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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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  • 909 MACEWEN DR, OSPREY, FL 34229

    $1,595,000649 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


  • 348 TROPIC DR, OSPREY, FL 34229

    $109,900255 Days on yellowkey   MLS ID: A4668240

    INCREASED by $900 (0.8%) on 04/28/2026

    For Sale A4668240 - 348 TROPIC DR, OSPREY, FL 34229 34 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 864
       Built: 1977
    Monthly Fee: $215
       Tax: $884 (2024)
    Community: Arbors
    Manufactured Home


    Estimated Monthly Payment: $891 (change assumption)
    Mortgage ($602) + Fees ($215) + Taxes in 2024 ($74)


    Taxes:$884

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 232 WOODLAND DR #232, OSPREY, FL 34229

    $259,900223 Days on yellowkey   MLS ID: A4671600

    0 Days Off yellowkey (back on 4/25/2026)

    REDUCED by $5,000 (1.9%) on 04/20/2026

    For Sale A4671600 - 232 WOODLAND DR #232, OSPREY, FL 34229 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1980   Tax: $2,202 (2025)
    Community: Pine Run Iii
    Condo


    Estimated Monthly Payment: $1,608 (change assumption)
    Mortgage ($1,424) + Taxes in 2025 ($184)


    Taxes:$2,202

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 313 LOOKOUT POINT DR, OSPREY, FL 34229

    $5,999,99978 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


  • 33 BISHOPS COURT RD #118, OSPREY, FL 34229

    $679,000158 Days on yellowkey   MLS ID: A4678425

    For Sale A4678425 - 33 BISHOPS COURT RD #118, OSPREY, FL 34229 69 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1890
       Built: 1984
    Monthly Fee: $400
       Tax: $3,750 (2025)
    Community: Oaks
    Spa: No

    Townhouse


    Estimated Monthly Payment: $4,433 (change assumption)
    Mortgage ($3,720) + Fees ($400) + Taxes in 2025 ($312)


    Taxes:$3,750

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 385 NORTH POINT RD #701, OSPREY, FL 34229

    $1,399,000120 Days on yellowkey   MLS ID: A4683454

    For Sale A4683454 - 385 NORTH POINT RD #701, OSPREY, FL 34229 97 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2594
       Built: 2000
    Monthly Fee: $400
       Tax: $6,082 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $8,572 (change assumption)
    Mortgage ($7,666) + Fees ($400) + Taxes in 2025 ($507)


    Taxes:$6,082

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 1602 SOUTHBAY DR, OSPREY, FL 34229

    $974,900281 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


  • 409 N POINT RD #601, OSPREY, FL 34229

    $1,250,000141 Days on yellowkey   MLS ID: A4679994

    For Sale A4679994 - 409 N POINT RD #601, OSPREY, FL 34229 63 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2004
    Monthly Fee: $400
       Tax: $10,238 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $8,102 (change assumption)
    Mortgage ($6,849) + Fees ($400) + Taxes in 2025 ($853)


    Taxes:$10,238

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 3603 N POINT RD #202, OSPREY, FL 34229

    $699,0001083 Days on yellowkey   MLS ID: A4575407

    For Sale A4575407 - 3603 N POINT RD #202, OSPREY, FL 34229 50 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 3147
       Built: 2007
    Monthly Fee: $400
       Tax: $4,135 (2022)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $4,575 (change assumption)
    Mortgage ($3,830) + Fees ($400) + Taxes in 2022 ($345)


    Taxes:$4,135

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2022

    Middle School: Laurel Nokomis Middle


  • 409 N POINT RD #502, OSPREY, FL 34229

    $599,000650 Days on yellowkey   MLS ID: A4621353

    For Sale A4621353 - 409 N POINT RD #502, OSPREY, FL 34229 48 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2055
       Built: 2004
    Monthly Fee: $400
       Tax: $4,345 (2023)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $4,044 (change assumption)
    Mortgage ($3,282) + Fees ($400) + Taxes in 2023 ($362)


    Taxes:$4,345

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2023

    Middle School: Brookside Middle


  • 448 E MACEWEN DR, OSPREY, FL 34229

    $2,100,00088 Days on yellowkey   MLS ID: A4687195

    For Sale A4687195 - 448 E MACEWEN DR, OSPREY, FL 34229 52 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3768
       Built: 1998
    Monthly Fee: $142
       Tax: $9,639 (2025)
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $12,452 (change assumption)
    Mortgage ($11,507) + Fees ($142) + Taxes in 2025 ($803)


    Taxes:$9,639

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 854 N CASEY KEY RD, OSPREY, FL 34229

    $4,750,000118 Days on yellowkey   MLS ID: N6143043

    1 Days Off yellowkey (back on 3/26/2026)

    For Sale N6143043 - 854 N CASEY KEY RD, OSPREY, FL 34229 23 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 3462
       Built: 1975
    Community: Acreage & Unrec
    Single Family


    Estimated Monthly Payment: $26,027 (change assumption)
    Mortgage ($26,027)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 700 FAITH AVE, OSPREY, FL 34229

    $1,200,000228 Days on yellowkey   MLS ID: A4667634

    For Sale A4667634 - 700 FAITH AVE, OSPREY, FL 34229 74 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2474
       Built: 1982
    Community: Trinity Acres
    Single Family


    Estimated Monthly Payment: $6,575 (change assumption)
    Mortgage ($6,575)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 530 N MAC EWEN DR, OSPREY, FL 34229

    $2,400,000124 Days on yellowkey   MLS ID: A4683029

    1 Days Off yellowkey (back on 3/20/2026)

    For Sale A4683029 - 530 N MAC EWEN DR, OSPREY, FL 34229 83 photos

    Bed: 4   Bath: 5.5
    Liv Area Sq Ft: 4346
       Built: 2002
    Community: Oaks 2 Ph 4-C Pt 3
    Single Family


    Estimated Monthly Payment: $13,150 (change assumption)
    Mortgage ($13,150)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1211 LOST CREEK CT, OSPREY, FL 34229

    $829,000   MLS ID: A4680671

    For Sale A4680671 - 1211 LOST CREEK CT, OSPREY, FL 34229 42 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2876
       Built: 2002
    Community: Rivendell Woodlands
    Single Family


    Estimated Monthly Payment: $4,542 (change assumption)
    Mortgage ($4,542)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 232 HIDDEN BAY DR #504, OSPREY, FL 34229

    $569,000   MLS ID: A4668602

    For Sale A4668602 - 232 HIDDEN BAY DR #504, OSPREY, FL 34229 63 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2000
       Built: 2001
    Community: Baypointe Vista 2
    Condo


    Estimated Monthly Payment: $3,118 (change assumption)
    Mortgage ($3,118)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None




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.