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Osprey Homes For Sale & Real Estate - 121 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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  • 854 MACEWEN DR, OSPREY, FL 34229

    $3,790,000178 Days on yellowkey   MLS ID: A4668918

    For Sale A4668918 - 854 MACEWEN DR, OSPREY, FL 34229 69 photos

    Bed: 4   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 9081
       Built: 2003
    Monthly Fee: $133
       Tax: $26,109 (2024)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,075 (change assumption)
    Mortgage ($20,767) + Fees ($133) + Taxes in 2024 ($2,176)


    Taxes:$26,109

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


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

    $599,0008 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


  • 665 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $719,000197 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


  • 480 ORISKANY CT, OSPREY, FL 34229

    $1,599,00044 Days on yellowkey   MLS ID: A4684136

    REDUCED by $96,000 (5.7%) on 04/12/2026

    For Sale A4684136 - 480 ORISKANY CT, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3208
       Built: 1999
    Monthly Fee: $142
       Tax: $6,365 (2024)
    Community: The Oaks Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,434 (change assumption)
    Mortgage ($8,761) + Fees ($142) + Taxes in 2024 ($530)


    Taxes:$6,365

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 664 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $887,00054 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

    $725,00083 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


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

    $679,900105 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


  • 1486 LANDVIEW LN, OSPREY, FL 34229

    $850,000155 Days on yellowkey   MLS ID: D6144630

    For Sale D6144630 - 1486 LANDVIEW LN, OSPREY, FL 34229 78 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1869
       Built: 1977
    Monthly Fee: $204
       Tax: $7,488 (2025)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $5,485 (change assumption)
    Mortgage ($4,657) + Fees ($204) + Taxes in 2025 ($624)


    Taxes:$7,488

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1337 COPPERWOOD DR, OSPREY, FL 34229

    $550,000197 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


  • 4226 FRONTIER LN #103, OSPREY, FL 34229

    $319,0008 Days on yellowkey   MLS ID: A4687965

    For Sale A4687965 - 4226 FRONTIER LN #103, OSPREY, FL 34229 36 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1135
       Built: 2018
    Monthly Fee: $475
       Tax: $3,542 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,518 (change assumption)
    Mortgage ($1,748) + Fees ($475) + Taxes in 2025 ($295)


    Taxes:$3,542

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 140 SUGAR MILL DR, OSPREY, FL 34229

    $1,695,00036 Days on yellowkey   MLS ID: A4684805

    For Sale A4684805 - 140 SUGAR MILL DR, OSPREY, FL 34229 74 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3286
       Built: 1989
    Monthly Fee: $483
       Tax: $12,040 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,774 (change assumption)
    Mortgage ($9,287) + Fees ($483) + Taxes in 2025 ($1,003)


    Taxes:$12,040

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 102 WINDWARD DR, OSPREY, FL 34229

    $690,000147 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


  • 172 SEA ANCHOR DR, OSPREY, FL 34229

    $895,000154 Days on yellowkey   MLS ID: A4671745

    For Sale A4671745 - 172 SEA ANCHOR DR, OSPREY, FL 34229 48 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2283
       Built: 1977
    Monthly Fee: $204
       Tax: $8,870 (2024)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $5,847 (change assumption)
    Mortgage ($4,904) + Fees ($204) + Taxes in 2024 ($739)


    Taxes:$8,870

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 7303 JESSIE HARBOR DR #7303, OSPREY, FL 34229

    $474,900280 Days on yellowkey   MLS ID: D6142543

    For Sale D6142543 - 7303 JESSIE HARBOR DR #7303, OSPREY, FL 34229 61 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1883
       Built: 1985   Tax: $4,800 (2024)
    Community: Heron House
    Condo


    Estimated Monthly Payment: $3,002 (change assumption)
    Mortgage ($2,602) + Taxes in 2024 ($400)


    Taxes:$4,800

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 120 VILLA DR #120, OSPREY, FL 34229

    $510,000365 Days on yellowkey   MLS ID: N6138441

    REDUCED by $5,000 (1.0%) on 04/01/2026

    For Sale N6138441 - 120 VILLA DR #120, OSPREY, FL 34229 55 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1404
       Built: 1978
    Monthly Fee: $529
       Tax: $5,056 (2025)
    Community: Sorrento Villas 1
    Villa


    Estimated Monthly Payment: $3,745 (change assumption)
    Mortgage ($2,794) + Fees ($529) + Taxes in 2025 ($421)


    Taxes:$5,056

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 472 PARK TRACE BLVD, OSPREY, FL 34229

    $609,00075 Days on yellowkey   MLS ID: A4680326

    For Sale A4680326 - 472 PARK TRACE BLVD, OSPREY, FL 34229 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2217
       Built: 2002
    Monthly Fee: $58
       Tax: $5,925 (2025)
    Community: Park Trace Estates
    Single Family


    Estimated Monthly Payment: $3,889 (change assumption)
    Mortgage ($3,337) + Fees ($58) + Taxes in 2025 ($494)


    Taxes:$5,925

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1116 BEACHCOMBER CT #3, OSPREY, FL 34229

    $545,00012 Days on yellowkey   MLS ID: A4688310

    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


  • 296 PINE RANCH TRL, OSPREY, FL 34229

    $1,250,000326 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


  • 107 SORRENTO DR, OSPREY, FL 34229

    $425,00042 Days on yellowkey   MLS ID: N6143210

    REDUCED by $24,000 (5.3%) on 04/12/2026

    For Sale N6143210 - 107 SORRENTO DR, OSPREY, FL 34229 51 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1284
       Built: 1963
    Monthly Fee: $10
       Tax: $2,566 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $2,553 (change assumption)
    Mortgage ($2,329) + Fees ($10) + Taxes in 2025 ($214)


    Taxes:$2,566

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 408 PARK TRACE BLVD, OSPREY, FL 34229

    $625,00041 Days on yellowkey   MLS ID: A4685004

    REDUCED by $5,000 (0.8%) on 04/11/2026

    For Sale A4685004 - 408 PARK TRACE BLVD, OSPREY, FL 34229 34 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 2003
    Monthly Fee: $54
       Tax: $4,652 (2025)
    Community: Park Trace Estates
    Single Family


    Estimated Monthly Payment: $3,866 (change assumption)
    Mortgage ($3,425) + Fees ($54) + Taxes in 2025 ($388)


    Taxes:$4,652

    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.