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Osprey Single Family Homes For Sale - 90 homes

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

Location: Osprey

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  • 852 MACEWEN DR, OSPREY, FL 34229

    $2,395,000314 Days on yellowkey   MLS ID: A4659276

    For Sale A4659276 - 852 MACEWEN DR, OSPREY, FL 34229 73 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4519
       Built: 1992
    Monthly Fee: $133
       Tax: $12,855 (2024)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,327 (change assumption)
    Mortgage ($13,123) + Fees ($133) + Taxes in 2024 ($1,071)


    Taxes:$12,855

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 204 WINDWARD DR, OSPREY, FL 34229

    $1,050,00019 Days on yellowkey   MLS ID: A4693139

    For Sale A4693139 - 204 WINDWARD DR, OSPREY, FL 34229 73 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 1986
    Monthly Fee: $86
       Tax: $4,761 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,236 (change assumption)
    Mortgage ($5,753) + Fees ($86) + Taxes in 2025 ($397)


    Taxes:$4,761

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 730 SARABAY RD, OSPREY, FL 34229

    $4,995,000192 Days on yellowkey   MLS ID: A4672618

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale A4672618 - 730 SARABAY RD, OSPREY, FL 34229 42 photos

    Bed: 4   Bath: 5.5   Gar: 7
    Liv Area Sq Ft: 6308
       Built: 2011   Tax: $47,200 (2024)
    Community: Sarabay Acres
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,303 (change assumption)
    Mortgage ($27,369) + Taxes in 2024 ($3,933)


    Taxes:$47,200

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 186 WINDWARD DR, OSPREY, FL 34229

    $599,900142 Days on yellowkey   MLS ID: N6142087

    0 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $49,600 (7.6%) on 05/07/2026

    For Sale N6142087 - 186 WINDWARD DR, OSPREY, FL 34229 93 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2505
       Built: 1983
    Monthly Fee: $204
       Tax: $7,566 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,122 (change assumption)
    Mortgage ($3,287) + Fees ($204) + Taxes in 2025 ($631)


    Taxes:$7,566

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 227 SAINT JAMES PARK, OSPREY, FL 34229

    $885,000122 Days on yellowkey   MLS ID: A4679867

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale A4679867 - 227 SAINT JAMES PARK, OSPREY, FL 34229 93 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2071
       Built: 1986
    Monthly Fee: $142
       Tax: $4,611 (2025)
    Community: Oaks 2 Ph 1
    Single Family


    Estimated Monthly Payment: $5,375 (change assumption)
    Mortgage ($4,849) + Fees ($142) + Taxes in 2025 ($384)


    Taxes:$4,611

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 447 N SHORE DR, OSPREY, FL 34229

    $499,00086 Days on yellowkey   MLS ID: A4684009

    REDUCED by $16,350 (3.2%) on 05/12/2026

    For Sale A4684009 - 447 N SHORE DR, OSPREY, FL 34229 45 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1874
       Built: 1964   Tax: $4,243 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $3,088 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($354)


    Taxes:$4,243

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 222 GLENWOOD AVE, OSPREY, FL 34229

    $275,00024 Days on yellowkey   MLS ID: TB8504427

    0 Days Off yellowkey (back on 5/9/2026)

    For Sale TB8504427 - 222 GLENWOOD AVE, OSPREY, FL 34229 53 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 952
       Built: 1990   Tax: $3,409 (2025)
    Community: Tb Ogburns Add
    Single Family


    Estimated Monthly Payment: $1,791 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($284)


    Taxes:$3,409

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 1361 NEW FOREST LN, OSPREY, FL 34229

    $550,00036 Days on yellowkey   MLS ID: A4691036

    For Sale A4691036 - 1361 NEW FOREST LN, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2074
       Built: 2002
    Monthly Fee: $292
       Tax: $5,783 (2025)
    Community: Rivendell Woodlands
    Single Family


    Estimated Monthly Payment: $3,788 (change assumption)
    Mortgage ($3,014) + Fees ($292) + Taxes in 2025 ($482)


    Taxes:$5,783

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 18 N CASEY KEY RD, OSPREY, FL 34229

    $1,750,000222 Days on yellowkey   MLS ID: A4669083

    REDUCED by $250,000 (12.5%) on 05/08/2026

    For Sale A4669083 - 18 N CASEY KEY RD, OSPREY, FL 34229 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1977
       Built: 1973   Tax: $24,015 (2024)
    Community: Casey Key
    Single Family


    Estimated Monthly Payment: $11,590 (change assumption)
    Mortgage ($9,589) + Taxes in 2024 ($2,001)


    Taxes:$24,015

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 678 FAITH AVE, OSPREY, FL 34229

    $749,000170 Days on yellowkey   MLS ID: A4674865

    REDUCED by $26,000 (3.4%) on 05/08/2026

    For Sale A4674865 - 678 FAITH AVE, OSPREY, FL 34229 51 photos

    Bed: 3   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2583
       Built: 1995   Tax: $5,871 (2025)
    Community: Trinity Acres
    Single Family


    Estimated Monthly Payment: $4,593 (change assumption)
    Mortgage ($4,104) + Taxes in 2025 ($489)


    Taxes:$5,871

    Elementary School: Pine View School

    High School: None

    Tax Year: 2025

    Middle School: Pine View School


  • 21 BAYHEAD LN, OSPREY, FL 34229

    $850,000257 Days on yellowkey   MLS ID: A4664085

    For Sale A4664085 - 21 BAYHEAD LN, OSPREY, FL 34229 92 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2246
       Built: 2002
    Monthly Fee: $458
       Tax: $4,221 (2024)
    Community: Bishopscourt At The Oaks Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,467 (change assumption)
    Mortgage ($4,657) + Fees ($458) + Taxes in 2024 ($352)


    Taxes:$4,221

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 236 SAINT JAMES PARK, OSPREY, FL 34229

    $2,700,000429 Days on yellowkey   MLS ID: A4644125

    For Sale A4644125 - 236 SAINT JAMES PARK, OSPREY, FL 34229 88 photos

    Bed: 6   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 6246
       Built: 1986
    Monthly Fee: $283
       Tax: $22,433 (2024)
    Community: Oaks 2 Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,947 (change assumption)
    Mortgage ($14,794) + Fees ($283) + Taxes in 2024 ($1,869)


    Taxes:$22,433

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 538 DOVE POINTE DR, OSPREY, FL 34229

    $1,950,000204 Days on yellowkey   MLS ID: A4669491

    For Sale A4669491 - 538 DOVE POINTE DR, OSPREY, FL 34229 75 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4346
       Built: 2002
    Monthly Fee: $133
       Tax: $17,098 (2024)
    Community: Oaks 2 Ph 4-C Pt 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,242 (change assumption)
    Mortgage ($10,685) + Fees ($133) + Taxes in 2024 ($1,425)


    Taxes:$17,098

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2024

    Middle School: Pine View School


  • 600 EAGLE WATCH LN, OSPREY, FL 34229

    $2,195,000221 Days on yellowkey   MLS ID: A4668497

    0 Days Off yellowkey (back on 5/6/2026)

    For Sale A4668497 - 600 EAGLE WATCH LN, OSPREY, FL 34229 91 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3681
       Built: 1992
    Monthly Fee: $133
       Tax: $14,836 (2024)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,396 (change assumption)
    Mortgage ($12,027) + Fees ($133) + Taxes in 2024 ($1,236)


    Taxes:$14,836

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 135 TINA ISLAND DR, OSPREY, FL 34229

    $3,295,00025 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: 1965
    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


  • 1486 LANDVIEW LN, OSPREY, FL 34229

    $850,000200 Days on yellowkey   MLS ID: D6144630

    0 Days Off yellowkey (back on 5/3/2026)

    For Sale D6144630 - 1486 LANDVIEW LN, OSPREY, FL 34229 78 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1869
       Built: 1977
    Monthly Fee: $204
       Tax: $7,488 (2025)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $5,485 (change assumption)
    Mortgage ($4,657) + Fees ($204) + Taxes in 2025 ($624)


    Taxes:$7,488

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 365 S SHORE DR, OSPREY, FL 34229

    $1,349,000149 Days on yellowkey   MLS ID: N6142101

    REDUCED by $31,000 (2.2%) on 05/02/2026

    For Sale N6142101 - 365 S SHORE DR, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1824
       Built: 1968   Tax: $7,804 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $8,042 (change assumption)
    Mortgage ($7,392) + Taxes in 2025 ($650)


    Taxes:$7,804

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 408 PARK TRACE BLVD, OSPREY, FL 34229

    $615,00086 Days on yellowkey   MLS ID: A4685004

    REDUCED by $10,000 (1.6%) on 04/24/2026

    For Sale A4685004 - 408 PARK TRACE BLVD, OSPREY, FL 34229 34 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 2003
    Monthly Fee: $54
       Tax: $4,652 (2025)
    Community: Park Trace Estates
    Single Family


    Estimated Monthly Payment: $3,811 (change assumption)
    Mortgage ($3,370) + Fees ($54) + Taxes in 2025 ($388)


    Taxes:$4,652

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 583 PINE RANCH EAST RD, OSPREY, FL 34229

    $569,000208 Days on yellowkey   MLS ID: A4670669

    For Sale A4670669 - 583 PINE RANCH EAST RD, OSPREY, FL 34229 55 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 1996
    Monthly Fee: $23
       Tax: $4,537 (2024)
    Community: Bay Oaks Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,519 (change assumption)
    Mortgage ($3,118) + Fees ($23) + Taxes in 2024 ($378)


    Taxes:$4,537

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 107 SORRENTO DR, OSPREY, FL 34229

    $425,00087 Days on yellowkey   MLS ID: N6143210

    REDUCED by $24,000 (5.3%) on 04/12/2026

    For Sale N6143210 - 107 SORRENTO DR, OSPREY, FL 34229 51 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1284
       Built: 1963
    Monthly Fee: $10
       Tax: $2,566 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $2,553 (change assumption)
    Mortgage ($2,329) + Fees ($10) + Taxes in 2025 ($214)


    Taxes:$2,566

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle




Why Bother Searching Elsewhere for Osprey Single Family Homes for Sale?

Osprey home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Osprey. You can use our website to view Multiple Listing Service (MLS) data on Osprey single family homes. 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 single family home 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.