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Osprey Homes For Sale & Real Estate - 121 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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  • 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


  • 4235 EXPEDITION WAY #102, OSPREY, FL 34229

    $379,90011 Days on yellowkey   MLS ID: N6143716

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale N6143716 - 4235 EXPEDITION WAY #102, OSPREY, FL 34229 71 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 2016   Tax: $4,410 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,449 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($367)


    Taxes:$4,410

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 409 N POINT RD #601, OSPREY, FL 34229

    $1,250,00071 Days on yellowkey   MLS ID: A4679994

    For Sale A4679994 - 409 N POINT RD #601, OSPREY, FL 34229 63 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2004
    Monthly Fee: $400
       Tax: $10,238 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $8,102 (change assumption)
    Mortgage ($6,849) + Fees ($400) + Taxes in 2025 ($853)


    Taxes:$10,238

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 348 TROPIC DR, OSPREY, FL 34229

    $109,000185 Days on yellowkey   MLS ID: A4668240

    For Sale A4668240 - 348 TROPIC DR, OSPREY, FL 34229 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 864
       Built: 1977
    Monthly Fee: $215
       Tax: $884 (2024)
    Community: Arbors
    Manufactured Home


    Estimated Monthly Payment: $886 (change assumption)
    Mortgage ($597) + Fees ($215) + Taxes in 2024 ($74)


    Taxes:$884

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 385 NORTH POINT RD #701, OSPREY, FL 34229

    $1,399,00050 Days on yellowkey   MLS ID: A4683454

    For Sale A4683454 - 385 NORTH POINT RD #701, OSPREY, FL 34229 97 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2594
       Built: 2000
    Monthly Fee: $400
       Tax: $6,082 (2025)
    Community: Meridan At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $8,572 (change assumption)
    Mortgage ($7,666) + Fees ($400) + Taxes in 2025 ($507)


    Taxes:$6,082

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 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


  • 409 N POINT RD #1001, OSPREY, FL 34229

    $2,750,0008 Days on yellowkey   MLS ID: A4689096

    1 Days Off yellowkey (back on 4/8/2026)

    For Sale A4689096 - 409 N POINT RD #1001, OSPREY, FL 34229 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3029
       Built: 2004
    Monthly Fee: $400
       Tax: $16,089 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $16,809 (change assumption)
    Mortgage ($15,068) + Fees ($400) + Taxes in 2025 ($1,341)


    Taxes:$16,089

    Elementary School: Pine View School

    High School: Riverview High

    Tax Year: 2025

    Middle School: Pine View School


  • 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


  • 570 BLACKBURN POINT RD #40, OSPREY, FL 34229

    $98,00012 Days on yellowkey   MLS ID: A4688762

    For Sale A4688762 - 570 BLACKBURN POINT RD #40, OSPREY, FL 34229 4 photos

    Bed:    Bath: 0.0
    Monthly Fee: $448
       Tax: $648 (2025)
    Community: Dry Slips At Bellagio Village
    Dock-Rackominium


    Estimated Monthly Payment: $1,039 (change assumption)
    Mortgage ($537) + Fees ($448) + Taxes in 2025 ($54)


    Taxes:$648

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14021 BELLAGIO WAY #309, OSPREY, FL 34229

    $899,99568 Days on yellowkey   MLS ID: A4681589

    For Sale A4681589 - 14021 BELLAGIO WAY #309, OSPREY, FL 34229 38 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2199
       Built: 2006
    Monthly Fee: $1,585
       Tax: $9,062 (2024)
    Community: Villas/Harbor Village
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,271 (change assumption)
    Mortgage ($4,931) + Fees ($1,585) + Taxes in 2024 ($755)


    Taxes:$9,062

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


  • 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229

    $329,90040 Days on yellowkey   MLS ID: N6143250

    For Sale N6143250 - 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229 68 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1528
       Built: 2018   Tax: $3,781 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,123 (change assumption)
    Mortgage ($1,808) + Taxes in 2025 ($315)


    Taxes:$3,781

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 14041 BELLAGIO WAY #218, OSPREY, FL 34229

    $999,000146 Days on yellowkey   MLS ID: A4672639

    REDUCED by $100,000 (9.1%) on 04/03/2026

    For Sale A4672639 - 14041 BELLAGIO WAY #218, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2374
       Built: 2006
    Monthly Fee: $1,649
       Tax: $6,459 (2024)
    Community: Villas At Bellagio Harbor Village
    Condo


    Estimated Monthly Payment: $7,661 (change assumption)
    Mortgage ($5,474) + Fees ($1,649) + Taxes in 2024 ($538)


    Taxes:$6,459

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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




Why Bother Searching Elsewhere for Osprey Homes for Sale and Other Real Estate?

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.