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Osprey Homes For Sale & Real Estate - 132 homes

Osprey homes for sale are located in Sarasota County, Florida. Find homes in Osprey for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Osprey houses.

Location: Osprey

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  • 811 SARABAY RD, OSPREY, FL 34229

    $449,000Listed 06/23/2026 7:24PM   MLS ID: A4697921

    For Sale A4697921 - 811 SARABAY RD, OSPREY, FL 34229 36 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1211
       Built: 1950   Tax: $1,130 (2025)
    Community: Harms Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,554 (change assumption)
    Mortgage ($2,460) + Taxes in 2025 ($94)


    Taxes:$1,130

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 403 LONGBOW TRL, OSPREY, FL 34229

    $1,095,000218 Days on yellowkey   MLS ID: A4672081

    For Sale A4672081 - 403 LONGBOW TRL, OSPREY, FL 34229 99 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2770
       Built: 1978
    Monthly Fee: $42
       Tax: $9,020 (2024)
    Community: Pine Ranch
    Single Family


    Estimated Monthly Payment: $6,794 (change assumption)
    Mortgage ($6,000) + Fees ($42) + Taxes in 2024 ($752)


    Taxes:$9,020

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 1527 BUOY LN, OSPREY, FL 34229

    $1,165,00077 Days on yellowkey   MLS ID: A4688266

    REDUCED by $34,000 (2.8%) on 06/23/2026

    For Sale A4688266 - 1527 BUOY LN, OSPREY, FL 34229 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2830
       Built: 1989
    Monthly Fee: $204
       Tax: $8,555 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,300 (change assumption)
    Mortgage ($6,383) + Fees ($204) + Taxes in 2025 ($713)


    Taxes:$8,555

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Venice Area Middle


  • 353 S SHORE DR, OSPREY, FL 34229

    $999,00083 Days on yellowkey   MLS ID: A4688006

    REDUCED by $26,000 (2.5%) on 06/09/2026

    For Sale A4688006 - 353 S SHORE DR, OSPREY, FL 34229 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 1968
    Monthly Fee: $11
       Tax: $3,904 (2025)
    Community: Sorrento Shores Rep Of 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,810 (change assumption)
    Mortgage ($5,474) + Fees ($11) + Taxes in 2025 ($325)


    Taxes:$3,904

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 14041 BELLAGIO WAY #318, OSPREY, FL 34229

    $999,00012 Days on yellowkey   MLS ID: A4696101

    For Sale A4696101 - 14041 BELLAGIO WAY #318, OSPREY, FL 34229 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2086
       Built: 2006
    Monthly Fee: $1,512
       Tax: $7,362 (2025)
    Community: Villas At Bellagio Harbor Village
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,599 (change assumption)
    Mortgage ($5,474) + Fees ($1,512) + Taxes in 2025 ($614)


    Taxes:$7,362

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 116 WOODLAND PL #116, OSPREY, FL 34229

    $254,90012 Days on yellowkey   MLS ID: A4696616

    REDUCED by $15,000 (5.6%) on 06/23/2026

    For Sale A4696616 - 116 WOODLAND PL #116, OSPREY, FL 34229 45 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1979
    Monthly Fee: $820
       Tax: $1,893 (2025)
    Community: Pine Run Ii
    Condo


    Estimated Monthly Payment: $2,374 (change assumption)
    Mortgage ($1,397) + Fees ($820) + Taxes in 2025 ($158)


    Taxes:$1,893

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 472 PARK TRACE BLVD, OSPREY, FL 34229

    $599,000144 Days on yellowkey   MLS ID: A4680326

    REDUCED by $10,000 (1.6%) on 06/23/2026

    For Sale A4680326 - 472 PARK TRACE BLVD, OSPREY, FL 34229 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2217
       Built: 2002
    Monthly Fee: $58
       Tax: $5,925 (2025)
    Community: Park Trace Estates
    Single Family


    Estimated Monthly Payment: $3,834 (change assumption)
    Mortgage ($3,282) + Fees ($58) + Taxes in 2025 ($494)


    Taxes:$5,925

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 347 BAYSHORE DR, OSPREY, FL 34229

    $739,00042 Days on yellowkey   MLS ID: A4693374

    For Sale A4693374 - 347 BAYSHORE DR, OSPREY, FL 34229 70 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2013   Tax: $879 (2025)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $4,122 (change assumption)
    Mortgage ($4,049) + Taxes in 2025 ($73)


    Taxes:$879

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 816 SHADOW BAY WAY, OSPREY, FL 34229

    $655,00042 Days on yellowkey   MLS ID: A4690226

    For Sale A4690226 - 816 SHADOW BAY WAY, OSPREY, FL 34229 66 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2251
       Built: 1998
    Monthly Fee: $120
       Tax: $4,453 (2025)
    Community: Rivendell
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,080 (change assumption)
    Mortgage ($3,589) + Fees ($120) + Taxes in 2025 ($371)


    Taxes:$4,453

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 433 E MACEWEN DR, OSPREY, FL 34229

    $2,189,000175 Days on yellowkey   MLS ID: A4676505

    REDUCED by $61,000 (2.7%) on 06/23/2026

    For Sale A4676505 - 433 E MACEWEN DR, OSPREY, FL 34229 72 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4012
       Built: 1998
    Monthly Fee: $142
       Tax: $17,426 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,588 (change assumption)
    Mortgage ($11,994) + Fees ($142) + Taxes in 2025 ($1,452)


    Taxes:$17,426

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 25 SUGAR MILL DR, OSPREY, FL 34229

    $1,489,000152 Days on yellowkey   MLS ID: A4678423

    0 Days Off yellowkey (back on 6/22/2026)

    REDUCED by $61,000 (3.9%) on 06/04/2026

    For Sale A4678423 - 25 SUGAR MILL DR, OSPREY, FL 34229 74 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3066
       Built: 1998
    Monthly Fee: $483
       Tax: $7,845 (2025)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,295 (change assumption)
    Mortgage ($8,159) + Fees ($483) + Taxes in 2025 ($654)


    Taxes:$7,845

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 401 WALLS WAY, OSPREY, FL 34229

    $1,775,000144 Days on yellowkey   MLS ID: A4680312

    1 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $25,000 (1.4%) on 05/31/2026

    For Sale A4680312 - 401 WALLS WAY, OSPREY, FL 34229 51 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4387
       Built: 1990
    Monthly Fee: $133
       Tax: $16,158 (2025)
    Community: Oaks 2 Ph 1
    Single Family


    Estimated Monthly Payment: $11,205 (change assumption)
    Mortgage ($9,726) + Fees ($133) + Taxes in 2025 ($1,347)


    Taxes:$16,158

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4424 CONCHFISH LN, OSPREY, FL 34229

    $585,00034 Days on yellowkey   MLS ID: A4691622

    REDUCED by $30,000 (4.9%) on 06/07/2026

    For Sale A4691622 - 4424 CONCHFISH LN, OSPREY, FL 34229 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2017
    Monthly Fee: $125
       Tax: $4,467 (2026)
    Community: Palms/Casey Key
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,703 (change assumption)
    Mortgage ($3,205) + Fees ($125) + Taxes in 2026 ($372)


    Taxes:$4,467

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2026

    Middle School: Sarasota Middle


  • 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229

    $318,000109 Days on yellowkey   MLS ID: N6143250

    REDUCED by $10,000 (3.0%) on 06/22/2026

    For Sale N6143250 - 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229 77 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1528
       Built: 2018   Tax: $3,781 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,057 (change assumption)
    Mortgage ($1,742) + Taxes in 2025 ($315)


    Taxes:$3,781

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 1474 LANDVIEW LN, OSPREY, FL 34229

    $1,475,00010 Days on yellowkey   MLS ID: A4696853

    For Sale A4696853 - 1474 LANDVIEW LN, OSPREY, FL 34229 74 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3246
       Built: 1977
    Monthly Fee: $219
       Tax: $9,834 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,120 (change assumption)
    Mortgage ($8,082) + Fees ($219) + Taxes in 2025 ($820)


    Taxes:$9,834

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 314 S SHORE DR, OSPREY, FL 34229

    $1,495,00029 Days on yellowkey   MLS ID: TB8510971

    REDUCED by $154,000 (9.3%) on 06/01/2026

    For Sale TB8510971 - 314 S SHORE DR, OSPREY, FL 34229 99 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3853
       Built: 1981
    Monthly Fee: $15
       Tax: $8,819 (2025)
    Community: Sorrento Shores Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,941 (change assumption)
    Mortgage ($8,192) + Fees ($15) + Taxes in 2025 ($735)


    Taxes:$8,819

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 173 NAVIGATION CIR #107, OSPREY, FL 34229

    $328,0008 Days on yellowkey   MLS ID: N6144704

    For Sale N6144704 - 173 NAVIGATION CIR #107, OSPREY, FL 34229 79 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1528
       Built: 2015   Tax: $2,892 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,797) + Taxes in 2025 ($241)


    Taxes:$2,892

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229

    $725,00062 Days on yellowkey   MLS ID: A4690942

    REDUCED by $10,000 (1.4%) on 06/16/2026

    For Sale A4690942 - 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229 71 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2004   Tax: $6,004 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $4,473 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($500)


    Taxes:$6,004

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 180 LOOKOUT POINT DR, OSPREY, FL 34229

    $2,199,900220 Days on yellowkey   MLS ID: A4672222

    REDUCED by $50,000 (2.2%) on 06/03/2026

    For Sale A4672222 - 180 LOOKOUT POINT DR, OSPREY, FL 34229 70 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3236
       Built: 1986
    Monthly Fee: $204
       Tax: $8,750 (2024)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,987 (change assumption)
    Mortgage ($12,054) + Fees ($204) + Taxes in 2024 ($729)


    Taxes:$8,750

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 113 BURNEY RD, OSPREY, FL 34229

    $999,50061 Days on yellowkey   MLS ID: A4690672

    0 Days Off yellowkey (back on 6/20/2026)

    For Sale A4690672 - 113 BURNEY RD, OSPREY, FL 34229 44 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2502
       Built: 2020   Tax: $10,455 (2025)
    Community: Bel-Air
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,348 (change assumption)
    Mortgage ($5,477) + Taxes in 2025 ($871)


    Taxes:$10,455

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School




Why Bother Searching Elsewhere for Osprey Homes for Sale and Other Real Estate?

Osprey home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Osprey . You can use our website to view Multiple Listing Service (MLS) data on Osprey Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Osprey listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information 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. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.