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 $375,000 and as high as $10,750,000 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 $2,750,000. Suppose a Townhome for sale in Osprey is what you are looking for, a two-bedroom, two bathroom 1,555 square foot villa or a two-bed, two-bath home as large as 2,125 sq ft ranging in price from $299,900 to $697,500.

We have detailed information regarding 20 communities in Osprey, including six non-gated communities of single family homes, two condo buildings, 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 169 properties are currently on the market (as of April 10th, 2026). 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

Reduced

$10,750,000

$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

399 Days

Reduced

$6,475,000

$7,100,000

Casey Key

121 N Casey Key Rd
Osprey, FL 34229

5

6

2

6,906 SqFt

Pool

Ocean Front

0.49 Acres

188 Days

$5.99 Million

Southbay Yacht And Racquet Club

313 Lookout Point Dr
Osprey, FL 34229

4

5

5

6,896 SqFt

Pool

Water Front

0.41 Acres

3 Days

Reduced

$4.995 Million

$5,495,000

MLS#MFRA4672618

730 Sarabay Rd
Osprey, FL 34229

4

6

7

8,156 SqFt

Pool

Water Front

2 Acres

142 Days

$4,250,000

MLS#MFRA4683138

324 Bayshore Dr
Osprey, FL 34229

4

5

2

7,971 SqFt

Pool

Water Front

0.47 Acres

45 Days

Reduced

$3,890,000

$3,950,000

The Oaks Club

854 Macewen Dr
Osprey, FL 34229

4

6

4

11,650 SqFt

Pool

0.78 Acres

173 Days

$3,750,000

MLS#MFRA4674771

1042 N Casey Key Rd
Osprey, FL 34229

4

5

2

6,556 SqFt

Pool

Water Front

0.68 Acres

119 Days

$3,250,000

Bayside

14401 Masthead Dr
Osprey, FL 34229

3

4

2

3,984 SqFt

Pool

Water Front

0.44 Acres

36 Days

$2,850,000

Oaks Bayside

662 Fernwalk Ln
Osprey, FL 34229

4

4

3

6,300 SqFt

Pool

0.44 Acres

71 Days

Under Contract

$2,750,000

The Oaks Preserve

409 N Point Rd #1001
Osprey, FL 34229

3

3

2

3,355 Sq Ft

Water Front

2.48 Acres

3 Days

Reduced

$2,700,000

$2,900,000

The Oaks Club

236 Saint James Park
Osprey, FL 34229

6

7

2

9,589 SqFt

Pool

0.56 Acres

379 Days

Reduced

$2.5 Million

$2,595,000

Oaks Bayside

49 Osprey Point Dr
Osprey, FL 34229

4

4

2

5,227 SqFt

Pool

Water Front

0.4 Acres

148 Days

169 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, Ruskin, Nokomis, Longboat Key, Lakewood Ranch, Englewood, Bradenton, North Port, 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.