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Windward Bay Homes for Sale in Longboat Key - 11 homes

Windward Bay homes for sale are located in Manatee County, Florida. Find Windward Bay Homes in Longboat Key for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Windward Bay, Longboat Key homes.

Location: Windward Bay, Longboat Key

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  • 4760 GULF OF MEXICO DR. VILLA 7, LONGBOAT KEY, FL 34228

    $549,999142 Days on yellowkey   MLS ID: A4671823

    REDUCED by $24,501 (4.3%) on 04/01/2026

    For Sale A4671823 - 4760 GULF OF MEXICO DR. VILLA 7, LONGBOAT KEY, FL 34228 75 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 931
       Built: 1974
    Monthly Fee: $21
       Tax: $1,629 (2025)
    Community: Windward Bay Amd
    Villa


    Estimated Monthly Payment: $3,170 (change assumption)
    Mortgage ($3,014) + Fees ($21) + Taxes in 2025 ($136)


    Taxes:$1,629

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228

    $699,000151 Days on yellowkey   MLS ID: A4670932

    For Sale A4670932 - 4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228 72 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1325
       Built: 1975   Tax: $8,395 (2025)
    Community: Windward Bay Amd
    Condo


    Estimated Monthly Payment: $4,530 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($700)


    Taxes:$8,395

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228

    $739,00010 Days on yellowkey   MLS ID: A4685838

    For Sale A4685838 - 4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228 61 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1325
       Built: 1975   Tax: $2,843 (2025)
    Community: Windward Bay Amd
    Condo


    Estimated Monthly Payment: $4,286 (change assumption)
    Mortgage ($4,049) + Taxes in 2025 ($237)


    Taxes:$2,843

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4720 GULF OF MEXICO DR #Villa 2, LONGBOAT KEY, FL 34228

    $599,00042 Days on yellowkey   MLS ID: A4679458

    For Sale A4679458 - 4720 GULF OF MEXICO DR #Villa 2, LONGBOAT KEY, FL 34228 59 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 912
       Built: 1974
    Monthly Fee: $1,305
       Tax: $1,356 (2025)
    Community: Windward Bay Amd
    Villa


    Estimated Monthly Payment: $4,700 (change assumption)
    Mortgage ($3,282) + Fees ($1,305) + Taxes in 2025 ($113)


    Taxes:$1,356

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4750 GULF OF MEXICO DR #Villa 8, LONGBOAT KEY, FL 34228

    $850,00066 Days on yellowkey   MLS ID: A4679944

    For Sale A4679944 - 4750 GULF OF MEXICO DR #Villa 8, LONGBOAT KEY, FL 34228 76 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1504
       Built: 1974   Tax: $2,954 (2025)
    Community: Windward Bay Amd
    Villa


    Estimated Monthly Payment: $4,904 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($246)


    Taxes:$2,954

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4540 GULF OF MEXICO DR #204, LONGBOAT KEY, FL 34228

    $595,000177 Days on yellowkey   MLS ID: A4667631

    For Sale A4667631 - 4540 GULF OF MEXICO DR #204, LONGBOAT KEY, FL 34228 75 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1312
       Built: 1975   Tax: $9,451 (2024)
    Community: Windward Bay
    Condo


    Estimated Monthly Payment: $4,048 (change assumption)
    Mortgage ($3,260) + Taxes in 2024 ($788)


    Taxes:$9,451

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 4860 GULF OF MEXICO DR #Villa 13, LONGBOAT KEY, FL 34228

    $505,000132 Days on yellowkey   MLS ID: A4673141

    REDUCED by $5,000 (1.0%) on 04/01/2026

    For Sale A4673141 - 4860 GULF OF MEXICO DR #Villa 13, LONGBOAT KEY, FL 34228 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1025
       Built: 1974   Tax: $2,052 (2025)
    Community: Windward Bay Amd
    Villa


    Estimated Monthly Payment: $2,938 (change assumption)
    Mortgage ($2,767) + Taxes in 2025 ($171)


    Taxes:$2,052

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: W.D. Sugg Middle


  • 4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228

    $649,90073 Days on yellowkey   MLS ID: A4679160

    REDUCED by $10,000 (1.5%) on 04/01/2026

    For Sale A4679160 - 4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228 75 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1523
       Built: 1975   Tax: $7,738 (2025)
    Community: Windward Bay Amd
    Condo


    Estimated Monthly Payment: $4,206 (change assumption)
    Mortgage ($3,561) + Taxes in 2025 ($645)


    Taxes:$7,738

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4900 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228

    $698,000149 Days on yellowkey   MLS ID: A4671087

    1 Days Off yellowkey (back on 2/18/2026)

    For Sale A4671087 - 4900 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228 40 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1312
       Built: 1975   Tax: $6,787 (2024)
    Community: Windward Bay
    Condo


    Estimated Monthly Payment: $4,390 (change assumption)
    Mortgage ($3,825) + Taxes in 2024 ($566)


    Taxes:$6,787

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4840 GULF OF MEXICO DR #Villa 15, LONGBOAT KEY, FL 34228

    $445,000324 Days on yellowkey   MLS ID: A4652683

    0 Days Off yellowkey (back on 3/24/2026)

    For Sale A4652683 - 4840 GULF OF MEXICO DR #Villa 15, LONGBOAT KEY, FL 34228 74 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1084
       Built: 1974
    Community: Windward Bay Amd
    Villa


    Estimated Monthly Payment: $2,438 (change assumption)
    Mortgage ($2,438)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 4976 GULF OF MEXICO DR #Villa 18, LONGBOAT KEY, FL 34228

    $675,000194 Days on yellowkey   MLS ID: A4665034

    For Sale A4665034 - 4976 GULF OF MEXICO DR #Villa 18, LONGBOAT KEY, FL 34228 47 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1900
       Built: 1974
    Community: Windward Bay Amd
    Condo


    Estimated Monthly Payment: $3,699 (change assumption)
    Mortgage ($3,699)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None




Why Bother Searching Elsewhere for Windward Bay Homes for Sale and Other Longboat Key Real Estate?

Windward Bay 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 Windward Bay. You can use our website to view Multiple Listing Service (MLS) data on Windward Bay 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 Windward Bay. Longboat Key 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.