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Homes For Sale in Osprey 34229 - 133 homes

34229 zip code is located in Sarasota County, Florida. Find homes for sale in Osprey 34229 from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Osprey 34229 homes for sale.

Location: Osprey , 34229

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  • 4424 CONCHFISH LN, OSPREY, FL 34229

    $585,00029 Days on yellowkey   MLS ID: A4691622

    REDUCED by $30,000 (4.9%) on 06/07/2026

    For Sale A4691622 - 4424 CONCHFISH LN, OSPREY, FL 34229 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2017
    Monthly Fee: $125
       Tax: $4,467 (2026)
    Community: Palms/Casey Key
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,703 (change assumption)
    Mortgage ($3,205) + Fees ($125) + Taxes in 2026 ($372)


    Taxes:$4,467

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2026

    Middle School: Sarasota Middle


  • 403 LONGBOW TRL, OSPREY, FL 34229

    $1,095,000213 Days on yellowkey   MLS ID: A4672081

    For Sale A4672081 - 403 LONGBOW TRL, OSPREY, FL 34229 99 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2770
       Built: 1978
    Monthly Fee: $42
       Tax: $9,020 (2024)
    Community: Pine Ranch
    Single Family


    Estimated Monthly Payment: $6,794 (change assumption)
    Mortgage ($6,000) + Fees ($42) + Taxes in 2024 ($752)


    Taxes:$9,020

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 523 OAK BAY DR, OSPREY, FL 34229

    $540,0006 Days on yellowkey   MLS ID: A4696725

    For Sale A4696725 - 523 OAK BAY DR, OSPREY, FL 34229 97 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 1998
    Monthly Fee: $25
       Tax: $3,448 (2025)
    Community: Bay Oaks Estates
    Single Family


    Estimated Monthly Payment: $3,271 (change assumption)
    Mortgage ($2,959) + Fees ($25) + Taxes in 2025 ($287)


    Taxes:$3,448

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 110 WOODLAND PL #110, OSPREY, FL 34229

    $225,0006 Days on yellowkey   MLS ID: A4696738

    For Sale A4696738 - 110 WOODLAND PL #110, OSPREY, FL 34229 50 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1979   Tax: $2,840 (2025)
    Community: Pine Run Ii
    Condo


    Estimated Monthly Payment: $1,470 (change assumption)
    Mortgage ($1,233) + Taxes in 2025 ($237)


    Taxes:$2,840

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 21 BAYHEAD LN, OSPREY, FL 34229

    $789,000276 Days on yellowkey   MLS ID: A4664085

    REDUCED by $61,000 (7.2%) on 06/12/2026

    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: $5,133 (change assumption)
    Mortgage ($4,323) + 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


  • 157 LOOKOUT POINT DR, OSPREY, FL 34229

    $875,00021 Days on yellowkey   MLS ID: A4694878

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale A4694878 - 157 LOOKOUT POINT DR, OSPREY, FL 34229 73 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1859
       Built: 1981
    Monthly Fee: $219
       Tax: $4,950 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,426 (change assumption)
    Mortgage ($4,794) + Fees ($219) + Taxes in 2025 ($413)


    Taxes:$4,950

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 557 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $599,0006 Days on yellowkey   MLS ID: A4696823

    For Sale A4696823 - 557 CRANE PRAIRIE WAY, OSPREY, FL 34229 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2172
       Built: 2005
    Monthly Fee: $397
       Tax: $3,953 (2025)
    Community: Willowbend Ph 4
    Single Family


    Estimated Monthly Payment: $4,009 (change assumption)
    Mortgage ($3,282) + Fees ($397) + Taxes in 2025 ($329)


    Taxes:$3,953

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,00064 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


  • 347 BAYSHORE DR, OSPREY, FL 34229

    $739,00037 Days on yellowkey   MLS ID: A4693374

    For Sale A4693374 - 347 BAYSHORE DR, OSPREY, FL 34229 71 photos

    Bed: 3   Bath: 2.5   Gar: 4
    Liv Area Sq Ft: 2216
       Built: 2013   Tax: $879 (2025)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $4,122 (change assumption)
    Mortgage ($4,049) + Taxes in 2025 ($73)


    Taxes:$879

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 97 SUGAR MILL DR, OSPREY, FL 34229

    $1,950,00048 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

    $2,650,00078 Days on yellowkey   MLS ID: A4688291

    0 Days Off yellowkey (back on 5/19/2026)

    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


  • 401 N POINT RD #603, OSPREY, FL 34229

    $629,000217 Days on yellowkey   MLS ID: A4671958

    REDUCED by $70,000 (10.0%) on 05/20/2026

    For Sale A4671958 - 401 N POINT RD #603, OSPREY, FL 34229 99 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 2003   Tax: $8,771 (2024)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $4,177 (change assumption)
    Mortgage ($3,446) + Taxes in 2024 ($731)


    Taxes:$8,771

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 402 MACEWEN DR, OSPREY, FL 34229

    $1,699,00065 Days on yellowkey   MLS ID: A4690018

    REDUCED by $51,000 (2.9%) on 05/12/2026

    For Sale A4690018 - 402 MACEWEN DR, OSPREY, FL 34229 81 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: $10,598 (change assumption)
    Mortgage ($9,309) + 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


  • 204 WINDWARD DR, OSPREY, FL 34229

    $999,00038 Days on yellowkey   MLS ID: A4693139

    REDUCED by $51,000 (4.9%) on 06/10/2026

    For Sale A4693139 - 204 WINDWARD DR, OSPREY, FL 34229 73 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 1986
    Monthly Fee: $219
       Tax: $4,761 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,090 (change assumption)
    Mortgage ($5,474) + Fees ($219) + Taxes in 2025 ($397)


    Taxes:$4,761

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 385 N POINT RD #503, OSPREY, FL 34229

    $690,000212 Days on yellowkey   MLS ID: A4672342

    For Sale A4672342 - 385 N POINT RD #503, OSPREY, FL 34229 97 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 2000
    Monthly Fee: $367
       Tax: $7,327 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $4,758 (change assumption)
    Mortgage ($3,781) + Fees ($367) + Taxes in 2024 ($611)


    Taxes:$7,327

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 292 TURQUOISE LN, OSPREY, FL 34229

    $1,050,00023 Days on yellowkey   MLS ID: A4694515

    For Sale A4694515 - 292 TURQUOISE LN, OSPREY, FL 34229 89 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2255
       Built: 2001
    Monthly Fee: $400
       Tax: $6,536 (2025)
    Community: Emerald Woods At Oaks 03 Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,698 (change assumption)
    Mortgage ($5,753) + Fees ($400) + Taxes in 2025 ($545)


    Taxes:$6,536

    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

    $625,00058 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


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

    $700,000324 Days on yellowkey   MLS ID: A4659785

    For Sale A4659785 - 401 N POINT RD #304, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2778
       Built: 2003
    Monthly Fee: $367
       Tax: $8,473 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,909 (change assumption)
    Mortgage ($3,836) + Fees ($367) + Taxes in 2024 ($706)


    Taxes:$8,473

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 3621 N POINT RD #301, OSPREY, FL 34229

    $625,000134 Days on yellowkey   MLS ID: A4681290

    For Sale A4681290 - 3621 N POINT RD #301, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2680
       Built: 2006   Tax: $6,143 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $3,937 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($512)


    Taxes:$6,143

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 362 MACEWEN DR, OSPREY, FL 34229

    $2,249,000157 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




Why Bother Searching Elsewhere for 34229 Homes for Sale and Other Osprey Real Estate?

34229, Osprey home, townhome, condo, villa, and other listing rental 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 the 34229 zip code. You can use our website to view Multiple Listing Service (MLS) data on 34229, Osprey 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 34229, 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.