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Osprey Homes For Sale & Real Estate - 129 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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  • 14401 MASTHEAD DR, OSPREY, FL 34229

    $2,995,000149 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


  • 403 LONGBOW TRL, OSPREY, FL 34229

    $1,095,000257 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


  • 321 LOOKOUT POINT DR, OSPREY, FL 34229

    $3,100,00036 Days on yellowkey   MLS ID: A4697345

    0 Days Off yellowkey (back on 6/27/2026)

    For Sale A4697345 - 321 LOOKOUT POINT DR, OSPREY, FL 34229 77 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3122
       Built: 1978
    Monthly Fee: $219
       Tax: $16,002 (2025)
    Community: Southbay Yacht & Racquet Club
    Single Family


    Estimated Monthly Payment: $18,538 (change assumption)
    Mortgage ($16,986) + Fees ($219) + Taxes in 2025 ($1,333)


    Taxes:$16,002

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 324 BAYSHORE DR, OSPREY, FL 34229

    $3,995,000158 Days on yellowkey   MLS ID: A4683138

    0 Days Off yellowkey (back on 6/26/2026)

    REDUCED by $255,000 (6.0%) on 04/29/2026

    For Sale A4683138 - 324 BAYSHORE DR, OSPREY, FL 34229 40 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4389
       Built: 2000   Tax: $23,356 (2025)
    Community: Bay Acres - Resub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,836 (change assumption)
    Mortgage ($21,890) + Taxes in 2025 ($1,946)


    Taxes:$23,356

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 135 TINA ISLAND DR, OSPREY, FL 34229

    $3,295,00088 Days on yellowkey   MLS ID: A4692366

    For Sale A4692366 - 135 TINA ISLAND DR, OSPREY, FL 34229 47 photos

    Bed: 3   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 2572
       Built: 2011
    Monthly Fee: $10
       Tax: $12,575 (2025)
    Community: Sorrento Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,112 (change assumption)
    Mortgage ($18,054) + Fees ($10) + Taxes in 2025 ($1,048)


    Taxes:$12,575

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 570 BLACKBURN POINT RD #11, OSPREY, FL 34229

    $39,500383 Days on yellowkey   MLS ID: A4658755

    For Sale A4658755 - 570 BLACKBURN POINT RD #11, OSPREY, FL 34229 4 photos

    Bed:    Bath: 0.0
    Built: 2006
       Tax: $196 (2024)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $233 (change assumption)
    Mortgage ($216) + Taxes in 2024 ($16)


    Taxes:$196

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1527 BUOY LN, OSPREY, FL 34229

    $1,165,000116 Days on yellowkey   MLS ID: A4688266

    REDUCED by $34,000 (2.8%) on 06/23/2026

    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: $7,300 (change assumption)
    Mortgage ($6,383) + 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


  • 314 S SHORE DR, OSPREY, FL 34229

    $1,495,00068 Days on yellowkey   MLS ID: TB8510971

    REDUCED by $154,000 (9.3%) on 06/01/2026

    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: $8,941 (change assumption)
    Mortgage ($8,192) + 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


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

    $700,000190 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


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

    $880,00050 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


  • 360 N POINT RD, OSPREY, FL 34229

    $1,495,00054 Days on yellowkey   MLS ID: A4695959

    For Sale A4695959 - 360 N POINT RD, OSPREY, FL 34229 49 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2913
       Built: 2022
    Monthly Fee: $400
       Tax: $9,588 (2025)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,391 (change assumption)
    Mortgage ($8,192) + Fees ($400) + Taxes in 2025 ($799)


    Taxes:$9,588

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 21 BAYHEAD LN, OSPREY, FL 34229

    $789,000320 Days on yellowkey   MLS ID: A4664085

    REDUCED by $61,000 (7.2%) on 06/12/2026

    For Sale A4664085 - 21 BAYHEAD LN, OSPREY, FL 34229 92 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2246
       Built: 2002
    Monthly Fee: $458
       Tax: $4,221 (2024)
    Community: Bishopscourt At The Oaks Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,133 (change assumption)
    Mortgage ($4,323) + Fees ($458) + Taxes in 2024 ($352)


    Taxes:$4,221

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 157 LOOKOUT POINT DR, OSPREY, FL 34229

    $875,00065 Days on yellowkey   MLS ID: A4694878

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale A4694878 - 157 LOOKOUT POINT DR, OSPREY, FL 34229 73 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1859
       Built: 1981
    Monthly Fee: $219
       Tax: $4,950 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,426 (change assumption)
    Mortgage ($4,794) + Fees ($219) + Taxes in 2025 ($413)


    Taxes:$4,950

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 449 WEBBS COVE, OSPREY, FL 34229

    $2,650,000122 Days on yellowkey   MLS ID: A4688291

    0 Days Off yellowkey (back on 5/19/2026)

    For Sale A4688291 - 449 WEBBS COVE, OSPREY, FL 34229 97 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 5287
       Built: 2006
    Monthly Fee: $492
       Tax: $10,623 (2025)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $15,897 (change assumption)
    Mortgage ($14,520) + Fees ($492) + Taxes in 2025 ($885)


    Taxes:$10,623

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 401 N POINT RD #603, OSPREY, FL 34229

    $629,000261 Days on yellowkey   MLS ID: A4671958

    REDUCED by $70,000 (10.0%) on 05/20/2026

    For Sale A4671958 - 401 N POINT RD #603, OSPREY, FL 34229 99 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 2003   Tax: $8,771 (2024)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $4,177 (change assumption)
    Mortgage ($3,446) + Taxes in 2024 ($731)


    Taxes:$8,771

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 385 N POINT RD #503, OSPREY, FL 34229

    $690,000256 Days on yellowkey   MLS ID: A4672342

    For Sale A4672342 - 385 N POINT RD #503, OSPREY, FL 34229 97 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 2000
    Monthly Fee: $367
       Tax: $7,327 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $4,758 (change assumption)
    Mortgage ($3,781) + Fees ($367) + Taxes in 2024 ($611)


    Taxes:$7,327

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 3621 N POINT RD #301, OSPREY, FL 34229

    $625,000178 Days on yellowkey   MLS ID: A4681290

    For Sale A4681290 - 3621 N POINT RD #301, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2680
       Built: 2006   Tax: $6,143 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $3,937 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($512)


    Taxes:$6,143

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 110 PINE AVE, OSPREY, FL 34229

    $649,000483 Days on yellowkey   MLS ID: A4646339

    REDUCED by $50,000 (7.2%) on 06/09/2026

    For Sale A4646339 - 110 PINE AVE, OSPREY, FL 34229 11 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 1977   Tax: $5,908 (2024)
    Community: Saunders V A Resub
    Single Family


    Estimated Monthly Payment: $4,048 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($492)


    Taxes:$5,908

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1140 BEACHCOMBER CT #11, OSPREY, FL 34229

    $525,000158 Days on yellowkey   MLS ID: A4683755

    For Sale A4683755 - 1140 BEACHCOMBER CT #11, OSPREY, FL 34229 52 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2040
       Built: 2005   Tax: $5,401 (2025)
    Community: Blackburn Point Marina Village
    Condo


    Estimated Monthly Payment: $3,327 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($450)


    Taxes:$5,401

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 393 N POINT RD #604, OSPREY, FL 34229

    $795,000545 Days on yellowkey   MLS ID: A4638035

    0 Days Off yellowkey (back on 6/5/2026)

    For Sale A4638035 - 393 N POINT RD #604, OSPREY, FL 34229 92 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2778
       Built: 2001
    Monthly Fee: $367
       Tax: $9,625 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $5,525 (change assumption)
    Mortgage ($4,356) + Fees ($367) + Taxes in 2024 ($802)


    Taxes:$9,625

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside 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.