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Osprey Single Family Homes For Sale - 89 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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  • 107 SORRENTO DR, OSPREY, FL 34229

    $425,00089 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


  • 408 YACHT HARBOR DR, OSPREY, FL 34229

    $1,375,00034 Days on yellowkey   MLS ID: A4691576

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale A4691576 - 408 YACHT HARBOR DR, OSPREY, FL 34229 46 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2624
       Built: 1976
    Monthly Fee: $219
       Tax: $9,482 (2025)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $8,543 (change assumption)
    Mortgage ($7,534) + Fees ($219) + Taxes in 2025 ($790)


    Taxes:$9,482

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 854 MACEWEN DR, OSPREY, FL 34229

    $3,690,000225 Days on yellowkey   MLS ID: A4668918

    REDUCED by $100,000 (2.6%) on 05/01/2026

    For Sale A4668918 - 854 MACEWEN DR, OSPREY, FL 34229 69 photos

    Bed: 4   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 9081
       Built: 2003
    Monthly Fee: $133
       Tax: $26,109 (2024)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,527 (change assumption)
    Mortgage ($20,219) + Fees ($133) + Taxes in 2024 ($2,176)


    Taxes:$26,109

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 650 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $799,990119 Days on yellowkey   MLS ID: A4680121

    For Sale A4680121 - 650 CRANE PRAIRIE WAY, OSPREY, FL 34229 64 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3183
       Built: 2005
    Monthly Fee: $427
       Tax: $8,138 (2025)
    Community: Willowbend Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,489 (change assumption)
    Mortgage ($4,383) + Fees ($427) + Taxes in 2025 ($678)


    Taxes:$8,138

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 324 BAYSHORE DR, OSPREY, FL 34229

    $3,995,00097 Days on yellowkey   MLS ID: A4683138

    REDUCED by $255,000 (6.0%) on 04/29/2026

    For Sale A4683138 - 324 BAYSHORE DR, OSPREY, FL 34229 40 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4389
       Built: 2000   Tax: $23,356 (2025)
    Community: Bay Acres - Resub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,836 (change assumption)
    Mortgage ($21,890) + Taxes in 2025 ($1,946)


    Taxes:$23,356

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 909 MACEWEN DR, OSPREY, FL 34229

    $1,595,000626 Days on yellowkey   MLS ID: A4621683

    For Sale A4621683 - 909 MACEWEN DR, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4241
       Built: 1991
    Monthly Fee: $133
       Tax: $9,867 (2023)
    Community: Oaks 2 Phase 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,695 (change assumption)
    Mortgage ($8,740) + Fees ($133) + Taxes in 2023 ($822)


    Taxes:$9,867

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2023

    Middle School: Laurel Nokomis Middle


  • 25 SUGAR MILL DR, OSPREY, FL 34229

    $1,550,000130 Days on yellowkey   MLS ID: A4678423

    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: $9,630 (change assumption)
    Mortgage ($8,493) + 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


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,00047 Days on yellowkey   MLS ID: A4685559

    For Sale A4685559 - 61 BAYHEAD LN, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3180
       Built: 1993
    Monthly Fee: $458
       Tax: $4,573 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,332 (change assumption)
    Mortgage ($6,493) + Fees ($458) + Taxes in 2025 ($381)


    Taxes:$4,573

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 113 BURNEY RD, OSPREY, FL 34229

    $999,50039 Days on yellowkey   MLS ID: A4690672

    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


  • 313 LOOKOUT POINT DR, OSPREY, FL 34229

    $5,999,99955 Days on yellowkey   MLS ID: A4688995

    For Sale A4688995 - 313 LOOKOUT POINT DR, OSPREY, FL 34229 100 photos

    Bed: 4   Bath: 4.5   Gar: 5
    Liv Area Sq Ft: 5337
       Built: 2016
    Monthly Fee: $219
       Tax: $20,559 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $34,808 (change assumption)
    Mortgage ($32,876) + Fees ($219) + Taxes in 2025 ($1,713)


    Taxes:$20,559

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 642 TRENTON WAY, OSPREY, FL 34229

    $2,150,00068 Days on yellowkey   MLS ID: A4686927

    For Sale A4686927 - 642 TRENTON WAY, OSPREY, FL 34229 86 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 3939
       Built: 2002
    Monthly Fee: $142
       Tax: $16,068 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,262 (change assumption)
    Mortgage ($11,781) + Fees ($142) + Taxes in 2025 ($1,339)


    Taxes:$16,068

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 362 MACEWEN DR, OSPREY, FL 34229

    $2,249,000140 Days on yellowkey   MLS ID: A4676567

    For Sale A4676567 - 362 MACEWEN DR, OSPREY, FL 34229 55 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4117
       Built: 1998
    Monthly Fee: $142
       Tax: $10,742 (2025)
    Community: The Oaks
    Single Family


    Estimated Monthly Payment: $13,360 (change assumption)
    Mortgage ($12,323) + Fees ($142) + Taxes in 2025 ($895)


    Taxes:$10,742

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1602 SOUTHBAY DR, OSPREY, FL 34229

    $974,900258 Days on yellowkey   MLS ID: A4665288

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale A4665288 - 1602 SOUTHBAY DR, OSPREY, FL 34229 56 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2980
       Built: 1986
    Monthly Fee: $204
       Tax: $9,955 (2024)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $6,375 (change assumption)
    Mortgage ($5,342) + Fees ($204) + Taxes in 2024 ($830)


    Taxes:$9,955

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 472 PARK TRACE BLVD, OSPREY, FL 34229

    $609,000122 Days on yellowkey   MLS ID: A4680326

    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: $3,889 (change assumption)
    Mortgage ($3,337) + 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


  • 32 BAY AVE, OSPREY, FL 34229

    $415,000233 Days on yellowkey   MLS ID: N6140978

    2 Days Off yellowkey (back on 4/9/2026)

    For Sale N6140978 - 32 BAY AVE, OSPREY, FL 34229 51 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 1962
    Monthly Fee: $13
       Tax: $3,612 (2024)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $2,588 (change assumption)
    Mortgage ($2,274) + Fees ($13) + Taxes in 2024 ($301)


    Taxes:$3,612

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1471 SHOAL WAY, OSPREY, FL 34229

    $1,499,00098 Days on yellowkey   MLS ID: A4683702

    For Sale A4683702 - 1471 SHOAL WAY, OSPREY, FL 34229 37 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2798
       Built: 1985
    Monthly Fee: $219
       Tax: $6,036 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,935 (change assumption)
    Mortgage ($8,213) + Fees ($219) + Taxes in 2025 ($503)


    Taxes:$6,036

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1527 BUOY LN, OSPREY, FL 34229

    $1,199,00055 Days on yellowkey   MLS ID: A4688266

    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: $7,487 (change assumption)
    Mortgage ($6,570) + 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


  • 1795 HIGHLAND RD, OSPREY, FL 34229

    $385,00086 Days on yellowkey   MLS ID: A4684679

    3 Days Off yellowkey (back on 4/6/2026)

    For Sale A4684679 - 1795 HIGHLAND RD, OSPREY, FL 34229 74 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1879
       Built: 1999
    Monthly Fee: $150
       Tax: $2,809 (2025)
    Community: Towns-End Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,494 (change assumption)
    Mortgage ($2,110) + Fees ($150) + Taxes in 2025 ($234)


    Taxes:$2,809

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 434 MACEWEN DR, OSPREY, FL 34229

    $1,465,00063 Days on yellowkey   MLS ID: A4687368

    0 Days Off yellowkey (back on 4/5/2026)

    For Sale A4687368 - 434 MACEWEN DR, OSPREY, FL 34229 55 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2414
       Built: 1997
    Monthly Fee: $142
       Tax: $11,162 (2025)
    Community: Oaks 2 Ph 3
    Single Family


    Estimated Monthly Payment: $9,099 (change assumption)
    Mortgage ($8,027) + Fees ($142) + Taxes in 2025 ($930)


    Taxes:$11,162

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 1016 SCHERER WAY, OSPREY, FL 34229

    $950,00064 Days on yellowkey   MLS ID: A4687161

    0 Days Off yellowkey (back on 3/30/2026)

    For Sale A4687161 - 1016 SCHERER WAY, OSPREY, FL 34229 76 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2921
       Built: 2003
    Monthly Fee: $115
       Tax: $5,442 (2025)
    Community: Rivendell Unit 5 The Woodlands
    Single Family


    Estimated Monthly Payment: $5,774 (change assumption)
    Mortgage ($5,205) + Fees ($115) + Taxes in 2025 ($453)


    Taxes:$5,442

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota 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.