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Longboat Key Homes For Sale & Real Estate - 391 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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  • 2301 GULF OF MEXICO DR #12N and 11N, LONGBOAT KEY, FL 34228

    $2,377,000190 Days on yellowkey   MLS ID: A4675054

    REDUCED by $111,000 (4.5%) on 04/21/2026

    For Sale A4675054 - 2301 GULF OF MEXICO DR #12N and 11N, LONGBOAT KEY, FL 34228 72 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2415
       Built: 1970   Tax: $13,538 (2025)
    Community: Islander Club Of Longboat
    Spa: No

    Condo


    Estimated Monthly Payment: $14,152 (change assumption)
    Mortgage ($13,024) + Taxes in 2025 ($1,128)


    Taxes:$13,538

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2301 GULF OF MEXICO DR #11N, LONGBOAT KEY, FL 34228

    $1,225,27725 Days on yellowkey   MLS ID: A4695843

    For Sale A4695843 - 2301 GULF OF MEXICO DR #11N, LONGBOAT KEY, FL 34228 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1235
       Built: 1970   Tax: $4,043 (2025)
    Community: Islander Club Of Longboat
    Condo


    Estimated Monthly Payment: $7,051 (change assumption)
    Mortgage ($6,714) + Taxes in 2025 ($337)


    Taxes:$4,043

    Elementary School: None

    High School: Pine View School

    Tax Year: 2025

    Middle School: None


  • 2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL 34228

    $1,225,27725 Days on yellowkey   MLS ID: A4695851

    For Sale A4695851 - 2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL 34228 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1235
       Built: 1970   Tax: $9,496 (2025)
    Community: Islander Club Of Longboat
    Spa: No

    Condo


    Estimated Monthly Payment: $7,505 (change assumption)
    Mortgage ($6,714) + Taxes in 2025 ($791)


    Taxes:$9,496

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2600 HARBOURSIDE DRIVE #R-13, LONGBOAT KEY, FL 34228

    $400,0003 Days on yellowkey   MLS ID: A4697978

    For Sale A4697978 - 2600 HARBOURSIDE DRIVE #R-13, LONGBOAT KEY, FL 34228 19 photos

    Bed:    Bath: 0.0
    Built: 1985

    Monthly Fee: $540
       Tax: $3,753 (2025)
    Community: 7981 Longboat Key Moorings Marina
    Dock-Rackominium


    Estimated Monthly Payment: $3,044 (change assumption)
    Mortgage ($2,192) + Fees ($540) + Taxes in 2025 ($313)


    Taxes:$3,753

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 4320 FALMOUTH DR #103, LONGBOAT KEY, FL 34228

    $499,000142 Days on yellowkey   MLS ID: A4681530

    REDUCED by $26,000 (5.0%) on 05/26/2026

    For Sale A4681530 - 4320 FALMOUTH DR #103, LONGBOAT KEY, FL 34228 66 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1969   Tax: $6,901 (2024)
    Community: Longboat Harbour
    Spa: No

    Condo


    Estimated Monthly Payment: $3,309 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($575)


    Taxes:$6,901

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4350 CHATHAM DR #105, LONGBOAT KEY, FL 34228

    $310,00010 Days on yellowkey   MLS ID: A4697241

    For Sale A4697241 - 4350 CHATHAM DR #105, LONGBOAT KEY, FL 34228 54 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 747
       Built: 1969
    Monthly Fee: $1,147
       Tax: $1,457 (2025)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $2,967 (change assumption)
    Mortgage ($1,699) + Fees ($1,147) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 500 HARBOR COVE CIR, LONGBOAT KEY, FL 34228

    $12,250,0006 Days on yellowkey   MLS ID: A4697649

    For Sale A4697649 - 500 HARBOR COVE CIR, LONGBOAT KEY, FL 34228 15 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5120
       Built: 2026   Tax: $20,619 (2025)
    Community: Bay Isles
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $68,840 (change assumption)
    Mortgage ($67,122) + Taxes in 2025 ($1,718)


    Taxes:$20,619

    Elementary School: Southside Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Booker Middle


  • 5841 GULF OF MEXICO DR #236, LONGBOAT KEY, FL 34228

    $475,000159 Days on yellowkey   MLS ID: A4679009

    REDUCED by $20,000 (4.0%) on 06/25/2026

    For Sale A4679009 - 5841 GULF OF MEXICO DR #236, LONGBOAT KEY, FL 34228 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 450
       Built: 1953   Tax: $4,409 (2024)
    Community: Silver Sands
    Condo


    Estimated Monthly Payment: $2,970 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($367)


    Taxes:$4,409

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: W.D. Sugg Middle


  • 1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228

    $2,745,000243 Days on yellowkey   MLS ID: A4669837

    REDUCED by $10,000 (0.4%) on 06/23/2026

    For Sale A4669837 - 1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228 63 photos

    Bed: 3   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3045
       Built: 1996   Tax: $25,341 (2024)
    Community: Water Club 01 At Longboat Key
    Condo


    Estimated Monthly Payment: $17,152 (change assumption)
    Mortgage ($15,041) + Taxes in 2024 ($2,112)


    Taxes:$25,341

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228

    $1,180,000121 Days on yellowkey   MLS ID: A4684021

    REDUCED by $15,000 (1.3%) on 06/25/2026

    For Sale A4684021 - 1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228 39 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2092
       Built: 1982   Tax: $11,749 (2025)
    Community: Players Club Iii
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,445 (change assumption)
    Mortgage ($6,466) + Taxes in 2025 ($979)


    Taxes:$11,749

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 7143 LA LENAIRE DR, LONGBOAT KEY, FL 34228

    $5,995,00032 Days on yellowkey   MLS ID: A4694196

    For Sale A4694196 - 7143 LA LENAIRE DR, LONGBOAT KEY, FL 34228 78 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2721
       Built: 2010
    Monthly Fee: $317
       Tax: $17,255 (2025)
    Community: Jew Fish Key
    Single Family


    Estimated Monthly Payment: $34,603 (change assumption)
    Mortgage ($32,848) + Fees ($317) + Taxes in 2025 ($1,438)


    Taxes:$17,255

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4350 CHATHAM DR #Unit E-208, LONGBOAT KEY, FL 34228

    $640,000212 Days on yellowkey   MLS ID: A4672221

    REDUCED by $35,000 (5.2%) on 06/17/2026

    For Sale A4672221 - 4350 CHATHAM DR #Unit E-208, LONGBOAT KEY, FL 34228 86 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1316
       Built: 1969   Tax: $6,535 (2025)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $4,051 (change assumption)
    Mortgage ($3,507) + Taxes in 2025 ($545)


    Taxes:$6,535

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1930 HARBOURSIDE DR #122, LONGBOAT KEY, FL 34228

    $515,00054 Days on yellowkey   MLS ID: A4692494

    REDUCED by $34,000 (6.2%) on 06/25/2026

    For Sale A4692494 - 1930 HARBOURSIDE DR #122, LONGBOAT KEY, FL 34228 63 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1192
       Built: 1982   Tax: $6,584 (2025)
    Community: Fairway Bay 1
    Spa: Yes

    Condo


    Estimated Monthly Payment: $3,371 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($549)


    Taxes:$6,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228

    $1,675,000103 Days on yellowkey   MLS ID: A4686539

    REDUCED by $25,000 (1.5%) on 06/25/2026

    For Sale A4686539 - 2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1470
       Built: 1973   Tax: $13,728 (2025)
    Community: Sea Gate Club
    Spa: Yes

    Condo


    Estimated Monthly Payment: $10,322 (change assumption)
    Mortgage ($9,178) + Taxes in 2025 ($1,144)


    Taxes:$13,728

    Elementary School: Southside Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Booker Middle


  • 1965 GULF OF MEXICO DR #G5-103, LONGBOAT KEY, FL 34228

    $649,00036 Days on yellowkey   MLS ID: A4694695

    For Sale A4694695 - 1965 GULF OF MEXICO DR #G5-103, LONGBOAT KEY, FL 34228 66 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 933
       Built: 1977
    Monthly Fee: $1,500
       Tax: $3,123 (2025)
    Community: Seaplace Iii
    Spa: Yes

    Condo


    Estimated Monthly Payment: $5,316 (change assumption)
    Mortgage ($3,556) + Fees ($1,500) + Taxes in 2025 ($260)


    Taxes:$3,123

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 1925 GULF OF MEXICO DR #G8-302, LONGBOAT KEY, FL 34228

    $629,000101 Days on yellowkey   MLS ID: A4686871

    REDUCED by $20,000 (3.1%) on 05/15/2026

    For Sale A4686871 - 1925 GULF OF MEXICO DR #G8-302, LONGBOAT KEY, FL 34228 82 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1257
       Built: 1978
    Monthly Fee: $1,467
       Tax: $6,897 (2025)
    Community: Seaplace Vi
    Spa: Yes

    Condo


    Estimated Monthly Payment: $5,488 (change assumption)
    Mortgage ($3,446) + Fees ($1,467) + Taxes in 2025 ($575)


    Taxes:$6,897

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228

    $975,000198 Days on yellowkey   MLS ID: A4674194

    REDUCED by $25,000 (2.5%) on 06/25/2026

    For Sale A4674194 - 1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228 45 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1707
       Built: 1983   Tax: $11,336 (2025)
    Community: Players Club Iv
    Condo


    Estimated Monthly Payment: $6,287 (change assumption)
    Mortgage ($5,342) + Taxes in 2025 ($945)


    Taxes:$11,336

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 3460 WINDING OAKS DR #38, LONGBOAT KEY, FL 34228

    $1,150,00026 Days on yellowkey   MLS ID: A4695005

    For Sale A4695005 - 3460 WINDING OAKS DR #38, LONGBOAT KEY, FL 34228 55 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2608
       Built: 1988   Tax: $10,320 (2025)
    Community: Winding Oaks
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,161 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($860)


    Taxes:$10,320

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228

    $2,050,00011 Days on yellowkey   MLS ID: A4697202

    For Sale A4697202 - 2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228 59 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 3083
       Built: 1990   Tax: $20,065 (2025)
    Community: Marina Bay
    Condo


    Estimated Monthly Payment: $12,905 (change assumption)
    Mortgage ($11,233) + Taxes in 2025 ($1,672)


    Taxes:$20,065

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228

    $4,395,000229 Days on yellowkey   MLS ID: A4671696

    For Sale A4671696 - 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 92 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




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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.