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Osprey Homes For Sale & Real Estate - 132 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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  • 401 N POINT RD #504, OSPREY, FL 34229

    $880,0007 Days on yellowkey   MLS ID: A4696459

    For Sale A4696459 - 401 N POINT RD #504, OSPREY, FL 34229 54 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2778
       Built: 2003
    Monthly Fee: $400
       Tax: $8,767 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $5,952 (change assumption)
    Mortgage ($4,822) + Fees ($400) + Taxes in 2025 ($731)


    Taxes:$8,767

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 7204 JESSIE HARBOR DR #7204, OSPREY, FL 34229

    $395,000Listed 06/19/2026 9:35AM   MLS ID: A4697473

    For Sale A4697473 - 7204 JESSIE HARBOR DR #7204, OSPREY, FL 34229 43 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1255
       Built: 1985   Tax: $3,281 (2025)
    Community: Heron House
    Spa: No

    Condo


    Estimated Monthly Payment: $2,438 (change assumption)
    Mortgage ($2,164) + Taxes in 2025 ($273)


    Taxes:$3,281

    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

    $259,00039 Days on yellowkey   MLS ID: A4693150

    REDUCED by $10,000 (3.7%) on 06/19/2026

    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: $1,684 (change assumption)
    Mortgage ($1,419) + 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


  • 1474 LANDVIEW LN, OSPREY, FL 34229

    $1,475,0006 Days on yellowkey   MLS ID: A4696853

    For Sale A4696853 - 1474 LANDVIEW LN, OSPREY, FL 34229 74 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3246
       Built: 1977
    Monthly Fee: $219
       Tax: $9,834 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,120 (change assumption)
    Mortgage ($8,082) + Fees ($219) + Taxes in 2025 ($820)


    Taxes:$9,834

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 113 BURNEY RD, OSPREY, FL 34229

    $999,50057 Days on yellowkey   MLS ID: A4690672

    For Sale A4690672 - 113 BURNEY RD, OSPREY, FL 34229 44 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2502
       Built: 2020   Tax: $10,455 (2025)
    Community: Bel-Air
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,348 (change assumption)
    Mortgage ($5,477) + Taxes in 2025 ($871)


    Taxes:$10,455

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School


  • 730 FORDINGBRIDGE WAY, OSPREY, FL 34229

    $710,000Listed 06/19/2026 8:38AM   MLS ID: A4697358

    For Sale A4697358 - 730 FORDINGBRIDGE WAY, OSPREY, FL 34229 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2182
       Built: 2002
    Monthly Fee: $120
       Tax: $6,488 (2025)
    Community: Rivendell Woodlands
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,551 (change assumption)
    Mortgage ($3,890) + Fees ($120) + Taxes in 2025 ($541)


    Taxes:$6,488

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 433 E MACEWEN DR, OSPREY, FL 34229

    $2,250,000171 Days on yellowkey   MLS ID: A4676505

    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: $13,923 (change assumption)
    Mortgage ($12,328) + 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


  • 557 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $599,0007 Days on yellowkey   MLS ID: A4696823

    For Sale A4696823 - 557 CRANE PRAIRIE WAY, OSPREY, FL 34229 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2172
       Built: 2005
    Monthly Fee: $397
       Tax: $3,953 (2025)
    Community: Willowbend Ph 4
    Single Family


    Estimated Monthly Payment: $4,009 (change assumption)
    Mortgage ($3,282) + Fees ($397) + Taxes in 2025 ($329)


    Taxes:$3,953

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 180 LOOKOUT POINT DR, OSPREY, FL 34229

    $2,199,900216 Days on yellowkey   MLS ID: A4672222

    REDUCED by $50,000 (2.2%) on 06/03/2026

    For Sale A4672222 - 180 LOOKOUT POINT DR, OSPREY, FL 34229 70 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3236
       Built: 1986
    Monthly Fee: $204
       Tax: $8,750 (2024)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,987 (change assumption)
    Mortgage ($12,054) + Fees ($204) + Taxes in 2024 ($729)


    Taxes:$8,750

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 401 N POINT RD #301, OSPREY, FL 34229

    $475,000825 Days on yellowkey   MLS ID: A4603773

    SHORT SALE A4603773 - 401 N POINT RD #301, OSPREY, FL 34229 91 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2003
    Monthly Fee: $367
       Tax: $6,783 (2023)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $3,535 (change assumption)
    Mortgage ($2,603) + Fees ($367) + Taxes in 2023 ($565)


    Taxes:$6,783

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2023

    Middle School: Brookside Middle


  • 401 WALLS WAY, OSPREY, FL 34229

    $1,775,000140 Days on yellowkey   MLS ID: A4680312

    1 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $25,000 (1.4%) on 05/31/2026

    For Sale A4680312 - 401 WALLS WAY, OSPREY, FL 34229 51 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4387
       Built: 1990
    Monthly Fee: $133
       Tax: $16,158 (2025)
    Community: Oaks 2 Ph 1
    Single Family


    Estimated Monthly Payment: $11,205 (change assumption)
    Mortgage ($9,726) + Fees ($133) + Taxes in 2025 ($1,347)


    Taxes:$16,158

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $599,00073 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


  • 242 HIDDEN BAY DR #602, OSPREY, FL 34229

    $700,000147 Days on yellowkey   MLS ID: A4678883

    REDUCED by $19,000 (2.6%) on 04/23/2026

    For Sale A4678883 - 242 HIDDEN BAY DR #602, OSPREY, FL 34229 41 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1932
       Built: 1999   Tax: $7,518 (2025)
    Community: Baypointe Vista 1
    Condo


    Estimated Monthly Payment: $4,462 (change assumption)
    Mortgage ($3,836) + Taxes in 2025 ($626)


    Taxes:$7,518

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 14401 MASTHEAD DR, OSPREY, FL 34229

    $2,995,000106 Days on yellowkey   MLS ID: A4684834

    REDUCED by $155,000 (4.9%) on 06/12/2026

    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: $17,126 (change assumption)
    Mortgage ($16,411) + 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


  • 89 NAVIGATION CIR, OSPREY, FL 34229

    $345,00028 Days on yellowkey   MLS ID: A4694435

    For Sale A4694435 - 89 NAVIGATION CIR, OSPREY, FL 34229 61 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1449
       Built: 2014   Tax: $3,931 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,218 (change assumption)
    Mortgage ($1,890) + Taxes in 2025 ($328)


    Taxes:$3,931

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 173 NAVIGATION CIR #107, OSPREY, FL 34229

    $328,0004 Days on yellowkey   MLS ID: N6144704

    For Sale N6144704 - 173 NAVIGATION CIR #107, OSPREY, FL 34229 79 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1528
       Built: 2015   Tax: $2,892 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,797) + Taxes in 2025 ($241)


    Taxes:$2,892

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229

    $725,00058 Days on yellowkey   MLS ID: A4690942

    REDUCED by $10,000 (1.4%) on 06/16/2026

    For Sale A4690942 - 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229 71 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2004   Tax: $6,004 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $4,473 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($500)


    Taxes:$6,004

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 4428 CONCHFISH LN, OSPREY, FL 34229

    $548,000366 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


  • 4271 EXPEDITION WAY #103, OSPREY, FL 34229

    $270,00070 Days on yellowkey   MLS ID: A4689541

    REDUCED by $10,000 (3.6%) on 06/04/2026

    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: $1,772 (change assumption)
    Mortgage ($1,479) + 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


  • 408 PARK TRACE BLVD, OSPREY, FL 34229

    $595,000106 Days on yellowkey   MLS ID: A4685004

    2 Days Off yellowkey (back on 6/16/2026)

    REDUCED by $20,000 (3.3%) on 06/01/2026

    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: $3,702 (change assumption)
    Mortgage ($3,260) + 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.