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Longboat Key Homes For Sale & Real Estate - 399 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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  • 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


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

    $310,0008 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


  • 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


  • 3804 GULF OF MEXICO DR #B204, LONGBOAT KEY, FL 34228

    $339,00015 Days on yellowkey   MLS ID: A4696842

    For Sale A4696842 - 3804 GULF OF MEXICO DR #B204, LONGBOAT KEY, FL 34228 28 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 761
       Built: 1970   Tax: $1,343 (2025)
    Community: Beach Harbor Club
    Condo


    Estimated Monthly Payment: $1,969 (change assumption)
    Mortgage ($1,857) + Taxes in 2025 ($112)


    Taxes:$1,343

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $549,00052 Days on yellowkey   MLS ID: A4692494

    REDUCED by $10,000 (1.8%) on 06/19/2026

    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: $3,557 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($549)


    Taxes:$6,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3040 GRAND BAY BLVD #234, LONGBOAT KEY, FL 34228

    $1,150,000191 Days on yellowkey   MLS ID: A4675109

    0 Days Off yellowkey (back on 6/19/2026)

    REDUCED by $100,000 (8.0%) on 05/06/2026

    For Sale A4675109 - 3040 GRAND BAY BLVD #234, LONGBOAT KEY, FL 34228 55 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2550
       Built: 1996   Tax: $8,854 (2024)
    Community: Grand Bay 2
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,039 (change assumption)
    Mortgage ($6,301) + Taxes in 2024 ($738)


    Taxes:$8,854

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2600 HARBOURSIDE DR #C11, LONGBOAT KEY, FL 34228

    $479,5008 Days on yellowkey   MLS ID: A4697476

    For Sale A4697476 - 2600 HARBOURSIDE DR #C11, LONGBOAT KEY, FL 34228 6 photos

    Bed:    Bath: 0.0
    Built: 1983
       Tax: $2,837 (2025)
    Community: Longboat Key Moorings
    Dock-Rackominium


    Estimated Monthly Payment: $2,864 (change assumption)
    Mortgage ($2,627) + Taxes in 2025 ($236)


    Taxes:$2,837

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 510 PUTTER LN, LONGBOAT KEY, FL 34228

    $2,875,000172 Days on yellowkey   MLS ID: A4676878

    0 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $50,000 (1.7%) on 05/13/2026

    For Sale A4676878 - 510 PUTTER LN, LONGBOAT KEY, FL 34228 74 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2253
       Built: 1968   Tax: $17,343 (2024)
    Community: Country Club Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $17,198 (change assumption)
    Mortgage ($15,753) + Taxes in 2024 ($1,445)


    Taxes:$17,343

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 3710 GULF OF MEXICO DR #E22, LONGBOAT KEY, FL 34228

    $310,0008 Days on yellowkey   MLS ID: A4697004

    For Sale A4697004 - 3710 GULF OF MEXICO DR #E22, LONGBOAT KEY, FL 34228 37 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 680
       Built: 1976
    Monthly Fee: $290
       Tax: $2,208 (2025)
    Community: Gulfshore Of Longboat Key
    Spa: No

    Mobile Home


    Estimated Monthly Payment: $2,173 (change assumption)
    Mortgage ($1,699) + Fees ($290) + Taxes in 2025 ($184)


    Taxes:$2,208

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 455 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228

    $2,095,00086 Days on yellowkey   MLS ID: A4686984

    REDUCED by $100,000 (4.6%) on 05/04/2026

    For Sale A4686984 - 455 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228 48 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2410
       Built: 1990   Tax: $18,228 (2025)
    Community: Pierre
    Spa: Yes

    Condo


    Estimated Monthly Payment: $12,998 (change assumption)
    Mortgage ($11,479) + Taxes in 2025 ($1,519)


    Taxes:$18,228

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1211 GULF OF MEXICO DR #609, LONGBOAT KEY, FL 34228

    $1,395,00015 Days on yellowkey   MLS ID: A4696671

    2 Days Off yellowkey (back on 6/15/2026)

    For Sale A4696671 - 1211 GULF OF MEXICO DR #609, LONGBOAT KEY, FL 34228 45 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1827
       Built: 1985   Tax: $14,266 (2025)
    Community: Promenade
    Spa: Yes

    Condo


    Estimated Monthly Payment: $8,832 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($1,189)


    Taxes:$14,266

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228

    $899,00041 Days on yellowkey   MLS ID: A4693834

    0 Days Off yellowkey (back on 6/18/2026)

    For Sale A4693834 - 100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228 41 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1492
       Built: 1966   Tax: $3,929 (2025)
    Community: Sands Point
    Condo


    Estimated Monthly Payment: $5,253 (change assumption)
    Mortgage ($4,926) + Taxes in 2025 ($327)


    Taxes:$3,929

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL 34228

    $1,650,00018 Days on yellowkey   MLS ID: A4696213

    1 Days Off yellowkey (back on 6/16/2026)

    For Sale A4696213 - 2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL 34228 100 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1468
       Built: 1972   Tax: $18,254 (2025)
    Community: Islands West
    Spa: Yes

    Condo


    Estimated Monthly Payment: $10,562 (change assumption)
    Mortgage ($9,041) + Taxes in 2025 ($1,521)


    Taxes:$18,254

    Elementary School: None

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 4976 GULF OF MEXICO DR #Villa 18, LONGBOAT KEY, FL 34228

    $600,000276 Days on yellowkey   MLS ID: A4665034

    REDUCED by $50,000 (7.7%) on 05/30/2026

    For Sale A4665034 - 4976 GULF OF MEXICO DR #Villa 18, LONGBOAT KEY, FL 34228 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1900
       Built: 1974   Tax: $5,878 (2024)
    Community: Windward Bay
    Spa: No

    Villa


    Estimated Monthly Payment: $3,777 (change assumption)
    Mortgage ($3,288) + Taxes in 2024 ($490)


    Taxes:$5,878

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 1914 HARBOUR LINKS CIR #10, LONGBOAT KEY, FL 34228

    $1,445,00086 Days on yellowkey   MLS ID: A4686139

    REDUCED by $50,000 (3.3%) on 05/20/2026

    For Sale A4686139 - 1914 HARBOUR LINKS CIR #10, LONGBOAT KEY, FL 34228 54 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2180
       Built: 2001   Tax: $12,540 (2025)
    Community: Emerald Pointe South
    Spa: No

    Condo


    Estimated Monthly Payment: $8,963 (change assumption)
    Mortgage ($7,918) + Taxes in 2025 ($1,045)


    Taxes:$12,540

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228

    $330,000161 Days on yellowkey   MLS ID: A4678473

    REDUCED by $20,000 (5.7%) on 06/18/2026

    For Sale A4678473 - 4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228 44 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 747
       Built: 1969
    Monthly Fee: $1,196
       Tax: $4,937 (2025)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $3,416 (change assumption)
    Mortgage ($1,808) + Fees ($1,196) + Taxes in 2025 ($411)


    Taxes:$4,937

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle




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.