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Homes For Sale in Osprey 34229 - 129 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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  • 480 ORISKANY CT, OSPREY, FL 34229

    $1,500,000152 Days on yellowkey   MLS ID: A4684136

    REDUCED by $35,000 (2.3%) on 07/09/2026

    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: $8,891 (change assumption)
    Mortgage ($8,219) + 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

    $1,649,00051 Days on yellowkey   MLS ID: A4695145

    For Sale A4695145 - 75 OSPREY POINT DR, OSPREY, FL 34229 70 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4001
       Built: 1983
    Monthly Fee: $950
       Tax: $14,636 (2025)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,205 (change assumption)
    Mortgage ($9,035) + Fees ($950) + Taxes in 2025 ($1,220)


    Taxes:$14,636

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 4226 FRONTIER LN #103, OSPREY, FL 34229

    $299,000116 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


  • 97 SUGAR MILL DR, OSPREY, FL 34229

    $1,950,00092 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


  • 6100 JESSIE HARBOR DR #202, OSPREY, FL 34229

    $850,00090 Days on yellowkey   MLS ID: A4690969

    For Sale A4690969 - 6100 JESSIE HARBOR DR #202, OSPREY, FL 34229 83 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 3771
       Built: 2005
    Monthly Fee: $1,101
       Tax: $8,698 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $6,483 (change assumption)
    Mortgage ($4,657) + Fees ($1,101) + Taxes in 2025 ($725)


    Taxes:$8,698

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 916 MACEWEN DR, OSPREY, FL 34229

    $1,900,00030 Days on yellowkey   MLS ID: A4698153

    For Sale A4698153 - 916 MACEWEN DR, OSPREY, FL 34229 97 photos

    Bed: 5   Bath: 7.5   Gar: 4
    Liv Area Sq Ft: 5986
       Built: 1991
    Monthly Fee: $283
       Tax: $11,835 (2025)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,680 (change assumption)
    Mortgage ($10,411) + Fees ($283) + Taxes in 2025 ($986)


    Taxes:$11,835

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 903 TRANQUILITY CIR, OSPREY, FL 34229

    $739,90011 Days on yellowkey   MLS ID: A4700143

    2 Days Off yellowkey (back on 7/27/2026)

    For Sale A4700143 - 903 TRANQUILITY CIR, OSPREY, FL 34229 35 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2622
       Built: 2002
    Monthly Fee: $158
       Tax: $4,479 (2025)
    Community: North Creek Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,585 (change assumption)
    Mortgage ($4,054) + Fees ($158) + Taxes in 2025 ($373)


    Taxes:$4,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 764 SARABAY RD #8, OSPREY, FL 34229

    $399,000156 Days on yellowkey   MLS ID: A4683747

    REDUCED by $26,000 (6.1%) on 07/27/2026

    For Sale A4683747 - 764 SARABAY RD #8, OSPREY, FL 34229 64 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1981
    Monthly Fee: $1,617
       Tax: $2,936 (2025)
    Community: Heron Bay Club Sec I
    Villa


    Estimated Monthly Payment: $4,048 (change assumption)
    Mortgage ($2,186) + Fees ($1,617) + Taxes in 2025 ($245)


    Taxes:$2,936

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School


  • 619 OAK RIVER CT, OSPREY, FL 34229

    $609,90079 Days on yellowkey   MLS ID: A4692331

    0 Days Off yellowkey (back on 7/18/2026)

    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


  • 754 PINE RUN DR #754, OSPREY, FL 34229

    $259,00082 Days on yellowkey   MLS ID: A4693150

    REDUCED by $10,000 (3.7%) on 06/19/2026

    For Sale A4693150 - 754 PINE RUN DR #754, OSPREY, FL 34229 45 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1379
       Built: 1973
    Monthly Fee: $917
       Tax: $3,176 (2025)
    Community: Pine Run I
    Spa: No

    Condo


    Estimated Monthly Payment: $2,601 (change assumption)
    Mortgage ($1,419) + Fees ($917) + Taxes in 2025 ($265)


    Taxes:$3,176

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1801 HIGHLAND RD, OSPREY, FL 34229

    $289,900319 Days on yellowkey   MLS ID: N6140508

    REDUCED by $10,000 (3.3%) on 06/03/2026

    For Sale N6140508 - 1801 HIGHLAND RD, OSPREY, FL 34229 39 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1165
       Built: 1999
    Monthly Fee: $150
       Tax: $2,578 (2025)
    Community: Towns-End Shores
    Spa: No

    Townhouse


    Estimated Monthly Payment: $1,953 (change assumption)
    Mortgage ($1,588) + Fees ($150) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


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

    $615,000553 Days on yellowkey   MLS ID: A4635708

    REDUCED by $45,000 (6.8%) on 07/27/2026

    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: $4,260 (change assumption)
    Mortgage ($3,370) + 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


  • 401 N POINT RD #1001, OSPREY, FL 34229

    $1,995,000181 Days on yellowkey   MLS ID: A4679998

    For Sale A4679998 - 401 N POINT RD #1001, OSPREY, FL 34229 60 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3029
       Built: 2003
    Monthly Fee: $400
       Tax: $10,201 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $12,181 (change assumption)
    Mortgage ($10,931) + Fees ($400) + Taxes in 2025 ($850)


    Taxes:$10,201

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School


  • 700 FAITH AVE, OSPREY, FL 34229

    $1,200,000266 Days on yellowkey   MLS ID: A4667634

    For Sale A4667634 - 700 FAITH AVE, OSPREY, FL 34229 74 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 1982   Tax: $9,155 (2024)
    Community: Trinity Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,338 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($763)


    Taxes:$9,155

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4213 EXPEDITION WAY #107, OSPREY, FL 34229

    $320,00030 Days on yellowkey   MLS ID: A4698337

    For Sale A4698337 - 4213 EXPEDITION WAY #107, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1430
       Built: 2016
    Monthly Fee: $475
       Tax: $3,428 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,514 (change assumption)
    Mortgage ($1,753) + Fees ($475) + Taxes in 2025 ($286)


    Taxes:$3,428

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 108 WOODLAND PL #108, OSPREY, FL 34229

    $285,00022 Days on yellowkey   MLS ID: A4699279

    For Sale A4699279 - 108 WOODLAND PL #108, OSPREY, FL 34229 50 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1316
       Built: 1979   Tax: $3,100 (2025)
    Community: Pine Run Ii
    Condo


    Estimated Monthly Payment: $1,820 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($258)


    Taxes:$3,100

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 433 E MACEWEN DR, OSPREY, FL 34229

    $2,189,000214 Days on yellowkey   MLS ID: A4676505

    REDUCED by $61,000 (2.7%) on 06/23/2026

    For Sale A4676505 - 433 E MACEWEN DR, OSPREY, FL 34229 78 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4012
       Built: 1998
    Monthly Fee: $142
       Tax: $17,426 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,588 (change assumption)
    Mortgage ($11,994) + Fees ($142) + Taxes in 2025 ($1,452)


    Taxes:$17,426

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 14041 BELLAGIO WAY #318, OSPREY, FL 34229

    $949,00051 Days on yellowkey   MLS ID: A4696101

    0 Days Off yellowkey (back on 7/26/2026)

    REDUCED by $50,000 (5.0%) on 07/07/2026

    For Sale A4696101 - 14041 BELLAGIO WAY #318, OSPREY, FL 34229 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2086
       Built: 2006
    Monthly Fee: $1,512
       Tax: $7,362 (2025)
    Community: Villas At Bellagio Harbor Village
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,325 (change assumption)
    Mortgage ($5,200) + Fees ($1,512) + Taxes in 2025 ($614)


    Taxes:$7,362

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 570 BLACKBURN POINT RD #36, OSPREY, FL 34229

    $99,5008 Days on yellowkey   MLS ID: A4700865

    For Sale A4700865 - 570 BLACKBURN POINT RD #36, OSPREY, FL 34229 4 photos

    Bed:    Bath: 0.0
    Monthly Fee: $448
       Tax: $648 (2025)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $1,047 (change assumption)
    Mortgage ($545) + Fees ($448) + Taxes in 2025 ($54)


    Taxes:$648

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 742 HARMS DR, OSPREY, FL 34229

    $499,900305 Days on yellowkey   MLS ID: A4666421

    REDUCED by $15,100 (2.9%) on 07/24/2026

    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: $3,207 (change assumption)
    Mortgage ($2,739) + 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




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.