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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

Condos & Apartments 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
Browse by Listing Type
attach_moneyFor Sale editFor Rent
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homeHouses apartmentCondos & Apartments holiday_villageTownhouses & Duplexes crop_landscapeLots & Land parkFarms & Ranches

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
View All Zip Codes
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  • List
409 POINT ROAD #803 For Sale
$985,000
409 POINT ROAD #803Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2423 sqft
  • Built 2004
  • MFRA4703407
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
14041 BELLAGIO WAY #214 For Rent
$6,000
14041 BELLAGIO WAY #214Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2089 sqft
  • Built 2006
  • MFRA4700702
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
108 WOODLAND PLACE #108 For Sale
$285,000
108 WOODLAND PLACE #108Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1474 sqft
  • Built 1979
  • A4699279
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
6100 JESSIE HARBOR DRIVE #202 For Rent
$5,500
6100 JESSIE HARBOR DRIVE #202Osprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 4209 sqft
  • Built 2005
  • A4698732
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
51 MAC EWEN DRIVE #8 For Rent
$1,600
51 MAC EWEN DRIVE #8Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 675 sqft
  • Built 1990
  • A4695928
184 EXPLORER DRIVE For Rent
$2,150
184 EXPLORER DRIVEOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 1430 sqft
  • Built 2016
  • A4695420
4296 EXPEDITION WAY #104 For Sale
$299,990
4296 EXPEDITION WAY #104Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1219 sqft
  • Built 2017
  • A4694926
260 HIDDEN BAY DRIVE #401 For Rent
$4,850
260 HIDDEN BAY DRIVE #401Osprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 2433 sqft
  • Built 2019
  • A4693277
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
4219 FRONTIER WAY #105 For Rent
$2,200
4219 FRONTIER WAY #105Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1560 sqft
  • Built 2017
  • N6144275
51 MACEWEN DRIVE #12 For Sale
$275,000
51 MACEWEN DRIVE #12Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 623 sqft
  • Built 1990
  • A4690540
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
14021 BELLAGIO WAY #404 For Sale
$1,100,000
14021 BELLAGIO WAY #404Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2526 sqft
  • Built 2006
  • N6144070
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
4226 FRONTIER LANE #103 For Sale
$299,000
4226 FRONTIER LANE #103Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1219 sqft
  • Built 2018
  • A4687965
51 MACEWEN DRIVE #12 For Rent
$2,250
51 MACEWEN DRIVE #12Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 623 sqft
  • Built 1990
  • A4686127
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
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
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
1811 HIGHLAND ROAD For Sale
$417,000
1811 HIGHLAND ROADOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 1725 sqft
  • Built 1997
  • TB8443161
1801 HIGHLAND ROAD For Sale
$289,900
1801 HIGHLAND ROADOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 2125 sqft
  • Built 1999
  • N6140508
5100 JESSIE HARBOR DRIVE #504 For Rent
$7,500
5100 JESSIE HARBOR DRIVE #504Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2304 sqft
  • Built 2004
  • A4651384
101 WOODLAND PLACE For Rent
$6,950
101 WOODLAND PLACEOsprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 2039 sqft
  • Built 1979
  • A4644465
3603 POINT ROAD #702 For Sale
$1,395,000
3603 POINT ROAD #702Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2904 sqft
  • Built 2007
  • A4642397
3603 POINT ROAD #602 For Rent
$5,900
3603 POINT ROAD #602Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2904 sqft
  • Built 2007
  • A4640065
385 POINT ROAD #402 For Sale
$615,000
385 POINT ROAD #402Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2250 sqft
  • Built 2000
  • A4635708
409 POINT ROAD #502 For Sale
$599,000
409 POINT ROAD #502Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2250 sqft
  • Built 2004
  • A4621353
14041 BELLAGIO WAY #316 For Rent
$8,000
14041 BELLAGIO WAY #316Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2386 sqft
  • Built 2006
  • A4622973
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
51 MAC EWEN DRIVE #1 For Rent
$2,500
51 MAC EWEN DRIVE #1Osprey, FL 34229
  • 1 bd
  • 1 ba
  • 623 sqft
  • Built 1990
  • A4589608
152 NAVIGATION CIRCLE #107 For Rent
$4,500
152 NAVIGATION CIRCLE #107Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 1889 sqft
  • Built 2016
  • A4517611
293 HIDDEN BAY DRIVE #203 For Rent
$5,000
293 HIDDEN BAY DRIVE #203Osprey, FL 34229
  • 2 bd
  • 2 ba
  • Built 2000
  • A4410764
50

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