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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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  • 75 OSPREY POINT DR, OSPREY, FL 34229

    $1,649,00013 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


  • 523 OAK BAY DR, OSPREY, FL 34229

    $540,00012 Days on yellowkey   MLS ID: A4696725

    For Sale A4696725 - 523 OAK BAY DR, OSPREY, FL 34229 97 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 1998
    Monthly Fee: $25
       Tax: $3,448 (2025)
    Community: Bay Oaks Estates
    Single Family


    Estimated Monthly Payment: $3,271 (change assumption)
    Mortgage ($2,959) + Fees ($25) + Taxes in 2025 ($287)


    Taxes:$3,448

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 21 BAYHEAD LN, OSPREY, FL 34229

    $789,000282 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

    $875,00027 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


  • 61 BAYHEAD LN, OSPREY, FL 34229

    $1,185,00070 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


  • 449 WEBBS COVE, OSPREY, FL 34229

    $2,650,00084 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

    $629,000223 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


  • 204 WINDWARD DR, OSPREY, FL 34229

    $999,00044 Days on yellowkey   MLS ID: A4693139

    REDUCED by $51,000 (4.9%) on 06/10/2026

    For Sale A4693139 - 204 WINDWARD DR, OSPREY, FL 34229 73 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 1986
    Monthly Fee: $219
       Tax: $4,761 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,090 (change assumption)
    Mortgage ($5,474) + Fees ($219) + Taxes in 2025 ($397)


    Taxes:$4,761

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


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

    $690,000218 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


  • 292 TURQUOISE LN, OSPREY, FL 34229

    $1,050,00029 Days on yellowkey   MLS ID: A4694515

    For Sale A4694515 - 292 TURQUOISE LN, OSPREY, FL 34229 89 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2255
       Built: 2001
    Monthly Fee: $400
       Tax: $6,536 (2025)
    Community: Emerald Woods At Oaks 03 Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,698 (change assumption)
    Mortgage ($5,753) + Fees ($400) + Taxes in 2025 ($545)


    Taxes:$6,536

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 409 NORTH POINT RD #401, OSPREY, FL 34229

    $625,00064 Days on yellowkey   MLS ID: A4690812

    For Sale A4690812 - 409 NORTH POINT RD #401, OSPREY, FL 34229 90 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2004
    Monthly Fee: $367
       Tax: $6,285 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $4,315 (change assumption)
    Mortgage ($3,425) + Fees ($367) + Taxes in 2025 ($524)


    Taxes:$6,285

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 401 N POINT RD #304, OSPREY, FL 34229

    $700,000330 Days on yellowkey   MLS ID: A4659785

    For Sale A4659785 - 401 N POINT RD #304, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2778
       Built: 2003
    Monthly Fee: $367
       Tax: $8,473 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,909 (change assumption)
    Mortgage ($3,836) + Fees ($367) + Taxes in 2024 ($706)


    Taxes:$8,473

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


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

    $625,000140 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


  • 362 MACEWEN DR, OSPREY, FL 34229

    $2,249,000163 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


  • 422 BLUE GARDEN LN, OSPREY, FL 34229

    $1,495,000282 Days on yellowkey   MLS ID: A4664436

    REDUCED by $55,000 (3.5%) on 05/28/2026

    For Sale A4664436 - 422 BLUE GARDEN LN, OSPREY, FL 34229 96 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3872
       Built: 1984
    Monthly Fee: $475
       Tax: $7,339 (2024)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,278 (change assumption)
    Mortgage ($8,192) + Fees ($475) + Taxes in 2024 ($612)


    Taxes:$7,339

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 17 BAYHEAD LN, OSPREY, FL 34229

    $1,295,000163 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

    $649,000445 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


  • 480 ORISKANY CT, OSPREY, FL 34229

    $1,535,000114 Days on yellowkey   MLS ID: A4684136

    REDUCED by $64,000 (4.0%) on 05/12/2026

    For Sale A4684136 - 480 ORISKANY CT, OSPREY, FL 34229 100 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3208
       Built: 1999
    Monthly Fee: $142
       Tax: $6,365 (2024)
    Community: The Oaks Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,083 (change assumption)
    Mortgage ($8,411) + Fees ($142) + Taxes in 2024 ($530)


    Taxes:$6,365

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 6100 JESSIE HARBOR DR #202, OSPREY, FL 34229

    $850,00052 Days on yellowkey   MLS ID: A4690969

    For Sale A4690969 - 6100 JESSIE HARBOR DR #202, OSPREY, FL 34229 83 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 3771
       Built: 2005
    Monthly Fee: $1,101
       Tax: $8,698 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $6,483 (change assumption)
    Mortgage ($4,657) + Fees ($1,101) + Taxes in 2025 ($725)


    Taxes:$8,698

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1140 BEACHCOMBER CT #11, OSPREY, FL 34229

    $525,000120 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




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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.