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Osprey Single Family Homes For Sale - 80 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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  • 352 GLENWOOD AVE, OSPREY, FL 34229

    $417,000394 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

    $427,00046 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

    $6,475,000257 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


  • 293 TURQUOISE LN, OSPREY, FL 34229

    $875,000524 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

    $535,00048 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

    $875,000118 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

    $749,00027 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

    $799,000441 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


  • 49 OSPREY POINT DR, OSPREY, FL 34229

    $2,399,000217 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

    $419,000174 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


  • 272 FOUR KNOT LN, OSPREY, FL 34229

    $1,095,00036 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

    $2,395,000333 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


  • 730 SARABAY RD, OSPREY, FL 34229

    $4,995,000211 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

    $599,900161 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


  • 447 N SHORE DR, OSPREY, FL 34229

    $499,000105 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

    $275,00043 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


  • 678 FAITH AVE, OSPREY, FL 34229

    $749,000189 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


  • 236 SAINT JAMES PARK, OSPREY, FL 34229

    $2,700,000448 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

    $1,950,000223 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

    $2,195,000240 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




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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.