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Homes For Sale in Osprey 34229 - 126 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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  • 447 N SHORE DR, OSPREY, FL 34229

    $515,35045 Days on yellowkey   MLS ID: A4684009

    REDUCED by $19,550 (3.7%) on 04/02/2026

    For Sale A4684009 - 447 N SHORE DR, OSPREY, FL 34229 45 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1874
       Built: 1964   Tax: $4,243 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $3,177 (change assumption)
    Mortgage ($2,824) + Taxes in 2025 ($354)


    Taxes:$4,243

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 664 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $887,00058 Days on yellowkey   MLS ID: A4681662

    REDUCED by $10,000 (1.1%) on 04/08/2026

    For Sale A4681662 - 664 CRANE PRAIRIE WAY, OSPREY, FL 34229 69 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2870
       Built: 2003
    Monthly Fee: $437
       Tax: $5,460 (2025)
    Community: Willowbend Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,752 (change assumption)
    Mortgage ($4,860) + Fees ($437) + Taxes in 2025 ($455)


    Taxes:$5,460

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 250 HIDDEN BAY DR #301, OSPREY, FL 34229

    $725,00087 Days on yellowkey   MLS ID: A4679278

    For Sale A4679278 - 250 HIDDEN BAY DR #301, OSPREY, FL 34229 58 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2168
       Built: 2017   Tax: $7,792 (2025)
    Community: Edgewater At Hidden Bay
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,622 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($649)


    Taxes:$7,792

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 522 LUMINARY BLVD, OSPREY, FL 34229

    $647,00072 Days on yellowkey   MLS ID: A4676528

    For Sale A4676528 - 522 LUMINARY BLVD, OSPREY, FL 34229 53 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2320
       Built: 2005
    Monthly Fee: $420
       Tax: $4,456 (2025)
    Community: Willowbend Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,336 (change assumption)
    Mortgage ($3,545) + Fees ($420) + Taxes in 2025 ($371)


    Taxes:$4,456

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 312 YACHT HARBOR DR, OSPREY, FL 34229

    $1,995,000198 Days on yellowkey   MLS ID: A4667293

    For Sale A4667293 - 312 YACHT HARBOR DR, OSPREY, FL 34229 69 photos

    Bed: 3   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 2572
       Built: 1978
    Monthly Fee: $219
       Tax: $14,066 (2024)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,322 (change assumption)
    Mortgage ($10,931) + Fees ($219) + Taxes in 2024 ($1,172)


    Taxes:$14,066

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 5100 JESSIE HARBOR DR #403, OSPREY, FL 34229

    $679,900109 Days on yellowkey   MLS ID: A4676382

    For Sale A4676382 - 5100 JESSIE HARBOR DR #403, OSPREY, FL 34229 44 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2004
    Monthly Fee: $1,027
       Tax: $5,647 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $5,223 (change assumption)
    Mortgage ($3,725) + Fees ($1,027) + Taxes in 2025 ($471)


    Taxes:$5,647

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 228 SAINT JAMES PARK, OSPREY, FL 34229

    $1,645,00030 Days on yellowkey   MLS ID: A4686681

    REDUCED by $50,000 (2.9%) on 04/18/2026

    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: $10,054 (change assumption)
    Mortgage ($9,013) + 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

    $1,590,000146 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


  • 102 WINDWARD DR, OSPREY, FL 34229

    $690,000151 Days on yellowkey   MLS ID: A4671793

    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: $4,295 (change assumption)
    Mortgage ($3,781) + 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


  • 232 WOODLAND DR #232, OSPREY, FL 34229

    $264,900157 Days on yellowkey   MLS ID: A4671600

    For Sale A4671600 - 232 WOODLAND DR #232, OSPREY, FL 34229 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1980   Tax: $2,202 (2025)
    Community: Pine Run Iii
    Condo


    Estimated Monthly Payment: $1,635 (change assumption)
    Mortgage ($1,451) + Taxes in 2025 ($184)


    Taxes:$2,202

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1337 COPPERWOOD DR, OSPREY, FL 34229

    $550,000201 Days on yellowkey   MLS ID: A4666722

    REDUCED by $19,000 (3.3%) on 04/02/2026

    For Sale A4666722 - 1337 COPPERWOOD DR, OSPREY, FL 34229 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2172
       Built: 2004
    Monthly Fee: $397
       Tax: $4,420 (2025)
    Community: Willowbend Phase 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,779 (change assumption)
    Mortgage ($3,014) + Fees ($397) + Taxes in 2025 ($368)


    Taxes:$4,420

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 4428 CONCHFISH LN, OSPREY, FL 34229

    $548,000305 Days on yellowkey   MLS ID: A4656074

    For Sale A4656074 - 4428 CONCHFISH LN, OSPREY, FL 34229 13 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1861
       Built: 2018
    Monthly Fee: $147
       Tax: $5,936 (2024)
    Community: Palms/Casey Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,644 (change assumption)
    Mortgage ($3,003) + Fees ($147) + Taxes in 2024 ($495)


    Taxes:$5,936

    Elementary School: Laurel Nokomis Elementary

    High School: Pine View School

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 296 PINE RANCH TRL, OSPREY, FL 34229

    $1,250,000330 Days on yellowkey   MLS ID: A4653218

    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: $7,307 (change assumption)
    Mortgage ($6,849) + Taxes in 2024 ($458)


    Taxes:$5,492

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229

    $329,50044 Days on yellowkey   MLS ID: N6143250

    REDUCED by $400 (0.1%) on 04/19/2026

    For Sale N6143250 - 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229 77 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1528
       Built: 2018   Tax: $3,781 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,120 (change assumption)
    Mortgage ($1,805) + Taxes in 2025 ($315)


    Taxes:$3,781

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 328 E BAY ST, OSPREY, FL 34229

    $429,900Listed 04/19/2026 9:21AM   MLS ID: O6400514

    For Sale O6400514 - 328 E BAY ST, OSPREY, FL 34229 28 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 884
       Built: 1986   Tax: $1,236 (2025)
    Community: Sarabay Acres
    Single Family


    Estimated Monthly Payment: $2,459 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($103)


    Taxes:$1,236

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 166 EDGEWOOD DR, OSPREY, FL 34229

    $167,00018 Days on yellowkey   MLS ID: A4687852

    0 Days Off yellowkey (back on 4/18/2026)

    For Sale A4687852 - 166 EDGEWOOD DR, OSPREY, FL 34229 76 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 959
       Built: 1977
    Monthly Fee: $215
       Tax: $919 (2025)
    Community: Arbors
    Manufactured Home


    Estimated Monthly Payment: $1,207 (change assumption)
    Mortgage ($915) + Fees ($215) + Taxes in 2025 ($77)


    Taxes:$919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1348 THORNAPPLE DR, OSPREY, FL 34229

    $535,00010 Days on yellowkey   MLS ID: A4687822

    0 Days Off yellowkey (back on 4/18/2026)

    For Sale A4687822 - 1348 THORNAPPLE DR, OSPREY, FL 34229 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2171
       Built: 2003
    Monthly Fee: $397
       Tax: $4,051 (2025)
    Community: Willowbend Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,666 (change assumption)
    Mortgage ($2,931) + Fees ($397) + Taxes in 2025 ($338)


    Taxes:$4,051

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 665 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $719,000201 Days on yellowkey   MLS ID: A4666718

    For Sale A4666718 - 665 CRANE PRAIRIE WAY, OSPREY, FL 34229 61 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 2003
    Monthly Fee: $420
       Tax: $4,513 (2025)
    Community: Willowbend Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,736 (change assumption)
    Mortgage ($3,940) + Fees ($420) + Taxes in 2025 ($376)


    Taxes:$4,513

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 14041 BELLAGIO WAY #218, OSPREY, FL 34229

    $999,000150 Days on yellowkey   MLS ID: A4672639

    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: 2374
       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


  • 1801 HIGHLAND RD, OSPREY, FL 34229

    $299,900215 Days on yellowkey   MLS ID: N6140508

    For Sale N6140508 - 1801 HIGHLAND RD, OSPREY, FL 34229 41 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: $2,008 (change assumption)
    Mortgage ($1,643) + 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




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.