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Longboat Key Homes For Sale & Real Estate - 344 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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  • 2341 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228

    $1,399,9906 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


  • 561 BIRDIE LN, LONGBOAT KEY, FL 34228

    $2,195,00011 Days on yellowkey   MLS ID: A4687002

    For Sale A4687002 - 561 BIRDIE LN, LONGBOAT KEY, FL 34228 49 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2256
       Built: 1967
    Monthly Fee: $17
       Tax: $15,946 (2025)
    Community: Country Club Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,373 (change assumption)
    Mortgage ($12,027) + Fees ($17) + Taxes in 2025 ($1,329)


    Taxes:$15,946

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 510 BOWSPRIT LN, LONGBOAT KEY, FL 34228

    $4,600,00017 Days on yellowkey   MLS ID: A4687207

    For Sale A4687207 - 510 BOWSPRIT LN, LONGBOAT KEY, FL 34228 80 photos

    Bed: 5   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 4389
       Built: 2013
    Monthly Fee: $21
       Tax: $35,060 (2025)
    Community: Country Club Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $28,148 (change assumption)
    Mortgage ($25,205) + Fees ($21) + Taxes in 2025 ($2,922)


    Taxes:$35,060

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $739,00018 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

    $950,00048 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

    $1,295,00048 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

    $475,00038 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

    $999,99967 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

    $599,00050 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

    $660,00080 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

    $13,995,00087 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

    $530,00098 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


  • 4370 CHATHAM DR #104, LONGBOAT KEY, FL 34228

    $470,000129 Days on yellowkey   MLS ID: A4674307

    For Sale A4674307 - 4370 CHATHAM DR #104, LONGBOAT KEY, FL 34228 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1969   Tax: $5,334 (2024)
    Community: Longboat Harbour
    Spa: No

    Condo


    Estimated Monthly Payment: $3,020 (change assumption)
    Mortgage ($2,575) + Taxes in 2024 ($445)


    Taxes:$5,334

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $595,000185 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


  • 2045 GULF OF MEXICO DR #M1-511, LONGBOAT KEY, FL 34228

    $749,0003 Days on yellowkey   MLS ID: A4689590

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale A4689590 - 2045 GULF OF MEXICO DR #M1-511, LONGBOAT KEY, FL 34228 58 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1076
       Built: 1974
    Monthly Fee: $1,278
       Tax: $9,430 (2025)
    Community: Seaplace Ii
    Condo


    Estimated Monthly Payment: $6,168 (change assumption)
    Mortgage ($4,104) + Fees ($1,278) + Taxes in 2025 ($786)


    Taxes:$9,430

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228

    $950,00099 Days on yellowkey   MLS ID: A4676681

    For Sale A4676681 - 100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228 34 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1492
       Built: 1966   Tax: $3,929 (2025)
    Community: Sands Point
    Condo


    Estimated Monthly Payment: $5,533 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($327)


    Taxes:$3,929

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 3131 BAYOU SOUND, LONGBOAT KEY, FL 34228

    $1,650,00048 Days on yellowkey   MLS ID: A4683048

    For Sale A4683048 - 3131 BAYOU SOUND, LONGBOAT KEY, FL 34228 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3023
       Built: 1978
    Monthly Fee: $104
       Tax: $15,562 (2025)
    Community: Bay Isles
    Single Family


    Estimated Monthly Payment: $10,442 (change assumption)
    Mortgage ($9,041) + Fees ($104) + Taxes in 2025 ($1,297)


    Taxes:$15,562

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 340 GULF OF MEXICO DR #112, LONGBOAT KEY, FL 34228

    $1,775,000166 Days on yellowkey   MLS ID: A4670120

    For Sale A4670120 - 340 GULF OF MEXICO DR #112, LONGBOAT KEY, FL 34228 50 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2298
       Built: 1991   Tax: $12,180 (2024)
    Community: Tangerine Bay Club
    Spa: Yes

    Condo


    Estimated Monthly Payment: $10,741 (change assumption)
    Mortgage ($9,726) + Taxes in 2024 ($1,015)


    Taxes:$12,180

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228

    $399,00087 Days on yellowkey   MLS ID: A4678473

    For Sale A4678473 - 4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228 44 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 747
       Built: 1969
    Monthly Fee: $1,196
       Tax: $4,937 (2025)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $3,794 (change assumption)
    Mortgage ($2,186) + Fees ($1,196) + Taxes in 2025 ($411)


    Taxes:$4,937

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


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

    $549,999150 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




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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.