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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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  • 852 MACEWEN DR, OSPREY, FL 34229

    $2,395,000315 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


  • 393 N POINT RD #301, OSPREY, FL 34229

    $625,00097 Days on yellowkey   MLS ID: A4682548

    0 Days Off yellowkey (back on 5/13/2026)

    For Sale A4682548 - 393 N POINT RD #301, OSPREY, FL 34229 85 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2594
       Built: 2001
    Monthly Fee: $400
       Tax: $3,652 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $4,129 (change assumption)
    Mortgage ($3,425) + Fees ($400) + Taxes in 2025 ($304)


    Taxes:$3,652

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 227 SAINT JAMES PARK, OSPREY, FL 34229

    $885,000123 Days on yellowkey   MLS ID: A4679867

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale A4679867 - 227 SAINT JAMES PARK, OSPREY, FL 34229 93 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2071
       Built: 1986
    Monthly Fee: $142
       Tax: $4,611 (2025)
    Community: Oaks 2 Ph 1
    Single Family


    Estimated Monthly Payment: $5,375 (change assumption)
    Mortgage ($4,849) + Fees ($142) + Taxes in 2025 ($384)


    Taxes:$4,611

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 393 N POINT RD #604, OSPREY, FL 34229

    $795,000483 Days on yellowkey   MLS ID: A4638035

    For Sale A4638035 - 393 N POINT RD #604, OSPREY, FL 34229 92 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2778
       Built: 2001
    Monthly Fee: $367
       Tax: $9,625 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $5,525 (change assumption)
    Mortgage ($4,356) + Fees ($367) + Taxes in 2024 ($802)


    Taxes:$9,625

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 51 MACEWEN DR #5, OSPREY, FL 34229

    $235,00041 Days on yellowkey   MLS ID: A4689838

    REDUCED by $65,000 (21.7%) on 05/11/2026

    For Sale A4689838 - 51 MACEWEN DR #5, OSPREY, FL 34229 44 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 595
       Built: 1990
    Monthly Fee: $142
       Tax: $3,079 (2025)
    Community: Windsor Lodge At The Oaks
    Condo


    Estimated Monthly Payment: $1,686 (change assumption)
    Mortgage ($1,288) + Fees ($142) + Taxes in 2025 ($257)


    Taxes:$3,079

    Elementary School: Laurel Nokomis Elementary

    High School: Pine View School

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 21 BAYHEAD LN, OSPREY, FL 34229

    $850,000258 Days on yellowkey   MLS ID: A4664085

    For Sale A4664085 - 21 BAYHEAD LN, OSPREY, FL 34229 92 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2246
       Built: 2002
    Monthly Fee: $458
       Tax: $4,221 (2024)
    Community: Bishopscourt At The Oaks Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,467 (change assumption)
    Mortgage ($4,657) + Fees ($458) + Taxes in 2024 ($352)


    Taxes:$4,221

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 236 SAINT JAMES PARK, OSPREY, FL 34229

    $2,700,000430 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

    $1,950,000205 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

    $2,195,000222 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


  • 51 MACEWEN DR #12, OSPREY, FL 34229

    $275,00026 Days on yellowkey   MLS ID: A4690540

    For Sale A4690540 - 51 MACEWEN DR #12, OSPREY, FL 34229 71 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 623
       Built: 1990
    Monthly Fee: $142
       Tax: $3,079 (2025)
    Community: Oaks
    Condo


    Estimated Monthly Payment: $1,905 (change assumption)
    Mortgage ($1,507) + Fees ($142) + Taxes in 2025 ($257)


    Taxes:$3,079

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 583 PINE RANCH EAST RD, OSPREY, FL 34229

    $569,000209 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


  • 51 MACEWEN DR #11, OSPREY, FL 34229

    $235,000128 Days on yellowkey   MLS ID: A4679180

    For Sale A4679180 - 51 MACEWEN DR #11, OSPREY, FL 34229 42 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 623
       Built: 1990
    Monthly Fee: $142
       Tax: $2,367 (2025)
    Community: The Oaks Club
    Spa: No

    Condo


    Estimated Monthly Payment: $1,627 (change assumption)
    Mortgage ($1,288) + Fees ($142) + Taxes in 2025 ($197)


    Taxes:$2,367

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 854 MACEWEN DR, OSPREY, FL 34229

    $3,690,000224 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


  • 385 N POINT RD #402, OSPREY, FL 34229

    $660,000491 Days on yellowkey   MLS ID: A4635708

    For Sale A4635708 - 385 N POINT RD #402, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2055
       Built: 2000
    Monthly Fee: $400
       Tax: $5,877 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $4,506 (change assumption)
    Mortgage ($3,616) + Fees ($400) + Taxes in 2024 ($490)


    Taxes:$5,877

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 909 MACEWEN DR, OSPREY, FL 34229

    $1,595,000625 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

    $1,550,000129 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


  • 385 N POINT RD #304, OSPREY, FL 34229

    $1,100,000135 Days on yellowkey   MLS ID: A4678422

    For Sale A4678422 - 385 N POINT RD #304, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2778
       Built: 2000
    Monthly Fee: $400
       Tax: $5,845 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $6,914 (change assumption)
    Mortgage ($6,027) + Fees ($400) + Taxes in 2025 ($487)


    Taxes:$5,845

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 393 N POINT RD #401, OSPREY, FL 34229

    $785,00069 Days on yellowkey   MLS ID: A4686928

    0 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $50,000 (6.0%) on 03/31/2026

    For Sale A4686928 - 393 N POINT RD #401, OSPREY, FL 34229 63 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2001
    Monthly Fee: $400
       Tax: $5,733 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $5,179 (change assumption)
    Mortgage ($4,301) + Fees ($400) + Taxes in 2025 ($478)


    Taxes:$5,733

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,00046 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


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

    $679,000134 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


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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.