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

    $389,000Listed 04/08/2026 8:34PM   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

    $850,000Listed 04/08/2026 4:59PM   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

    $999,99963 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

    $739,000Listed 04/08/2026 9:05PM   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

    $1,499,90048 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

    $699,00090 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

    $850,000287 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


  • 3030 GRAND BAY BLVD #PH3101, LONGBOAT KEY, FL 34228

    $8,999,00034 Days on yellowkey   MLS ID: A4685052

    For Sale A4685052 - 3030 GRAND BAY BLVD #PH3101, LONGBOAT KEY, FL 34228 49 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4413
       Built: 1998   Tax: $36,728 (2025)
    Community: Grand Bay 3
    Spa: Yes

    Condo


    Estimated Monthly Payment: $52,369 (change assumption)
    Mortgage ($49,308) + Taxes in 2025 ($3,061)


    Taxes:$36,728

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3488 MISTLETOE LN, LONGBOAT KEY, FL 34228

    $3,980,000162 Days on yellowkey   MLS ID: A4670010

    For Sale A4670010 - 3488 MISTLETOE LN, LONGBOAT KEY, FL 34228 82 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3341
       Built: 1989
    Monthly Fee: $1,083
       Tax: $25,296 (2025)
    Community: Coreys Landing
    Spa: No

    Single Family


    Estimated Monthly Payment: $24,999 (change assumption)
    Mortgage ($21,808) + Fees ($1,083) + Taxes in 2025 ($2,108)


    Taxes:$25,296

    Elementary School: Southside Elementary

    High School: Sarasota High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $1,950,0007 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


  • 450 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228

    $650,000187 Days on yellowkey   MLS ID: A4667364

    For Sale A4667364 - 450 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1474
       Built: 1970   Tax: $6,830 (2024)
    Community: Bay Harbour Apts
    Condo


    Estimated Monthly Payment: $4,131 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($569)


    Taxes:$6,830

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4360 CHATHAM DR #305, LONGBOAT KEY, FL 34228

    $338,90083 Days on yellowkey   MLS ID: A4678390

    For Sale A4678390 - 4360 CHATHAM DR #305, LONGBOAT KEY, FL 34228 69 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 747
       Built: 1969   Tax: $4,654 (2024)
    Community: Longboat Harbour
    Spa: No

    Condo


    Estimated Monthly Payment: $2,245 (change assumption)
    Mortgage ($1,857) + Taxes in 2024 ($388)


    Taxes:$4,654

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228

    $1,559,00034 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


  • 6701 GULF OF MEXICO DR #332, LONGBOAT KEY, FL 34228

    $795,000Listed 04/08/2026 2:09PM   MLS ID: A4689175

    For Sale A4689175 - 6701 GULF OF MEXICO DR #332, LONGBOAT KEY, FL 34228 30 photos

    Bed: 1   Bath: 2.0
    Liv Area Sq Ft: 990
       Built: 1971   Tax: $3,403 (2025)
    Community: Whitney Beach Iii
    Condo


    Estimated Monthly Payment: $4,640 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($284)


    Taxes:$3,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228

    $1,200,000Listed 04/08/2026 7:32AM   MLS ID: A4689076

    For Sale A4689076 - 1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228 67 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1192
       Built: 1982   Tax: $9,436 (2024)
    Community: Fairway Bay 1
    Condo


    Estimated Monthly Payment: $7,362 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($786)


    Taxes:$9,436

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


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

    $505,000136 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


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

    $595,000106 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


  • 1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228

    $1,299,00056 Days on yellowkey   MLS ID: A4680710

    For Sale A4680710 - 1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228 55 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1748
       Built: 1982
    Monthly Fee: $146
       Tax: $11,598 (2025)
    Community: Fairway Bay 1
    Spa: Yes

    Townhouse


    Estimated Monthly Payment: $8,230 (change assumption)
    Mortgage ($7,118) + Fees ($146) + Taxes in 2025 ($966)


    Taxes:$11,598

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228

    $4,395,000149 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


  • 4561 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228

    $2,950,000118 Days on yellowkey   MLS ID: A4674911

    For Sale A4674911 - 4561 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228 71 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3260
       Built: 1999   Tax: $29,736 (2024)
    Community: The Grande At Longboat Key
    Spa: Yes

    Condo


    Estimated Monthly Payment: $18,642 (change assumption)
    Mortgage ($16,164) + Taxes in 2024 ($2,478)


    Taxes:$29,736

    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.