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Longboat Key Homes For Sale & Real Estate - 385 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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  • 524 HALYARD LN, LONGBOAT KEY, FL 34228

    $5,495,000233 Days on yellowkey   MLS ID: A4663499

    For Sale A4663499 - 524 HALYARD LN, LONGBOAT KEY, FL 34228 77 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


  • 530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228

    $4,795,000180 Days on yellowkey   MLS ID: A4669195

    For Sale A4669195 - 530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228 100 photos

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

    Single Family


    Estimated Monthly Payment: $27,279 (change assumption)
    Mortgage ($26,273) + 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


  • 1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228

    $4,750,000202 Days on yellowkey   MLS ID: A4666688

    For Sale A4666688 - 1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228 93 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4209
       Built: 1987   Tax: $16,980 (2024)
    Community: Bay Isles
    Single Family


    Estimated Monthly Payment: $27,442 (change assumption)
    Mortgage ($26,027) + Taxes in 2024 ($1,415)


    Taxes:$16,980

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 578 - 580 COMPANION WAY, LONGBOAT KEY, FL 34228

    $999,00067 Days on yellowkey   MLS ID: A4682264

    REDUCED by $1,000 (0.1%) on 04/19/2026

    For Sale A4682264 - 578 - 580 COMPANION WAY, LONGBOAT KEY, FL 34228 70 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1792
       Built: 1963   Tax: $11,672 (2025)
    Community: Longboat Key
    Spa: No

    Apartment


    Estimated Monthly Payment: $6,447 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($973)


    Taxes:$11,672

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 578 COMPANION WAY, LONGBOAT KEY, FL 34228

    $999,00067 Days on yellowkey   MLS ID: A4682186

    REDUCED by $1,000 (0.1%) on 04/19/2026

    For Sale A4682186 - 578 COMPANION WAY, LONGBOAT KEY, FL 34228 51 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1792
       Built: 1963   Tax: $11,672 (2025)
    Community: Longboat Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,447 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($973)


    Taxes:$11,672

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


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

    $1,690,000321 Days on yellowkey   MLS ID: A4654664

    REDUCED by $60,000 (3.4%) on 04/18/2026

    For Sale A4654664 - 2425 GULF OF MEXICO DR #14B, LONGBOAT KEY, FL 34228 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1470
       Built: 1973   Tax: $18,495 (2024)
    Community: Sea Gate Club
    Spa: Yes

    Condo


    Estimated Monthly Payment: $10,801 (change assumption)
    Mortgage ($9,260) + Taxes in 2024 ($1,541)


    Taxes:$18,495

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 612 JUAN ANASCO DR, LONGBOAT KEY, FL 34228

    $22,500,000410 Days on yellowkey   MLS ID: A4643123

    For Sale A4643123 - 612 JUAN ANASCO DR, LONGBOAT KEY, FL 34228 94 photos

    Bed: 6   Bath: 8.0   Gar: 9
    Liv Area Sq Ft: 9243
       Built: 2024   Tax: $32,107 (2024)
    Community: Sleepy Lagoon Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $125,960 (change assumption)
    Mortgage ($123,285) + Taxes in 2024 ($2,676)


    Taxes:$32,107

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3598 FAIR OAKS LN, LONGBOAT KEY, FL 34228

    $2,795,00097 Days on yellowkey   MLS ID: A4677923

    1 Days Off yellowkey (back on 4/18/2026)

    For Sale A4677923 - 3598 FAIR OAKS LN, LONGBOAT KEY, FL 34228 43 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3417
       Built: 1996
    Monthly Fee: $833
       Tax: $15,229 (2025)
    Community: Queens Harbour
    Spa: No

    Single Family


    Estimated Monthly Payment: $17,417 (change assumption)
    Mortgage ($15,315) + Fees ($833) + Taxes in 2025 ($1,269)


    Taxes:$15,229

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4485 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228

    $760,000122 Days on yellowkey   MLS ID: A4675789

    For Sale A4675789 - 4485 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228 70 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1022
       Built: 1973
    Monthly Fee: $1,050
       Tax: $4,183 (2024)
    Community: Arbomar Apts
    Condo


    Estimated Monthly Payment: $5,563 (change assumption)
    Mortgage ($4,164) + Fees ($1,050) + Taxes in 2024 ($349)


    Taxes:$4,183

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 550 YARDARM LN, LONGBOAT KEY, FL 34228

    $3,795,000150 Days on yellowkey   MLS ID: A4672604

    For Sale A4672604 - 550 YARDARM LN, LONGBOAT KEY, FL 34228 79 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4281
       Built: 2006
    Monthly Fee: $23
       Tax: $16,615 (2024)
    Community: Country Club Shores Sec 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,202 (change assumption)
    Mortgage ($20,794) + Fees ($23) + Taxes in 2024 ($1,385)


    Taxes:$16,615

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $675,000142 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


  • 597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228

    $3,890,000426 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


  • 4420 EXETER DR #303, LONGBOAT KEY, FL 34228

    $625,00083 Days on yellowkey   MLS ID: TB8455704

    REDUCED by $24,900 (3.8%) on 04/18/2026

    For Sale TB8455704 - 4420 EXETER DR #303, LONGBOAT KEY, FL 34228 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1152
       Built: 1970
    Monthly Fee: $1,412
       Tax: $3,678 (2025)
    Community: Longboat Harbour
    Spa: No

    Condo


    Estimated Monthly Payment: $5,143 (change assumption)
    Mortgage ($3,425) + Fees ($1,412) + Taxes in 2025 ($306)


    Taxes:$3,678

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 563 SPANISH DR S, LONGBOAT KEY, FL 34228

    $615,00061 Days on yellowkey   MLS ID: A4682513

    For Sale A4682513 - 563 SPANISH DR S, LONGBOAT KEY, FL 34228 44 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1516
       Built: 1971
    Monthly Fee: $1,340
       Tax: $7,899 (2024)
    Community: Spanish Main Yacht Club Condo
    Villa


    Estimated Monthly Payment: $5,368 (change assumption)
    Mortgage ($3,370) + Fees ($1,340) + Taxes in 2024 ($658)


    Taxes:$7,899

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 569 BAYVIEW DR, LONGBOAT KEY, FL 34228

    $4,850,000255 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


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

    $799,00080 Days on yellowkey   MLS ID: A4679944

    REDUCED by $51,000 (6.0%) on 04/15/2026

    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: $4,624 (change assumption)
    Mortgage ($4,378) + 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


  • 3533 FAIR OAKS LN, LONGBOAT KEY, FL 34228

    $2,995,00096 Days on yellowkey   MLS ID: A4678167

    For Sale A4678167 - 3533 FAIR OAKS LN, LONGBOAT KEY, FL 34228 78 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3909
       Built: 1999
    Monthly Fee: $833
       Tax: $24,710 (2025)
    Community: Queens Harbour
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,303 (change assumption)
    Mortgage ($16,411) + Fees ($833) + Taxes in 2025 ($2,059)


    Taxes:$24,710

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 415 L AMBIANCE DR #B202, LONGBOAT KEY, FL 34228

    $2,150,000164 Days on yellowkey   MLS ID: A4670048

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale A4670048 - 415 L AMBIANCE DR #B202, LONGBOAT KEY, FL 34228 59 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2385
       Built: 1992   Tax: $23,948 (2025)
    Community: L Ambiance 1
    Spa: Yes

    Condo


    Estimated Monthly Payment: $13,776 (change assumption)
    Mortgage ($11,781) + Taxes in 2025 ($1,996)


    Taxes:$23,948

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228

    $1,950,00017 Days on yellowkey   MLS ID: A4688148

    For Sale A4688148 - 1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228 41 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2476
       Built: 2002   Tax: $19,319 (2025)
    Community: Bay Isles
    Spa: Yes

    Condo


    Estimated Monthly Payment: $12,295 (change assumption)
    Mortgage ($10,685) + Taxes in 2025 ($1,610)


    Taxes:$19,319

    Elementary School: Southside Elementary

    High School: Sarasota High

    Tax Year: 2025

    Middle School: Booker Middle


  • 636 TARAWITT DR, LONGBOAT KEY, FL 34228

    $799,000382 Days on yellowkey   MLS ID: TB8368182

    1 Days Off yellowkey (back on 3/19/2026)

    For Sale TB8368182 - 636 TARAWITT DR, LONGBOAT KEY, FL 34228 69 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1248
       Built: 1961   Tax: $6,715 (2024)
    Community: Longboat Key
    Single Family


    Estimated Monthly Payment: $4,938 (change assumption)
    Mortgage ($4,378) + Taxes in 2024 ($560)


    Taxes:$6,715

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.