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Osprey Homes For Sale & Real Estate - 126 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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  • 1801 HIGHLAND RD, OSPREY, FL 34229

    $299,900216 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


  • 730 SARABAY RD, OSPREY, FL 34229

    $4,995,000152 Days on yellowkey   MLS ID: A4672618

    For Sale A4672618 - 730 SARABAY RD, OSPREY, FL 34229 42 photos

    Bed: 4   Bath: 5.5   Gar: 7
    Liv Area Sq Ft: 6308
       Built: 2011   Tax: $47,200 (2024)
    Community: Sarabay Acres
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,303 (change assumption)
    Mortgage ($27,369) + Taxes in 2024 ($3,933)


    Taxes:$47,200

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 353 S SHORE DR, OSPREY, FL 34229

    $1,150,00019 Days on yellowkey   MLS ID: A4688006

    REDUCED by $50,000 (4.2%) on 04/18/2026

    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: $6,637 (change assumption)
    Mortgage ($6,301) + 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


  • 403 LONGBOW TRL, OSPREY, FL 34229

    $1,095,000154 Days on yellowkey   MLS ID: A4672081

    For Sale A4672081 - 403 LONGBOW TRL, OSPREY, FL 34229 99 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2770
       Built: 1978
    Monthly Fee: $42
       Tax: $9,020 (2024)
    Community: Pine Ranch
    Single Family


    Estimated Monthly Payment: $6,794 (change assumption)
    Mortgage ($6,000) + Fees ($42) + Taxes in 2024 ($752)


    Taxes:$9,020

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 819 SHADOW BAY WAY, OSPREY, FL 34229

    $615,00049 Days on yellowkey   MLS ID: N6143162

    0 Days Off yellowkey (back on 4/10/2026)

    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


  • 172 SEA ANCHOR DR, OSPREY, FL 34229

    $895,000159 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


  • 14041 BELLAGIO WAY #214, OSPREY, FL 34229

    $700,0006 Days on yellowkey   MLS ID: A4689731

    For Sale A4689731 - 14041 BELLAGIO WAY #214, OSPREY, FL 34229 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1799
       Built: 2006
    Monthly Fee: $1,248
       Tax: $6,254 (2025)
    Community: Villas At Bellagio Harbor Village
    Spa: No

    Condo


    Estimated Monthly Payment: $5,605 (change assumption)
    Mortgage ($3,836) + Fees ($1,248) + Taxes in 2025 ($521)


    Taxes:$6,254

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4271 EXPEDITION WAY #103, OSPREY, FL 34229

    $290,00010 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


  • 313 LOOKOUT POINT DR, OSPREY, FL 34229

    $5,999,99913 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
    Monthly Fee: $219
       Tax: $20,559 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $34,808 (change assumption)
    Mortgage ($32,876) + Fees ($219) + 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


  • 583 PINE RANCH EAST RD, OSPREY, FL 34229

    $569,000168 Days on yellowkey   MLS ID: A4670669

    For Sale A4670669 - 583 PINE RANCH EAST RD, OSPREY, FL 34229 55 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 1996
    Monthly Fee: $23
       Tax: $4,537 (2024)
    Community: Bay Oaks Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,519 (change assumption)
    Mortgage ($3,118) + Fees ($23) + Taxes in 2024 ($378)


    Taxes:$4,537

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 745 FORDINGBRIDGE WAY, OSPREY, FL 34229

    $640,00042 Days on yellowkey   MLS ID: N6143319

    REDUCED by $10,000 (1.5%) on 04/17/2026

    For Sale N6143319 - 745 FORDINGBRIDGE WAY, OSPREY, FL 34229 53 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1893
       Built: 2002
    Monthly Fee: $120
       Tax: $4,308 (2025)
    Community: Rivendell Woodlands
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,986 (change assumption)
    Mortgage ($3,507) + Fees ($120) + Taxes in 2025 ($359)


    Taxes:$4,308

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 759 FORDINGBRIDGE WAY, OSPREY, FL 34229

    $727,0004 Days on yellowkey   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


  • 402 MACEWEN DR, OSPREY, FL 34229

    $1,750,0006 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


  • 32 SIESTA CIR W, OSPREY, FL 34229

    $69,0006 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


  • 4284 EXPEDITION WAY #NA, OSPREY, FL 34229

    $339,90066 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

    $200,000186 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


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,0005 Days 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


  • 479 SOUTH CREEK DR, OSPREY, FL 34229

    $2,495,000140 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

    $289,00010 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


  • 238 PALM AIR DR, OSPREY, FL 34229

    $179,9006 Days on yellowkey   MLS ID: A4689837

    For Sale A4689837 - 238 PALM AIR DR, OSPREY, FL 34229 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1152
       Built: 1986
    Monthly Fee: $215
       Tax: $1,562 (2025)
    Community: Arbors
    Manufactured Home


    Estimated Monthly Payment: $1,331 (change assumption)
    Mortgage ($986) + Fees ($215) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    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.