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Displaying: For Sale

Location: Osprey

Property Type(s): Single Family

Price: $1,000,000+

Osprey - 48 properties found

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  • 365 S SHORE DR, OSPREY, FL 34229

    $1,349,000123 Days on yellowkey   MLS ID: N6142101

    REDUCED by $31,000 (2.2%) on 05/02/2026

    For Sale N6142101 - 365 S SHORE DR, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1824
       Built: 1968   Tax: $7,804 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $8,042 (change assumption)
    Mortgage ($7,392) + Taxes in 2025 ($650)


    Taxes:$7,804

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 97 SUGAR MILL DR, OSPREY, FL 34229

    $1,950,0003 Days on yellowkey   MLS ID: A4691789

    For Sale A4691789 - 97 SUGAR MILL DR, OSPREY, FL 34229 61 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4885
       Built: 1990
    Monthly Fee: $483
       Tax: $16,651 (2025)
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $12,555 (change assumption)
    Mortgage ($10,685) + Fees ($483) + Taxes in 2025 ($1,388)


    Taxes:$16,651

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 449 WEBBS COVE, OSPREY, FL 34229

    $2,650,00033 Days on yellowkey   MLS ID: A4688291

    For Sale A4688291 - 449 WEBBS COVE, OSPREY, FL 34229 97 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 5287
       Built: 2006
    Monthly Fee: $492
       Tax: $10,623 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $15,897 (change assumption)
    Mortgage ($14,520) + Fees ($492) + Taxes in 2025 ($885)


    Taxes:$10,623

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 408 YACHT HARBOR DR, OSPREY, FL 34229

    $1,375,0006 Days on yellowkey   MLS ID: A4691576

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale A4691576 - 408 YACHT HARBOR DR, OSPREY, FL 34229 46 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2624
       Built: 1976
    Monthly Fee: $219
       Tax: $9,482 (2025)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $8,543 (change assumption)
    Mortgage ($7,534) + Fees ($219) + Taxes in 2025 ($790)


    Taxes:$9,482

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14401 MASTHEAD DR, OSPREY, FL 34229

    $3,150,00060 Days on yellowkey   MLS ID: A4684834

    REDUCED by $100,000 (3.1%) on 05/01/2026

    For Sale A4684834 - 14401 MASTHEAD DR, OSPREY, FL 34229 96 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2665
       Built: 2017
    Monthly Fee: $643
       Tax: $874 (2025)
    Community: Bayside
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,976 (change assumption)
    Mortgage ($17,260) + Fees ($643) + Taxes in 2025 ($73)


    Taxes:$874

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 422 BLUE GARDEN LN, OSPREY, FL 34229

    $1,550,000231 Days on yellowkey   MLS ID: A4664436

    REDUCED by $50,000 (3.1%) on 05/01/2026

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

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3872
       Built: 1984
    Monthly Fee: $475
       Tax: $7,339 (2024)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,580 (change assumption)
    Mortgage ($8,493) + Fees ($475) + Taxes in 2024 ($612)


    Taxes:$7,339

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 296 PINE RANCH TRL, OSPREY, FL 34229

    $1,150,000345 Days on yellowkey   MLS ID: A4653218

    REDUCED by $100,000 (8.0%) on 05/01/2026

    For Sale A4653218 - 296 PINE RANCH TRL, OSPREY, FL 34229 82 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3481
       Built: 1995   Tax: $5,492 (2024)
    Community: Pine Ranch East
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,759 (change assumption)
    Mortgage ($6,301) + Taxes in 2024 ($458)


    Taxes:$5,492

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 854 MACEWEN DR, OSPREY, FL 34229

    $3,690,000197 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


  • 49 OSPREY POINT DR, OSPREY, FL 34229

    $2,500,000172 Days on yellowkey   MLS ID: A4671762

    For Sale A4671762 - 49 OSPREY POINT DR, OSPREY, FL 34229 96 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3953
       Built: 1989
    Monthly Fee: $475
       Tax: $14,206 (2024)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $15,357 (change assumption)
    Mortgage ($13,698) + Fees ($475) + Taxes in 2024 ($1,184)


    Taxes:$14,206

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 236 SAINT JAMES PARK, OSPREY, FL 34229

    $2,700,000403 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


  • 140 SUGAR MILL DR, OSPREY, FL 34229

    $1,399,00055 Days on yellowkey   MLS ID: A4684805

    REDUCED by $296,000 (17.5%) on 04/24/2026

    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: $9,152 (change assumption)
    Mortgage ($7,666) + 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


  • 17 BAYHEAD LN, OSPREY, FL 34229

    $1,295,000112 Days on yellowkey   MLS ID: A4676710

    REDUCED by $5,000 (0.4%) on 04/29/2026

    For Sale A4676710 - 17 BAYHEAD LN, OSPREY, FL 34229 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2850
       Built: 1992
    Monthly Fee: $458
       Tax: $6,642 (2024)
    Community: Bishops Court At Oaks Preserve
    Single Family


    Estimated Monthly Payment: $8,107 (change assumption)
    Mortgage ($7,096) + Fees ($458) + Taxes in 2024 ($554)


    Taxes:$6,642

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 324 BAYSHORE DR, OSPREY, FL 34229

    $3,995,00069 Days on yellowkey   MLS ID: A4683138

    REDUCED by $255,000 (6.0%) on 04/29/2026

    For Sale A4683138 - 324 BAYSHORE DR, OSPREY, FL 34229 40 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4389
       Built: 2000   Tax: $23,356 (2025)
    Community: Bay Acres - Resub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,836 (change assumption)
    Mortgage ($21,890) + Taxes in 2025 ($1,946)


    Taxes:$23,356

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 909 MACEWEN DR, OSPREY, FL 34229

    $1,595,000598 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


  • 402 MACEWEN DR, OSPREY, FL 34229

    $1,750,00020 Days on yellowkey   MLS ID: A4690018

    For Sale A4690018 - 402 MACEWEN DR, OSPREY, FL 34229 78 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3565
       Built: 1999
    Monthly Fee: $142
       Tax: $13,762 (2025)
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $10,878 (change assumption)
    Mortgage ($9,589) + Fees ($142) + Taxes in 2025 ($1,147)


    Taxes:$13,762

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 25 SUGAR MILL DR, OSPREY, FL 34229

    $1,550,000102 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


  • 353 S SHORE DR, OSPREY, FL 34229

    $1,150,00033 Days on yellowkey   MLS ID: A4688006

    REDUCED by $50,000 (4.2%) on 04/18/2026

    For Sale A4688006 - 353 S SHORE DR, OSPREY, FL 34229 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 1968
    Monthly Fee: $10
       Tax: $3,904 (2025)
    Community: Sorrento Shores Rep Of 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,637 (change assumption)
    Mortgage ($6,301) + Fees ($10) + Taxes in 2025 ($325)


    Taxes:$3,904

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 480 ORISKANY CT, OSPREY, FL 34229

    $1,599,00063 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


  • 75 OSPREY POINT DR, OSPREY, FL 34229

    $1,695,000166 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


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,00019 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


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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.