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Osprey Condos For Sale - 33 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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  • 260 HIDDEN BAY DR #304, OSPREY, FL 34229

    $694,00057 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


  • 135 WOODLAND PL, OSPREY, FL 34229

    $269,00016 Days on yellowkey   MLS ID: A4687664

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale A4687664 - 135 WOODLAND PL, OSPREY, FL 34229 82 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1316
       Built: 1979   Tax: $2,660 (2025)
    Community: Pine Run Ii
    Condo


    Estimated Monthly Payment: $1,696 (change assumption)
    Mortgage ($1,474) + Taxes in 2025 ($222)


    Taxes:$2,660

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 232 WOODLAND DR #232, OSPREY, FL 34229

    $264,900153 Days on yellowkey   MLS ID: A4671600

    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: $1,635 (change assumption)
    Mortgage ($1,451) + 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


  • 4173 FRONTIER LN #4173, OSPREY, FL 34229

    $289,0005 Days on yellowkey   MLS ID: A4689582

    For Sale A4689582 - 4173 FRONTIER LN #4173, OSPREY, FL 34229 51 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1135
       Built: 2019   Tax: $2,478 (2025)
    Community: Bay Street Village
    Condo


    Estimated Monthly Payment: $1,790 (change assumption)
    Mortgage ($1,584) + Taxes in 2025 ($206)


    Taxes:$2,478

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $599,0008 Days on yellowkey   MLS ID: C7524397

    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


  • 250 HIDDEN BAY DR #301, OSPREY, FL 34229

    $725,00083 Days on yellowkey   MLS ID: A4679278

    For Sale A4679278 - 250 HIDDEN BAY DR #301, OSPREY, FL 34229 58 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2168
       Built: 2017   Tax: $7,792 (2025)
    Community: Edgewater At Hidden Bay
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,622 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($649)


    Taxes:$7,792

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 5100 JESSIE HARBOR DR #403, OSPREY, FL 34229

    $679,900105 Days on yellowkey   MLS ID: A4676382

    For Sale A4676382 - 5100 JESSIE HARBOR DR #403, OSPREY, FL 34229 44 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2004
    Monthly Fee: $1,027
       Tax: $5,647 (2025)
    Community: Blackburn Harbor Residences
    Condo


    Estimated Monthly Payment: $5,223 (change assumption)
    Mortgage ($3,725) + Fees ($1,027) + Taxes in 2025 ($471)


    Taxes:$5,647

    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

    $319,0008 Days on yellowkey   MLS ID: A4687965

    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: $2,518 (change assumption)
    Mortgage ($1,748) + 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


  • 7303 JESSIE HARBOR DR #7303, OSPREY, FL 34229

    $474,900280 Days on yellowkey   MLS ID: D6142543

    For Sale D6142543 - 7303 JESSIE HARBOR DR #7303, OSPREY, FL 34229 61 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1883
       Built: 1985   Tax: $4,800 (2024)
    Community: Heron House
    Condo


    Estimated Monthly Payment: $3,002 (change assumption)
    Mortgage ($2,602) + Taxes in 2024 ($400)


    Taxes:$4,800

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1116 BEACHCOMBER CT #3, OSPREY, FL 34229

    $545,00012 Days on yellowkey   MLS ID: A4688310

    For Sale A4688310 - 1116 BEACHCOMBER CT #3, OSPREY, FL 34229 65 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2040
       Built: 2005
    Monthly Fee: $1,133
       Tax: $5,376 (2025)
    Community: Blackburn Point Marina Village
    Condo


    Estimated Monthly Payment: $4,567 (change assumption)
    Mortgage ($2,986) + Fees ($1,133) + Taxes in 2025 ($448)


    Taxes:$5,376

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 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


  • 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


  • 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


  • 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


  • 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


  • 242 HIDDEN BAY DR #602, OSPREY, FL 34229

    $719,00082 Days on yellowkey   MLS ID: A4678883

    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: $4,566 (change assumption)
    Mortgage ($3,940) + 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


  • 244 WOODLAND DR #244, OSPREY, FL 34229

    $200,000181 Days on yellowkey   MLS ID: A4667419

    For Sale A4667419 - 244 WOODLAND DR #244, OSPREY, FL 34229 41 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1980   Tax: $2,685 (2025)
    Community: Pine Run Iii
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,096) + Taxes in 2025 ($224)


    Taxes:$2,685

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $785,00023 Days on yellowkey   MLS ID: A4686928

    REDUCED by $50,000 (6.0%) on 03/31/2026

    For Sale A4686928 - 393 N POINT RD #401, OSPREY, FL 34229 63 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2594
       Built: 2001
    Monthly Fee: $400
       Tax: $5,733 (2025)
    Community: Meridian At The Oaks Preserve
    Condo


    Estimated Monthly Payment: $5,179 (change assumption)
    Mortgage ($4,301) + Fees ($400) + Taxes in 2025 ($478)


    Taxes:$5,733

    Elementary School: Gulf Gate Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Brookside Middle


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Why Bother Searching Elsewhere for Osprey Condos for Sale and Other Condominiums?

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 condos for sale in Osprey. You can use our website to view Multiple Listing Service (MLS) data on Osprey condos. 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 condo 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.