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Longboat Key Homes For Sale & Real Estate - 337 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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  • 548 GUNWALE LN, LONGBOAT KEY, FL 34228

    $2,200,00070 Days on yellowkey   MLS ID: A4680965

    For Sale A4680965 - 548 GUNWALE LN, LONGBOAT KEY, FL 34228 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 1967
    Monthly Fee: $17
       Tax: $9,801 (2025)
    Community: Country Club Shores Sec 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,888 (change assumption)
    Mortgage ($12,054) + Fees ($17) + Taxes in 2025 ($817)


    Taxes:$9,801

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $505,000140 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


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

    $675,000136 Days on yellowkey   MLS ID: A4672221

    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: $4,243 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($545)


    Taxes:$6,535

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7030 POINSETTIA AVE, LONGBOAT KEY, FL 34228

    $1,199,00024 Days on yellowkey   MLS ID: A4686787

    For Sale A4686787 - 7030 POINSETTIA AVE, LONGBOAT KEY, FL 34228 62 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1402
       Built: 1934   Tax: $6,672 (2025)
    Community: Longbeach On Longboat Key
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,126 (change assumption)
    Mortgage ($6,570) + Taxes in 2025 ($556)


    Taxes:$6,672

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 569 BAYVIEW DR, LONGBOAT KEY, FL 34228

    $4,850,000249 Days on yellowkey   MLS ID: A4661312

    For Sale A4661312 - 569 BAYVIEW DR, LONGBOAT KEY, FL 34228 89 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4106
       Built: 2025   Tax: $12,064 (2024)
    Community: Bayview Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,580 (change assumption)
    Mortgage ($26,575) + Taxes in 2024 ($1,005)


    Taxes:$12,064

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 5260 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228

    $595,000110 Days on yellowkey   MLS ID: A4675930

    For Sale A4675930 - 5260 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228 34 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1173
       Built: 1974
    Monthly Fee: $1,763
       Tax: $1,961 (2025)
    Community: The Banyan Bay Club
    Condo


    Estimated Monthly Payment: $5,187 (change assumption)
    Mortgage ($3,260) + Fees ($1,763) + Taxes in 2025 ($163)


    Taxes:$1,961

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 311 FIREHOUSE CT, LONGBOAT KEY, FL 34228

    $2,399,000202 Days on yellowkey   MLS ID: A4665445

    For Sale A4665445 - 311 FIREHOUSE CT, LONGBOAT KEY, FL 34228 79 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2352
       Built: 2005
    Monthly Fee: $467
       Tax: $29,195 (2025)
    Community: Conrad Beach
    Single Family


    Estimated Monthly Payment: $16,045 (change assumption)
    Mortgage ($13,145) + Fees ($467) + Taxes in 2025 ($2,433)


    Taxes:$29,195

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 6841 LONGBOAT DR S, LONGBOAT KEY, FL 34228

    $1,050,000116 Days on yellowkey   MLS ID: A4674302

    0 Days Off yellowkey (back on 4/9/2026)

    REDUCED by $45,000 (4.1%) on 04/01/2026

    For Sale A4674302 - 6841 LONGBOAT DR S, LONGBOAT KEY, FL 34228 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1380
       Built: 1935   Tax: $13,113 (2025)
    Community: Longbeach On Longboat Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,846 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($1,093)


    Taxes:$13,113

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 729 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228

    $449,00032 Days on yellowkey   MLS ID: A4685189

    For Sale A4685189 - 729 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228 73 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 630
       Built: 1966   Tax: $1,994 (2025)
    Community: Saint Judes Apts
    Spa: No

    Condo


    Estimated Monthly Payment: $2,626 (change assumption)
    Mortgage ($2,460) + Taxes in 2025 ($166)


    Taxes:$1,994

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 6750 GULF OF MEXICO DR #152, LONGBOAT KEY, FL 34228

    $375,00017 Days on yellowkey   MLS ID: A4686698

    REDUCED by $24,000 (6.0%) on 04/09/2026

    For Sale A4686698 - 6750 GULF OF MEXICO DR #152, LONGBOAT KEY, FL 34228 41 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 990
       Built: 1970   Tax: $2,215 (2025)
    Community: Whitney Beach
    Condo


    Estimated Monthly Payment: $2,239 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($185)


    Taxes:$2,215

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228

    $1,559,00038 Days on yellowkey   MLS ID: A4684840

    For Sale A4684840 - 3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228 58 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2579
       Built: 1998
    Monthly Fee: $833
       Tax: $17,916 (2025)
    Community: Bay Isles
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,868 (change assumption)
    Mortgage ($8,542) + Fees ($833) + Taxes in 2025 ($1,493)


    Taxes:$17,916

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228

    $3,890,000420 Days on yellowkey   MLS ID: A4640902

    For Sale A4640902 - 597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228 92 photos

    Bed: 5   Bath: 6.0   Gar: 5
    Liv Area Sq Ft: 4176
       Built: 2025   Tax: $7,998 (2024)
    Community: Buttonwood Harbor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,981 (change assumption)
    Mortgage ($21,315) + Taxes in 2024 ($666)


    Taxes:$7,998

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


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

    $389,0005 Days on yellowkey   MLS ID: R4911020

    For Sale R4911020 - 3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228 38 photos

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


    Estimated Monthly Payment: $2,366 (change assumption)
    Mortgage ($2,131) + Taxes in 2025 ($234)


    Taxes:$2,813

    Elementary School: None

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228

    $850,0005 Days on yellowkey   MLS ID: A4689278

    For Sale A4689278 - 815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228 57 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1601
       Built: 1981   Tax: $7,370 (2025)
    Community: Bayport Bch & Ten Ph E
    Condo


    Estimated Monthly Payment: $5,272 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($614)


    Taxes:$7,370

    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


  • 706 BAYPORT WAY #706, LONGBOAT KEY, FL 34228

    $739,0005 Days on yellowkey   MLS ID: A4688503

    For Sale A4688503 - 706 BAYPORT WAY #706, LONGBOAT KEY, FL 34228 58 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1601
       Built: 1980
    Monthly Fee: $1,978
       Tax: $6,727 (2025)
    Community: Bayport Bch & Ten Ph C
    Condo


    Estimated Monthly Payment: $6,588 (change assumption)
    Mortgage ($4,049) + Fees ($1,978) + Taxes in 2025 ($561)


    Taxes:$6,727

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 765 SAINT JUDES DR N, LONGBOAT KEY, FL 34228

    $1,499,90052 Days on yellowkey   MLS ID: A4683420

    REDUCED by $80,100 (5.1%) on 04/08/2026

    For Sale A4683420 - 765 SAINT JUDES DR N, LONGBOAT KEY, FL 34228 65 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1900
       Built: 1963   Tax: $14,125 (2025)
    Community: Longboat Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,396 (change assumption)
    Mortgage ($8,218) + Taxes in 2025 ($1,177)


    Taxes:$14,125

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4805 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228

    $699,00094 Days on yellowkey   MLS ID: A4677568

    1 Days Off yellowkey (back on 4/6/2026)

    For Sale A4677568 - 4805 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228 58 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1393
       Built: 1970   Tax: $6,331 (2024)
    Community: Westchester Apts
    Spa: No

    Condo


    Estimated Monthly Payment: $4,358 (change assumption)
    Mortgage ($3,830) + Taxes in 2024 ($528)


    Taxes:$6,331

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2181 HARBOURSIDE DR #1403, LONGBOAT KEY, FL 34228

    $850,000291 Days on yellowkey   MLS ID: A4656539

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale A4656539 - 2181 HARBOURSIDE DR #1403, LONGBOAT KEY, FL 34228 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2219
       Built: 1984   Tax: $9,674 (2024)
    Community: Harbor Oaks Ph I & Ii
    Spa: No

    Condo


    Estimated Monthly Payment: $5,464 (change assumption)
    Mortgage ($4,657) + Taxes in 2024 ($806)


    Taxes:$9,674

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Pine View School




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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.