info@rrgrouptampa.com Renaissance Realty Group
Traffic Dashboard
Home Home
  • Search
  • Communities
    • Tampa
    • Clearwater
    • Saint Petersburg
    • Hillsborough County
    • Pasco County
    • Pinellas County
  • Buy
    • Buying Info
  • Sell
    • Selling Info
  • Property Management
  • Resources
    • Claim Your Free Book
  • About
    • Learn More
    • Meet the Team
    • Our Testimonials
  • Articles
  • Contact
Traffic Dashboard
Renaissance Realty Group
info@rrgrouptampa.com
  • 118 South Fremont Avenue
    Tampa, FL 33606
Home
  • Search
  • Communities
  • Buy
  • Sell
  • Property Management
  • Resources
  • About
  • Articles
  • Contact
Legal
  • Privacy
  • Terms
  • DMCA
  • Accessibility
  • Fair Housing
Account
  • Dashboard
  • Logout
  • Login
Renaissance Realty Group - Footer Logo
©2026 Renaissance Realty Group. All rights reserved.
Website built by CloseHack.
Miami Association of REALTORS®

MIAMI ASSOCIATION OF REALTORS® All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Multiple Listing Service. Real estate listings held by brokerage firms other than Marjo Realty Co. may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS.

Beaches MLS

© BEACHES MLS. All rights reserved. Information Deemed Reliable, but Not Guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

My Florida Regional MLS DBA Stellar MLS

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: Renaissance Realty Group

Back

Little Sarasota Bay Waterfront

Listings 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.

Renaissance Realty Group
Renaissance Realty Group Renaissance Realty Group

Get more information about Osprey

Osprey, FL 4 photos
Photo: Trish Hartmann
Listings 171
Population 6,690
County Sarasota County
Osprey Listings Market Stats Subdivisions Zip Codes Neighborhood FAQs Nearby

Houses in Osprey, FL

homeMore houses
649 CRANE PRAIRIE WAY
$639,000
MFRA4702490
For Sale
649 CRANE PRAIRIE WAY Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2803 sq ft
366 S CREEK COURT
$1,049,000
MFRA4708943
For Sale
366 S CREEK COURT Osprey, FL 34229
4 Beds bathtub 3 Baths straighten 3652 sq ft
401 N POINT ROAD #404
$1,025,000
MFRA4708169
For Sale
401 N POINT ROAD #404 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 3106 sq ft
422 BLUE GARDEN LANE
$1,445,000
MFRA4707058
For Sale
422 BLUE GARDEN LANE Osprey, FL 34229
3 Beds bathtub 3.5 Baths straighten 4702 sq ft
275 LOOKOUT POINT DRIVE
$4,590,000
MFRA4707430
For Sale
275 LOOKOUT POINT DRIVE Osprey, FL 34229
5 Beds bathtub 5 Baths straighten 7781 sq ft
250 HIDDEN BAY DRIVE #302
$625,000
MFRA4706421
For Sale
250 HIDDEN BAY DRIVE #302 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2241 sq ft
401 POINT ROAD #703
$1,200,000
MFRA4707244
For Sale
401 POINT ROAD #703 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2423 sq ft
1036 OAK MEADOW LANE
$630,000
MFRA4701532
For Sale
1036 OAK MEADOW LANE Osprey, FL 34229
4 Beds bathtub 2 Baths straighten 2947 sq ft
385 NORTH POINT ROAD #701
$1,399,000
MFRA4707336
For Sale
385 NORTH POINT ROAD #701 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2837 sq ft
650 OAKS CREEK COURT
$3,700,000
MFRA4707301
For Sale
650 OAKS CREEK COURT Osprey, FL 34229
4 Beds bathtub 4 Baths straighten 5920 sq ft
7303 JESSIE HARBOR DRIVE #7303
$449,000
MFRA4706429
For Sale
7303 JESSIE HARBOR DRIVE #7303 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2163 sq ft
385 N POINT ROAD #401
$695,000
MFRA4707057
For Sale
385 N POINT ROAD #401 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2837 sq ft
124 TURQUOISE LANE
$4,500
MFRA4707451
For Rent
124 TURQUOISE LANE Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 3084 sq ft
324 OSPREY POINT DRIVE
$3,700,000
MFRA4706333
For Sale
324 OSPREY POINT DRIVE Osprey, FL 34229
5 Beds bathtub 5 Baths straighten 7471 sq ft
17 BAYHEAD LANE
$1,270,000
MFRA4706711
For Sale
17 BAYHEAD LANE Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 3060 sq ft
3621 N POINT ROAD #403
$700,000
MFRA4705730
For Sale
3621 N POINT ROAD #403 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2968 sq ft
700 SHADOW BAY WAY
$655,000
MFRO6442446
For Sale
700 SHADOW BAY WAY Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 3625 sq ft
109 WOODLAND PLACE
$244,900
MFRA4705745
For Sale
109 WOODLAND PLACE Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1387 sq ft
402 MACEWEN DRIVE
$1,590,000
MFRA4706228
For Sale
402 MACEWEN DRIVE Osprey, FL 34229
3 Beds bathtub 3.5 Baths straighten 5020 sq ft
141 SUGAR MILL DRIVE
$1,700,000
MFRA4705716
For Sale
141 SUGAR MILL DRIVE Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 4402 sq ft
1417 LANDVIEW LANE
$1,349,999
MFRA4705553
For Sale
1417 LANDVIEW LANE Osprey, FL 34229
4 Beds bathtub 4 Baths straighten 4113 sq ft
1328 THORNAPPLE DRIVE
$749,900
MFRA4705435
For Sale
1328 THORNAPPLE DRIVE Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2183 sq ft
2046 CORDES STREET
$565,000
MFRA4705136
For Sale
2046 CORDES STREET Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 4972 sq ft
210 PATTERSON AVENUE
$950,000
MFRA4704911
For Sale
210 PATTERSON AVENUE Osprey, FL 34229
3 Beds bathtub 1.5 Baths straighten 2084 sq ft

Townhouses & Duplexes in Osprey, FL

holiday_villageMore townhouses
1819 HIGHLAND ROAD
$319,000
MFRA4703963
For Sale
1819 HIGHLAND ROAD Osprey, FL 34229
2 Beds bathtub 2.5 Baths straighten 1897 sq ft
4296 EXPEDITION WAY #104
$289,000
MFRA4694926
For Sale
4296 EXPEDITION WAY #104 Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1219 sq ft
1811 HIGHLAND ROAD
$409,900
MFRTB8443161
For Sale
1811 HIGHLAND ROAD Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1725 sq ft
101 WOODLAND PLACE
$5,500
MFRA4644465
For Rent
101 WOODLAND PLACE Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 2039 sq ft

Condos & Apartments in Osprey, FL

apartmentMore condos
401 N POINT ROAD #404
$1,025,000
MFRA4708169
For Sale
401 N POINT ROAD #404 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 3106 sq ft
250 HIDDEN BAY DRIVE #302
$625,000
MFRA4706421
For Sale
250 HIDDEN BAY DRIVE #302 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2241 sq ft
401 POINT ROAD #703
$1,200,000
MFRA4707244
For Sale
401 POINT ROAD #703 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2423 sq ft
385 NORTH POINT ROAD #701
$1,399,000
MFRA4707336
For Sale
385 NORTH POINT ROAD #701 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2837 sq ft
7303 JESSIE HARBOR DRIVE #7303
$449,000
MFRA4706429
For Sale
7303 JESSIE HARBOR DRIVE #7303 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2163 sq ft
385 N POINT ROAD #401
$695,000
MFRA4707057
For Sale
385 N POINT ROAD #401 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2837 sq ft
3621 N POINT ROAD #403
$700,000
MFRA4705730
For Sale
3621 N POINT ROAD #403 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2968 sq ft
109 WOODLAND PLACE
$244,900
MFRA4705745
For Sale
109 WOODLAND PLACE Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1387 sq ft
4248 EXPEDITION WAY
$2,095
MFRA4704095
For Rent
4248 EXPEDITION WAY Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 1510 sq ft
1140 BEACHCOMBER COURT #11
$540,000
MFRW7888943
For Sale
1140 BEACHCOMBER COURT #11 Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 2718 sq ft
242 HIDDEN BAY DRIVE #602
$700,000
MFRA4678883
For Sale
242 HIDDEN BAY DRIVE #602 Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 2032 sq ft
5100 JESSIE HARBOR DRIVE #404
$599,000
MFRA4703484
For Sale
5100 JESSIE HARBOR DRIVE #404 Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 2304 sq ft
409 POINT ROAD #803
$985,000
MFRA4703407
For Sale
409 POINT ROAD #803 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2423 sq ft
260 HIDDEN BAY DRIVE #402
$775,000
MFRA4701000
For Sale
260 HIDDEN BAY DRIVE #402 Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 2109 sq ft
14041 BELLAGIO WAY #214
$5,000
MFRA4700702
For Rent
14041 BELLAGIO WAY #214 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2089 sq ft
2309 JESSIE HARBOR DRIVE #2402
$480,000
MFRA4698434
For Sale
2309 JESSIE HARBOR DRIVE #2402 Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 2446 sq ft
6100 JESSIE HARBOR DRIVE #202
$4,995
MFRA4698732
For Rent
6100 JESSIE HARBOR DRIVE #202 Osprey, FL 34229
3 Beds bathtub 3.5 Baths straighten 4209 sq ft
7204 JESSIE HARBOR DRIVE #7204
$395,000
MFRA4697473
For Sale
7204 JESSIE HARBOR DRIVE #7204 Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1410 sq ft
116 WOODLAND PLACE #116
$249,900
MFRA4696616
For Sale
116 WOODLAND PLACE #116 Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1483 sq ft
51 MAC EWEN DRIVE #8
$1,600
MFRA4695928
For Rent
51 MAC EWEN DRIVE #8 Osprey, FL 34229
1 Beds bathtub 1 Baths straighten 675 sq ft
260 HIDDEN BAY DRIVE #401
$4,395
MFRA4693277
For Rent
260 HIDDEN BAY DRIVE #401 Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 2433 sq ft
280 HIDDEN BAY DRIVE #302
$719,000
MFRA4690813
For Sale
280 HIDDEN BAY DRIVE #302 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2241 sq ft
4219 FRONTIER WAY #105
$2,000
MFRN6144275
For Rent
4219 FRONTIER WAY #105 Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1560 sq ft
51 MACEWEN DRIVE #12
$275,000
MFRA4690540
For Sale
51 MACEWEN DRIVE #12 Osprey, FL 34229
1 Beds bathtub 1 Baths straighten 623 sq ft

For Rent in Osprey, FL

editMore rentals
124 TURQUOISE LANE
$4,500
MFRA4707451
For Rent
124 TURQUOISE LANE Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 3084 sq ft
4248 EXPEDITION WAY
$2,095
MFRA4704095
For Rent
4248 EXPEDITION WAY Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 1510 sq ft
14041 BELLAGIO WAY #214
$5,000
MFRA4700702
For Rent
14041 BELLAGIO WAY #214 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2089 sq ft
4401 CONCHFISH LANE
$3,295
MFRA4700255
For Rent
4401 CONCHFISH LANE Osprey, FL 34229
4 Beds bathtub 3 Baths straighten 2824 sq ft
534 OAK BAY DRIVE
$3,750
MFRA4699469
For Rent
534 OAK BAY DRIVE Osprey, FL 34229
4 Beds bathtub 3 Baths straighten 2787 sq ft
6100 JESSIE HARBOR DRIVE #202
$4,995
MFRA4698732
For Rent
6100 JESSIE HARBOR DRIVE #202 Osprey, FL 34229
3 Beds bathtub 3.5 Baths straighten 4209 sq ft
51 MAC EWEN DRIVE #8
$1,600
MFRA4695928
For Rent
51 MAC EWEN DRIVE #8 Osprey, FL 34229
1 Beds bathtub 1 Baths straighten 675 sq ft
260 HIDDEN BAY DRIVE #401
$4,395
MFRA4693277
For Rent
260 HIDDEN BAY DRIVE #401 Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 2433 sq ft
4219 FRONTIER WAY #105
$2,000
MFRN6144275
For Rent
4219 FRONTIER WAY #105 Osprey, FL 34229
2 Beds bathtub 2 Baths straighten 1560 sq ft
51 MACEWEN DRIVE #12
$2,250
MFRA4686127
For Rent
51 MACEWEN DRIVE #12 Osprey, FL 34229
1 Beds bathtub 1 Baths straighten 623 sq ft
2068 PREYMORE STREET
$3,500
MFRA4673066
For Rent
2068 PREYMORE STREET Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2213 sq ft
521 HABITAT BOULEVARD
$5,900
MFRA4661768
For Rent
521 HABITAT BOULEVARD Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2284 sq ft
852 MACEWEN DRIVE
$7,000
MFRA4659277
For Rent
852 MACEWEN DRIVE Osprey, FL 34229
3 Beds bathtub 3.5 Baths straighten 6019 sq ft
5100 JESSIE HARBOR DRIVE #504
$6,950
MFRA4651384
For Rent
5100 JESSIE HARBOR DRIVE #504 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2304 sq ft
101 WOODLAND PLACE
$5,500
MFRA4644465
For Rent
101 WOODLAND PLACE Osprey, FL 34229
3 Beds bathtub 2.5 Baths straighten 2039 sq ft
3603 POINT ROAD #602
$5,900
MFRA4640065
For Rent
3603 POINT ROAD #602 Osprey, FL 34229
3 Beds bathtub 3 Baths straighten 2904 sq ft
293 TURQUOISE LANE
$5,750
MFRA4594860
For Rent
293 TURQUOISE LANE Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 2998 sq ft
51 MAC EWEN DRIVE #1
$2,500
MFRA4589608
For Rent
51 MAC EWEN DRIVE #1 Osprey, FL 34229
1 Beds bathtub 1 Baths straighten 623 sq ft
152 NAVIGATION CIRCLE #107
$4,500
MFRA4517611
For Rent
152 NAVIGATION CIRCLE #107 Osprey, FL 34229
3 Beds bathtub 2 Baths straighten 1889 sq ft
293 HIDDEN BAY DRIVE #203
$5,000
MFRA4410764
For Rent
293 HIDDEN BAY DRIVE #203 Osprey, FL 34229
2 Beds bathtub 2 Baths

Lots & Land in Osprey, FL

crop_landscapeMore land
2301 S TAMIAMI TRAIL
$2,850,000
MFRA4702316
For Sale
2301 S TAMIAMI TRAIL Osprey, FL 34229
458 SHORE DRIVE
$600,000
MFRN6144855
For Sale
458 SHORE DRIVE Osprey, FL 34229
3820 PARROT BAY COURT
$825,000
MFRA4698462
For Sale
3820 PARROT BAY COURT Osprey, FL 34229
143 OSPREY POINT DRIVE
$575,000
MFRA4694133
For Sale
143 OSPREY POINT DRIVE Osprey, FL 34229
216 OSPREY POINT DRIVE
$695,000
MFRA4696023
For Sale
216 OSPREY POINT DRIVE Osprey, FL 34229
410 BLUE GARDEN LANE
$699,000
MFRA4679677
For Sale
410 BLUE GARDEN LANE Osprey, FL 34229
2099 S TAMIAMI TRAIL
$1,250,000
MFRA4677875
For Sale
2099 S TAMIAMI TRAIL Osprey, FL 34229
456 WASHINGTON AVENUE
$299,999
MFRA4623594
For Sale
456 WASHINGTON AVENUE Osprey, FL 34229

MARKET SNAPSHOT

The Market at a Glance

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

New This Week 8
Went Under Contract 0
Price Reductions 0
Median Sale Price $640,000 -0.8%
Price per Sq Ft $232
Avg Days on Market 102
Homes Sold 60
Sale-to-List Ratio 94.0%
Months of Inventory 6.4

Price & Sales History

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

Renaissance Realty Group
Renaissance Realty Group Renaissance Realty Group info@rrgrouptampa.com

Zip Codes

BROWSE BY ZIP

Browse listings by postal code in this area.

011 homes for saleMedian sale$295K1 sale in the last 90 days
002 homes for saleMedian sale$295K
0002 homes for saleMedian sale$295K
00006 homes for saleMedian sale$295K
0000025 homes for saleMedian sale$85KPer sq ft$211 sale in the last 90 days
0060223 homes for saleMedian sale$560.3KPer sq ft$2282 sales in the last 90 days
0060333 homes for saleMedian sale$195KPer sq ft$1493 sales in the last 90 days
0061232 homes for saleMedian sale$205KPer sq ft$1319 sales in the last 90 days
0062356 homes for saleMedian sale$275KPer sq ft$22111 sales in the last 90 days
0064113 homes for saleMedian sale$399KPer sq ft$1601 sale in the last 90 days
00646135 homes for saleMedian sale$1.2MPer sq ft$51622 sales in the last 90 days
0066233 homes for saleMedian sale$482.5KPer sq ft$3864 sales in the last 90 days
View All Zip Codes
Get Alerts Advanced Search
  • Grid
  • Map
  • List
649 CRANE PRAIRIE WAY For Sale
$639,000
649 CRANE PRAIRIE WAYOsprey, FL 34229
  • 3 bd
  • 3 ba
  • 2803 sqft
  • Built 2004
  • MFRA4702490
366 S CREEK COURT For Sale
$1,049,000
366 S CREEK COURTOsprey, FL 34229
  • 4 bd
  • 3 ba
  • 3652 sqft
  • Built 2004
  • MFRA4708943
401 N POINT ROAD #404 For Sale
$1,025,000
401 N POINT ROAD #404Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 3106 sqft
  • Built 2003
  • MFRA4708169
422 BLUE GARDEN LANE For Sale
$1,445,000
422 BLUE GARDEN LANEOsprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 4702 sqft
  • Built 1984
  • MFRA4707058
275 LOOKOUT POINT DRIVE For Sale
$4,590,000
275 LOOKOUT POINT DRIVEOsprey, FL 34229
  • 5 bd
  • 5 ba
  • 7781 sqft
  • Built 2007
  • MFRA4707430
250 HIDDEN BAY DRIVE #302 For Sale
$625,000
250 HIDDEN BAY DRIVE #302Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2241 sqft
  • Built 2017
  • MFRA4706421
401 POINT ROAD #703 For Sale
$1,200,000
401 POINT ROAD #703Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2423 sqft
  • Built 2003
  • MFRA4707244
1036 OAK MEADOW LANE For Sale
$630,000
1036 OAK MEADOW LANEOsprey, FL 34229
  • 4 bd
  • 2 ba
  • 2947 sqft
  • Built 2001
  • MFRA4701532
385 NORTH POINT ROAD #701 For Sale
$1,399,000
385 NORTH POINT ROAD #701Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2837 sqft
  • Built 2000
  • MFRA4707336
650 OAKS CREEK COURT For Sale
$3,700,000
650 OAKS CREEK COURTOsprey, FL 34229
  • 4 bd
  • 4 ba
  • 5920 sqft
  • Built 2024
  • MFRA4707301
7303 JESSIE HARBOR DRIVE #7303 For Sale
$449,000
7303 JESSIE HARBOR DRIVE #7303Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2163 sqft
  • Built 1985
  • MFRA4706429
385 N POINT ROAD #401 For Sale
$695,000
385 N POINT ROAD #401Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2837 sqft
  • Built 2000
  • MFRA4707057
124 TURQUOISE LANE For Rent
$4,500
124 TURQUOISE LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 3084 sqft
  • Built 2002
  • MFRA4707451
324 OSPREY POINT DRIVE For Sale
$3,700,000
324 OSPREY POINT DRIVEOsprey, FL 34229
  • 5 bd
  • 5 ba
  • 7471 sqft
  • Built 1998
  • MFRA4706333
17 BAYHEAD LANE For Sale
$1,270,000
17 BAYHEAD LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 3060 sqft
  • Built 1992
  • MFRA4706711
3621 N POINT ROAD #403 For Sale
$700,000
3621 N POINT ROAD #403Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2968 sqft
  • Built 2007
  • MFRA4705730
700 SHADOW BAY WAY For Sale
$655,000
700 SHADOW BAY WAYOsprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 3625 sqft
  • Built 2002
  • MFRO6442446
109 WOODLAND PLACE For Sale
$244,900
109 WOODLAND PLACEOsprey, FL 34229
  • 2 bd
  • 2 ba
  • 1387 sqft
  • Built 1979
  • MFRA4705745
402 MACEWEN DRIVE For Sale
$1,590,000
402 MACEWEN DRIVEOsprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 5020 sqft
  • Built 1999
  • MFRA4706228
141 SUGAR MILL DRIVE For Sale
$1,700,000
141 SUGAR MILL DRIVEOsprey, FL 34229
  • 3 bd
  • 3 ba
  • 4402 sqft
  • Built 2016
  • MFRA4705716
1417 LANDVIEW LANE For Sale
$1,349,999
1417 LANDVIEW LANEOsprey, FL 34229
  • 4 bd
  • 4 ba
  • 4113 sqft
  • Built 2014
  • MFRA4705553
1328 THORNAPPLE DRIVE For Sale
$749,900
1328 THORNAPPLE DRIVEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2183 sqft
  • Built 2003
  • MFRA4705435
2046 CORDES STREET For Sale
$565,000
2046 CORDES STREETOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 4972 sqft
  • Built 1998
  • MFRA4705136
210 PATTERSON AVENUE For Sale
$950,000
210 PATTERSON AVENUEOsprey, FL 34229
  • 3 bd
  • 1.5 ba
  • 2084 sqft
  • Built 1950
  • MFRA4704911
1216 CASEY KEY ROAD For Sale
$9,750,000
1216 CASEY KEY ROADOsprey, FL 34229
  • 5 bd
  • 7 ba
  • 15522 sqft
  • Built 1999
  • MFRA4704643
4248 EXPEDITION WAY For Rent
$2,095
4248 EXPEDITION WAYOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 1510 sqft
  • Built 2017
  • MFRA4704095
583 PINE RANCH EAST ROAD For Sale
$529,000
583 PINE RANCH EAST ROADOsprey, FL 34229
  • 4 bd
  • 2 ba
  • 3162 sqft
  • Built 1996
  • MFRA4704589
226 SAINT JAMES PARK For Sale
$1,495,000
226 SAINT JAMES PARKOsprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 3789 sqft
  • Built 1988
  • MFRA4704489
154 LOOKOUT POINT DRIVE For Sale
$2,095,000
154 LOOKOUT POINT DRIVEOsprey, FL 34229
  • 4 bd
  • 3.5 ba
  • 6200 sqft
  • Built 1979
  • MFRTB8543439
296 PINE RANCH TRAIL For Sale
$1,100,000
296 PINE RANCH TRAILOsprey, FL 34229
  • 5 bd
  • 3.5 ba
  • 4500 sqft
  • Built 1995
  • MFRA4704317
1819 HIGHLAND ROAD For Sale
$319,000
1819 HIGHLAND ROADOsprey, FL 34229
  • 2 bd
  • 2.5 ba
  • 1897 sqft
  • Built 1998
  • MFRA4703963
1140 BEACHCOMBER COURT #11 For Sale
$540,000
1140 BEACHCOMBER COURT #11Osprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 2718 sqft
  • Built 2005
  • MFRW7888943
242 HIDDEN BAY DRIVE #602 For Sale
$700,000
242 HIDDEN BAY DRIVE #602Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 2032 sqft
  • Built 1999
  • MFRA4678883
5100 JESSIE HARBOR DRIVE #404 For Sale
$599,000
5100 JESSIE HARBOR DRIVE #404Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 2304 sqft
  • Built 2004
  • MFRA4703484
409 POINT ROAD #803 For Sale
$985,000
409 POINT ROAD #803Osprey, FL 34229
  • 3 bd
  • 3 ba
  • 2423 sqft
  • Built 2004
  • MFRA4703407
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
$699,000
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
570 BLACKBURN POINT ROAD #36 For Sale
$99,500
570 BLACKBURN POINT ROAD #36Osprey, FL 34229
  • MFRA4700865
14041 BELLAGIO WAY #214 For Rent
$5,000
14041 BELLAGIO WAY #214Osprey, FL 34229
  • 3 bd
  • 2 ba
  • 2089 sqft
  • Built 2006
  • MFRA4700702
599 PINE RANCH EAST ROAD For Sale
$815,000
599 PINE RANCH EAST ROADOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 2815 sqft
  • Built 1995
  • MFRA4660895
4401 CONCHFISH LANE For Rent
$3,295
4401 CONCHFISH LANEOsprey, FL 34229
  • 4 bd
  • 3 ba
  • 2824 sqft
  • Built 2018
  • MFRA4700255
534 OAK BAY DRIVE For Rent
$3,750
534 OAK BAY DRIVEOsprey, FL 34229
  • 4 bd
  • 3 ba
  • 2787 sqft
  • Built 1996
  • MFRA4699469
2309 JESSIE HARBOR DRIVE #2402 For Sale
$480,000
2309 JESSIE HARBOR DRIVE #2402Osprey, FL 34229
  • 3 bd
  • 2.5 ba
  • 2446 sqft
  • Built 2006
  • MFRA4698434
6100 JESSIE HARBOR DRIVE #202 For Rent
$4,995
6100 JESSIE HARBOR DRIVE #202Osprey, FL 34229
  • 3 bd
  • 3.5 ba
  • 4209 sqft
  • Built 2005
  • MFRA4698732
206 FOUR KNOT LANE For Sale
$1,690,000
206 FOUR KNOT LANEOsprey, FL 34229
  • 3 bd
  • 2 ba
  • 3837 sqft
  • Built 1991
  • MFRA4695429
570 BLACKBURN POINT ROAD #23 For Sale
$89,000
570 BLACKBURN POINT ROAD #23Osprey, FL 34229
  • Built 2006
  • MFRA4697977
7204 JESSIE HARBOR DRIVE #7204 For Sale
$395,000
7204 JESSIE HARBOR DRIVE #7204Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1410 sqft
  • Built 1985
  • MFRA4697473
116 WOODLAND PLACE #116 For Sale
$249,900
116 WOODLAND PLACE #116Osprey, FL 34229
  • 2 bd
  • 2 ba
  • 1483 sqft
  • Built 1979
  • MFRA4696616
75 OSPREY POINT DRIVE For Sale
$1,595,000
75 OSPREY POINT DRIVEOsprey, FL 34229
  • 4 bd
  • 4 ba
  • 5028 sqft
  • Built 1983
  • MFRA4695145
104

Nearby Cities

All Cities
  • Nokomis4.6 mi414 Listings
  • Sarasota7.9 mi3.3K Listings
  • North Venice7.3 mi27 Listings
  • Siesta Key6.4 mi3 Listings
  • Venice11 mi1.2K Listings
  • Longboat Key16 mi342 Listings
  • Bradenton19 mi2.5K Listings
  • Lakewood Ranch18 mi424 Listings
  • University Park14 mi27 Listings
  • North Port21 mi3K Listings
  • Englewood20 mi904 Listings
  • Port Charlotte24 mi4.8K Listings

Similar Searches

  • For Sale in Osprey
  • Rentals in Osprey
  • Houses in Osprey
  • Condos & Apartments in Osprey
  • Townhouses & Duplexes in Osprey
  • Lots & Land in Osprey
  • Farms & Ranches in Osprey

Featured Areas

All Areas
  • Hillsborough County9375 Listings
  • Pinellas County9093 Listings
  • Pasco County6636 Listings
  • Tampa2596 Listings
  • Clearwater24 Listings
  • Saint Petersburg1 Listings

Featured Searches

Advanced Search
  • $200k to $300k Homes
  • $300k to $400k Homes
  • $400k to $500k Homes
  • Acreage
  • Commercial Properties
  • Farms & Ranches
  • Golf Course Homes
  • Homes Listed this Week
  • Homes with 2+ Beds
  • Homes with Pools
  • Large Houses (2k+ sqft)
  • Luxury Condos ($400k+)
  • Multi-Family Homes
  • New Construction
  • Oceanfront Condos
  • Rentals Under $2k
  • Rentals with Pets
  • Under $200k Homes
  • Under $250k Homes
  • Water View Homes
  • Water View Homes

Popular Cities

All Cities
  • Miami9426 Listings
  • Orlando5598 Listings
  • Port Charlotte4794 Listings
  • ocala4607 Listings
  • Fort Lauderdale4466 Listings
  • Tampa4460 Listings
  • West Palm Beach4052 Listings
  • Boca Raton3997 Listings
  • Kissimmee3794 Listings
  • Delray Beach3475 Listings

Popular Subdivisions

All Subdivisions
  • Grove at Grand Bay205 Listings
  • Icon Brickell III - W Residences129 Listings
  • Mystic Pointe 100 -600117 Listings
  • Winston Towers87 Listings
  • Paramount at Miami World Center85 Listings
  • Vizcayne73 Listings
  • Beachwalk73 Listings
  • Paraiso Bay71 Listings
  • H3 - Hollywood Station71 Listings
  • St. Tropez70 Listings

Popular Zip Codes

All Zips
  • Homes in 33993436 Listings
  • Homes in 33974626 Listings
  • Homes in 33972388 Listings
  • Homes in 33909242 Listings
  • Homes in 33971308 Listings
  • Homes in 3412080 Listings
  • Homes in 339811641 Listings
  • Homes in 3390842 Listings
  • Homes in 331601928 Listings
  • Homes in 33955958 Listings

Recent Articles

All Articles
  • How Much Home Can You Afford?
  • Capital Gains Exclusion for Surviving Spouses
  • Benefits of Homeownership
  • How to Market Your Summer Vacation Home
  • Finding the Best First-Time Homebuyer Programs
  • The Perks of Buying a Waterfront Property in Fall
  • 4 Reasons to Buy a Home in Fall
  • Market-Specific Home Buying Strategies
  • Tips for Selling Your Home in Hillsboro Beach, Florida
  • Experience the Best of Hillsboro Beach, Florida: Explore our Homes for Sale!

City Guide

About Osprey

Real Estate & Housing

Osprey's residential landscape is built around water, golf, and low-density living. Established waterfront neighborhoods such as Sorrento Shores offer direct boating access on Little Sarasota Bay, while Osprey Harbor Village provides Mediterranean-style condominium living near the water. The Oaks community includes estate and golf-course homes around championship courses, and communities like Rivendell add preserve-backed single-family options. Nearby Casey Key is known for larger Gulf-front and bayfront estates. The overall housing stock skews toward established, mid-to-upscale single-family homes and condominiums rather than dense new tract development, giving Osprey a settled, residential character.

Neighborhoods

Several distinct communities define Osprey. The Oaks is a golf and country-club community with sub-neighborhoods such as Oaks Bayside and Oaks Clubside set around championship courses and Little Sarasota Bay. Sorrento Shores is a well-established waterfront neighborhood near Blackburn Point Road with bay access and boat docks. Osprey Harbor Village offers Mediterranean-style condominiums overlooking the bay, and Rivendell is a popular community with scenic preserve surroundings. Across the water, Casey Key and Nokomis provide barrier-island living with Gulf beaches, extending Osprey's reach to the shoreline even though the community itself sits on the mainland side of the bay.

Lifestyle in Osprey

Life in Osprey revolves around the water and the outdoors. Residents boat and paddle on Little Sarasota Bay, play golf at The Oaks, and spend mornings at Historic Spanish Point or hiking the trails of Oscar Scherer State Park. The community skews toward established households and retirees drawn to its quiet, low-density character, yet it remains within minutes of downtown Sarasota's arts, dining, and healthcare and the beaches and shops of Venice and Nokomis. Osprey's own commercial scene is modest—marinas, a handful of restaurants, and neighborhood services—so much of daily shopping and entertainment happens in the neighboring cities, keeping the community itself calm and residential.

Schools & Education

Osprey is served by Sarasota County Schools, the public district that covers the entire county with neighborhood elementary, middle, and high schools in the surrounding area. Families also have access to a range of private and charter schools in Sarasota and Venice. The community's school-age population is relatively small, reflecting its mix of established households and retirees, but the broader Sarasota County system provides well-regarded educational options for families who choose to live in Osprey.

Getting Around

Osprey lies along the Tamiami Trail (U.S. 41), the primary north-south corridor connecting Sarasota to Venice, which places both cities within a short drive. Interstate 75 runs inland just to the east, offering faster regional travel to Tampa, Bradenton, and Fort Myers. Blackburn Point Road and the Blackburn Point Bridge link the community toward Casey Key and the Gulf beaches. Because Osprey is primarily residential, most residents rely on cars for commuting, shopping, and beach access, a typical pattern for the Sarasota County coast.

Parks & Recreation

Osprey's two signature attractions are Oscar Scherer State Park and Historic Spanish Point. Oscar Scherer, set between Sarasota and Venice, preserves habitat for the threatened Florida scrub-jay, offers hiking and biking trails and Lake Osprey for fishing, and draws hundreds of thousands of visitors each year. Historic Spanish Point, on a peninsula in Little Sarasota Bay, is a botanical, archaeological, and historic site operated by Marie Selby Botanical Gardens. Boating and paddlecraft on the bay, golf at The Oaks, and the Gulf beaches of Casey Key and Nokomis round out a recreation-rich setting that is central to Osprey's identity.

About Osprey

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.

Still have questions about Osprey?

Get in touch
  • Local Guide
  • Cities

Explore the area

Nearby cities

Anna Maria, FL73 homes for saleMedian$1,630,000+2.0%Days on market132Per sq ft$782
Bradenton, FL2,485 homes for saleMedian$429,000+4.1%Days on market85Per sq ft$197
Bradenton Beach, FL94 homes for saleMedian$965,000+48.0%Days on market88Per sq ft$534
Cortez, FL22 homes for saleMedian$872,000−35.4%Days on market120Per sq ft$408
Ellenton, FL106 homes for saleMedian$459,750+21.8%Days on market86Per sq ft$160
Englewood, FL904 homes for saleMedian$379,000+15.9%Days on market91Per sq ft$207
Holmes Beach, FL108 homes for saleMedian$1,200,000+37.9%Days on market167Per sq ft$611
Lakewood Ranch, FL424 homes for saleMedian$595,000+2.6%Days on market81Per sq ft$239
Longboat Key, FL342 homes for saleMedian$900,000−7.7%Days on market147Per sq ft$593
Myakka City, FL87 homes for saleMedian$761,250−17.7%Days on market76Per sq ft$276
Nokomis, FL414 homes for saleMedian$505,000+8.6%Days on market70Per sq ft$208
North Port, FL3,032 homes for saleMedian$318,500−0.5%Days on market92Per sq ft$178
North Venice, FL27 homes for saleMedian$619,500+5.9%Days on market118Per sq ft$1,806
Palmetto, FL694 homes for saleMedian$391,312+5.8%Days on market89Per sq ft$182
Parrish, FL1,046 homes for saleMedian$402,610−3.5%Days on market87Per sq ft$162
Placida, FL649 homes for saleMedian$585,000−10.0%Days on market179Per sq ft$313
Port Charlotte, FL4,794 homes for saleMedian$315,000+4.3%Days on market115Per sq ft$150
Punta Gorda, FL2,643 homes for saleMedian$355,000−1.4%Days on market130Per sq ft$184
Rotonda West, FL669 homes for saleMedian$400,000+8.1%Days on market114Per sq ft$155
Sarasota, FL3,285 homes for saleMedian$498,900+2.4%Days on market90Per sq ft$293
Siesta Key, FL3 homes for saleMedian$1,525,000−37.6%Days on market151Per sq ft$673
Terra Ceia, FL19 homes for saleMedian$1,550,000+34.5%Days on market230Per sq ft$271
University Park, FL27 homes for saleMedian$641,245−23.8%Days on market70Per sq ft$231
Venice, FL1,173 homes for saleMedian$400,000+1.3%Days on market86Per sq ft$196
24