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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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  • 320 TROPIC DR, OSPREY, FL 34229

    $195,00044 Days on yellowkey   MLS ID: A4692490

    For Sale A4692490 - 320 TROPIC DR, OSPREY, FL 34229 37 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1199
       Built: 1980
    Monthly Fee: $430
       Tax: $1,983 (2025)
    Community: Arbors
    Manufactured Home


    Estimated Monthly Payment: $1,664 (change assumption)
    Mortgage ($1,068) + Fees ($430) + Taxes in 2025 ($165)


    Taxes:$1,983

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18 N CASEY KEY RD, OSPREY, FL 34229

    $1,750,000247 Days on yellowkey   MLS ID: A4669083

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

    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


  • 4296 EXPEDITION WAY #104, OSPREY, FL 34229

    $299,99025 Days on yellowkey   MLS ID: A4694926

    For Sale A4694926 - 4296 EXPEDITION WAY #104, OSPREY, FL 34229 49 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1135
       Built: 2017   Tax: $3,507 (2025)
    Community: Bay Street Village
    Townhouse


    Estimated Monthly Payment: $1,936 (change assumption)
    Mortgage ($1,644) + Taxes in 2025 ($292)


    Taxes:$3,507

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 352 GLENWOOD AVE, OSPREY, FL 34229

    $417,000400 Days on yellowkey   MLS ID: N6138982

    REDUCED by $12,500 (2.9%) on 05/29/2026

    For Sale N6138982 - 352 GLENWOOD AVE, OSPREY, FL 34229 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1300
       Built: 2021   Tax: $4,355 (2024)
    Community: Siesta Rev Resub Of Pt
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,285) + Taxes in 2024 ($363)


    Taxes:$4,355

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 212 WASHINGTON AVE, OSPREY, FL 34229

    $427,00052 Days on yellowkey   MLS ID: O6404307

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6404307 - 212 WASHINGTON AVE, OSPREY, FL 34229 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1478
       Built: 1999   Tax: $3,294 (2025)
    Community: Ogburns T B Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,614 (change assumption)
    Mortgage ($2,340) + Taxes in 2025 ($275)


    Taxes:$3,294

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 121 N CASEY KEY RD, OSPREY, FL 34229

    $6,475,000263 Days on yellowkey   MLS ID: A4667263

    For Sale A4667263 - 121 N CASEY KEY RD, OSPREY, FL 34229 65 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4096
       Built: 1969
    Monthly Fee: $33
       Tax: $37,172 (2024)
    Community: Casey Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $38,609 (change assumption)
    Mortgage ($35,479) + Fees ($33) + Taxes in 2024 ($3,098)


    Taxes:$37,172

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 14021 BELLAGIO WAY #404, OSPREY, FL 34229

    $1,175,00058 Days on yellowkey   MLS ID: N6144070

    REDUCED by $114,000 (8.8%) on 05/28/2026

    For Sale N6144070 - 14021 BELLAGIO WAY #404, OSPREY, FL 34229 77 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2187
       Built: 2006
    Monthly Fee: $1,644
       Tax: $5,636 (2025)
    Community: Villas At Bellagio Harbor Village
    Condo


    Estimated Monthly Payment: $8,552 (change assumption)
    Mortgage ($6,438) + Fees ($1,644) + Taxes in 2025 ($470)


    Taxes:$5,636

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 293 TURQUOISE LN, OSPREY, FL 34229

    $875,000530 Days on yellowkey   MLS ID: A4633961

    REDUCED by $35,000 (3.8%) on 05/28/2026

    For Sale A4633961 - 293 TURQUOISE LN, OSPREY, FL 34229 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2271
       Built: 2001
    Monthly Fee: $400
       Tax: $7,520 (2024)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,821 (change assumption)
    Mortgage ($4,794) + Fees ($400) + Taxes in 2024 ($627)


    Taxes:$7,520

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 4429 CONCHFISH LN, OSPREY, FL 34229

    $535,00054 Days on yellowkey   MLS ID: A4689967

    For Sale A4689967 - 4429 CONCHFISH LN, OSPREY, FL 34229 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2018
    Monthly Fee: $147
       Tax: $5,968 (2025)
    Community: Palms/Casey Key
    Single Family


    Estimated Monthly Payment: $3,576 (change assumption)
    Mortgage ($2,931) + Fees ($147) + Taxes in 2025 ($497)


    Taxes:$5,968

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 664 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $875,000124 Days on yellowkey   MLS ID: A4681662

    0 Days Off yellowkey (back on 5/24/2026)

    REDUCED by $12,000 (1.4%) on 05/14/2026

    For Sale A4681662 - 664 CRANE PRAIRIE WAY, OSPREY, FL 34229 63 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2870
       Built: 2003
    Monthly Fee: $437
       Tax: $5,460 (2025)
    Community: Willowbend Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,686 (change assumption)
    Mortgage ($4,794) + Fees ($437) + Taxes in 2025 ($455)


    Taxes:$5,460

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 103 BISHOPS COURT RD, OSPREY, FL 34229

    $749,00033 Days on yellowkey   MLS ID: A4694468

    For Sale A4694468 - 103 BISHOPS COURT RD, OSPREY, FL 34229 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2034
       Built: 2000
    Monthly Fee: $425
       Tax: $3,743 (2025)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,841 (change assumption)
    Mortgage ($4,104) + Fees ($425) + Taxes in 2025 ($312)


    Taxes:$3,743

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School


  • 13 BAYHEAD LN, OSPREY, FL 34229

    $799,000447 Days on yellowkey   MLS ID: A4645829

    REDUCED by $51,000 (6.0%) on 05/13/2026

    For Sale A4645829 - 13 BAYHEAD LN, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2310
       Built: 2001
    Monthly Fee: $425
       Tax: $3,620 (2024)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,105 (change assumption)
    Mortgage ($4,378) + Fees ($425) + Taxes in 2024 ($302)


    Taxes:$3,620

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 5100 JESSIE HARBOR DR #403, OSPREY, FL 34229

    $650,000175 Days on yellowkey   MLS ID: A4676382

    REDUCED by $29,900 (4.4%) on 05/21/2026

    For Sale A4676382 - 5100 JESSIE HARBOR DR #403, OSPREY, FL 34229 44 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2004
    Monthly Fee: $1,027
       Tax: $5,647 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $5,059 (change assumption)
    Mortgage ($3,562) + Fees ($1,027) + Taxes in 2025 ($471)


    Taxes:$5,647

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 49 OSPREY POINT DR, OSPREY, FL 34229

    $2,399,000223 Days on yellowkey   MLS ID: A4671762

    REDUCED by $101,000 (4.0%) on 05/03/2026

    For Sale A4671762 - 49 OSPREY POINT DR, OSPREY, FL 34229 96 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3953
       Built: 1989
    Monthly Fee: $475
       Tax: $14,206 (2024)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,804 (change assumption)
    Mortgage ($13,145) + Fees ($475) + Taxes in 2024 ($1,184)


    Taxes:$14,206

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 524 SARABAY RD, OSPREY, FL 34229

    $419,000180 Days on yellowkey   MLS ID: A4676179

    For Sale A4676179 - 524 SARABAY RD, OSPREY, FL 34229 41 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1760
       Built: 1956   Tax: $1,926 (2025)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $2,456 (change assumption)
    Mortgage ($2,296) + Taxes in 2025 ($161)


    Taxes:$1,926

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 120 VILLA DR #120, OSPREY, FL 34229

    $497,000435 Days on yellowkey   MLS ID: N6138441

    REDUCED by $13,000 (2.5%) on 04/25/2026

    For Sale N6138441 - 120 VILLA DR #120, OSPREY, FL 34229 55 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1404
       Built: 1978
    Monthly Fee: $529
       Tax: $5,056 (2025)
    Community: Sorrento Villas 1
    Villa


    Estimated Monthly Payment: $3,674 (change assumption)
    Mortgage ($2,723) + Fees ($529) + Taxes in 2025 ($421)


    Taxes:$5,056

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 280 HIDDEN BAY DR #302, OSPREY, FL 34229

    $749,00044 Days on yellowkey   MLS ID: A4690813

    For Sale A4690813 - 280 HIDDEN BAY DR #302, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1937
       Built: 2024   Tax: $7,907 (2025)
    Community: Edgewater/Hidden Bay Ph 3
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,763 (change assumption)
    Mortgage ($4,104) + Taxes in 2025 ($659)


    Taxes:$7,907

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 272 FOUR KNOT LN, OSPREY, FL 34229

    $1,095,00042 Days on yellowkey   MLS ID: N6144313

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale N6144313 - 272 FOUR KNOT LN, OSPREY, FL 34229 80 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2723
       Built: 1978
    Monthly Fee: $219
       Tax: $5,738 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,697 (change assumption)
    Mortgage ($6,000) + Fees ($219) + Taxes in 2025 ($478)


    Taxes:$5,738

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 852 MACEWEN DR, OSPREY, FL 34229

    $2,395,000339 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


  • 14041 BELLAGIO WAY #218, OSPREY, FL 34229

    $999,000216 Days on yellowkey   MLS ID: A4672639

    0 Days Off yellowkey (back on 5/14/2026)

    REDUCED by $100,000 (9.1%) on 04/03/2026

    For Sale A4672639 - 14041 BELLAGIO WAY #218, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2086
       Built: 2006
    Monthly Fee: $1,649
       Tax: $6,459 (2024)
    Community: Villas At Bellagio Harbor Village
    Condo


    Estimated Monthly Payment: $7,661 (change assumption)
    Mortgage ($5,474) + Fees ($1,649) + Taxes in 2024 ($538)


    Taxes:$6,459

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.