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Osprey Single Family Homes For Sale - 75 homes

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

Location: Osprey

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  • 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


  • 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


  • 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


  • 362 MACEWEN DR, OSPREY, FL 34229

    $2,249,00093 Days on yellowkey   MLS ID: A4676567

    For Sale A4676567 - 362 MACEWEN DR, OSPREY, FL 34229 55 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4117
       Built: 1998
    Monthly Fee: $142
       Tax: $10,742 (2025)
    Community: The Oaks
    Single Family


    Estimated Monthly Payment: $13,360 (change assumption)
    Mortgage ($12,323) + Fees ($142) + Taxes in 2025 ($895)


    Taxes:$10,742

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 32 BAY AVE, OSPREY, FL 34229

    $415,000186 Days on yellowkey   MLS ID: N6140978

    2 Days Off yellowkey (back on 4/9/2026)

    For Sale N6140978 - 32 BAY AVE, OSPREY, FL 34229 51 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 1962
    Monthly Fee: $13
       Tax: $3,612 (2024)
    Community: Bay Acres - Resub
    Single Family


    Estimated Monthly Payment: $2,588 (change assumption)
    Mortgage ($2,274) + Fees ($13) + Taxes in 2024 ($301)


    Taxes:$3,612

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 819 SHADOW BAY WAY, OSPREY, FL 34229

    $615,00044 Days on yellowkey   MLS ID: N6143162

    REDUCED by $24,000 (3.8%) on 04/08/2026

    For Sale N6143162 - 819 SHADOW BAY WAY, OSPREY, FL 34229 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2145
       Built: 2002
    Monthly Fee: $170
       Tax: $6,288 (2024)
    Community: Rivendell
    Single Family


    Estimated Monthly Payment: $4,064 (change assumption)
    Mortgage ($3,370) + Fees ($170) + Taxes in 2024 ($524)


    Taxes:$6,288

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Venice Area Middle


  • 1471 SHOAL WAY, OSPREY, FL 34229

    $1,499,00051 Days on yellowkey   MLS ID: A4683702

    For Sale A4683702 - 1471 SHOAL WAY, OSPREY, FL 34229 37 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2798
       Built: 1985
    Monthly Fee: $219
       Tax: $6,036 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,935 (change assumption)
    Mortgage ($8,213) + Fees ($219) + Taxes in 2025 ($503)


    Taxes:$6,036

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 313 LOOKOUT POINT DR, OSPREY, FL 34229

    $5,999,9998 Days on yellowkey   MLS ID: A4688995

    For Sale A4688995 - 313 LOOKOUT POINT DR, OSPREY, FL 34229 100 photos

    Bed: 4   Bath: 4.5   Gar: 5
    Liv Area Sq Ft: 5337
       Built: 2016   Tax: $20,559 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $34,589 (change assumption)
    Mortgage ($32,876) + Taxes in 2025 ($1,713)


    Taxes:$20,559

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1527 BUOY LN, OSPREY, FL 34229

    $1,199,0008 Days on yellowkey   MLS ID: A4688266

    For Sale A4688266 - 1527 BUOY LN, OSPREY, FL 34229 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2830
       Built: 1989
    Monthly Fee: $204
       Tax: $8,555 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,487 (change assumption)
    Mortgage ($6,570) + Fees ($204) + Taxes in 2025 ($713)


    Taxes:$8,555

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Venice Area Middle


  • 571 PINE RANCH EAST RD, OSPREY, FL 34229

    $650,000201 Days on yellowkey   MLS ID: A4665938

    2 Days Off yellowkey (back on 4/6/2026)

    For Sale A4665938 - 571 PINE RANCH EAST RD, OSPREY, FL 34229 88 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2746
       Built: 1995
    Monthly Fee: $25
       Tax: $6,575 (2024)
    Community: Bay Oaks Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,134 (change assumption)
    Mortgage ($3,562) + Fees ($25) + Taxes in 2024 ($548)


    Taxes:$6,575

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 1795 HIGHLAND RD, OSPREY, FL 34229

    $385,00039 Days on yellowkey   MLS ID: A4684679

    3 Days Off yellowkey (back on 4/6/2026)

    For Sale A4684679 - 1795 HIGHLAND RD, OSPREY, FL 34229 74 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1879
       Built: 1999
    Monthly Fee: $150
       Tax: $2,809 (2025)
    Community: Towns-End Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,494 (change assumption)
    Mortgage ($2,110) + Fees ($150) + Taxes in 2025 ($234)


    Taxes:$2,809

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 156 BISHOPSCOURT RD, OSPREY, FL 34229

    $1,299,00067 Days on yellowkey   MLS ID: A4681468

    For Sale A4681468 - 156 BISHOPSCOURT RD, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3112
       Built: 1990
    Monthly Fee: $916
       Tax: $8,109 (2024)
    Community: Bishopscourt At The Oaks Preserve
    Single Family


    Estimated Monthly Payment: $8,709 (change assumption)
    Mortgage ($7,118) + Fees ($916) + Taxes in 2024 ($676)


    Taxes:$8,109

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 434 MACEWEN DR, OSPREY, FL 34229

    $1,465,00016 Days on yellowkey   MLS ID: A4687368

    0 Days Off yellowkey (back on 4/5/2026)

    For Sale A4687368 - 434 MACEWEN DR, OSPREY, FL 34229 55 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2414
       Built: 1997
    Monthly Fee: $142
       Tax: $11,162 (2025)
    Community: Oaks 2 Ph 3
    Single Family


    Estimated Monthly Payment: $9,099 (change assumption)
    Mortgage ($8,027) + Fees ($142) + Taxes in 2025 ($930)


    Taxes:$11,162

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 3936 WAYPOINT AVE, OSPREY, FL 34229

    $1,039,00014 Days on yellowkey   MLS ID: A4687847

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

    For Sale A4687847 - 3936 WAYPOINT AVE, OSPREY, FL 34229 29 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2323
       Built: 2016
    Monthly Fee: $521
       Tax: $10,336 (2024)
    Community: Bayside
    Single Family


    Estimated Monthly Payment: $7,075 (change assumption)
    Mortgage ($5,693) + Fees ($521) + Taxes in 2024 ($861)


    Taxes:$10,336

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 353 S SHORE DR, OSPREY, FL 34229

    $1,200,00014 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
    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


  • 437 S SHORE DR, OSPREY, FL 34229

    $525,00021 Days on yellowkey   MLS ID: N6143587

    For Sale N6143587 - 437 S SHORE DR, OSPREY, FL 34229 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1947
       Built: 1976
    Monthly Fee: $10
       Tax: $4,187 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $3,236 (change assumption)
    Mortgage ($2,877) + Fees ($10) + Taxes in 2025 ($349)


    Taxes:$4,187

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 365 S SHORE DR, OSPREY, FL 34229

    $1,380,000104 Days on yellowkey   MLS ID: N6142101

    For Sale N6142101 - 365 S SHORE DR, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1824
       Built: 1968   Tax: $7,804 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $8,212 (change assumption)
    Mortgage ($7,561) + Taxes in 2025 ($650)


    Taxes:$7,804

    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

    $2,495,000135 Days on yellowkey   MLS ID: N6141722

    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
    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




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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.