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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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  • 204 WINDWARD DR, OSPREY, FL 34229

    $1,050,00019 Days on yellowkey   MLS ID: A4693139

    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: $86
       Tax: $4,761 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,236 (change assumption)
    Mortgage ($5,753) + Fees ($86) + 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


  • 4284 EXPEDITION WAY #NA, OSPREY, FL 34229

    $325,000106 Days on yellowkey   MLS ID: A4681835

    REDUCED by $14,900 (4.4%) on 05/12/2026

    For Sale A4681835 - 4284 EXPEDITION WAY #NA, OSPREY, FL 34229 40 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1430
       Built: 2017   Tax: $2,934 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,025 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($244)


    Taxes:$2,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 730 SARABAY RD, OSPREY, FL 34229

    $4,995,000192 Days on yellowkey   MLS ID: A4672618

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale A4672618 - 730 SARABAY RD, OSPREY, FL 34229 42 photos

    Bed: 4   Bath: 5.5   Gar: 7
    Liv Area Sq Ft: 6308
       Built: 2011   Tax: $47,200 (2024)
    Community: Sarabay Acres
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,303 (change assumption)
    Mortgage ($27,369) + Taxes in 2024 ($3,933)


    Taxes:$47,200

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 186 WINDWARD DR, OSPREY, FL 34229

    $599,900142 Days on yellowkey   MLS ID: N6142087

    0 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $49,600 (7.6%) on 05/07/2026

    For Sale N6142087 - 186 WINDWARD DR, OSPREY, FL 34229 93 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2505
       Built: 1983
    Monthly Fee: $204
       Tax: $7,566 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,122 (change assumption)
    Mortgage ($3,287) + Fees ($204) + Taxes in 2025 ($631)


    Taxes:$7,566

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 227 SAINT JAMES PARK, OSPREY, FL 34229

    $885,000122 Days on yellowkey   MLS ID: A4679867

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale A4679867 - 227 SAINT JAMES PARK, OSPREY, FL 34229 93 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2071
       Built: 1986
    Monthly Fee: $142
       Tax: $4,611 (2025)
    Community: Oaks 2 Ph 1
    Single Family


    Estimated Monthly Payment: $5,375 (change assumption)
    Mortgage ($4,849) + Fees ($142) + Taxes in 2025 ($384)


    Taxes:$4,611

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 320 TROPIC DR, OSPREY, FL 34229

    $195,00019 Days on yellowkey   MLS ID: A4692490

    For Sale A4692490 - 320 TROPIC DR, OSPREY, FL 34229 37 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1199
       Built: 1980
    Monthly Fee: $430
       Tax: $1,438 (2024)
    Community: Arbors
    Manufactured Home


    Estimated Monthly Payment: $1,618 (change assumption)
    Mortgage ($1,068) + Fees ($430) + Taxes in 2024 ($120)


    Taxes:$1,438

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 447 N SHORE DR, OSPREY, FL 34229

    $499,00086 Days on yellowkey   MLS ID: A4684009

    REDUCED by $16,350 (3.2%) on 05/12/2026

    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: $3,088 (change assumption)
    Mortgage ($2,734) + 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


  • 4271 EXPEDITION WAY #103, OSPREY, FL 34229

    $280,00050 Days on yellowkey   MLS ID: A4689541

    REDUCED by $10,000 (3.4%) on 05/12/2026

    For Sale A4689541 - 4271 EXPEDITION WAY #103, OSPREY, FL 34229 35 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1135
       Built: 2017   Tax: $3,507 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $1,826 (change assumption)
    Mortgage ($1,534) + Taxes in 2025 ($292)


    Taxes:$3,507

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1811 HIGHLAND RD, OSPREY, FL 34229

    $417,000211 Days on yellowkey   MLS ID: TB8443161

    REDUCED by $5,000 (1.2%) on 05/12/2026

    For Sale TB8443161 - 1811 HIGHLAND RD, OSPREY, FL 34229 19 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1725
       Built: 1997
    Monthly Fee: $150
       Tax: $4,299 (2024)
    Community: Towns-End Shores
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,793 (change assumption)
    Mortgage ($2,285) + Fees ($150) + Taxes in 2024 ($358)


    Taxes:$4,299

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 393 N POINT RD #604, OSPREY, FL 34229

    $795,000482 Days on yellowkey   MLS ID: A4638035

    For Sale A4638035 - 393 N POINT RD #604, OSPREY, FL 34229 92 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2778
       Built: 2001
    Monthly Fee: $367
       Tax: $9,625 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $5,525 (change assumption)
    Mortgage ($4,356) + Fees ($367) + Taxes in 2024 ($802)


    Taxes:$9,625

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 14021 BELLAGIO WAY #309, OSPREY, FL 34229

    $899,995113 Days on yellowkey   MLS ID: A4681589

    For Sale A4681589 - 14021 BELLAGIO WAY #309, OSPREY, FL 34229 38 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2199
       Built: 2006
    Monthly Fee: $1,585
       Tax: $9,062 (2024)
    Community: Villas/Harbor Village
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,271 (change assumption)
    Mortgage ($4,931) + Fees ($1,585) + Taxes in 2024 ($755)


    Taxes:$9,062

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 51 MACEWEN DR #5, OSPREY, FL 34229

    $235,00040 Days on yellowkey   MLS ID: A4689838

    REDUCED by $65,000 (21.7%) on 05/11/2026

    For Sale A4689838 - 51 MACEWEN DR #5, OSPREY, FL 34229 44 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 595
       Built: 1990
    Monthly Fee: $142
       Tax: $3,079 (2025)
    Community: Windsor Lodge At The Oaks
    Condo


    Estimated Monthly Payment: $1,686 (change assumption)
    Mortgage ($1,288) + Fees ($142) + Taxes in 2025 ($257)


    Taxes:$3,079

    Elementary School: Laurel Nokomis Elementary

    High School: Pine View School

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 222 GLENWOOD AVE, OSPREY, FL 34229

    $275,00024 Days on yellowkey   MLS ID: TB8504427

    0 Days Off yellowkey (back on 5/9/2026)

    For Sale TB8504427 - 222 GLENWOOD AVE, OSPREY, FL 34229 53 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 952
       Built: 1990   Tax: $3,409 (2025)
    Community: Tb Ogburns Add
    Single Family


    Estimated Monthly Payment: $1,791 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($284)


    Taxes:$3,409

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 1361 NEW FOREST LN, OSPREY, FL 34229

    $550,00036 Days on yellowkey   MLS ID: A4691036

    For Sale A4691036 - 1361 NEW FOREST LN, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2074
       Built: 2002
    Monthly Fee: $292
       Tax: $5,783 (2025)
    Community: Rivendell Woodlands
    Single Family


    Estimated Monthly Payment: $3,788 (change assumption)
    Mortgage ($3,014) + Fees ($292) + Taxes in 2025 ($482)


    Taxes:$5,783

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 18 N CASEY KEY RD, OSPREY, FL 34229

    $1,750,000222 Days on yellowkey   MLS ID: A4669083

    REDUCED by $250,000 (12.5%) on 05/08/2026

    For Sale A4669083 - 18 N CASEY KEY RD, OSPREY, FL 34229 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1977
       Built: 1973   Tax: $24,015 (2024)
    Community: Casey Key
    Single Family


    Estimated Monthly Payment: $11,590 (change assumption)
    Mortgage ($9,589) + Taxes in 2024 ($2,001)


    Taxes:$24,015

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 1116 BEACHCOMBER CT #3, OSPREY, FL 34229

    $545,00057 Days on yellowkey   MLS ID: A4688310

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

    For Sale A4688310 - 1116 BEACHCOMBER CT #3, OSPREY, FL 34229 65 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2040
       Built: 2005
    Monthly Fee: $1,133
       Tax: $5,376 (2025)
    Community: Blackburn Point Marina Village
    Condo


    Estimated Monthly Payment: $4,567 (change assumption)
    Mortgage ($2,986) + Fees ($1,133) + Taxes in 2025 ($448)


    Taxes:$5,376

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 678 FAITH AVE, OSPREY, FL 34229

    $749,000170 Days on yellowkey   MLS ID: A4674865

    REDUCED by $26,000 (3.4%) on 05/08/2026

    For Sale A4674865 - 678 FAITH AVE, OSPREY, FL 34229 51 photos

    Bed: 3   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2583
       Built: 1995   Tax: $5,871 (2025)
    Community: Trinity Acres
    Single Family


    Estimated Monthly Payment: $4,593 (change assumption)
    Mortgage ($4,104) + Taxes in 2025 ($489)


    Taxes:$5,871

    Elementary School: Pine View School

    High School: None

    Tax Year: 2025

    Middle School: Pine View School


  • 21 BAYHEAD LN, OSPREY, FL 34229

    $850,000257 Days on yellowkey   MLS ID: A4664085

    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: $5,467 (change assumption)
    Mortgage ($4,657) + 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


  • 570 BLACKBURN POINT RD #LNG42, OSPREY, FL 34229

    $35,900142 Days on yellowkey   MLS ID: A4677438

    REDUCED by $3,100 (7.9%) on 05/06/2026

    For Sale A4677438 - 570 BLACKBURN POINT RD #LNG42, OSPREY, FL 34229 15 photos

    Bed:    Bath: 0.0    Tax: $278 (2025)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $220 (change assumption)
    Mortgage ($197) + Taxes in 2025 ($23)


    Taxes:$278

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 764 SARABAY RD #8, OSPREY, FL 34229

    $450,00093 Days on yellowkey   MLS ID: A4683747

    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: $1,650
       Tax: $2,936 (2025)
    Community: Heron Bay Club Sec I
    Villa


    Estimated Monthly Payment: $4,360 (change assumption)
    Mortgage ($2,466) + Fees ($1,650) + 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




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.