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Longboat Key Homes For Sale & Real Estate - 364 homes

Longboat Key homes for sale are located in Sarasota County, Florida. Find homes in Longboat Key for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Longboat Key houses.

Location: Longboat Key

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  • 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228

    $4,395,000154 Days on yellowkey   MLS ID: A4671696

    For Sale A4671696 - 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 91 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5080
       Built: 1996
    Monthly Fee: $208
       Tax: $42,201 (2024)
    Community: Bay Isles
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,806 (change assumption)
    Mortgage ($24,082) + Fees ($208) + Taxes in 2024 ($3,517)


    Taxes:$42,201

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 569 JUAN ANASCO DR, LONGBOAT KEY, FL 34228

    $1,700,000172 Days on yellowkey   MLS ID: A4669634

    For Sale A4669634 - 569 JUAN ANASCO DR, LONGBOAT KEY, FL 34228 81 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2804
       Built: 1996
    Monthly Fee: $3
       Tax: $22,111 (2024)
    Community: Sleepy Lagoon Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,160 (change assumption)
    Mortgage ($9,315) + Fees ($3) + Taxes in 2024 ($1,843)


    Taxes:$22,111

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 3617 FAIR OAKS PL, LONGBOAT KEY, FL 34228

    $2,050,000219 Days on yellowkey   MLS ID: A4663935

    For Sale A4663935 - 3617 FAIR OAKS PL, LONGBOAT KEY, FL 34228 33 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2950
       Built: 1995
    Monthly Fee: $746
       Tax: $16,463 (2025)
    Community: Queens Harbour
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,350 (change assumption)
    Mortgage ($11,233) + Fees ($746) + Taxes in 2025 ($1,372)


    Taxes:$16,463

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 524 HALYARD LN, LONGBOAT KEY, FL 34228

    $5,495,000228 Days on yellowkey   MLS ID: A4663499

    For Sale A4663499 - 524 HALYARD LN, LONGBOAT KEY, FL 34228 91 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3737
       Built: 2025
    Monthly Fee: $21
       Tax: $17,932 (2024)
    Community: Country Club Shores Iv
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,624 (change assumption)
    Mortgage ($30,109) + Fees ($21) + Taxes in 2024 ($1,494)


    Taxes:$17,932

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Brookside Middle


  • 5005 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228

    $3,995,000242 Days on yellowkey   MLS ID: A4661988

    For Sale A4661988 - 5005 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228 82 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4044
       Built: 2018
    Monthly Fee: $766
       Tax: $49,274 (2024)
    Community: Bonaire
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,762 (change assumption)
    Mortgage ($21,890) + Fees ($766) + Taxes in 2024 ($4,106)


    Taxes:$49,274

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3210 BAYOU SOUND, LONGBOAT KEY, FL 34228

    $1,299,000273 Days on yellowkey   MLS ID: A4658086

    For Sale A4658086 - 3210 BAYOU SOUND, LONGBOAT KEY, FL 34228 59 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2091
       Built: 1978
    Monthly Fee: $104
       Tax: $15,679 (2024)
    Community: The Bayou
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,528 (change assumption)
    Mortgage ($7,118) + Fees ($104) + Taxes in 2024 ($1,307)


    Taxes:$15,679

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4234 GULF OF MEXICO DR #Q2, LONGBOAT KEY, FL 34228

    $648,800399 Days on yellowkey   MLS ID: A4643486

    For Sale A4643486 - 4234 GULF OF MEXICO DR #Q2, LONGBOAT KEY, FL 34228 67 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1150
       Built: 1973   Tax: $6,219 (2025)
    Community: Pelican Harbour & Beach Club
    Condo


    Estimated Monthly Payment: $4,073 (change assumption)
    Mortgage ($3,555) + Taxes in 2025 ($518)


    Taxes:$6,219

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228

    $389,0006 Days on yellowkey   MLS ID: R4911020

    For Sale R4911020 - 3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228 77 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1046
       Built: 1970
    Monthly Fee: $1,457
       Tax: $2,813 (2025)
    Community: Beach Harbor Club
    Condo


    Estimated Monthly Payment: $3,823 (change assumption)
    Mortgage ($2,131) + Fees ($1,457) + Taxes in 2025 ($234)


    Taxes:$2,813

    Elementary School: None

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $689,000160 Days on yellowkey   MLS ID: A4670932

    REDUCED by $10,000 (1.4%) on 04/08/2026

    For Sale A4670932 - 4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228 73 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1325
       Built: 1975   Tax: $8,395 (2025)
    Community: Windward Bay Amd
    Spa: No

    Condo


    Estimated Monthly Payment: $4,475 (change assumption)
    Mortgage ($3,775) + 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


  • 1912 HARBOURSIDE DR #602, LONGBOAT KEY, FL 34228

    $549,900179 Days on yellowkey   MLS ID: A4668394

    For Sale A4668394 - 1912 HARBOURSIDE DR #602, LONGBOAT KEY, FL 34228 44 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1590
       Built: 1982   Tax: $6,146 (2024)
    Community: Fairway Bay 1
    Spa: Yes

    Condo


    Estimated Monthly Payment: $3,525 (change assumption)
    Mortgage ($3,013) + Taxes in 2024 ($512)


    Taxes:$6,146

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Pine View School


  • 2341 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228

    $1,399,9907 Days on yellowkey   MLS ID: A4688219

    For Sale A4688219 - 2341 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228 52 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2282
       Built: 1986
    Monthly Fee: $1,617
       Tax: $11,814 (2025)
    Community: Harbour Oaks 2
    Spa: No

    Villa


    Estimated Monthly Payment: $10,272 (change assumption)
    Mortgage ($7,671) + Fees ($1,617) + Taxes in 2025 ($984)


    Taxes:$11,814

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $739,00019 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


  • 2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228

    $950,00049 Days on yellowkey   MLS ID: A4683180

    For Sale A4683180 - 2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228 97 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2282
       Built: 1986
    Monthly Fee: $143
       Tax: $10,215 (2025)
    Community: Harbour Oaks 2
    Villa


    Estimated Monthly Payment: $6,200 (change assumption)
    Mortgage ($5,205) + Fees ($143) + Taxes in 2025 ($851)


    Taxes:$10,215

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 550 DE NARVAEZ DR, LONGBOAT KEY, FL 34228

    $1,295,00049 Days on yellowkey   MLS ID: A4683082

    For Sale A4683082 - 550 DE NARVAEZ DR, LONGBOAT KEY, FL 34228 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1758
       Built: 1977   Tax: $6,151 (2025)
    Community: Sleepy Lagoon Park
    Single Family


    Estimated Monthly Payment: $7,608 (change assumption)
    Mortgage ($7,096) + Taxes in 2025 ($513)


    Taxes:$6,151

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228

    $475,00039 Days on yellowkey   MLS ID: A4681154

    For Sale A4681154 - 3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228 45 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 740
       Built: 2026
    Monthly Fee: $290
       Tax: $2,070 (2025)
    Community: Gulfshore Of Longboat Key
    Manufactured Home


    Estimated Monthly Payment: $3,065 (change assumption)
    Mortgage ($2,603) + Fees ($290) + Taxes in 2025 ($173)


    Taxes:$2,070

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228

    $999,99968 Days on yellowkey   MLS ID: A4680786

    For Sale A4680786 - 552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 46 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 1960   Tax: $17,419 (2024)
    Community: Sleepy Lagoon Park
    Single Family


    Estimated Monthly Payment: $6,931 (change assumption)
    Mortgage ($5,479) + Taxes in 2024 ($1,452)


    Taxes:$17,419

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


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

    $599,00051 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


  • 4310 FALMOUTH DR #102, LONGBOAT KEY, FL 34228

    $660,00081 Days on yellowkey   MLS ID: A4679011

    REDUCED by $5,000 (0.8%) on 04/12/2026

    For Sale A4679011 - 4310 FALMOUTH DR #102, LONGBOAT KEY, FL 34228 99 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1969
    Monthly Fee: $1,410
       Tax: $6,739 (2024)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $5,588 (change assumption)
    Mortgage ($3,616) + Fees ($1,410) + Taxes in 2024 ($562)


    Taxes:$6,739

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 6489 GULFSIDE RD, LONGBOAT KEY, FL 34228

    $13,995,00088 Days on yellowkey   MLS ID: A4677413

    For Sale A4677413 - 6489 GULFSIDE RD, LONGBOAT KEY, FL 34228 68 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 6616
       Built: 2026   Tax: $42,641 (2025)
    Community: Sleepy Lagoon
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $80,236 (change assumption)
    Mortgage ($76,683) + Taxes in 2025 ($3,553)


    Taxes:$42,641

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228

    $530,00099 Days on yellowkey   MLS ID: A4676925

    For Sale A4676925 - 4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228 60 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1969   Tax: $6,041 (2024)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $3,407 (change assumption)
    Mortgage ($2,904) + Taxes in 2024 ($503)


    Taxes:$6,041

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle




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