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Osprey Homes For Sale & Real Estate - 140 homes

Osprey homes for sale are located in Sarasota County, Florida. Find homes in Osprey for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Osprey houses.

Location: Osprey

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  • 347 BAYSHORE DR, OSPREY, FL 34229

    $699,00064 Days on yellowkey   MLS ID: A4693374

    REDUCED by $40,000 (5.4%) on 07/07/2026

    For Sale A4693374 - 347 BAYSHORE DR, OSPREY, FL 34229 70 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2013   Tax: $879 (2025)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $3,903 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($73)


    Taxes:$879

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 448 E MACEWEN DR, OSPREY, FL 34229

    $2,100,000109 Days on yellowkey   MLS ID: A4687195

    0 Days Off yellowkey (back on 7/11/2026)

    For Sale A4687195 - 448 E MACEWEN DR, OSPREY, FL 34229 52 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3768
       Built: 1998
    Monthly Fee: $142
       Tax: $9,639 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,452 (change assumption)
    Mortgage ($11,507) + Fees ($142) + Taxes in 2025 ($803)


    Taxes:$9,639

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 18 N CASEY KEY RD, OSPREY, FL 34229

    $1,750,000268 Days on yellowkey   MLS ID: A4669083

    0 Days Off yellowkey (back on 6/1/2026)

    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


  • 619 OAK RIVER CT, OSPREY, FL 34229

    $609,90062 Days on yellowkey   MLS ID: A4692331

    2 Days Off yellowkey (back on 7/10/2026)

    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


  • 422 BLUE GARDEN LN, OSPREY, FL 34229

    $1,445,000303 Days on yellowkey   MLS ID: A4664436

    REDUCED by $50,000 (3.3%) on 07/10/2026

    For Sale A4664436 - 422 BLUE GARDEN LN, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3872
       Built: 1984
    Monthly Fee: $475
       Tax: $7,339 (2024)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,004 (change assumption)
    Mortgage ($7,918) + Fees ($475) + Taxes in 2024 ($612)


    Taxes:$7,339

    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

    $318,000131 Days on yellowkey   MLS ID: N6143250

    REDUCED by $10,000 (3.0%) on 06/22/2026

    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: $2,057 (change assumption)
    Mortgage ($1,742) + Taxes in 2025 ($315)


    Taxes:$3,781

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 127 PARK TRACE BLVD, OSPREY, FL 34229

    $795,00072 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


  • 329 BAY VISTA AVE, OSPREY, FL 34229

    $445,0006 Days on yellowkey   MLS ID: A4699464

    For Sale A4699464 - 329 BAY VISTA AVE, OSPREY, FL 34229 30 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1346
       Built: 1963   Tax: $4,306 (2025)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $2,797 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($359)


    Taxes:$4,306

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 759 FORDINGBRIDGE WAY, OSPREY, FL 34229

    $715,00090 Days on yellowkey   MLS ID: O6399774

    REDUCED by $34,000 (4.5%) on 07/09/2026

    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: $4,567 (change assumption)
    Mortgage ($3,918) + Fees ($55) + Taxes in 2025 ($594)


    Taxes:$7,129

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 429 PATTERSON AVE, OSPREY, FL 34229

    $449,00019 Days on yellowkey   MLS ID: A4697505

    1 Days Off yellowkey (back on 7/8/2026)

    For Sale A4697505 - 429 PATTERSON AVE, OSPREY, FL 34229 46 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1173
       Built: 1979   Tax: $4,251 (2025)
    Community: Osprey Park 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,814 (change assumption)
    Mortgage ($2,460) + Taxes in 2025 ($354)


    Taxes:$4,251

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: None


  • 433 E MACEWEN DR, OSPREY, FL 34229

    $2,189,000197 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 72 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


  • 811 SARABAY RD, OSPREY, FL 34229

    $449,00022 Days on yellowkey   MLS ID: A4697921

    For Sale A4697921 - 811 SARABAY RD, OSPREY, FL 34229 36 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1211
       Built: 1950   Tax: $1,130 (2025)
    Community: Harms Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,554 (change assumption)
    Mortgage ($2,460) + Taxes in 2025 ($94)


    Taxes:$1,130

    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

    $265,00096 Days on yellowkey   MLS ID: A4689541

    REDUCED by $5,000 (1.9%) on 07/06/2026

    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: $1,744 (change assumption)
    Mortgage ($1,452) + 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


  • 816 SHADOW BAY WAY, OSPREY, FL 34229

    $655,00064 Days on yellowkey   MLS ID: A4690226

    0 Days Off yellowkey (back on 7/8/2026)

    For Sale A4690226 - 816 SHADOW BAY WAY, OSPREY, FL 34229 66 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2251
       Built: 1998
    Monthly Fee: $120
       Tax: $4,453 (2025)
    Community: Rivendell
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,080 (change assumption)
    Mortgage ($3,589) + Fees ($120) + Taxes in 2025 ($371)


    Taxes:$4,453

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 121 N CASEY KEY RD, OSPREY, FL 34229

    $6,475,000284 Days on yellowkey   MLS ID: A4667263

    For Sale A4667263 - 121 N CASEY KEY RD, OSPREY, FL 34229 66 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4096
       Built: 1969
    Monthly Fee: $33
       Tax: $37,172 (2024)
    Community: Casey Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $38,609 (change assumption)
    Mortgage ($35,479) + Fees ($33) + Taxes in 2024 ($3,098)


    Taxes:$37,172

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 260 HIDDEN BAY DR #304, OSPREY, FL 34229

    $694,000148 Days on yellowkey   MLS ID: N6142969

    REDUCED by $5,000 (0.7%) on 04/14/2026

    For Sale N6142969 - 260 HIDDEN BAY DR #304, OSPREY, FL 34229 70 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1950
       Built: 2019   Tax: $6,342 (2025)
    Community: Edgewater/Hidden Bay Ph 2 Bldg
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,331 (change assumption)
    Mortgage ($3,803) + Taxes in 2025 ($529)


    Taxes:$6,342

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4213 EXPEDITION WAY #107, OSPREY, FL 34229

    $320,00013 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


  • OSPREY, FL 34229

    $799,0009 Days on yellowkey   MLS ID: A4699089

    For Sale A4699089 - OSPREY, FL 34229 45 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2607
       Built: 2001
    Monthly Fee: $58
       Tax: $5,777 (2025)
    Community: Park Trace Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,917 (change assumption)
    Mortgage ($4,378) + Fees ($58) + Taxes in 2025 ($481)


    Taxes:$5,777

    Elementary School: Pine View School

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 14021 BELLAGIO WAY #404, OSPREY, FL 34229

    $1,100,00079 Days on yellowkey   MLS ID: N6144070

    REDUCED by $75,000 (6.4%) on 07/07/2026

    For Sale N6144070 - 14021 BELLAGIO WAY #404, OSPREY, FL 34229 70 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2187
       Built: 2006
    Monthly Fee: $1,644
       Tax: $5,636 (2025)
    Community: Villas At Bellagio Harbor Village
    Condo


    Estimated Monthly Payment: $8,141 (change assumption)
    Mortgage ($6,027) + Fees ($1,644) + Taxes in 2025 ($470)


    Taxes:$5,636

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 480 BLACKBURN POINT RD #5, OSPREY, FL 34229

    $249,00013 Days on yellowkey   MLS ID: A4698854

    1 Days Off yellowkey (back on 7/6/2026)

    For Sale A4698854 - 480 BLACKBURN POINT RD #5, OSPREY, FL 34229 5 photos

    Bed:    Bath: 0.0
    Built: 2006
       Tax: $1,092 (2025)
    Community: Wet Slips At Bellagio Harbor Village
    Dock-Rackominium


    Estimated Monthly Payment: $1,455 (change assumption)
    Mortgage ($1,364) + Taxes in 2025 ($91)


    Taxes:$1,092

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for Osprey Homes for Sale and Other Real Estate?

Osprey home, townhome, condo, villa, and other listing sales 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 Osprey. You can use our website to view Multiple Listing Service (MLS) data on 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 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.