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Oaks Single Family Homes For Sale in Osprey - 26 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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  • 75 OSPREY POINT DR, OSPREY, FL 34229

    $1,695,000147 Days on yellowkey   MLS ID: A4672439

    For Sale A4672439 - 75 OSPREY POINT DR, OSPREY, FL 34229 92 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4001
       Built: 1983
    Monthly Fee: $967
       Tax: $14,229 (2024)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,440 (change assumption)
    Mortgage ($9,287) + Fees ($967) + Taxes in 2024 ($1,186)


    Taxes:$14,229

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 228 SAINT JAMES PARK, OSPREY, FL 34229

    $1,695,00026 Days on yellowkey   MLS ID: A4686681

    For Sale A4686681 - 228 SAINT JAMES PARK, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2425
       Built: 1997
    Monthly Fee: $142
       Tax: $10,787 (2025)
    Community: Oaks 2 Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,328 (change assumption)
    Mortgage ($9,287) + Fees ($142) + Taxes in 2025 ($899)


    Taxes:$10,787

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 76 OSPREY POINT DR, OSPREY, FL 34229

    $1,590,000142 Days on yellowkey   MLS ID: A4672843

    For Sale A4672843 - 76 OSPREY POINT DR, OSPREY, FL 34229 66 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4364
       Built: 1986
    Monthly Fee: $475
       Tax: $13,509 (2024)
    Community: Oaks Bayside
    Single Family


    Estimated Monthly Payment: $10,313 (change assumption)
    Mortgage ($8,712) + Fees ($475) + Taxes in 2024 ($1,126)


    Taxes:$13,509

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 854 MACEWEN DR, OSPREY, FL 34229

    $3,790,000178 Days on yellowkey   MLS ID: A4668918

    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: $23,075 (change assumption)
    Mortgage ($20,767) + 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


  • 480 ORISKANY CT, OSPREY, FL 34229

    $1,599,00044 Days on yellowkey   MLS ID: A4684136

    REDUCED by $96,000 (5.7%) on 04/12/2026

    For Sale A4684136 - 480 ORISKANY CT, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3208
       Built: 1999
    Monthly Fee: $142
       Tax: $6,365 (2024)
    Community: The Oaks Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,434 (change assumption)
    Mortgage ($8,761) + Fees ($142) + Taxes in 2024 ($530)


    Taxes:$6,365

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 140 SUGAR MILL DR, OSPREY, FL 34229

    $1,695,00036 Days on yellowkey   MLS ID: A4684805

    For Sale A4684805 - 140 SUGAR MILL DR, OSPREY, FL 34229 74 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3286
       Built: 1989
    Monthly Fee: $483
       Tax: $12,040 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,774 (change assumption)
    Mortgage ($9,287) + Fees ($483) + Taxes in 2025 ($1,003)


    Taxes:$12,040

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 362 MACEWEN DR, OSPREY, FL 34229

    $2,249,00093 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


  • 571 PINE RANCH EAST RD, OSPREY, FL 34229

    $650,000201 Days on yellowkey   MLS ID: A4665938

    2 Days Off yellowkey (back on 4/6/2026)

    For Sale A4665938 - 571 PINE RANCH EAST RD, OSPREY, FL 34229 88 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2746
       Built: 1995
    Monthly Fee: $25
       Tax: $6,575 (2024)
    Community: Bay Oaks Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,134 (change assumption)
    Mortgage ($3,562) + Fees ($25) + Taxes in 2024 ($548)


    Taxes:$6,575

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 156 BISHOPSCOURT RD, OSPREY, FL 34229

    $1,299,00067 Days on yellowkey   MLS ID: A4681468

    For Sale A4681468 - 156 BISHOPSCOURT RD, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3112
       Built: 1990
    Monthly Fee: $916
       Tax: $8,109 (2024)
    Community: Bishopscourt At The Oaks Preserve
    Single Family


    Estimated Monthly Payment: $8,709 (change assumption)
    Mortgage ($7,118) + Fees ($916) + Taxes in 2024 ($676)


    Taxes:$8,109

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 434 MACEWEN DR, OSPREY, FL 34229

    $1,465,00016 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


  • 597 OAK RIVER CT, OSPREY, FL 34229

    $699,000129 Days on yellowkey   MLS ID: A4673797

    0 Days Off yellowkey (back on 4/3/2026)

    For Sale A4673797 - 597 OAK RIVER CT, OSPREY, FL 34229 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2111
       Built: 1994
    Monthly Fee: $25
       Tax: $5,289 (2025)
    Community: Bay Oaks Estates
    Single Family


    Estimated Monthly Payment: $4,296 (change assumption)
    Mortgage ($3,830) + Fees ($25) + Taxes in 2025 ($441)


    Taxes:$5,289

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 538 DOVE POINTE DR, OSPREY, FL 34229

    $1,950,000159 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
    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


  • 13 BAYHEAD LN, OSPREY, FL 34229

    $850,000377 Days on yellowkey   MLS ID: A4645829

    For Sale A4645829 - 13 BAYHEAD LN, OSPREY, FL 34229 62 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 2310
       Built: 2001
    Monthly Fee: $425
       Tax: $3,620 (2024)
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $5,384 (change assumption)
    Mortgage ($4,657) + 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


  • 448 E MACEWEN DR, OSPREY, FL 34229

    $2,100,00018 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


  • 642 TRENTON WAY, OSPREY, FL 34229

    $2,150,00021 Days on yellowkey   MLS ID: A4686927

    For Sale A4686927 - 642 TRENTON WAY, OSPREY, FL 34229 86 photos

    Bed: 4   Bath: 4.5
    Liv Area Sq Ft: 3939
       Built: 2002
    Community: Oaks 2 Ph 2
    Single Family


    Estimated Monthly Payment: $11,781 (change assumption)
    Mortgage ($11,781)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 422 BLUE GARDEN LN, OSPREY, FL 34229

    $1,600,000212 Days on yellowkey   MLS ID: A4664436

    For Sale A4664436 - 422 BLUE GARDEN LN, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 3872
       Built: 1984
    Community: The Oaks Bayside
    Single Family


    Estimated Monthly Payment: $8,767 (change assumption)
    Mortgage ($8,767)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 230 OSPREY POINT DR, OSPREY, FL 34229

    $2,495,00023 Days on yellowkey   MLS ID: A4683382

    For Sale A4683382 - 230 OSPREY POINT DR, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 3586
       Built: 2014
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $13,671 (change assumption)
    Mortgage ($13,671)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 401 WALLS WAY, OSPREY, FL 34229

    $1,800,00075 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


  • 20 BAYHEAD LN, OSPREY, FL 34229

    $1,575,00097 Days on yellowkey   MLS ID: A4674649

    For Sale A4674649 - 20 BAYHEAD LN, OSPREY, FL 34229 73 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3486
       Built: 2017
    Community: Bishops Court At The Oaks Preserve
    Single Family


    Estimated Monthly Payment: $8,630 (change assumption)
    Mortgage ($8,630)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 227 SAINT JAMES PARK, OSPREY, FL 34229

    $885,00077 Days on yellowkey   MLS ID: A4679867

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

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 2071
       Built: 1986
    Community: Oaks 2 Ph 1
    Single Family


    Estimated Monthly Payment: $4,849 (change assumption)
    Mortgage ($4,849)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


12


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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.