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Osprey Homes For Sale & Real Estate - 140 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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  • 242 HIDDEN BAY DR #602, OSPREY, FL 34229

    $700,000173 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


  • 4226 FRONTIER LN #103, OSPREY, FL 34229

    $299,00099 Days on yellowkey   MLS ID: A4687965

    REDUCED by $20,000 (6.3%) on 05/16/2026

    For Sale A4687965 - 4226 FRONTIER LN #103, OSPREY, FL 34229 36 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1135
       Built: 2018
    Monthly Fee: $475
       Tax: $3,542 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,408 (change assumption)
    Mortgage ($1,638) + Fees ($475) + Taxes in 2025 ($295)


    Taxes:$3,542

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


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

    $395,00026 Days on yellowkey   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


  • 557 CRANE PRAIRIE WAY, OSPREY, FL 34229

    $599,00033 Days on yellowkey   MLS ID: A4696823

    0 Days Off yellowkey (back on 6/19/2026)

    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


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

    $880,00033 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


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

    $475,000851 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


  • 360 N POINT RD, OSPREY, FL 34229

    $1,495,00037 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


  • 75 OSPREY POINT DR, OSPREY, FL 34229

    $1,649,00034 Days on yellowkey   MLS ID: A4695145

    For Sale A4695145 - 75 OSPREY POINT DR, OSPREY, FL 34229 70 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4001
       Built: 1983
    Monthly Fee: $950
       Tax: $14,636 (2025)
    Community: Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,205 (change assumption)
    Mortgage ($9,035) + Fees ($950) + Taxes in 2025 ($1,220)


    Taxes:$14,636

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 21 BAYHEAD LN, OSPREY, FL 34229

    $789,000303 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

    $875,00048 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

    $2,650,000105 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

    $629,000244 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

    $690,000239 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

    $625,000161 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


  • 17 BAYHEAD LN, OSPREY, FL 34229

    $1,295,000184 Days on yellowkey   MLS ID: A4676710

    REDUCED by $5,000 (0.4%) on 04/29/2026

    For Sale A4676710 - 17 BAYHEAD LN, OSPREY, FL 34229 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2850
       Built: 1992
    Monthly Fee: $458
       Tax: $6,642 (2024)
    Community: Bishops Court At Oaks Preserve
    Single Family


    Estimated Monthly Payment: $8,107 (change assumption)
    Mortgage ($7,096) + Fees ($458) + Taxes in 2024 ($554)


    Taxes:$6,642

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 110 PINE AVE, OSPREY, FL 34229

    $649,000466 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

    $525,000141 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

    $795,000528 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


  • 570 BLACKBURN POINT RD #13, OSPREY, FL 34229

    $109,000217 Days on yellowkey   MLS ID: A4674344

    For Sale A4674344 - 570 BLACKBURN POINT RD #13, OSPREY, FL 34229 4 photos

    Bed:    Bath: 0.0    Tax: $644 (2024)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $651 (change assumption)
    Mortgage ($597) + Taxes in 2024 ($54)


    Taxes:$644

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 570 BLACKBURN POINT RD #43, OSPREY, FL 34229

    $115,000216 Days on yellowkey   MLS ID: A4672823

    For Sale A4672823 - 570 BLACKBURN POINT RD #43, OSPREY, FL 34229 4 photos

    Bed:    Bath: 0.0
    Monthly Fee: $414
       Tax: $620 (2024)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $1,096 (change assumption)
    Mortgage ($630) + Fees ($414) + Taxes in 2024 ($52)


    Taxes:$620

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.