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Homes For Sale in Osprey 34229 - 145 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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  • 140 SUGAR MILL DR, OSPREY, FL 34229

    $1,399,00081 Days on yellowkey   MLS ID: A4684805

    0 Days Off yellowkey (back on 5/3/2026)

    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


  • 102 WINDWARD DR, OSPREY, FL 34229

    $650,000192 Days on yellowkey   MLS ID: A4671793

    0 Days Off yellowkey (back on 5/7/2026)

    REDUCED by $40,000 (5.8%) on 04/26/2026

    For Sale A4671793 - 102 WINDWARD DR, OSPREY, FL 34229 78 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2134
       Built: 1986
    Monthly Fee: $219
       Tax: $3,540 (2024)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $4,076 (change assumption)
    Mortgage ($3,562) + Fees ($219) + Taxes in 2024 ($295)


    Taxes:$3,540

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 32 SIESTA CIR W, OSPREY, FL 34229

    $69,00046 Days on yellowkey   MLS ID: A4690063

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale A4690063 - 32 SIESTA CIR W, OSPREY, FL 34229 3 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 480
       Built: 1968
    Monthly Fee: $215
       Tax: $555 (2025)
    Community: Arbors
    Mobile Home


    Estimated Monthly Payment: $639 (change assumption)
    Mortgage ($378) + Fees ($215) + Taxes in 2025 ($46)


    Taxes:$555

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 49 OSPREY POINT DR, OSPREY, FL 34229

    $2,399,000198 Days on yellowkey   MLS ID: A4671762

    REDUCED by $101,000 (4.0%) on 05/03/2026

    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: $14,804 (change assumption)
    Mortgage ($13,145) + 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


  • 449 WEBBS COVE, OSPREY, FL 34229

    $2,650,00059 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 #301, OSPREY, FL 34229

    $475,000805 Days on yellowkey   MLS ID: A4603773

    SHORT SALE A4603773 - 401 N POINT RD #301, OSPREY, FL 34229 91 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2003
    Monthly Fee: $367
       Tax: $6,783 (2023)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $3,535 (change assumption)
    Mortgage ($2,603) + Fees ($367) + Taxes in 2023 ($565)


    Taxes:$6,783

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2023

    Middle School: Brookside Middle


  • 17 BAYHEAD LN, OSPREY, FL 34229

    $1,295,000138 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


  • 524 SARABAY RD, OSPREY, FL 34229

    $419,000155 Days on yellowkey   MLS ID: A4676179

    For Sale A4676179 - 524 SARABAY RD, OSPREY, FL 34229 41 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1760
       Built: 1956   Tax: $1,926 (2025)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $2,456 (change assumption)
    Mortgage ($2,296) + Taxes in 2025 ($161)


    Taxes:$1,926

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 120 VILLA DR #120, OSPREY, FL 34229

    $497,000410 Days on yellowkey   MLS ID: N6138441

    REDUCED by $13,000 (2.5%) on 04/25/2026

    For Sale N6138441 - 120 VILLA DR #120, OSPREY, FL 34229 55 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1404
       Built: 1978
    Monthly Fee: $529
       Tax: $5,056 (2025)
    Community: Sorrento Villas 1
    Villa


    Estimated Monthly Payment: $3,674 (change assumption)
    Mortgage ($2,723) + Fees ($529) + Taxes in 2025 ($421)


    Taxes:$5,056

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 280 HIDDEN BAY DR #302, OSPREY, FL 34229

    $749,00019 Days on yellowkey   MLS ID: A4690813

    For Sale A4690813 - 280 HIDDEN BAY DR #302, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1937
       Built: 2024   Tax: $7,907 (2025)
    Community: Edgewater/Hidden Bay Ph 3
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,763 (change assumption)
    Mortgage ($4,104) + Taxes in 2025 ($659)


    Taxes:$7,907

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 619 OAK RIVER CT, OSPREY, FL 34229

    $609,90016 Days on yellowkey   MLS ID: A4692331

    0 Days Off yellowkey (back on 5/16/2026)

    For Sale A4692331 - 619 OAK RIVER CT, OSPREY, FL 34229 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2047
       Built: 1997
    Monthly Fee: $25
       Tax: $5,484 (2025)
    Community: Bay Oaks Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,824 (change assumption)
    Mortgage ($3,342) + Fees ($25) + Taxes in 2025 ($457)


    Taxes:$5,484

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 403 LONGBOW TRL, OSPREY, FL 34229

    $1,095,000194 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


  • 759 FORDINGBRIDGE WAY, OSPREY, FL 34229

    $770,00044 Days on yellowkey   MLS ID: O6399774

    INCREASED by $43,000 (5.9%) on 05/16/2026

    For Sale O6399774 - 759 FORDINGBRIDGE WAY, OSPREY, FL 34229 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2950
       Built: 2002
    Monthly Fee: $55
       Tax: $7,129 (2025)
    Community: Rivendell Woodlands
    Single Family


    Estimated Monthly Payment: $4,868 (change assumption)
    Mortgage ($4,219) + Fees ($55) + Taxes in 2025 ($594)


    Taxes:$7,129

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 742 HARMS DR, OSPREY, FL 34229

    $515,000242 Days on yellowkey   MLS ID: A4666421

    For Sale A4666421 - 742 HARMS DR, OSPREY, FL 34229 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1293
       Built: 1981   Tax: $5,620 (2024)
    Community: Harms Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,290 (change assumption)
    Mortgage ($2,822) + Taxes in 2024 ($468)


    Taxes:$5,620

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 272 FOUR KNOT LN, OSPREY, FL 34229

    $1,095,00017 Days on yellowkey   MLS ID: N6144313

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale N6144313 - 272 FOUR KNOT LN, OSPREY, FL 34229 80 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2723
       Built: 1978
    Monthly Fee: $219
       Tax: $5,738 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,697 (change assumption)
    Mortgage ($6,000) + Fees ($219) + Taxes in 2025 ($478)


    Taxes:$5,738

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 4226 FRONTIER LN #103, OSPREY, FL 34229

    $299,00053 Days on yellowkey   MLS ID: A4687965

    REDUCED by $20,000 (6.3%) on 05/16/2026

    For Sale A4687965 - 4226 FRONTIER LN #103, OSPREY, FL 34229 36 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1135
       Built: 2018
    Monthly Fee: $475
       Tax: $3,542 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,408 (change assumption)
    Mortgage ($1,638) + Fees ($475) + Taxes in 2025 ($295)


    Taxes:$3,542

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 6100 JESSIE HARBOR DR #603, OSPREY, FL 34229

    $849,000143 Days on yellowkey   MLS ID: A4676824

    1 Days Off yellowkey (back on 3/31/2026)

    For Sale A4676824 - 6100 JESSIE HARBOR DR #603, OSPREY, FL 34229 43 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2630
       Built: 2005
    Monthly Fee: $1,101
       Tax: $7,091 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $6,344 (change assumption)
    Mortgage ($4,652) + Fees ($1,101) + Taxes in 2025 ($591)


    Taxes:$7,091

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 852 MACEWEN DR, OSPREY, FL 34229

    $2,395,000314 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


  • 14041 BELLAGIO WAY #218, OSPREY, FL 34229

    $999,000191 Days on yellowkey   MLS ID: A4672639

    0 Days Off yellowkey (back on 5/14/2026)

    REDUCED by $100,000 (9.1%) on 04/03/2026

    For Sale A4672639 - 14041 BELLAGIO WAY #218, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2086
       Built: 2006
    Monthly Fee: $1,649
       Tax: $6,459 (2024)
    Community: Villas At Bellagio Harbor Village
    Condo


    Estimated Monthly Payment: $7,661 (change assumption)
    Mortgage ($5,474) + Fees ($1,649) + Taxes in 2024 ($538)


    Taxes:$6,459

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $625,00096 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




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.