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Osprey Homes For Sale & Real Estate - 125 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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  • 402 MACEWEN DR, OSPREY, FL 34229

    $1,750,0002 Days on yellowkey   MLS ID: A4690018

    For Sale A4690018 - 402 MACEWEN DR, OSPREY, FL 34229 78 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3565
       Built: 1999
    Monthly Fee: $142
       Tax: $13,762 (2025)
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $10,878 (change assumption)
    Mortgage ($9,589) + Fees ($142) + Taxes in 2025 ($1,147)


    Taxes:$13,762

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


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

    $329,90041 Days on yellowkey   MLS ID: N6143250

    For Sale N6143250 - 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229 68 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: $2,123 (change assumption)
    Mortgage ($1,808) + Taxes in 2025 ($315)


    Taxes:$3,781

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 32 SIESTA CIR W, OSPREY, FL 34229

    $69,0002 Days on yellowkey   MLS ID: A4690063

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale A4690063 - 32 SIESTA CIR W, OSPREY, FL 34229 3 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 480
       Built: 1968
    Monthly Fee: $215
       Tax: $555 (2025)
    Community: Arbors
    Mobile Home


    Estimated Monthly Payment: $639 (change assumption)
    Mortgage ($378) + Fees ($215) + Taxes in 2025 ($46)


    Taxes:$555

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 522 LUMINARY BLVD, OSPREY, FL 34229

    $647,00069 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


  • 4271 EXPEDITION WAY #103, OSPREY, FL 34229

    $290,0006 Days on yellowkey   MLS ID: A4689541

    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: $1,881 (change assumption)
    Mortgage ($1,589) + 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


  • 353 S SHORE DR, OSPREY, FL 34229

    $1,200,00015 Days on yellowkey   MLS ID: A4688006

    For Sale A4688006 - 353 S SHORE DR, OSPREY, FL 34229 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 1968
    Monthly Fee: $10
       Tax: $3,904 (2025)
    Community: Sorrento Shores Rep Of 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,910 (change assumption)
    Mortgage ($6,575) + Fees ($10) + Taxes in 2025 ($325)


    Taxes:$3,904

    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

    $339,90062 Days on yellowkey   MLS ID: A4681835

    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: $2,107 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($244)


    Taxes:$2,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 244 WOODLAND DR #244, OSPREY, FL 34229

    $200,000182 Days on yellowkey   MLS ID: A4667419

    For Sale A4667419 - 244 WOODLAND DR #244, OSPREY, FL 34229 41 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1980   Tax: $2,685 (2025)
    Community: Pine Run Iii
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,096) + Taxes in 2025 ($224)


    Taxes:$2,685

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $725,00084 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


  • 759 FORDINGBRIDGE WAY, OSPREY, FL 34229

    $727,000Listed 04/16/2026 12:39PM   MLS ID: O6399774

    For Sale O6399774 - 759 FORDINGBRIDGE WAY, OSPREY, FL 34229 50 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: $4,633 (change assumption)
    Mortgage ($3,983) + Fees ($55) + Taxes in 2025 ($594)


    Taxes:$7,129

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 447 N SHORE DR, OSPREY, FL 34229

    $515,35042 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


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,0001 Day on yellowkey   MLS ID: A4685559

    For Sale A4685559 - 61 BAYHEAD LN, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3180
       Built: 1993
    Monthly Fee: $458
       Tax: $4,573 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,332 (change assumption)
    Mortgage ($6,493) + Fees ($458) + Taxes in 2025 ($381)


    Taxes:$4,573

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 166 EDGEWOOD DR, OSPREY, FL 34229

    $167,00015 Days on yellowkey   MLS ID: A4687852

    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


  • 665 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $719,000198 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


  • 664 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $887,00055 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


  • 479 SOUTH CREEK DR, OSPREY, FL 34229

    $2,495,000136 Days on yellowkey   MLS ID: N6141722

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale N6141722 - 479 SOUTH CREEK DR, OSPREY, FL 34229 73 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4261
       Built: 1995
    Monthly Fee: $150
       Tax: $11,095 (2024)
    Community: South Creek
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,745 (change assumption)
    Mortgage ($13,671) + Fees ($150) + Taxes in 2024 ($925)


    Taxes:$11,095

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 4173 FRONTIER LN #4173, OSPREY, FL 34229

    $289,0006 Days on yellowkey   MLS ID: A4689582

    2 Days Off yellowkey (back on 4/15/2026)

    For Sale A4689582 - 4173 FRONTIER LN #4173, OSPREY, FL 34229 51 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1135
       Built: 2019   Tax: $2,478 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $1,790 (change assumption)
    Mortgage ($1,584) + Taxes in 2025 ($206)


    Taxes:$2,478

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1801 HIGHLAND RD, OSPREY, FL 34229

    $299,900212 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


  • 14041 BELLAGIO WAY #218, OSPREY, FL 34229

    $999,000147 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


  • 1348 THORNAPPLE DR, OSPREY, FL 34229

    $535,0007 Days on yellowkey   MLS ID: A4687822

    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




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.