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Longboat Key Homes For Sale & Real Estate - 394 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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  • 1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228

    $4,550,000270 Days on yellowkey   MLS ID: A4666688

    REDUCED by $200,000 (4.2%) on 04/29/2026

    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: $26,346 (change assumption)
    Mortgage ($24,931) + Taxes in 2024 ($1,415)


    Taxes:$16,980

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 569 JUAN ANASCO DR, LONGBOAT KEY, FL 34228

    $1,700,000245 Days on yellowkey   MLS ID: A4669634

    For Sale A4669634 - 569 JUAN ANASCO DR, LONGBOAT KEY, FL 34228 81 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2804
       Built: 1996
    Monthly Fee: $3
       Tax: $22,111 (2024)
    Community: Sleepy Lagoon Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,160 (change assumption)
    Mortgage ($9,315) + Fees ($3) + Taxes in 2024 ($1,843)


    Taxes:$22,111

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 1211 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228

    $1,000,00038 Days on yellowkey   MLS ID: A4694082

    For Sale A4694082 - 1211 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228 55 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1827
       Built: 1985   Tax: $6,388 (2025)
    Community: Promenade
    Spa: Yes

    Condo


    Estimated Monthly Payment: $6,012 (change assumption)
    Mortgage ($5,479) + Taxes in 2025 ($532)


    Taxes:$6,388

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3301 BAYOU RD, LONGBOAT KEY, FL 34228

    $1,250,00050 Days on yellowkey   MLS ID: A4692818

    For Sale A4692818 - 3301 BAYOU RD, LONGBOAT KEY, FL 34228 64 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2827
       Built: 1993
    Monthly Fee: $104
       Tax: $12,771 (2025)
    Community: Bay Isles
    Single Family


    Estimated Monthly Payment: $8,017 (change assumption)
    Mortgage ($6,849) + Fees ($104) + Taxes in 2025 ($1,064)


    Taxes:$12,771

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 660 LINLEY ST, LONGBOAT KEY, FL 34228

    $799,00010 Days on yellowkey   MLS ID: A4697248

    For Sale A4697248 - 660 LINLEY ST, LONGBOAT KEY, FL 34228 64 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1564
       Built: 1952   Tax: $4,889 (2025)
    Community: Longbeach Rev Of R P Jordans Sub
    Single Family


    Estimated Monthly Payment: $4,785 (change assumption)
    Mortgage ($4,378) + Taxes in 2025 ($407)


    Taxes:$4,889

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 842 BAYPORT WAY, LONGBOAT KEY, FL 34228

    $625,00087 Days on yellowkey   MLS ID: A4687058

    REDUCED by $50,000 (7.4%) on 06/16/2026

    For Sale A4687058 - 842 BAYPORT WAY, LONGBOAT KEY, FL 34228 54 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1260
       Built: 1983   Tax: $5,662 (2025)
    Community: Bayport Bch & Ten Ph F
    Spa: No

    Condo


    Estimated Monthly Payment: $3,896 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($472)


    Taxes:$5,662

    Elementary School: Southside Elementary

    High School: None

    Tax Year: 2025

    Middle School: Booker Middle


  • 3131 BAYOU SOUND, LONGBOAT KEY, FL 34228

    $1,650,000122 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


  • 775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228

    $2,195,000126 Days on yellowkey   MLS ID: A4683021

    For Sale A4683021 - 775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228 41 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2122
       Built: 1984   Tax: $17,930 (2025)
    Community: Beaches Of Longboat Key
    Condo


    Estimated Monthly Payment: $13,521 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($1,494)


    Taxes:$17,930

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 6489 GULFSIDE RD, LONGBOAT KEY, FL 34228

    $13,995,000161 Days on yellowkey   MLS ID: A4677413

    For Sale A4677413 - 6489 GULFSIDE RD, LONGBOAT KEY, FL 34228 75 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


  • 2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228

    $899,000119 Days on yellowkey   MLS ID: A4683112

    For Sale A4683112 - 2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228 53 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1235
       Built: 1970   Tax: $7,576 (2025)
    Community: Islander Club Of Longboat
    Condo


    Estimated Monthly Payment: $5,557 (change assumption)
    Mortgage ($4,926) + Taxes in 2025 ($631)


    Taxes:$7,576

    Elementary School: Southside Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Booker Middle


  • 775 LONGBOAT CLUB RD #807, LONGBOAT KEY, FL 34228

    $1,995,000259 Days on yellowkey   MLS ID: A4667077

    0 Days Off yellowkey (back on 6/20/2026)

    REDUCED by $300,000 (13.1%) on 06/09/2026

    For Sale A4667077 - 775 LONGBOAT CLUB RD #807, LONGBOAT KEY, FL 34228 71 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1842
       Built: 1984   Tax: $10,487 (2024)
    Community: Beaches Of Longboat Key Ph-1
    Condo


    Estimated Monthly Payment: $11,805 (change assumption)
    Mortgage ($10,931) + Taxes in 2024 ($874)


    Taxes:$10,487

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Pine View School


  • 3806 GULF OF MEXICO DR #C209, LONGBOAT KEY, FL 34228

    $335,00036 Days on yellowkey   MLS ID: A4693850

    2 Days Off yellowkey (back on 6/20/2026)

    For Sale A4693850 - 3806 GULF OF MEXICO DR #C209, LONGBOAT KEY, FL 34228 38 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1046
       Built: 1970
    Monthly Fee: $1,346
       Tax: $2,934 (2025)
    Community: Beach Harbor Club
    Condo


    Estimated Monthly Payment: $3,426 (change assumption)
    Mortgage ($1,836) + Fees ($1,346) + Taxes in 2025 ($245)


    Taxes:$2,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 605 SUTTON PL #201, LONGBOAT KEY, FL 34228

    $619,00091 Days on yellowkey   MLS ID: A4687586

    For Sale A4687586 - 605 SUTTON PL #201, LONGBOAT KEY, FL 34228 46 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1148
       Built: 1973   Tax: $6,756 (2025)
    Community: Sutton Place
    Condo


    Estimated Monthly Payment: $3,955 (change assumption)
    Mortgage ($3,392) + Taxes in 2025 ($563)


    Taxes:$6,756

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 605 SUTTON PL #102, LONGBOAT KEY, FL 34228

    $485,000141 Days on yellowkey   MLS ID: A4681310

    For Sale A4681310 - 605 SUTTON PL #102, LONGBOAT KEY, FL 34228 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 992
       Built: 1973
    Monthly Fee: $1,642
       Tax: $6,934 (2024)
    Community: Sutton Place
    Condo


    Estimated Monthly Payment: $4,877 (change assumption)
    Mortgage ($2,657) + Fees ($1,642) + Taxes in 2024 ($578)


    Taxes:$6,934

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 530 CHIPPING LN, LONGBOAT KEY, FL 34228

    $5,799,000111 Days on yellowkey   MLS ID: A4685275

    For Sale A4685275 - 530 CHIPPING LN, LONGBOAT KEY, FL 34228 49 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4216
       Built: 2026
    Monthly Fee: $21
       Tax: $16,910 (2025)
    Community: Country Club Shores Sec 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $33,205 (change assumption)
    Mortgage ($31,775) + Fees ($21) + Taxes in 2025 ($1,409)


    Taxes:$16,910

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3563 FAIR OAKS LN, LONGBOAT KEY, FL 34228

    $2,650,00027 Days on yellowkey   MLS ID: A4695291

    1 Days Off yellowkey (back on 6/20/2026)

    For Sale A4695291 - 3563 FAIR OAKS LN, LONGBOAT KEY, FL 34228 46 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3544
       Built: 1996
    Monthly Fee: $833
       Tax: $16,169 (2025)
    Community: Queens Harbour
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,701 (change assumption)
    Mortgage ($14,520) + Fees ($833) + Taxes in 2025 ($1,347)


    Taxes:$16,169

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 4234 GULF OF MEXICO DR #M1, LONGBOAT KEY, FL 34228

    $649,0007 Days on yellowkey   MLS ID: A4696419

    For Sale A4696419 - 4234 GULF OF MEXICO DR #M1, LONGBOAT KEY, FL 34228 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1150
       Built: 1973   Tax: $2,383 (2025)
    Community: Pelican Harbour & Beach Club
    Condo


    Estimated Monthly Payment: $3,755 (change assumption)
    Mortgage ($3,556) + Taxes in 2025 ($199)


    Taxes:$2,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 757 HIDEAWAY BAY DR, LONGBOAT KEY, FL 34228

    $7,488,000263 Days on yellowkey   MLS ID: A4667459

    For Sale A4667459 - 757 HIDEAWAY BAY DR, LONGBOAT KEY, FL 34228 58 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4507
       Built: 2007
    Monthly Fee: $58
       Tax: $29,603 (2024)
    Community: Hideaway Bay Sub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $43,554 (change assumption)
    Mortgage ($41,029) + Fees ($58) + Taxes in 2024 ($2,467)


    Taxes:$29,603

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1561 GULF OF MEXICO DR #403, LONGBOAT KEY, FL 34228

    $13,000,000592 Days on yellowkey   MLS ID: A4627926

    For Sale A4627926 - 1561 GULF OF MEXICO DR #403, LONGBOAT KEY, FL 34228 71 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4187
       Built: 2024   Tax: $81,320 (2025)
    Community: St. Regis Longboat Key
    Condo


    Estimated Monthly Payment: $78,008 (change assumption)
    Mortgage ($71,231) + Taxes in 2025 ($6,777)


    Taxes:$81,320

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 408 GULF OF MEXICO DR #1332, LONGBOAT KEY, FL 34228

    $69,00081 Days on yellowkey   MLS ID: A4688941

    REDUCED by $6,000 (8.0%) on 06/19/2026

    For Sale A4688941 - 408 GULF OF MEXICO DR #1332, LONGBOAT KEY, FL 34228 5 photos

    Bed:    Bath: 0.0
    Built: 2006
       Tax: $1,058 (2025)
    Community: Boathouse On Longboat
    Dock-Rackominium


    Estimated Monthly Payment: $466 (change assumption)
    Mortgage ($378) + Taxes in 2025 ($88)


    Taxes:$1,058

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for Longboat Key Homes for Sale and Other Real Estate?

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.