Osprey Real Estate

Some of the best housing options in Sarasota County are in the Osprey Real Estate market, with a variety of single family homes for sale priced between $249,900 and as high as $11,750,000 two to six bedroom homes that range in size from 1,616 to 15,522 square feet. Options for Condos in Osprey range from $175,000 for an apartment with one bedroom and one bathroom to three bedrooms and three bathroom luxury condominiums that sell for up to $1,549,000.

We have detailed information regarding 17 communities in Osprey, including four non-gated communities of single family homes, one condo building, four waterfront condo complexes, three gated communities, and four waterfront communities including some new construction opportunities and open houses. Osprey real estate activity on the MLS indicates 140 properties are currently on the market (as of October 9th, 2025). Whether relocating to Osprey from another state or upsizing or downsizing, whichever of the many luxury homes for sale in Osprey you choose, our professional Realtors in Osprey Florida can guide you through the home-buying process.

Osprey Homes For Sale

$11,750,000

MLS#MFRA4643654

1216 N Casey Key Rd
Osprey, FL 34229

5

8

4

15,522 SqFt

Pool

Ocean Front

1.1 Acres

216 Days

$7,100,000

Casey Key

121 N Casey Key Rd
Osprey, FL 34229

4

6

2

6,906 SqFt

Pool

Water Front

0.49 Acres

5 Days

Reduced

$5,990,000

$6,790,000

Casey Key

144 N Casey Key Rd
Osprey, FL 34229

4

6

3

10,722 SqFt

Pool

Water Front

0.55 Acres

62 Days

Reduced

$5,700,000

$6,750,000

MLS#MFRA4657777

622 Bayshore Dr
Osprey, FL 34229

6

5

3

5,832 SqFt

Pool

Water Front

0.78 Acres

98 Days

$5.5 Million

MLS#MFRA4662210

614 Bayshore Dr
Osprey, FL 34229

3

5

5

6,347 SqFt

Pool

Water Front

0.52 Acres

55 Days

New Construction

$5 Million

Oaks Bayside

101 Osprey Point Dr
Osprey, FL 34229

4

6

3

6,841 SqFt

Pool

Water Front

0.93 Acres

22 Days

$4,750,000

MLS#MFRN6137711

1049 N Casey Key Rd
Osprey, FL 34229

3

3

5

3,373 SqFt

Water Front

1.06 Acres

212 Days

Reduced

$3,400,000

$3,450,000

Sorrento Shores

135 Tina Island Dr
Osprey, FL 34229

3

5

4

2,572 SqFt

Water Front

0.37 Acres

21 Days

Under Contract

$3,325,000

$3,900,000

Oaks Bayside

112 Osprey Point Dr
Osprey, FL 34229

4

6

3

11,076 SqFt

Pool

Water Front

0.6 Acres

158 Days

Reduced

$2.995 Million

$3,150,000

Oaks Bayside

662 Fernwalk Ln
Osprey, FL 34229

4

4

3

6,300 SqFt

Pool

0.44 Acres

252 Days

$2.9 Million

The Oaks Club

236 Saint James Park
Osprey, FL 34229

6

7

2

9,589 SqFt

Pool

0.56 Acres

196 Days

$2,850,000

Southbay Yacht And Racquet Club

225 Harbor House Dr
Osprey, FL 34229

6

4

2

6,289 SqFt

Pool

0.26 Acres

14 Days

140 Active Listings in Osprey, FL

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Living in Osprey affords you easy access to nearby golf courses, fine dining, entertainment venues and various other amenities and conveniences in the city of Osprey. Tamiami Trail, FL70, or I-75 provide an easy transition to nearby cities such as Sarasota, Nokomis, Lakewood Ranch, Longboat Key, Bradenton, North Port, Englewood, and Venice.

Boating and watersports are integral to the coastal Florida lifestyle, offering year-round access to to both fresh and saltwater ecosystems, vibrant marine life, and a culture centered around outdoor leisure and recreation. Osprey real estate prices are directly correlated to it's proximity to these amenities.

Additionally, two local airports are easily accessible - Sarasota Bradenton International (SRQ), and Punta Gorda (PGD). Finally, for private air travel, you may utilize Venice Municipal (VNC).

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. 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.