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Osprey Homes For Sale & Real Estate - 140 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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  • 385 N POINT RD #304, OSPREY, FL 34229

    $1,100,000179 Days on yellowkey   MLS ID: A4678422

    For Sale A4678422 - 385 N POINT RD #304, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2778
       Built: 2000
    Monthly Fee: $400
       Tax: $5,845 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $6,914 (change assumption)
    Mortgage ($6,027) + Fees ($400) + Taxes in 2025 ($487)


    Taxes:$5,845

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 780 SARABAY RD #16, OSPREY, FL 34229

    $425,000Listed 07/14/2026 10:10AM   MLS ID: TB8528486

    For Sale TB8528486 - 780 SARABAY RD #16, OSPREY, FL 34229 50 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 1981
    Monthly Fee: $1,617
       Tax: $5,281 (2024)
    Community: Heron Bay Club Sec I
    Spa: Yes

    Villa


    Estimated Monthly Payment: $4,386 (change assumption)
    Mortgage ($2,329) + Fees ($1,617) + Taxes in 2024 ($440)


    Taxes:$5,281

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 401 WALLS WAY, OSPREY, FL 34229

    $1,775,000165 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


  • 730 FORDINGBRIDGE WAY, OSPREY, FL 34229

    $685,00025 Days on yellowkey   MLS ID: A4697358

    2 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $25,000 (3.5%) on 07/05/2026

    For Sale A4697358 - 730 FORDINGBRIDGE WAY, OSPREY, FL 34229 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2182
       Built: 2002
    Monthly Fee: $120
       Tax: $6,488 (2025)
    Community: Rivendell Woodlands
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,414 (change assumption)
    Mortgage ($3,753) + Fees ($120) + Taxes in 2025 ($541)


    Taxes:$6,488

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 204 WINDWARD DR, OSPREY, FL 34229

    $850,00064 Days on yellowkey   MLS ID: A4693139

    REDUCED by $75,000 (8.1%) on 07/13/2026

    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: $219
       Tax: $4,761 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,273 (change assumption)
    Mortgage ($4,657) + Fees ($219) + 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


  • 51 MACEWEN DR #11, OSPREY, FL 34229

    $235,000172 Days on yellowkey   MLS ID: A4679180

    For Sale A4679180 - 51 MACEWEN DR #11, OSPREY, FL 34229 42 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 623
       Built: 1990
    Monthly Fee: $142
       Tax: $2,367 (2025)
    Community: The Oaks Club
    Spa: No

    Condo


    Estimated Monthly Payment: $1,627 (change assumption)
    Mortgage ($1,288) + Fees ($142) + Taxes in 2025 ($197)


    Taxes:$2,367

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 173 NAVIGATION CIR #107, OSPREY, FL 34229

    $319,50029 Days on yellowkey   MLS ID: N6144704

    REDUCED by $8,500 (2.6%) on 07/13/2026

    For Sale N6144704 - 173 NAVIGATION CIR #107, OSPREY, FL 34229 71 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: $1,992 (change assumption)
    Mortgage ($1,751) + Taxes in 2025 ($241)


    Taxes:$2,892

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 408 PARK TRACE BLVD, OSPREY, FL 34229

    $595,000131 Days on yellowkey   MLS ID: A4685004

    2 Days Off yellowkey (back on 6/16/2026)

    REDUCED by $20,000 (3.3%) on 06/01/2026

    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: $3,702 (change assumption)
    Mortgage ($3,260) + Fees ($54) + Taxes in 2025 ($388)


    Taxes:$4,652

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 206 FOUR KNOT LN, OSPREY, FL 34229

    $1,850,00020 Days on yellowkey   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


  • 480 ORISKANY CT, OSPREY, FL 34229

    $1,500,000134 Days on yellowkey   MLS ID: A4684136

    REDUCED by $35,000 (2.3%) on 07/09/2026

    For Sale A4684136 - 480 ORISKANY CT, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3208
       Built: 1999
    Monthly Fee: $142
       Tax: $6,365 (2024)
    Community: The Oaks Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,891 (change assumption)
    Mortgage ($8,219) + Fees ($142) + Taxes in 2024 ($530)


    Taxes:$6,365

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 1495 LANDVIEW LN, OSPREY, FL 34229

    $799,90020 Days on yellowkey   MLS ID: A4697993

    For Sale A4697993 - 1495 LANDVIEW LN, OSPREY, FL 34229 75 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 1988
    Monthly Fee: $219
       Tax: $5,328 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,046 (change assumption)
    Mortgage ($4,383) + Fees ($219) + Taxes in 2025 ($444)


    Taxes:$5,328

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 116 WOODLAND PL #116, OSPREY, FL 34229

    $254,90033 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


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

    $725,00083 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


  • 1801 HIGHLAND RD, OSPREY, FL 34229

    $289,900301 Days on yellowkey   MLS ID: N6140508

    REDUCED by $10,000 (3.3%) on 06/03/2026

    For Sale N6140508 - 1801 HIGHLAND RD, OSPREY, FL 34229 41 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1165
       Built: 1999
    Monthly Fee: $150
       Tax: $2,578 (2025)
    Community: Towns-End Shores
    Spa: No

    Townhouse


    Estimated Monthly Payment: $1,953 (change assumption)
    Mortgage ($1,588) + Fees ($150) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 4428 CONCHFISH LN, OSPREY, FL 34229

    $548,000391 Days on yellowkey   MLS ID: A4656074

    For Sale A4656074 - 4428 CONCHFISH LN, OSPREY, FL 34229 13 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1861
       Built: 2018
    Monthly Fee: $147
       Tax: $5,936 (2024)
    Community: Palms/Casey Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,644 (change assumption)
    Mortgage ($3,003) + Fees ($147) + Taxes in 2024 ($495)


    Taxes:$5,936

    Elementary School: Laurel Nokomis Elementary

    High School: Pine View School

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 120 WOODLAND PL #120, OSPREY, FL 34229

    $299,0003 Days on yellowkey   MLS ID: D6148025

    For Sale D6148025 - 120 WOODLAND PL #120, OSPREY, FL 34229 65 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1979   Tax: $2,712 (2025)
    Community: Pine Run Ii
    Spa: No

    Condo


    Estimated Monthly Payment: $1,864 (change assumption)
    Mortgage ($1,638) + Taxes in 2025 ($226)


    Taxes:$2,712

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 2251 JESSIE HARBOR DR #2101, OSPREY, FL 34229

    $359,00011 Days on yellowkey   MLS ID: A4698891

    For Sale A4698891 - 2251 JESSIE HARBOR DR #2101, OSPREY, FL 34229 68 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1400
       Built: 2006   Tax: $4,920 (2025)
    Community: Blackburn Harbor Waterfront Vi
    Condo


    Estimated Monthly Payment: $2,377 (change assumption)
    Mortgage ($1,967) + Taxes in 2025 ($410)


    Taxes:$4,920

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 2309 JESSIE HARBOR DR #2402, OSPREY, FL 34229

    $497,00012 Days on yellowkey   MLS ID: A4698434

    For Sale A4698434 - 2309 JESSIE HARBOR DR #2402, OSPREY, FL 34229 93 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2006
       Built: 2006   Tax: $5,978 (2025)
    Community: Blackburn Harbor Waterfront Villas
    Spa: No

    Condo


    Estimated Monthly Payment: $3,221 (change assumption)
    Mortgage ($2,723) + Taxes in 2025 ($498)


    Taxes:$5,978

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 108 WOODLAND PL #108, OSPREY, FL 34229

    $285,0004 Days on yellowkey   MLS ID: A4699279

    For Sale A4699279 - 108 WOODLAND PL #108, OSPREY, FL 34229 50 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1316
       Built: 1979   Tax: $3,100 (2025)
    Community: Pine Run Ii
    Condo


    Estimated Monthly Payment: $1,820 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($258)


    Taxes:$3,100

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 89 NAVIGATION CIR, OSPREY, FL 34229

    $320,00053 Days on yellowkey   MLS ID: A4694435

    REDUCED by $25,000 (7.2%) on 06/27/2026

    For Sale A4694435 - 89 NAVIGATION CIR, OSPREY, FL 34229 61 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1449
       Built: 2014   Tax: $3,931 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,081 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($328)


    Taxes:$3,931

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle




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.