REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search


Displaying: For Sale

Location: Osprey

Property Type(s): Single Family

Price: $1,000,000+

Osprey - 38 properties found

Sort:
  • 365 S SHORE DR, OSPREY, FL 34229

    $1,349,000174 Days on yellowkey   MLS ID: N6142101

    REDUCED by $31,000 (2.2%) on 05/02/2026

    For Sale N6142101 - 365 S SHORE DR, OSPREY, FL 34229 95 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1824
       Built: 1968   Tax: $7,804 (2025)
    Community: Sorrento Shores
    Single Family


    Estimated Monthly Payment: $8,042 (change assumption)
    Mortgage ($7,392) + Taxes in 2025 ($650)


    Taxes:$7,804

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 101 OSPREY POINT DR, OSPREY, FL 34229

    $4,790,00029 Days on yellowkey   MLS ID: A4694716

    For Sale A4694716 - 101 OSPREY POINT DR, OSPREY, FL 34229 65 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5087
       Built: 1985
    Monthly Fee: $950
       Tax: $12,940 (2025)
    Community: The Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $28,274 (change assumption)
    Mortgage ($26,246) + Fees ($950) + Taxes in 2025 ($1,078)


    Taxes:$12,940

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 18 N CASEY KEY RD, OSPREY, FL 34229

    $1,750,000247 Days on yellowkey   MLS ID: A4669083

    0 Days Off yellowkey (back on 6/1/2026)

    REDUCED by $250,000 (12.5%) on 05/08/2026

    For Sale A4669083 - 18 N CASEY KEY RD, OSPREY, FL 34229 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1977
       Built: 1973   Tax: $24,015 (2024)
    Community: Casey Key
    Single Family


    Estimated Monthly Payment: $11,590 (change assumption)
    Mortgage ($9,589) + Taxes in 2024 ($2,001)


    Taxes:$24,015

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 121 N CASEY KEY RD, OSPREY, FL 34229

    $6,475,000263 Days on yellowkey   MLS ID: A4667263

    For Sale A4667263 - 121 N CASEY KEY RD, OSPREY, FL 34229 65 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4096
       Built: 1969
    Monthly Fee: $33
       Tax: $37,172 (2024)
    Community: Casey Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $38,609 (change assumption)
    Mortgage ($35,479) + Fees ($33) + Taxes in 2024 ($3,098)


    Taxes:$37,172

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 49 OSPREY POINT DR, OSPREY, FL 34229

    $2,399,000223 Days on yellowkey   MLS ID: A4671762

    REDUCED by $101,000 (4.0%) on 05/03/2026

    For Sale A4671762 - 49 OSPREY POINT DR, OSPREY, FL 34229 96 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3953
       Built: 1989
    Monthly Fee: $475
       Tax: $14,206 (2024)
    Community: Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,804 (change assumption)
    Mortgage ($13,145) + Fees ($475) + Taxes in 2024 ($1,184)


    Taxes:$14,206

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Sarasota Middle


  • 272 FOUR KNOT LN, OSPREY, FL 34229

    $1,095,00042 Days on yellowkey   MLS ID: N6144313

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale N6144313 - 272 FOUR KNOT LN, OSPREY, FL 34229 80 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2723
       Built: 1978
    Monthly Fee: $219
       Tax: $5,738 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,697 (change assumption)
    Mortgage ($6,000) + Fees ($219) + Taxes in 2025 ($478)


    Taxes:$5,738

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 852 MACEWEN DR, OSPREY, FL 34229

    $2,395,000339 Days on yellowkey   MLS ID: A4659276

    For Sale A4659276 - 852 MACEWEN DR, OSPREY, FL 34229 73 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4519
       Built: 1992
    Monthly Fee: $133
       Tax: $12,855 (2024)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,327 (change assumption)
    Mortgage ($13,123) + Fees ($133) + Taxes in 2024 ($1,071)


    Taxes:$12,855

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 236 SAINT JAMES PARK, OSPREY, FL 34229

    $2,700,000454 Days on yellowkey   MLS ID: A4644125

    For Sale A4644125 - 236 SAINT JAMES PARK, OSPREY, FL 34229 88 photos

    Bed: 6   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 6246
       Built: 1986
    Monthly Fee: $283
       Tax: $22,433 (2024)
    Community: Oaks 2 Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,947 (change assumption)
    Mortgage ($14,794) + Fees ($283) + Taxes in 2024 ($1,869)


    Taxes:$22,433

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 538 DOVE POINTE DR, OSPREY, FL 34229

    $1,950,000229 Days on yellowkey   MLS ID: A4669491

    For Sale A4669491 - 538 DOVE POINTE DR, OSPREY, FL 34229 75 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4346
       Built: 2002
    Monthly Fee: $133
       Tax: $17,098 (2024)
    Community: Oaks 2 Ph 4-C Pt 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,242 (change assumption)
    Mortgage ($10,685) + Fees ($133) + Taxes in 2024 ($1,425)


    Taxes:$17,098

    Elementary School: Pine View School

    High School: Pine View School

    Tax Year: 2024

    Middle School: Pine View School


  • 135 TINA ISLAND DR, OSPREY, FL 34229

    $3,295,00050 Days on yellowkey   MLS ID: A4692366

    For Sale A4692366 - 135 TINA ISLAND DR, OSPREY, FL 34229 47 photos

    Bed: 3   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 2572
       Built: 1965
    Monthly Fee: $10
       Tax: $12,575 (2025)
    Community: Sorrento Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,112 (change assumption)
    Mortgage ($18,054) + Fees ($10) + Taxes in 2025 ($1,048)


    Taxes:$12,575

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 854 MACEWEN DR, OSPREY, FL 34229

    $3,690,000248 Days on yellowkey   MLS ID: A4668918

    REDUCED by $100,000 (2.6%) on 05/01/2026

    For Sale A4668918 - 854 MACEWEN DR, OSPREY, FL 34229 69 photos

    Bed: 4   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 9081
       Built: 2003
    Monthly Fee: $133
       Tax: $26,109 (2024)
    Community: Oaks 2 Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,527 (change assumption)
    Mortgage ($20,219) + Fees ($133) + Taxes in 2024 ($2,176)


    Taxes:$26,109

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2024

    Middle School: Laurel Nokomis Middle


  • 324 BAYSHORE DR, OSPREY, FL 34229

    $3,995,000120 Days on yellowkey   MLS ID: A4683138

    REDUCED by $255,000 (6.0%) on 04/29/2026

    For Sale A4683138 - 324 BAYSHORE DR, OSPREY, FL 34229 40 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4389
       Built: 2000   Tax: $23,356 (2025)
    Community: Bay Acres - Resub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,836 (change assumption)
    Mortgage ($21,890) + Taxes in 2025 ($1,946)


    Taxes:$23,356

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Laurel Nokomis Middle


  • 909 MACEWEN DR, OSPREY, FL 34229

    $1,595,000649 Days on yellowkey   MLS ID: A4621683

    For Sale A4621683 - 909 MACEWEN DR, OSPREY, FL 34229 62 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4241
       Built: 1991
    Monthly Fee: $133
       Tax: $9,867 (2023)
    Community: Oaks 2 Phase 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,695 (change assumption)
    Mortgage ($8,740) + Fees ($133) + Taxes in 2023 ($822)


    Taxes:$9,867

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2023

    Middle School: Laurel Nokomis Middle


  • 313 LOOKOUT POINT DR, OSPREY, FL 34229

    $5,999,99978 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
    Monthly Fee: $219
       Tax: $20,559 (2025)
    Community: Southbay Yacht & Racquet Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $34,808 (change assumption)
    Mortgage ($32,876) + Fees ($219) + 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


  • 448 E MACEWEN DR, OSPREY, FL 34229

    $2,100,00088 Days on yellowkey   MLS ID: A4687195

    For Sale A4687195 - 448 E MACEWEN DR, OSPREY, FL 34229 52 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3768
       Built: 1998
    Monthly Fee: $142
       Tax: $9,639 (2025)
    Community: Oaks
    Single Family


    Estimated Monthly Payment: $12,452 (change assumption)
    Mortgage ($11,507) + Fees ($142) + Taxes in 2025 ($803)


    Taxes:$9,639

    Elementary School: Laurel Nokomis Elementary

    High School: Venice Senior High

    Tax Year: 2025

    Middle School: Sarasota Middle


  • 854 N CASEY KEY RD, OSPREY, FL 34229

    $4,750,000118 Days on yellowkey   MLS ID: N6143043

    1 Days Off yellowkey (back on 3/26/2026)

    For Sale N6143043 - 854 N CASEY KEY RD, OSPREY, FL 34229 23 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 3462
       Built: 1975
    Community: Acreage & Unrec
    Single Family


    Estimated Monthly Payment: $26,027 (change assumption)
    Mortgage ($26,027)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 700 FAITH AVE, OSPREY, FL 34229

    $1,200,000228 Days on yellowkey   MLS ID: A4667634

    For Sale A4667634 - 700 FAITH AVE, OSPREY, FL 34229 74 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2474
       Built: 1982
    Community: Trinity Acres
    Single Family


    Estimated Monthly Payment: $6,575 (change assumption)
    Mortgage ($6,575)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 530 N MAC EWEN DR, OSPREY, FL 34229

    $2,400,000124 Days on yellowkey   MLS ID: A4683029

    1 Days Off yellowkey (back on 3/20/2026)

    For Sale A4683029 - 530 N MAC EWEN DR, OSPREY, FL 34229 83 photos

    Bed: 4   Bath: 5.5
    Liv Area Sq Ft: 4346
       Built: 2002
    Community: Oaks 2 Ph 4-C Pt 3
    Single Family


    Estimated Monthly Payment: $13,150 (change assumption)
    Mortgage ($13,150)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


12




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.