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Oaks Single Family Homes For Sale in Osprey - 36 homes

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

Location: Oaks, Osprey

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  • 236 SAINT JAMES PARK, OSPREY, FL 34229

    $2,700,000429 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

    $1,950,000204 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

    $2,195,000221 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


  • 583 PINE RANCH EAST RD, OSPREY, FL 34229

    $569,000208 Days on yellowkey   MLS ID: A4670669

    For Sale A4670669 - 583 PINE RANCH EAST RD, OSPREY, FL 34229 55 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 1996
    Monthly Fee: $23
       Tax: $4,537 (2024)
    Community: Bay Oaks Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,519 (change assumption)
    Mortgage ($3,118) + Fees ($23) + Taxes in 2024 ($378)


    Taxes:$4,537

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 854 MACEWEN DR, OSPREY, FL 34229

    $3,690,000223 Days on yellowkey   MLS ID: A4668918

    REDUCED by $100,000 (2.6%) on 05/01/2026

    For Sale A4668918 - 854 MACEWEN DR, OSPREY, FL 34229 69 photos

    Bed: 4   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 9081
       Built: 2003
    Monthly Fee: $133
       Tax: $26,109 (2024)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,527 (change assumption)
    Mortgage ($20,219) + Fees ($133) + Taxes in 2024 ($2,176)


    Taxes:$26,109

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 909 MACEWEN DR, OSPREY, FL 34229

    $1,595,000624 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


  • 25 SUGAR MILL DR, OSPREY, FL 34229

    $1,550,000128 Days on yellowkey   MLS ID: A4678423

    For Sale A4678423 - 25 SUGAR MILL DR, OSPREY, FL 34229 74 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3066
       Built: 1998
    Monthly Fee: $483
       Tax: $7,845 (2025)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,630 (change assumption)
    Mortgage ($8,493) + Fees ($483) + Taxes in 2025 ($654)


    Taxes:$7,845

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,00045 Days on yellowkey   MLS ID: A4685559

    For Sale A4685559 - 61 BAYHEAD LN, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3180
       Built: 1993
    Monthly Fee: $458
       Tax: $4,573 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,332 (change assumption)
    Mortgage ($6,493) + Fees ($458) + Taxes in 2025 ($381)


    Taxes:$4,573

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 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


  • 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


  • 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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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.