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Osprey Condos For Sale - 45 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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  • 7204 JESSIE HARBOR DR #7204, OSPREY, FL 34229

    $395,00043 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


  • 260 HIDDEN BAY DR #402, OSPREY, FL 34229

    $775,000Listed 07/31/2026 10:50AM   MLS ID: A4701000

    For Sale A4701000 - 260 HIDDEN BAY DR #402, OSPREY, FL 34229 58 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1950
       Built: 2019   Tax: $7,780 (2025)
    Community: Edgewater/Hidden Bay Bldg B Ph
    Spa: No

    Condo


    Estimated Monthly Payment: $4,895 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($648)


    Taxes:$7,780

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 701 PINE RUN DR #701, OSPREY, FL 34229

    $172,00013 Days on yellowkey   MLS ID: A4700416

    For Sale A4700416 - 701 PINE RUN DR #701, OSPREY, FL 34229 38 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 586
       Built: 1973   Tax: $1,648 (2025)
    Community: Pine Run I
    Condo


    Estimated Monthly Payment: $1,080 (change assumption)
    Mortgage ($942) + Taxes in 2025 ($137)


    Taxes:$1,648

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


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

    $497,00030 Days on yellowkey   MLS ID: A4698434

    For Sale A4698434 - 2309 JESSIE HARBOR DR #2402, OSPREY, FL 34229 85 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


  • 14021 BELLAGIO WAY #309, OSPREY, FL 34229

    $899,995176 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


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

    $725,000101 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


  • 4271 EXPEDITION WAY #103, OSPREY, FL 34229

    $260,000113 Days on yellowkey   MLS ID: A4689541

    REDUCED by $5,000 (1.9%) on 07/22/2026

    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: $1,717 (change assumption)
    Mortgage ($1,425) + 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


  • 4226 FRONTIER LN #103, OSPREY, FL 34229

    $299,000116 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


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

    $850,00090 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


  • 754 PINE RUN DR #754, OSPREY, FL 34229

    $259,00082 Days on yellowkey   MLS ID: A4693150

    REDUCED by $10,000 (3.7%) on 06/19/2026

    For Sale A4693150 - 754 PINE RUN DR #754, OSPREY, FL 34229 45 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1379
       Built: 1973
    Monthly Fee: $917
       Tax: $3,176 (2025)
    Community: Pine Run I
    Spa: No

    Condo


    Estimated Monthly Payment: $2,601 (change assumption)
    Mortgage ($1,419) + Fees ($917) + Taxes in 2025 ($265)


    Taxes:$3,176

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 385 N POINT RD #402, OSPREY, FL 34229

    $615,000553 Days on yellowkey   MLS ID: A4635708

    REDUCED by $45,000 (6.8%) on 07/27/2026

    For Sale A4635708 - 385 N POINT RD #402, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2055
       Built: 2000
    Monthly Fee: $400
       Tax: $5,877 (2024)
    Community: Meridian At The Oaks Preserve
    Spa: No

    Condo


    Estimated Monthly Payment: $4,260 (change assumption)
    Mortgage ($3,370) + Fees ($400) + Taxes in 2024 ($490)


    Taxes:$5,877

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2024

    Middle School: Brookside Middle


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

    $1,995,000181 Days on yellowkey   MLS ID: A4679998

    For Sale A4679998 - 401 N POINT RD #1001, OSPREY, FL 34229 60 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3029
       Built: 2003
    Monthly Fee: $400
       Tax: $10,201 (2025)
    Community: Meridian At The Oaks Preserve
    Spa: Yes

    Condo


    Estimated Monthly Payment: $12,181 (change assumption)
    Mortgage ($10,931) + Fees ($400) + Taxes in 2025 ($850)


    Taxes:$10,201

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2025

    Middle School: Pine View School


  • 4213 EXPEDITION WAY #107, OSPREY, FL 34229

    $320,00030 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


  • 108 WOODLAND PL #108, OSPREY, FL 34229

    $285,00022 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


  • 14041 BELLAGIO WAY #318, OSPREY, FL 34229

    $949,00051 Days on yellowkey   MLS ID: A4696101

    0 Days Off yellowkey (back on 7/26/2026)

    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


  • 120 WOODLAND PL #120, OSPREY, FL 34229

    $299,00021 Days on yellowkey   MLS ID: D6148025

    0 Days Off yellowkey (back on 7/16/2026)

    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


  • 14041 BELLAGIO WAY #214, OSPREY, FL 34229

    $700,000109 Days on yellowkey   MLS ID: A4689731

    For Sale A4689731 - 14041 BELLAGIO WAY #214, OSPREY, FL 34229 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1799
       Built: 2006
    Monthly Fee: $1,248
       Tax: $6,254 (2025)
    Community: Villas At Bellagio Harbor Village
    Spa: No

    Condo


    Estimated Monthly Payment: $5,605 (change assumption)
    Mortgage ($3,836) + Fees ($1,248) + Taxes in 2025 ($521)


    Taxes:$6,254

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $359,00029 Days on yellowkey   MLS ID: A4698891

    0 Days Off yellowkey (back on 7/20/2026)

    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


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

    $459,900868 Days on yellowkey   MLS ID: A4603773

    REDUCED by $15,100 (3.2%) on 07/20/2026

    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: $3,452 (change assumption)
    Mortgage ($2,520) + 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


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

    $318,000148 Days on yellowkey   MLS ID: N6143250

    0 Days Off yellowkey (back on 7/15/2026)

    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


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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.