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Osprey Condos For Sale - 47 condos

Osprey Condos for sale are located in Sarasota County, Florida. Find condos in Osprey for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Osprey condominiums.

Location: Osprey

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

    $1,100,000180 Days on yellowkey   MLS ID: A4678422

    For Sale A4678422 - 385 N POINT RD #304, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2778
       Built: 2000
    Monthly Fee: $400
       Tax: $5,845 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $6,914 (change assumption)
    Mortgage ($6,027) + Fees ($400) + Taxes in 2025 ($487)


    Taxes:$5,845

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


  • 51 MACEWEN DR #11, OSPREY, FL 34229

    $235,000173 Days on yellowkey   MLS ID: A4679180

    For Sale A4679180 - 51 MACEWEN DR #11, OSPREY, FL 34229 42 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 623
       Built: 1990
    Monthly Fee: $142
       Tax: $2,367 (2025)
    Community: The Oaks Club
    Spa: No

    Condo


    Estimated Monthly Payment: $1,627 (change assumption)
    Mortgage ($1,288) + Fees ($142) + Taxes in 2025 ($197)


    Taxes:$2,367

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 173 NAVIGATION CIR #107, OSPREY, FL 34229

    $319,50030 Days on yellowkey   MLS ID: N6144704

    REDUCED by $8,500 (2.6%) on 07/13/2026

    For Sale N6144704 - 173 NAVIGATION CIR #107, OSPREY, FL 34229 71 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1528
       Built: 2015   Tax: $2,892 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $1,992 (change assumption)
    Mortgage ($1,751) + Taxes in 2025 ($241)


    Taxes:$2,892

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 116 WOODLAND PL #116, OSPREY, FL 34229

    $254,90034 Days on yellowkey   MLS ID: A4696616

    REDUCED by $15,000 (5.6%) on 06/23/2026

    For Sale A4696616 - 116 WOODLAND PL #116, OSPREY, FL 34229 45 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1979
    Monthly Fee: $820
       Tax: $1,893 (2025)
    Community: Pine Run Ii
    Condo


    Estimated Monthly Payment: $2,374 (change assumption)
    Mortgage ($1,397) + Fees ($820) + Taxes in 2025 ($158)


    Taxes:$1,893

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229

    $725,00084 Days on yellowkey   MLS ID: A4690942

    REDUCED by $10,000 (1.4%) on 06/16/2026

    For Sale A4690942 - 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229 71 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2004   Tax: $6,004 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $4,473 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($500)


    Taxes:$6,004

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 120 WOODLAND PL #120, OSPREY, FL 34229

    $299,0004 Days on yellowkey   MLS ID: D6148025

    For Sale D6148025 - 120 WOODLAND PL #120, OSPREY, FL 34229 65 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1979   Tax: $2,712 (2025)
    Community: Pine Run Ii
    Spa: No

    Condo


    Estimated Monthly Payment: $1,864 (change assumption)
    Mortgage ($1,638) + Taxes in 2025 ($226)


    Taxes:$2,712

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 2251 JESSIE HARBOR DR #2101, OSPREY, FL 34229

    $359,00012 Days on yellowkey   MLS ID: A4698891

    For Sale A4698891 - 2251 JESSIE HARBOR DR #2101, OSPREY, FL 34229 68 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1400
       Built: 2006   Tax: $4,920 (2025)
    Community: Blackburn Harbor Waterfront Vi
    Condo


    Estimated Monthly Payment: $2,377 (change assumption)
    Mortgage ($1,967) + Taxes in 2025 ($410)


    Taxes:$4,920

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 2309 JESSIE HARBOR DR #2402, OSPREY, FL 34229

    $497,00013 Days on yellowkey   MLS ID: A4698434

    For Sale A4698434 - 2309 JESSIE HARBOR DR #2402, OSPREY, FL 34229 93 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2006
       Built: 2006   Tax: $5,978 (2025)
    Community: Blackburn Harbor Waterfront Villas
    Spa: No

    Condo


    Estimated Monthly Payment: $3,221 (change assumption)
    Mortgage ($2,723) + Taxes in 2025 ($498)


    Taxes:$5,978

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 108 WOODLAND PL #108, OSPREY, FL 34229

    $285,0005 Days on yellowkey   MLS ID: A4699279

    For Sale A4699279 - 108 WOODLAND PL #108, OSPREY, FL 34229 50 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1316
       Built: 1979   Tax: $3,100 (2025)
    Community: Pine Run Ii
    Condo


    Estimated Monthly Payment: $1,820 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($258)


    Taxes:$3,100

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 89 NAVIGATION CIR, OSPREY, FL 34229

    $320,00054 Days on yellowkey   MLS ID: A4694435

    REDUCED by $25,000 (7.2%) on 06/27/2026

    For Sale A4694435 - 89 NAVIGATION CIR, OSPREY, FL 34229 61 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1449
       Built: 2014   Tax: $3,931 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,081 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($328)


    Taxes:$3,931

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


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

    $318,000131 Days on yellowkey   MLS ID: N6143250

    REDUCED by $10,000 (3.0%) on 06/22/2026

    For Sale N6143250 - 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229 77 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: $2,057 (change assumption)
    Mortgage ($1,742) + Taxes in 2025 ($315)


    Taxes:$3,781

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 4271 EXPEDITION WAY #103, OSPREY, FL 34229

    $265,00096 Days on yellowkey   MLS ID: A4689541

    REDUCED by $5,000 (1.9%) on 07/06/2026

    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: $1,744 (change assumption)
    Mortgage ($1,452) + 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


  • 260 HIDDEN BAY DR #304, OSPREY, FL 34229

    $694,000148 Days on yellowkey   MLS ID: N6142969

    REDUCED by $5,000 (0.7%) on 04/14/2026

    For Sale N6142969 - 260 HIDDEN BAY DR #304, OSPREY, FL 34229 70 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1950
       Built: 2019   Tax: $6,342 (2025)
    Community: Edgewater/Hidden Bay Ph 2 Bldg
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,331 (change assumption)
    Mortgage ($3,803) + Taxes in 2025 ($529)


    Taxes:$6,342

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4213 EXPEDITION WAY #107, OSPREY, FL 34229

    $320,00013 Days on yellowkey   MLS ID: A4698337

    For Sale A4698337 - 4213 EXPEDITION WAY #107, OSPREY, FL 34229 39 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1430
       Built: 2016
    Monthly Fee: $475
       Tax: $3,428 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $2,514 (change assumption)
    Mortgage ($1,753) + Fees ($475) + Taxes in 2025 ($286)


    Taxes:$3,428

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 14021 BELLAGIO WAY #404, OSPREY, FL 34229

    $1,100,00079 Days on yellowkey   MLS ID: N6144070

    REDUCED by $75,000 (6.4%) on 07/07/2026

    For Sale N6144070 - 14021 BELLAGIO WAY #404, OSPREY, FL 34229 70 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2187
       Built: 2006
    Monthly Fee: $1,644
       Tax: $5,636 (2025)
    Community: Villas At Bellagio Harbor Village
    Condo


    Estimated Monthly Payment: $8,141 (change assumption)
    Mortgage ($6,027) + Fees ($1,644) + Taxes in 2025 ($470)


    Taxes:$5,636

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $850,00073 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


  • 14041 BELLAGIO WAY #318, OSPREY, FL 34229

    $949,00034 Days on yellowkey   MLS ID: A4696101

    REDUCED by $50,000 (5.0%) on 07/07/2026

    For Sale A4696101 - 14041 BELLAGIO WAY #318, OSPREY, FL 34229 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2086
       Built: 2006
    Monthly Fee: $1,512
       Tax: $7,362 (2025)
    Community: Villas At Bellagio Harbor Village
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,325 (change assumption)
    Mortgage ($5,200) + Fees ($1,512) + Taxes in 2025 ($614)


    Taxes:$7,362

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $560,00085 Days on yellowkey   MLS ID: A4690812

    REDUCED by $65,000 (10.4%) on 07/07/2026

    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: $3,959 (change assumption)
    Mortgage ($3,068) + 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


  • 232 WOODLAND DR #232, OSPREY, FL 34229

    $259,900244 Days on yellowkey   MLS ID: A4671600

    0 Days Off yellowkey (back on 4/25/2026)

    REDUCED by $5,000 (1.9%) on 04/20/2026

    For Sale A4671600 - 232 WOODLAND DR #232, OSPREY, FL 34229 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1980   Tax: $2,202 (2025)
    Community: Pine Run Iii
    Condo


    Estimated Monthly Payment: $1,608 (change assumption)
    Mortgage ($1,424) + Taxes in 2025 ($184)


    Taxes:$2,202

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229

    $599,00099 Days on yellowkey   MLS ID: C7524397

    4 Days Off yellowkey (back on 6/25/2026)

    For Sale C7524397 - 1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2006
       Built: 2004
    Monthly Fee: $980
       Tax: $6,502 (2025)
    Community: Blackburn Harbor Waterfront Vi
    Condo


    Estimated Monthly Payment: $4,804 (change assumption)
    Mortgage ($3,282) + Fees ($980) + Taxes in 2025 ($542)


    Taxes:$6,502

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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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.