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Osprey Homes For Sale & Real Estate - 136 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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  • 570 BLACKBURN POINT RD #23, OSPREY, FL 34229

    $98,000Listed 06/24/2026 11:07AM   MLS ID: A4697977

    For Sale A4697977 - 570 BLACKBURN POINT RD #23, OSPREY, FL 34229 3 photos

    Bed:    Bath: 0.0
    Built: 2006
       Tax: $378 (2025)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $568 (change assumption)
    Mortgage ($537) + Taxes in 2025 ($32)


    Taxes:$378

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14041 BELLAGIO WAY #318, OSPREY, FL 34229

    $999,00013 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


  • 1367 THORNAPPLE DR, OSPREY, FL 34229

    $579,00021 Days on yellowkey   MLS ID: A4695210

    For Sale A4695210 - 1367 THORNAPPLE DR, OSPREY, FL 34229 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2182
       Built: 2003
    Monthly Fee: $397
       Tax: $5,745 (2025)
    Community: Willowbend Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,048 (change assumption)
    Mortgage ($3,173) + Fees ($397) + Taxes in 2025 ($479)


    Taxes:$5,745

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 206 FOUR KNOT LN, OSPREY, FL 34229

    $1,850,000Listed 06/24/2026 12:21PM   MLS ID: A4695429

    For Sale A4695429 - 206 FOUR KNOT LN, OSPREY, FL 34229 99 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2411
       Built: 1991
    Monthly Fee: $219
       Tax: $9,449 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,143 (change assumption)
    Mortgage ($10,137) + Fees ($219) + Taxes in 2025 ($787)


    Taxes:$9,449

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 919 TRANQUILITY CIR, OSPREY, FL 34229

    $774,900Listed 06/24/2026 10:34AM   MLS ID: N6144801

    For Sale N6144801 - 919 TRANQUILITY CIR, OSPREY, FL 34229 62 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2854
       Built: 2001
    Monthly Fee: $158
       Tax: $6,634 (2025)
    Community: North Creek Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,957 (change assumption)
    Mortgage ($4,246) + Fees ($158) + Taxes in 2025 ($553)


    Taxes:$6,634

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 135 TINA ISLAND DR, OSPREY, FL 34229

    $3,295,00050 Days on yellowkey   MLS ID: A4692366

    For Sale A4692366 - 135 TINA ISLAND DR, OSPREY, FL 34229 47 photos

    Bed: 3   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 2572
       Built: 2011
    Monthly Fee: $10
       Tax: $12,575 (2025)
    Community: Sorrento Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,112 (change assumption)
    Mortgage ($18,054) + Fees ($10) + Taxes in 2025 ($1,048)


    Taxes:$12,575

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 14041 BELLAGIO WAY #214, OSPREY, FL 34229

    $700,00071 Days on yellowkey   MLS ID: A4689731

    For Sale A4689731 - 14041 BELLAGIO WAY #214, OSPREY, FL 34229 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1799
       Built: 2006
    Monthly Fee: $1,248
       Tax: $6,254 (2025)
    Community: Villas At Bellagio Harbor Village
    Spa: No

    Condo


    Estimated Monthly Payment: $5,605 (change assumption)
    Mortgage ($3,836) + Fees ($1,248) + Taxes in 2025 ($521)


    Taxes:$6,254

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 116 WOODLAND PL #116, OSPREY, FL 34229

    $254,90013 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


  • 14401 MASTHEAD DR, OSPREY, FL 34229

    $2,995,000111 Days on yellowkey   MLS ID: A4684834

    REDUCED by $155,000 (4.9%) on 06/12/2026

    For Sale A4684834 - 14401 MASTHEAD DR, OSPREY, FL 34229 96 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2665
       Built: 2017
    Monthly Fee: $643
       Tax: $874 (2025)
    Community: Bayside
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,126 (change assumption)
    Mortgage ($16,411) + Fees ($643) + Taxes in 2025 ($73)


    Taxes:$874

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 570 BLACKBURN POINT RD #11, OSPREY, FL 34229

    $39,500345 Days on yellowkey   MLS ID: A4658755

    For Sale A4658755 - 570 BLACKBURN POINT RD #11, OSPREY, FL 34229 4 photos

    Bed:    Bath: 0.0
    Built: 2006
       Tax: $196 (2024)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $233 (change assumption)
    Mortgage ($216) + Taxes in 2024 ($16)


    Taxes:$196

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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

    $1,095,000219 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

    $1,165,00078 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

    $999,00084 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


  • 472 PARK TRACE BLVD, OSPREY, FL 34229

    $599,000145 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

    $739,00043 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

    $655,00043 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

    $2,189,000176 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

    $1,489,000153 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

    $1,775,000145 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




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.