area: 2,298 Sq. Ft.
OSPREY, FL | Closed
Listed: Jul, 15, 2025
Price: $649,995
Living Area: 2,298 Sq. Ft.
563 PINE RANCH EAST ROAD
OSPREY, FL | Closed
Listed: Sep, 19, 2025
Price: $675,000
Living Area: 2,346 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 19, 2025
Price: $675,000
Living Area: 2,346 Sq. Ft.
402 WALLS WAY
OSPREY, FL | Closed
Listed: Mar, 20, 2025
Price: $1,450,000
Living Area: 3,464 Sq. Ft.
OSPREY, FL | Closed
Listed: Mar, 20, 2025
Price: $1,450,000
Living Area: 3,464 Sq. Ft.
158 EDGEWOOD DRIVE
OSPREY, FL | Closed
Listed: Sep, 26, 2025
Price: $236,000
Living Area: 1,480 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 26, 2025
Price: $236,000
Living Area: 1,480 Sq. Ft.
708 ANNA HOPE LANE
OSPREY, FL | Closed
Listed: Sep, 24, 2025
Price: $549,000
Living Area: 2,133 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 24, 2025
Price: $549,000
Living Area: 2,133 Sq. Ft.
4267 EXPEDITION WAY
OSPREY, FL | Closed
Listed: Jun, 23, 2025
Price: $310,000
Living Area: 1,135 Sq. Ft.
OSPREY, FL | Closed
Listed: Jun, 23, 2025
Price: $310,000
Living Area: 1,135 Sq. Ft.
866 PLACID LAKE DRIVE
OSPREY, FL | Closed
Listed: Oct, 11, 2025
Price: $674,900
Living Area: 2,171 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 11, 2025
Price: $674,900
Living Area: 2,171 Sq. Ft.
813 OAK POND DRIVE
OSPREY, FL | Closed
Listed: Jun, 24, 2025
Price: $550,000
Living Area: 1,981 Sq. Ft.
OSPREY, FL | Closed
Listed: Jun, 24, 2025
Price: $550,000
Living Area: 1,981 Sq. Ft.
226 WOODLAND DRIVE
OSPREY, FL | Closed
Listed: Nov, 24, 2025
Price: $200,000
Living Area: 865 Sq. Ft.
OSPREY, FL | Closed
Listed: Nov, 24, 2025
Price: $200,000
Living Area: 865 Sq. Ft.
570 BLACKBURN POINT ROAD 13
OSPREY, FL | Active
Listed: Dec, 09, 2025
Price: $109,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 09, 2025
Price: $109,000
Living Area: 0 Sq. Ft.
570 BLACKBURN POINT ROAD 19
OSPREY, FL | Closed
Listed: Sep, 09, 2025
Price: $145,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 09, 2025
Price: $145,000
Living Area: 0 Sq. Ft.
570 BLACKBURN POINT ROAD Lido 25
OSPREY, FL | Closed
Listed: Nov, 14, 2025
Price: $98,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Closed
Listed: Nov, 14, 2025
Price: $98,000
Living Area: 0 Sq. Ft.
1235 YACHT HARBOR DRIVE
OSPREY, FL | Pending
Listed: Dec, 02, 2025
Price: $1,175,000
Living Area: 2,698 Sq. Ft.
OSPREY, FL | Pending
Listed: Dec, 02, 2025
Price: $1,175,000
Living Area: 2,698 Sq. Ft.
523 HABITAT BOULEVARD
OSPREY, FL | Closed
Listed: Jul, 14, 2025
Price: $785,500
Living Area: 2,314 Sq. Ft.
OSPREY, FL | Closed
Listed: Jul, 14, 2025
Price: $785,500
Living Area: 2,314 Sq. Ft.
447 OAK POINT ROAD
OSPREY, FL | Closed
Listed: Aug, 22, 2025
Price: $545,000
Living Area: 2,688 Sq. Ft.
OSPREY, FL | Closed
Listed: Aug, 22, 2025
Price: $545,000
Living Area: 2,688 Sq. Ft.
5100 JESSIE HARBOR DRIVE 403
OSPREY, FL | Active
Listed: Dec, 31, 2025
Price: $679,900
Living Area: 2,143 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 31, 2025
Price: $679,900
Living Area: 2,143 Sq. Ft.
7303 JESSIE HARBOR DRIVE 7303
OSPREY, FL | Active
Listed: Jul, 03, 2025
Price: $474,900
Living Area: 1,883 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 03, 2025
Price: $474,900
Living Area: 1,883 Sq. Ft.
1019 SCHERER WAY
OSPREY, FL | Pending
Listed: Jan, 03, 2026
Price: $735,000
Living Area: 2,498 Sq. Ft.
OSPREY, FL | Pending
Listed: Jan, 03, 2026
Price: $735,000
Living Area: 2,498 Sq. Ft.
409 N POINT ROAD 1003
OSPREY, FL | Closed
Listed: Dec, 09, 2025
Price: $1,800,000
Living Area: 2,778 Sq. Ft.
OSPREY, FL | Closed
Listed: Dec, 09, 2025
Price: $1,800,000
Living Area: 2,778 Sq. Ft.
14041 BELLAGIO WAY 414
OSPREY, FL | Pending
Listed: Jul, 08, 2025
Price: $700,000
Living Area: 1,799 Sq. Ft.
OSPREY, FL | Pending
Listed: Jul, 08, 2025
Price: $700,000
Living Area: 1,799 Sq. Ft.
238 WOODLAND DRIVE 238
OSPREY, FL | Pending
Listed: Oct, 08, 2025
Price: $184,900
Living Area: 865 Sq. Ft.
OSPREY, FL | Pending
Listed: Oct, 08, 2025
Price: $184,900
Living Area: 865 Sq. Ft.
260 HIDDEN BAY DRIVE 504
OSPREY, FL | Active
Listed: Sep, 06, 2025
Price: $5,000
Living Area: 1,950 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 06, 2025
Price: $5,000
Living Area: 1,950 Sq. Ft.
851 PLACID LAKE DRIVE
OSPREY, FL | Active
Listed: Jan, 19, 2026
Price: $720,000
Living Area: 3,395 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 19, 2026
Price: $720,000
Living Area: 3,395 Sq. Ft.
584 MEADOW SWEET CIRCLE
OSPREY, FL | Pending
Listed: Jan, 26, 2026
Price: $595,000
Living Area: 2,151 Sq. Ft.
OSPREY, FL | Pending
Listed: Jan, 26, 2026
Price: $595,000
Living Area: 2,151 Sq. Ft.
4284 EXPEDITION WAY NA
OSPREY, FL | Active
Listed: Feb, 13, 2026
Price: $350,000
Living Area: 1,430 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 13, 2026
Price: $350,000
Living Area: 1,430 Sq. Ft.
827 PLACID LAKE DRIVE
OSPREY, FL | Active
Listed: Jul, 29, 2025
Price: $529,900
Living Area: 1,875 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 29, 2025
Price: $529,900
Living Area: 1,875 Sq. Ft.
4256 EXPEDITION WAY 107
OSPREY, FL | Pending
Listed: Sep, 13, 2025
Price: $2,250
Living Area: 1,430 Sq. Ft.
OSPREY, FL | Pending
Listed: Sep, 13, 2025
Price: $2,250
Living Area: 1,430 Sq. Ft.
133 OSPREY POINT DRIVE
OSPREY, FL | Pending
Listed: Sep, 07, 2025
Price: $1,350,000
Living Area: 3,679 Sq. Ft.
OSPREY, FL | Pending
Listed: Sep, 07, 2025
Price: $1,350,000
Living Area: 3,679 Sq. Ft.
340 OSPREY POINT DR
OSPREY, FL | Closed
Listed: Apr, 04, 2025
Price: $2,395,000
Living Area: 6,001 Sq. Ft.
OSPREY, FL | Closed
Listed: Apr, 04, 2025
Price: $2,395,000
Living Area: 6,001 Sq. Ft.
811 SHADOW BAY WAY
OSPREY, FL | Pending
Listed: Feb, 02, 2026
Price: $525,000
Living Area: 1,760 Sq. Ft.
OSPREY, FL | Pending
Listed: Feb, 02, 2026
Price: $525,000
Living Area: 1,760 Sq. Ft.
3976 DESTINATION DRIVE 102
OSPREY, FL | Active
Listed: Jan, 16, 2026
Price: $479,000
Living Area: 1,050 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 16, 2026
Price: $479,000
Living Area: 1,050 Sq. Ft.
401 WALLS WAY
OSPREY, FL | Active
Listed: Jan, 30, 2026
Price: $1,800,000
Living Area: 4,387 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 30, 2026
Price: $1,800,000
Living Area: 4,387 Sq. Ft.
711 SHADOW BAY WAY
OSPREY, FL | Active
Listed: Dec, 12, 2025
Price: $600,000
Living Area: 2,133 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 12, 2025
Price: $600,000
Living Area: 2,133 Sq. Ft.
3603 N POINT ROAD 602
OSPREY, FL | Active
Listed: Feb, 18, 2025
Price: $5,900
Living Area: 2,545 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 18, 2025
Price: $5,900
Living Area: 2,545 Sq. Ft.
409 N POINT ROAD 502
OSPREY, FL | Active
Listed: Sep, 12, 2024
Price: $599,000
Living Area: 2,055 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 12, 2024
Price: $599,000
Living Area: 2,055 Sq. Ft.
3621 N POINT ROAD 603
OSPREY, FL | Active
Listed: Jan, 19, 2026
Price: $1,295,000
Living Area: 2,680 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 19, 2026
Price: $1,295,000
Living Area: 2,680 Sq. Ft.
659 RIVENDELL BOULEVARD
OSPREY, FL | Active
Listed: Feb, 14, 2026
Price: $679,000
Living Area: 2,292 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 14, 2026
Price: $679,000
Living Area: 2,292 Sq. Ft.
305 BAY VISTA AVENUE
OSPREY, FL | Active
Listed: Sep, 16, 2025
Price: $2,500
Living Area: 1,069 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 16, 2025
Price: $2,500
Living Area: 1,069 Sq. Ft.
409 N POINT ROAD 802
OSPREY, FL | Active
Listed: Sep, 09, 2025
Price: $6,000
Living Area: 2,055 Sq. Ft.
OSPREY, FL | Active
Listed: Sep, 09, 2025
Price: $6,000
Living Area: 2,055 Sq. Ft.
264 SARATOGA COURT
OSPREY, FL | Closed
Listed: Sep, 11, 2025
Price: $2,300,000
Living Area: 3,857 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 11, 2025
Price: $2,300,000
Living Area: 3,857 Sq. Ft.
393 N POINT ROAD 1002
OSPREY, FL | Active
Listed: Oct, 13, 2025
Price: $2,350,000
Living Area: 3,738 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 13, 2025
Price: $2,350,000
Living Area: 3,738 Sq. Ft.
110 PINE AVENUE
OSPREY, FL | Active
Listed: Apr, 05, 2025
Price: $699,000
Living Area: 2,058 Sq. Ft.
OSPREY, FL | Active
Listed: Apr, 05, 2025
Price: $699,000
Living Area: 2,058 Sq. Ft.
622 BAYSHORE DRIVE
OSPREY, FL | Closed
Listed: Jul, 03, 2025
Price: $5,700,000
Living Area: 4,893 Sq. Ft.
OSPREY, FL | Closed
Listed: Jul, 03, 2025
Price: $5,700,000
Living Area: 4,893 Sq. Ft.
385 N POINT ROAD 903
OSPREY, FL | Closed
Listed: Oct, 14, 2025
Price: $1,100,000
Living Area: 2,778 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 14, 2025
Price: $1,100,000
Living Area: 2,778 Sq. Ft.
137 WOODLAND PLACE
OSPREY, FL | Closed
Listed: Nov, 17, 2025
Price: $1,500
Living Area: 1,325 Sq. Ft.
OSPREY, FL | Closed
Listed: Nov, 17, 2025
Price: $1,500
Living Area: 1,325 Sq. Ft.
362 PINE RUN DRIVE
OSPREY, FL | Active
Listed: Nov, 10, 2025
Price: $235,000
Living Area: 1,224 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 10, 2025
Price: $235,000
Living Area: 1,224 Sq. Ft.
678 CRANE PRAIRIE WAY
OSPREY, FL | Closed
Listed: Nov, 03, 2025
Price: $867,000
Living Area: 2,483 Sq. Ft.
OSPREY, FL | Closed
Listed: Nov, 03, 2025
Price: $867,000
Living Area: 2,483 Sq. Ft.
570 BLACKBURN POINT ROAD 2
OSPREY, FL | Closed
Listed: Oct, 21, 2025
Price: $79,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 21, 2025
Price: $79,000
Living Area: 0 Sq. Ft.
293 HIDDEN BAY DRIVE 203
OSPREY, FL | Active
Listed: Aug, 12, 2018
Price: $5,000
Living Area: 1,568 Sq. Ft.
OSPREY, FL | Active
Listed: Aug, 12, 2018
Price: $5,000
Living Area: 1,568 Sq. Ft.
180 LOOKOUT POINT DRIVE
OSPREY, FL | Active
Listed: Nov, 14, 2025
Price: $2,299,900
Living Area: 3,236 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 14, 2025
Price: $2,299,900
Living Area: 3,236 Sq. Ft.
3983 DESTINATION DRIVE 102
OSPREY, FL | Active
Listed: Dec, 10, 2025
Price: $1,050,000
Living Area: 2,030 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 10, 2025
Price: $1,050,000
Living Area: 2,030 Sq. Ft.
432 SORRENTO DRIVE
OSPREY, FL | Closed
Listed: Oct, 24, 2025
Price: $2,550,000
Living Area: 3,640 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 24, 2025
Price: $2,550,000
Living Area: 3,640 Sq. Ft.
852 MACEWEN DRIVE
OSPREY, FL | Active
Listed: Jul, 20, 2025
Price: $7,000
Living Area: 4,519 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 20, 2025
Price: $7,000
Living Area: 4,519 Sq. Ft.
852 MACEWEN DRIVE
OSPREY, FL | Active
Listed: Jul, 20, 2025
Price: $2,495,000
Living Area: 4,519 Sq. Ft.
OSPREY, FL | Active
Listed: Jul, 20, 2025
Price: $2,495,000
Living Area: 4,519 Sq. Ft.
1128 Beachcomber Court 7
Osprey, FL | Closed
Listed: Nov, 23, 2021
Price: $499,900
Living Area: 2,162 Sq. Ft.
Osprey, FL | Closed
Listed: Nov, 23, 2021
Price: $499,900
Living Area: 2,162 Sq. Ft.
3976 DESTINATION DRIVE A411
OSPREY, FL | Active
Listed: Jun, 03, 2025
Price: $1,000,000
Living Area: 2,314 Sq. Ft.
OSPREY, FL | Active
Listed: Jun, 03, 2025
Price: $1,000,000
Living Area: 2,314 Sq. Ft.
494 MEADOW SWEET CIRCLE
OSPREY, FL | Pending
Listed: Jan, 15, 2026
Price: $595,000
Living Area: 1,791 Sq. Ft.
OSPREY, FL | Pending
Listed: Jan, 15, 2026
Price: $595,000
Living Area: 1,791 Sq. Ft.
538 DOVE POINTE DRIVE
OSPREY, FL | Active
Listed: Nov, 07, 2025
Price: $2,100,000
Living Area: 4,346 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 07, 2025
Price: $2,100,000
Living Area: 4,346 Sq. Ft.
3957 WAYPOINT AVENUE
OSPREY, FL | Closed
Listed: Sep, 29, 2025
Price: $925,000
Living Area: 2,328 Sq. Ft.
OSPREY, FL | Closed
Listed: Sep, 29, 2025
Price: $925,000
Living Area: 2,328 Sq. Ft.
315 BAYSHORE DRIVE
OSPREY, FL | Pending
Listed: Nov, 10, 2025
Price: $549,900
Living Area: 2,384 Sq. Ft.
OSPREY, FL | Pending
Listed: Nov, 10, 2025
Price: $549,900
Living Area: 2,384 Sq. Ft.
409 N POINT ROAD 501
OSPREY, FL | Closed
Listed: Jun, 03, 2024
Price: $795,000
Living Area: 2,594 Sq. Ft.
OSPREY, FL | Closed
Listed: Jun, 03, 2024
Price: $795,000
Living Area: 2,594 Sq. Ft.
3603 N POINT ROAD 702
OSPREY, FL | Active
Listed: Feb, 28, 2025
Price: $1,395,000
Living Area: 2,545 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 28, 2025
Price: $1,395,000
Living Area: 2,545 Sq. Ft.
409 NORTH POINT ROAD 902
OSPREY, FL | Active
Listed: Jan, 08, 2026
Price: $1,275,000
Living Area: 2,055 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 08, 2026
Price: $1,275,000
Living Area: 2,055 Sq. Ft.
121 N CASEY KEY ROAD
OSPREY, FL | Active
Listed: Oct, 04, 2025
Price: $6,800,000
Living Area: 4,096 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 04, 2025
Price: $6,800,000
Living Area: 4,096 Sq. Ft.
144 N CASEY KEY ROAD
OSPREY, FL | Active
Listed: Aug, 08, 2025
Price: $5,495,000
Living Area: 5,397 Sq. Ft.
OSPREY, FL | Active
Listed: Aug, 08, 2025
Price: $5,495,000
Living Area: 5,397 Sq. Ft.
49 OSPREY POINT DRIVE
OSPREY, FL | Active
Listed: Nov, 11, 2025
Price: $2,500,000
Living Area: 3,953 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 11, 2025
Price: $2,500,000
Living Area: 3,953 Sq. Ft.
352 GLENWOOD AVE
OSPREY, FL | Active
Listed: May, 20, 2025
Price: $429,500
Living Area: 1,300 Sq. Ft.
OSPREY, FL | Active
Listed: May, 20, 2025
Price: $429,500
Living Area: 1,300 Sq. Ft.
327 PARK TRACE BOULEVARD
OSPREY, FL | Pending
Listed: Oct, 27, 2025
Price: $849,000
Living Area: 2,935 Sq. Ft.
OSPREY, FL | Pending
Listed: Oct, 27, 2025
Price: $849,000
Living Area: 2,935 Sq. Ft.
403 LONGBOW TRAIL
OSPREY, FL | Active
Listed: Nov, 17, 2025
Price: $1,197,000
Living Area: 2,770 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 17, 2025
Price: $1,197,000
Living Area: 2,770 Sq. Ft.
385 N POINT ROAD 404
OSPREY, FL | Closed
Listed: Jul, 21, 2025
Price: $889,000
Living Area: 2,778 Sq. Ft.
OSPREY, FL | Closed
Listed: Jul, 21, 2025
Price: $889,000
Living Area: 2,778 Sq. Ft.
889 MACEWEN DRIVE
OSPREY, FL | Closed
Listed: Oct, 29, 2025
Price: $2,300,000
Living Area: 3,235 Sq. Ft.
OSPREY, FL | Closed
Listed: Oct, 29, 2025
Price: $2,300,000
Living Area: 3,235 Sq. Ft.
124 REVOLUTION WAY
OSPREY, FL | Active
Listed: Jan, 17, 2026
Price: $399,000
Living Area: 1,574 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 17, 2026
Price: $399,000
Living Area: 1,574 Sq. Ft.
866 OAK BRIAR LANE
OSPREY, FL | Closed
Listed: Jun, 09, 2025
Price: $699,900
Living Area: 2,434 Sq. Ft.
OSPREY, FL | Closed
Listed: Jun, 09, 2025
Price: $699,900
Living Area: 2,434 Sq. Ft.
570 BLACKBURN POINT ROAD 33
OSPREY, FL | Pending
Listed: Dec, 08, 2025
Price: $103,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Pending
Listed: Dec, 08, 2025
Price: $103,000
Living Area: 0 Sq. Ft.
370 SUGAR MILL DRIVE
OSPREY, FL | Closed
Listed: Jan, 14, 2026
Price: $2,450,000
Living Area: 4,783 Sq. Ft.
OSPREY, FL | Closed
Listed: Jan, 14, 2026
Price: $2,450,000
Living Area: 4,783 Sq. Ft.
162 WILLOW BEND WAY
OSPREY, FL | Pending
Listed: Jan, 30, 2026
Price: $689,000
Living Area: 2,661 Sq. Ft.
OSPREY, FL | Pending
Listed: Jan, 30, 2026
Price: $689,000
Living Area: 2,661 Sq. Ft.
3621 N POINT ROAD 301
OSPREY, FL | Active
Listed: Feb, 04, 2026
Price: $625,000
Living Area: 2,680 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 04, 2026
Price: $625,000
Living Area: 2,680 Sq. Ft.
280 HIDDEN BAY DRIVE 202
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $3,895
Living Area: 1,937 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $3,895
Living Area: 1,937 Sq. Ft.
280 HIDDEN BAY DRIVE 202
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $3,695
Living Area: 1,937 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 29, 2026
Price: $3,695
Living Area: 1,937 Sq. Ft.
566 OAK BAY DRIVE
OSPREY, FL | Pending
Listed: Jan, 23, 2026
Price: $530,000
Living Area: 2,559 Sq. Ft.
OSPREY, FL | Pending
Listed: Jan, 23, 2026
Price: $530,000
Living Area: 2,559 Sq. Ft.
177 NAVIGATION CIRCLE
OSPREY, FL | Pending
Listed: Feb, 03, 2026
Price: $369,000
Living Area: 1,581 Sq. Ft.
OSPREY, FL | Pending
Listed: Feb, 03, 2026
Price: $369,000
Living Area: 1,581 Sq. Ft.
903 TRANQUILITY CIRCLE
OSPREY, FL | Active
Listed: Oct, 24, 2025
Price: $879,000
Living Area: 2,622 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 24, 2025
Price: $879,000
Living Area: 2,622 Sq. Ft.
296 PINE RANCH TRAIL
OSPREY, FL | Active
Listed: May, 21, 2025
Price: $1,295,000
Living Area: 3,481 Sq. Ft.
OSPREY, FL | Active
Listed: May, 21, 2025
Price: $1,295,000
Living Area: 3,481 Sq. Ft.
409 N POINT ROAD 603
OSPREY, FL | Active
Listed: Mar, 08, 2024
Price: $595,000
Living Area: 2,203 Sq. Ft.
OSPREY, FL | Active
Listed: Mar, 08, 2024
Price: $595,000
Living Area: 2,203 Sq. Ft.
312 YACHT HARBOR DRIVE
OSPREY, FL | Active
Listed: Oct, 03, 2025
Price: $2,299,000
Living Area: 2,572 Sq. Ft.
OSPREY, FL | Active
Listed: Oct, 03, 2025
Price: $2,299,000
Living Area: 2,572 Sq. Ft.
919 TRANQUILITY CIRCLE CIRCLE
OSPREY, FL | Active
Listed: Jan, 19, 2026
Price: $825,000
Living Area: 2,854 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 19, 2026
Price: $825,000
Living Area: 2,854 Sq. Ft.
6100 JESSIE HARBOR DRIVE 603
OSPREY, FL | Active
Listed: Jan, 07, 2026
Price: $884,000
Living Area: 2,630 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 07, 2026
Price: $884,000
Living Area: 2,630 Sq. Ft.
242 HIDDEN BAY DRIVE 302
OSPREY, FL | Active
Listed: Jan, 13, 2026
Price: $699,000
Living Area: 2,032 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 13, 2026
Price: $699,000
Living Area: 2,032 Sq. Ft.
2099 S TAMIAMI TRAIL N
OSPREY, FL | Active
Listed: Feb, 09, 2026
Price: $1,400,000
Living Area: 1 Sq. Ft.
OSPREY, FL | Active
Listed: Feb, 09, 2026
Price: $1,400,000
Living Area: 1 Sq. Ft.
2099 S TAMIAMI TRAIL
OSPREY, FL | Active
Listed: Jan, 12, 2026
Price: $1,400,000
Living Area: 0 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 12, 2026
Price: $1,400,000
Living Area: 0 Sq. Ft.
524 SARABAY ROAD
OSPREY, FL | Active
Listed: Dec, 26, 2025
Price: $424,000
Living Area: 1,760 Sq. Ft.
OSPREY, FL | Active
Listed: Dec, 26, 2025
Price: $424,000
Living Area: 1,760 Sq. Ft.
650 CRANE PRAIRIE WAY
OSPREY, FL | Active
Listed: Jan, 23, 2026
Price: $799,990
Living Area: 3,183 Sq. Ft.
OSPREY, FL | Active
Listed: Jan, 23, 2026
Price: $799,990
Living Area: 3,183 Sq. Ft.
583 PINE RANCH EAST ROAD
OSPREY, FL | Active
Listed: Nov, 03, 2025
Price: $579,000
Living Area: 2,203 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 03, 2025
Price: $579,000
Living Area: 2,203 Sq. Ft.
14041 BELLAGIO WAY 218
OSPREY, FL | Active
Listed: Nov, 19, 2025
Price: $1,150,000
Living Area: 2,374 Sq. Ft.
OSPREY, FL | Active
Listed: Nov, 19, 2025
Price: $1,150,000
Living Area: 2,374 Sq. Ft.
