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

    $850,00027 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


  • 1042 N CASEY KEY RD, OSPREY, FL 34229

    $3,750,000169 Days on yellowkey   MLS ID: A4674771

    For Sale A4674771 - 1042 N CASEY KEY RD, OSPREY, FL 34229 58 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4781
       Built: 1995   Tax: $18,245 (2025)
    Community: Palmer
    Single Family


    Estimated Monthly Payment: $22,068 (change assumption)
    Mortgage ($20,547) + Taxes in 2025 ($1,520)


    Taxes:$18,245

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School


  • 314 S SHORE DR, OSPREY, FL 34229

    $1,649,0005 Days on yellowkey   MLS ID: TB8510971

    For Sale TB8510971 - 314 S SHORE DR, OSPREY, FL 34229 99 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3853
       Built: 1981
    Monthly Fee: $15
       Tax: $8,819 (2025)
    Community: Sorrento Shores Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,785 (change assumption)
    Mortgage ($9,035) + Fees ($15) + Taxes in 2025 ($735)


    Taxes:$8,819

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


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

    $328,00085 Days on yellowkey   MLS ID: N6143250

    REDUCED by $1,000 (0.3%) on 05/20/2026

    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: $2,112 (change assumption)
    Mortgage ($1,797) + Taxes in 2025 ($315)


    Taxes:$3,781

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 4428 CONCHFISH LN, OSPREY, FL 34229

    $548,000346 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


  • 347 BAYSHORE DR, OSPREY, FL 34229

    $739,00018 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


  • 664 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $875,00099 Days on yellowkey   MLS ID: A4681662

    0 Days Off yellowkey (back on 5/24/2026)

    REDUCED by $12,000 (1.4%) on 05/14/2026

    For Sale A4681662 - 664 CRANE PRAIRIE WAY, OSPREY, FL 34229 63 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: $5,686 (change assumption)
    Mortgage ($4,794) + 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


  • 1337 COPPERWOOD DR, OSPREY, FL 34229

    $550,000242 Days on yellowkey   MLS ID: A4666722

    2 Days Off yellowkey (back on 5/18/2026)

    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


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

    $269,00019 Days on yellowkey   MLS ID: A4693150

    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   Tax: $3,176 (2025)
    Community: Pine Run I
    Spa: No

    Condo


    Estimated Monthly Payment: $1,739 (change assumption)
    Mortgage ($1,474) + 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


  • 296 PINE RANCH TRL, OSPREY, FL 34229

    $1,150,000371 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


  • 103 BISHOPS COURT RD, OSPREY, FL 34229

    $749,0008 Days on yellowkey   MLS ID: A4694468

    For Sale A4694468 - 103 BISHOPS COURT RD, OSPREY, FL 34229 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2034
       Built: 2000
    Monthly Fee: $425
       Tax: $3,743 (2025)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,841 (change assumption)
    Mortgage ($4,104) + Fees ($425) + Taxes in 2025 ($312)


    Taxes:$3,743

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School


  • 1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229

    $599,00053 Days on yellowkey   MLS ID: C7524397

    For Sale C7524397 - 1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2006
       Built: 2004
    Monthly Fee: $980
       Tax: $6,502 (2025)
    Community: Blackburn Harbor Waterfront Vi
    Condo


    Estimated Monthly Payment: $4,804 (change assumption)
    Mortgage ($3,282) + Fees ($980) + Taxes in 2025 ($542)


    Taxes:$6,502

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 127 PARK TRACE BLVD, OSPREY, FL 34229

    $795,00026 Days on yellowkey   MLS ID: A4692408

    1 Days Off yellowkey (back on 5/22/2026)

    For Sale A4692408 - 127 PARK TRACE BLVD, OSPREY, FL 34229 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2463
       Built: 2003   Tax: $4,379 (2025)
    Community: Park Trace Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,721 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($365)


    Taxes:$4,379

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 13 BAYHEAD LN, OSPREY, FL 34229

    $799,000422 Days on yellowkey   MLS ID: A4645829

    REDUCED by $51,000 (6.0%) on 05/13/2026

    For Sale A4645829 - 13 BAYHEAD LN, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2310
       Built: 2001
    Monthly Fee: $425
       Tax: $3,620 (2024)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,105 (change assumption)
    Mortgage ($4,378) + Fees ($425) + Taxes in 2024 ($302)


    Taxes:$3,620

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 76 OSPREY POINT DR, OSPREY, FL 34229

    $1,545,000187 Days on yellowkey   MLS ID: A4672843

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

    REDUCED by $45,000 (2.8%) on 04/20/2026

    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
    Single Family


    Estimated Monthly Payment: $10,066 (change assumption)
    Mortgage ($8,466) + 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


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

    $650,000150 Days on yellowkey   MLS ID: A4676382

    REDUCED by $29,900 (4.4%) on 05/21/2026

    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: $5,059 (change assumption)
    Mortgage ($3,562) + 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


  • 4424 CONCHFISH LN, OSPREY, FL 34229

    $615,00010 Days on yellowkey   MLS ID: A4691622

    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: $3,867 (change assumption)
    Mortgage ($3,370) + 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


  • 104 PARK TRACE BLVD, OSPREY, FL 34229

    $550,000173 Days on yellowkey   MLS ID: A4674221

    REDUCED by $25,000 (4.3%) on 05/20/2026

    For Sale A4674221 - 104 PARK TRACE BLVD, OSPREY, FL 34229 47 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2557
       Built: 2002
    Monthly Fee: $58
       Tax: $7,427 (2024)
    Community: Park Trace Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,691 (change assumption)
    Mortgage ($3,014) + Fees ($58) + Taxes in 2024 ($619)


    Taxes:$7,427

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 562 OAK BAY DR, OSPREY, FL 34229

    $530,00033 Days on yellowkey   MLS ID: A4690387

    1 Days Off yellowkey (back on 5/20/2026)

    REDUCED by $30,000 (5.4%) on 05/09/2026

    For Sale A4690387 - 562 OAK BAY DR, OSPREY, FL 34229 79 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2414
       Built: 1995
    Monthly Fee: $25
       Tax: $3,524 (2025)
    Community: Bay Oaks Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,223 (change assumption)
    Mortgage ($2,904) + Fees ($25) + Taxes in 2025 ($294)


    Taxes:$3,524

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


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

    $629,000198 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




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.