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Osprey Homes For Sale & Real Estate - 145 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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  • 4429 CONCHFISH LN, OSPREY, FL 34229

    $535,00030 Days on yellowkey   MLS ID: A4689967

    For Sale A4689967 - 4429 CONCHFISH LN, OSPREY, FL 34229 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2018
    Monthly Fee: $147
       Tax: $5,968 (2025)
    Community: Palms/Casey Key
    Single Family


    Estimated Monthly Payment: $3,576 (change assumption)
    Mortgage ($2,931) + Fees ($147) + Taxes in 2025 ($497)


    Taxes:$5,968

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 14401 MASTHEAD DR, OSPREY, FL 34229

    $3,150,00087 Days on yellowkey   MLS ID: A4684834

    REDUCED by $100,000 (3.1%) on 05/01/2026

    For Sale A4684834 - 14401 MASTHEAD DR, OSPREY, FL 34229 96 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2665
       Built: 2017
    Monthly Fee: $643
       Tax: $874 (2025)
    Community: Bayside
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,976 (change assumption)
    Mortgage ($17,260) + Fees ($643) + Taxes in 2025 ($73)


    Taxes:$874

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 401 N POINT RD #504, OSPREY, FL 34229

    $990,000369 Days on yellowkey   MLS ID: A4653470

    For Sale A4653470 - 401 N POINT RD #504, OSPREY, FL 34229 92 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2778
       Built: 2003
    Monthly Fee: $367
       Tax: $8,767 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $6,522 (change assumption)
    Mortgage ($5,425) + Fees ($367) + Taxes in 2025 ($731)


    Taxes:$8,767

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 101 OSPREY POINT DR, OSPREY, FL 34229

    $4,790,0005 Days on yellowkey   MLS ID: A4694716

    For Sale A4694716 - 101 OSPREY POINT DR, OSPREY, FL 34229 65 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5087
       Built: 1985
    Monthly Fee: $950
       Tax: $12,940 (2025)
    Community: The Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $28,274 (change assumption)
    Mortgage ($26,246) + Fees ($950) + Taxes in 2025 ($1,078)


    Taxes:$12,940

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 292 TURQUOISE LN, OSPREY, FL 34229

    $1,050,0005 Days on yellowkey   MLS ID: A4694515

    For Sale A4694515 - 292 TURQUOISE LN, OSPREY, FL 34229 89 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2255
       Built: 2001
    Monthly Fee: $400
       Tax: $6,536 (2025)
    Community: Emerald Woods At Oaks 03 Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,698 (change assumption)
    Mortgage ($5,753) + Fees ($400) + Taxes in 2025 ($545)


    Taxes:$6,536

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


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

    $850,00028 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


  • 314 S SHORE DR, OSPREY, FL 34229

    $1,649,0006 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

    $328,00086 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

    $548,000347 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

    $739,00019 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

    $875,000100 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

    $550,000243 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

    $269,00020 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

    $1,150,000372 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

    $749,0009 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

    $599,00054 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

    $795,00027 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

    $799,000423 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

    $1,545,000188 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

    $650,000151 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




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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.