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(813) 710-6443 Stephanie@KeysToCastles.com
  • 26929 Coral Vine Lane
    Wesley Chapel, FL 33544
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website. Listing Information presented by local MLS brokerage: Stephanie LeFew | Keys To Castles Group

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Little Sarasota Bay Waterfront

For Sale in Osprey, FL

Welcome to Osprey, a waterfront community on Little Sarasota Bay in Sarasota County, Florida, set between Sarasota and Venice and minutes from Casey Key.

Osprey is an unincorporated community in Sarasota County, Florida, situated on Little Sarasota Bay along the Gulf Coast between Sarasota and Venice. Its history stretches back to the late nineteenth century, when the Osprey post office was established in 1884, and the area has long been defined by its waterfront setting, its early pioneer families, and, more recently, a collection of established residential neighborhoods and country-club communities. With a population of roughly 6,700, Osprey offers a low-density, bay-oriented way of life. Waterfront and boating communities such as Sorrento Shores and Osprey Harbor Village sit along the bay, while the master-planned neighborhoods of The Oaks wrap around championship golf courses. Casey Key, a narrow barrier island with Gulf-front homes, lies just across the bay to the west, placing the open Gulf beaches within a few minutes' drive of most Osprey addresses. Osprey is also notable for its natural and historic assets, which set it apart from the purely residential stretches of the Sarasota County coast. Historic Spanish Point, a peninsula operated by Marie Selby Botanical Gardens, preserves archaeological and pioneer history along the bay, while Oscar Scherer State Park protects scrub habitat and the threatened Florida scrub-jay, with hiking trails and Lake Osprey drawing hundreds of thousands of visitors each year. Day-to-day life in Osprey is quiet and car-dependent, typical of the Gulf Coast's established residential communities. Residents boat and paddle on the bay, play golf, and take short drives to the arts, dining, and healthcare of Sarasota to the north or the beaches and shops of Venice and Nokomis to the south. The community's own commercial scene is modest—marinas, restaurants, and neighborhood services—so much of daily shopping and entertainment happens in the neighboring cities. These anchors, combined with a settled, low-density housing stock and direct access to the Gulf shoreline, make Osprey a distinctive coastal address for people seeking quiet, established living along the water.

Population 6,690
County Sarasota County
Active Listings 160
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Frequently Asked Questions

Where is Osprey, Florida?

Osprey is an unincorporated community in Sarasota County, Florida, on Little Sarasota Bay along the Gulf Coast. It sits between the cities of Sarasota and Venice, with Casey Key and the Gulf beaches immediately to the west.

What is Historic Spanish Point?

Historic Spanish Point is a waterside archaeological and historic site on a peninsula in Little Sarasota Bay at Osprey. Operated by Marie Selby Botanical Gardens, it preserves pioneer and prehistoric history alongside botanical gardens and a short trail network.

What school district serves Osprey?

Osprey is served by Sarasota County Schools, the public school district covering all of Sarasota County, with neighborhood schools in the surrounding area plus private and charter options in nearby Sarasota and Venice.

Is Osprey close to the beach?

Yes. Osprey sits on the mainland side of Little Sarasota Bay, with Casey Key, Nokomis, and the Gulf of Mexico beaches just across the water to the west, typically a short drive across Blackburn Point Road.

MARKET SNAPSHOT

The Market at a Glance

How homes have been selling here over the last 90 days.

home_work New This Week 3
Went Under Contract 0
trending_down Price Reductions 0
payments Median Sale Price $645,000 -4.8%
square_foot Price per Sq Ft $254
schedule Avg Days on Market 92
sell Homes Sold 57
percent Sale-to-List Ratio 95.0%
inventory_2 Months of Inventory 6.4

Price & Sales History

Market data reflects closed sales over the last 90 days and is provided for informational purposes.

BROWSE BY ZIP

Zip Codes

Browse listings by postal code in this area.

000003 homes for saleMedian sale$370KPer sq ft$199 sales in the last 90 days
0060225 homes for saleMedian sale$417.5KPer sq ft$3124 sales in the last 90 days
0060318 homes for saleMedian sale$235KPer sq ft$7273 sales in the last 90 days
0061228 homes for saleMedian sale$160KPer sq ft$1685 sales in the last 90 days
0062358 homes for saleMedian sale$240KPer sq ft$19214 sales in the last 90 days
006418 homes for saleMedian sale$262KPer sq ft$1762 sales in the last 90 days
00646139 homes for saleMedian sale$1.5MPer sq ft$59625 sales in the last 90 days
0066239 homes for saleMedian sale$463KPer sq ft$2939 sales in the last 90 days
0067422 homes for saleMedian sale$190KPer sq ft$1293 sales in the last 90 days
0067798 homes for saleMedian sale$508KPer sq ft$37517 sales in the last 90 days
0068030 homes for saleMedian sale$143KPer sq ft$1345 sales in the last 90 days
0069232 homes for saleMedian sale$345KPer sq ft$20613 sales in the last 90 days
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432 S SHORE DRIVE For Sale
$529,900
432 S SHORE DRIVEOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 2642 sqft
  • Built 1988
  • MFRA4703634
409 POINT ROAD #803 For Sale
$985,000
409 POINT ROAD #803Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2423 sqft
  • Built 2004
  • MFRA4703407
264 WOODS POINT ROAD For Sale
$700,000
264 WOODS POINT ROADOsprey, FL 34229
  • 3 bd
  • 3 ba
  • 3694 sqft
  • Built 1992
  • MFRA4703025
108 VILLA DRIVE #108 For Sale
$319,000
108 VILLA DRIVE #108Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1593 sqft
  • Built 1976
  • MFRTB8539148
480 BLACKBURN POINT ROAD #6 For Sale
$269,000
480 BLACKBURN POINT ROAD #6Osprey, FL 34229
  • Built 2006
  • MFRA4703031
524 SARABAY ROAD For Sale
$419,000
524 SARABAY ROADOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 1760 sqft
  • Built 1956
  • MFRA4676179
299 TURQUOISE LANE For Sale
$739,000
299 TURQUOISE LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2934 sqft
  • Built 2001
  • MFRA4701662
260 HIDDEN BAY DRIVE #402 For Sale
$775,000
260 HIDDEN BAY DRIVE #402Osprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 2109 sqft
  • Built 2019
  • MFRA4701000
1036 OAK MEADOW LANE For Sale
$630,000
1036 OAK MEADOW LANEOsprey, FL 34229
  • 4 bd
  • 2 ba
  • 2947 sqft
  • Built 2001
  • MFRA4701532
547 MEADOW SWEET CIRCLE For Sale
$550,000
547 MEADOW SWEET CIRCLEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2329 sqft
  • Built 2002
  • MFRA4701316
570 BLACKBURN POINT ROAD #36 For Sale
$99,500
570 BLACKBURN POINT ROAD #36Osprey, FL 34229
  • MFRA4700865
916 MACEWEN DRIVE For Sale
$1,900,000
916 MACEWEN DRIVEOsprey, FL 34229
  • 5 bd
  • 7.5 ba
  • 7976 sqft
  • Built 1991
  • MFRA4698153
599 PINE RANCH EAST ROAD For Sale
$825,000
599 PINE RANCH EAST ROADOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2815 sqft
  • Built 1995
  • MFRA4660895
701 PINE RUN DRIVE #701 For Sale
$172,000
701 PINE RUN DRIVE #701Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 658 sqft
  • Built 1973
  • MFRA4700416
780 SARABAY ROAD #16 For Sale
$425,000
780 SARABAY ROAD #16Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1974 sqft
  • Built 1981
  • TB8528486
108 WOODLAND PLACE #108 For Sale
$285,000
108 WOODLAND PLACE #108Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1474 sqft
  • Built 1979
  • A4699279
329 BAY VISTA AVENUE For Sale
$399,000
329 BAY VISTA AVENUEOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 1784 sqft
  • Built 1963
  • A4699464
Address Not Shown For Sale
$799,000
Address Not ShownOsprey, FL 34229
  • 4 bd
  • 3 ba
  • 3527 sqft
  • Built 2001
  • A4699089
2309 JESSIE HARBOR DRIVE #2402 For Sale
$497,000
2309 JESSIE HARBOR DRIVE #2402Osprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 2446 sqft
  • Built 2006
  • A4698434
1495 LANDVIEW LANE For Sale
$760,000
1495 LANDVIEW LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 3355 sqft
  • Built 1988
  • A4697993
206 FOUR KNOT LANE For Sale
$1,775,000
206 FOUR KNOT LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 3837 sqft
  • Built 1991
  • A4695429
570 BLACKBURN POINT ROAD #23 For Sale
$89,000
570 BLACKBURN POINT ROAD #23Osprey, FL 34229
  • Built 2006
  • A4697977
7204 JESSIE HARBOR DRIVE #7204 For Sale
$395,000
7204 JESSIE HARBOR DRIVE #7204Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1410 sqft
  • Built 1985
  • A4697473
110 WOODLAND PLACE #110 For Sale
$215,000
110 WOODLAND PLACE #110Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1400 sqft
  • Built 1979
  • A4696738
401 POINT ROAD #504 For Sale
$795,000
401 POINT ROAD #504Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 3106 sqft
  • Built 2003
  • A4696459
116 WOODLAND PLACE #116 For Sale
$249,900
116 WOODLAND PLACE #116Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1483 sqft
  • Built 1979
  • A4696616
75 OSPREY POINT DRIVE For Sale
$1,595,000
75 OSPREY POINT DRIVEOsprey, FL 34229
  • 4 bd
  • 4 ba
  • 5028 sqft
  • Built 1983
  • A4695145
360 N POINT ROAD For Sale
$1,495,000
360 N POINT ROADOsprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 3523 sqft
  • Built 2022
  • A4695959
4296 EXPEDITION WAY #104 For Sale
$299,990
4296 EXPEDITION WAY #104Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1219 sqft
  • Built 2017
  • A4694926
101 OSPREY POINT DRIVE For Sale
$4,790,000
101 OSPREY POINT DRIVEOsprey, FL 34229
  • 4 bd
  • 5.5 ba
  • 6841 sqft
  • Built 1985
  • A4694716
103 BISHOPS COURT ROAD For Sale
$749,000
103 BISHOPS COURT ROADOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2804 sqft
  • Built 2000
  • A4694468
280 HIDDEN BAY DRIVE #302 For Sale
$749,000
280 HIDDEN BAY DRIVE #302Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2241 sqft
  • Built 2024
  • A4690813
156 BISHOPS COURT ROAD For Sale
$1,289,000
156 BISHOPS COURT ROADOsprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 4484 sqft
  • Built 1990
  • A4691664
51 MACEWEN DRIVE #12 For Sale
$275,000
51 MACEWEN DRIVE #12Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 623 sqft
  • Built 1990
  • A4690540
135 TINA ISLAND DRIVE For Sale
$3,295,000
135 TINA ISLAND DRIVEOsprey, FL 34229
  • 3 bd
  • 4.5 ba
  • 6254 sqft
  • Built 2011
  • A4692366
184 EXPLORER DRIVE For Sale
$294,900
184 EXPLORER DRIVEOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 1397 sqft
  • Built 2016
  • A4692249
6100 JESSIE HARBOR DRIVE #202 For Sale
$850,000
6100 JESSIE HARBOR DRIVE #202Osprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 4209 sqft
  • Built 2005
  • A4690969
212 WASHINGTON AVENUE For Sale
$420,000
212 WASHINGTON AVENUEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2093 sqft
  • Built 1999
  • O6404307
97 SUGAR MILL DRIVE For Sale
$1,950,000
97 SUGAR MILL DRIVEOsprey, FL 34229
  • 5 bd
  • 5.5 ba
  • 6062 sqft
  • Built 1990
  • A4691789
14021 BELLAGIO WAY #404 For Sale
$1,100,000
14021 BELLAGIO WAY #404Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2526 sqft
  • Built 2006
  • N6144070
1361 NEW FOREST LANE For Sale
$525,000
1361 NEW FOREST LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2798 sqft
  • Built 2002
  • A4691036
5100 JESSIE HARBOR DRIVE #304 For Sale
$699,000
5100 JESSIE HARBOR DRIVE #304Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 2304 sqft
  • Built 2004
  • A4690942
409 NORTH POINT ROAD #401 For Sale
$560,000
409 NORTH POINT ROAD #401Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2837 sqft
  • Built 2004
  • A4690812
51 MACEWEN DRIVE #5 For Sale
$235,000
51 MACEWEN DRIVE #5Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 675 sqft
  • Built 1990
  • A4689838
51 MAC EWEN DRIVE #14 For Sale
$285,000
51 MAC EWEN DRIVE #14Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 595 sqft
  • Built 1990
  • A4690371
14041 BELLAGIO WAY #214 For Sale
$700,000
14041 BELLAGIO WAY #214Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2089 sqft
  • Built 2006
  • A4689731
4271 EXPEDITION WAY #103 For Sale
$260,000
4271 EXPEDITION WAY #103Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1219 sqft
  • Built 2017
  • A4689541
759 FORDINGBRIDGE WAY For Sale
$700,000
759 FORDINGBRIDGE WAYOsprey, FL 34229
  • 4 bd
  • 3.5 ba
  • 3538 sqft
  • Built 2002
  • O6399774
61 BAYHEAD LANE For Sale
$1,185,000
61 BAYHEAD LANEOsprey, FL 34229
  • 3 bd
  • 3 ba
  • 3871 sqft
  • Built 1993
  • A4685559
1527 BUOY LANE For Sale
$1,165,000
1527 BUOY LANEOsprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 3685 sqft
  • Built 1989
  • A4688266
313 LOOKOUT POINT DRIVE For Sale
$5,999,999
313 LOOKOUT POINT DRIVEOsprey, FL 34229
  • 4 bd
  • 4.5 ba
  • 6896 sqft
  • Built 2016
  • A4688995
4226 FRONTIER LANE #103 For Sale
$299,000
4226 FRONTIER LANE #103Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1219 sqft
  • Built 2018
  • A4687965
14401 MASTHEAD DRIVE For Sale
$2,850,000
14401 MASTHEAD DRIVEOsprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 3984 sqft
  • Built 2017
  • A4684834
447 SHORE DRIVE For Sale
$474,000
447 SHORE DRIVEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2486 sqft
  • Built 1964
  • A4684009
107 SORRENTO DRIVE For Sale
$425,000
107 SORRENTO DRIVEOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 2091 sqft
  • Built 1963
  • N6143210
570 BLACKBURN POINT ROAD #26 For Sale
$36,000
570 BLACKBURN POINT ROAD #26Osprey, FL 34229
  • A4680901
14021 BELLAGIO WAY #309 For Sale
$899,995
14021 BELLAGIO WAY #309Osprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 2430 sqft
  • Built 2006
  • A4681589
3621 N POINT ROAD #301 For Sale
$525,000
3621 N POINT ROAD #301Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2968 sqft
  • Built 2006
  • A4681290
409 POINT ROAD #601 For Sale
$1,250,000
409 POINT ROAD #601Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2837 sqft
  • Built 2004
  • A4679994
401 POINT ROAD #1001 For Sale
$1,995,000
401 POINT ROAD #1001Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 3355 sqft
  • Built 2003
  • A4679998
242 HIDDEN BAY DRIVE #602 For Sale
$700,000
242 HIDDEN BAY DRIVE #602Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 2032 sqft
  • Built 1999
  • A4678883
385 N POINT ROAD #304 For Sale
$1,100,000
385 N POINT ROAD #304Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 3106 sqft
  • Built 2000
  • A4678422
570 BLACKBURN POINT ROAD #43 For Sale
$115,000
570 BLACKBURN POINT ROAD #43Osprey, FL 34229
  • A4672823
570 BLACKBURN POINT ROAD #13 For Sale
$109,000
570 BLACKBURN POINT ROAD #13Osprey, FL 34229
  • A4674344
385 N POINT ROAD #503 For Sale
$690,000
385 N POINT ROAD #503Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2423 sqft
  • Built 2000
  • A4672342
403 LONGBOW TRAIL For Sale
$1,095,000
403 LONGBOW TRAILOsprey, FL 34229
  • 4 bd
  • 3 ba
  • 3963 sqft
  • Built 1978
  • A4672081
180 LOOKOUT POINT DRIVE For Sale
$2,199,900
180 LOOKOUT POINT DRIVEOsprey, FL 34229
  • 5 bd
  • 3.5 ba
  • 3877 sqft
  • Built 1986
  • A4672222
49 OSPREY POINT DRIVE For Sale
$2,399,000
49 OSPREY POINT DRIVEOsprey, FL 34229
  • 4 bd
  • 3.5 ba
  • 5227 sqft
  • Built 1989
  • A4671762
401 N POINT ROAD #603 For Sale
$629,000
401 N POINT ROAD #603Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2423 sqft
  • Built 2003
  • A4671958
538 DOVE POINTE DRIVE For Sale
$1,950,000
538 DOVE POINTE DRIVEOsprey, FL 34229
  • 4 bd
  • 5.5 ba
  • 5837 sqft
  • Built 2002
  • A4669491
1811 HIGHLAND ROAD For Sale
$417,000
1811 HIGHLAND ROADOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 1725 sqft
  • Built 1997
  • TB8443161
121 CASEY KEY ROAD For Sale
$6,475,000
121 CASEY KEY ROADOsprey, FL 34229
  • 5 bd
  • 5.5 ba
  • 6906 sqft
  • Built 1969
  • A4667263
1801 HIGHLAND ROAD For Sale
$289,900
1801 HIGHLAND ROADOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 2125 sqft
  • Built 1999
  • N6140508
21 BAYHEAD LANE For Sale
$789,000
21 BAYHEAD LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 3119 sqft
  • Built 2002
  • A4664085
852 MACEWEN DRIVE For Sale
$2,395,000
852 MACEWEN DRIVEOsprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 6019 sqft
  • Built 1992
  • A4659276
570 BLACKBURN POINT ROAD #11 For Sale
$39,500
570 BLACKBURN POINT ROAD #11Osprey, FL 34229
  • Built 2006
  • A4658755
4428 CONCHFISH LANE For Sale
$525,000
4428 CONCHFISH LANEOsprey, FL 34229
  • 4 bd
  • 2 ba
  • 2657 sqft
  • Built 2018
  • A4656074
110 PINE AVENUE For Sale
$649,000
110 PINE AVENUEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2480 sqft
  • Built 1977
  • A4646339
13 BAYHEAD LANE For Sale
$769,000
13 BAYHEAD LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 3093 sqft
  • Built 2001
  • A4645829
236 SAINT JAMES PARK For Sale
$2,700,000
236 SAINT JAMES PARKOsprey, FL 34229
  • 6 bd
  • 6.5 ba
  • 9589 sqft
  • Built 1986
  • A4644125
909 MACEWEN DRIVE For Sale
$1,595,000
909 MACEWEN DRIVEOsprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 5495 sqft
  • Built 1991
  • A4621683
3603 POINT ROAD #702 For Sale
$1,395,000
3603 POINT ROAD #702Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2904 sqft
  • Built 2007
  • A4642397
385 POINT ROAD #402 For Sale
$615,000
385 POINT ROAD #402Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2250 sqft
  • Built 2000
  • A4635708
293 TURQUOISE LANE For Sale
$875,000
293 TURQUOISE LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2998 sqft
  • Built 2001
  • A4633961
409 POINT ROAD #502 For Sale
$599,000
409 POINT ROAD #502Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2250 sqft
  • Built 2004
  • A4621353
401 N POINT ROAD #301 For Sale
$459,900
401 N POINT ROAD #301Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2837 sqft
  • Built 2003
  • A4603773
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