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Oaks Homes for Sale in Osprey - 55 homes

Oaks homes for sale are located in Sarasota County, Florida. Find Oaks Homes in Osprey for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Oaks, Osprey homes.

Location: Oaks, Osprey

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  • 642 TRENTON WAY, OSPREY, FL 34229

    $2,150,00066 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

    $2,249,000138 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


  • 409 NORTH POINT RD #401, OSPREY, FL 34229

    $625,00039 Days on yellowkey   MLS ID: A4690812

    For Sale A4690812 - 409 NORTH POINT RD #401, OSPREY, FL 34229 90 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2004
    Monthly Fee: $367
       Tax: $6,285 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $4,315 (change assumption)
    Mortgage ($3,425) + Fees ($367) + Taxes in 2025 ($524)


    Taxes:$6,285

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


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

    $1,399,00095 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


  • 51 MAC EWEN DR #14, OSPREY, FL 34229

    $285,00040 Days on yellowkey   MLS ID: A4690371

    For Sale A4690371 - 51 MAC EWEN DR #14, OSPREY, FL 34229 19 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 595
       Built: 1990
    Monthly Fee: $142
       Tax: $2,483 (2026)
    Community: Windsor Lodge At The Oaks
    Condo


    Estimated Monthly Payment: $1,911 (change assumption)
    Mortgage ($1,562) + Fees ($142) + Taxes in 2026 ($207)


    Taxes:$2,483

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2026

    Middle School: Sarasota Middle


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

    $1,250,000116 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


  • 409 N POINT RD #1001, OSPREY, FL 34229

    $2,750,00053 Days on yellowkey   MLS ID: A4689096

    1 Days Off yellowkey (back on 4/8/2026)

    For Sale A4689096 - 409 N POINT RD #1001, OSPREY, FL 34229 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3029
       Built: 2004
    Monthly Fee: $400
       Tax: $16,089 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $16,809 (change assumption)
    Mortgage ($15,068) + Fees ($400) + Taxes in 2025 ($1,341)


    Taxes:$16,089

    Elementary School: Pine View School

    High School: Riverview High

    Tax Year: 2025

    Middle School: Pine View School


  • 434 MACEWEN DR, OSPREY, FL 34229

    $1,465,00061 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


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

    $699,0001058 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

    $599,000625 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

    $2,100,00063 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


  • 401 WALLS WAY, OSPREY, FL 34229

    $1,800,000120 Days on yellowkey   MLS ID: A4680312

    For Sale A4680312 - 401 WALLS WAY, OSPREY, FL 34229 51 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 4387
       Built: 1990
    Community: Oaks 2 Ph 1
    Single Family


    Estimated Monthly Payment: $9,863 (change assumption)
    Mortgage ($9,863)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 530 N MAC EWEN DR, OSPREY, FL 34229

    $2,400,00099 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


  • 433 E MACEWEN DR, OSPREY, FL 34229

    $2,250,000   MLS ID: A4676505

    For Sale A4676505 - 433 E MACEWEN DR, OSPREY, FL 34229 72 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 4012
       Built: 1998
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $12,328 (change assumption)
    Mortgage ($12,328)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 360 N POINT RD, OSPREY, FL 34229

    $1,499,000   MLS ID: A4617671

    For Sale A4617671 - 360 N POINT RD, OSPREY, FL 34229 57 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 2913
       Built: 2023
    Community: Oaks 3 Ph 1
    Single Family


    Estimated Monthly Payment: $8,213 (change assumption)
    Mortgage ($8,213)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


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Why Bother Searching Elsewhere for Oaks Homes for Sale and Other Osprey Real Estate?

Oaks 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 Oaks. You can use our website to view Multiple Listing Service (MLS) data on Oaks 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 Oaks. 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.