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

    $1,690,000389 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


  • 691 TARAWITT DR, LONGBOAT KEY, FL 34228

    $850,000163 Days on yellowkey   MLS ID: A4678131

    For Sale A4678131 - 691 TARAWITT DR, LONGBOAT KEY, FL 34228 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1500
       Built: 1960   Tax: $13,845 (2024)
    Community: Longboat Key
    Single Family


    Estimated Monthly Payment: $5,811 (change assumption)
    Mortgage ($4,657) + Taxes in 2024 ($1,154)


    Taxes:$13,845

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 3810 GULF OF MEXICO DR #F206, LONGBOAT KEY, FL 34228

    $325,00092 Days on yellowkey   MLS ID: A4686238

    5 Days Off yellowkey (back on 4/16/2026)

    For Sale A4686238 - 3810 GULF OF MEXICO DR #F206, LONGBOAT KEY, FL 34228 57 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1007
       Built: 1970   Tax: $3,657 (2025)
    Community: Beach Harbor Club
    Condo


    Estimated Monthly Payment: $2,086 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($305)


    Taxes:$3,657

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 726 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228

    $1,090,000113 Days on yellowkey   MLS ID: A4684733

    For Sale A4684733 - 726 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1384
       Built: 1963   Tax: $15,835 (2024)
    Community: Longboat Key
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,292 (change assumption)
    Mortgage ($5,972) + Taxes in 2024 ($1,320)


    Taxes:$15,835

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: W.D. Sugg Middle


  • 519 ROUNTREE DR, LONGBOAT KEY, FL 34228

    $6,488,00072 Days on yellowkey   MLS ID: A4690210

    For Sale A4690210 - 519 ROUNTREE DR, LONGBOAT KEY, FL 34228 88 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3554
       Built: 2025
    Monthly Fee: $250
       Tax: $9,330 (2024)
    Community: Longboat Key Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $36,577 (change assumption)
    Mortgage ($35,550) + Fees ($250) + Taxes in 2024 ($778)


    Taxes:$9,330

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2425 GULF OF MEXICO DR #8C, LONGBOAT KEY, FL 34228

    $1,550,00072 Days on yellowkey   MLS ID: A4688797

    For Sale A4688797 - 2425 GULF OF MEXICO DR #8C, LONGBOAT KEY, FL 34228 91 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1470
       Built: 1973   Tax: $17,374 (2025)
    Community: Sea Gate Club
    Condo


    Estimated Monthly Payment: $9,941 (change assumption)
    Mortgage ($8,493) + Taxes in 2025 ($1,448)


    Taxes:$17,374

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 408 GULF OF MEXICO DR #1214, LONGBOAT KEY, FL 34228

    $99,00074 Days on yellowkey   MLS ID: A4689763

    For Sale A4689763 - 408 GULF OF MEXICO DR #1214, LONGBOAT KEY, FL 34228 10 photos

    Bed:    Bath: 0.0
    Built: 2006
       Tax: $563 (2025)
    Community: Boathouse On Longboat
    Dock-Rackominium


    Estimated Monthly Payment: $589 (change assumption)
    Mortgage ($542) + Taxes in 2025 ($47)


    Taxes:$563

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1445 GULF OF MEXICO DR #501, LONGBOAT KEY, FL 34228

    $1,499,00088 Days on yellowkey   MLS ID: A4687339

    0 Days Off yellowkey (back on 4/10/2026)

    For Sale A4687339 - 1445 GULF OF MEXICO DR #501, LONGBOAT KEY, FL 34228 72 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2642
       Built: 1982   Tax: $19,801 (2025)
    Community: Players Club Iii
    Condo


    Estimated Monthly Payment: $9,864 (change assumption)
    Mortgage ($8,213) + Taxes in 2025 ($1,650)


    Taxes:$19,801

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 340 GULF OF MEXICO DR #112, LONGBOAT KEY, FL 34228

    $1,775,000240 Days on yellowkey   MLS ID: A4670120

    For Sale A4670120 - 340 GULF OF MEXICO DR #112, LONGBOAT KEY, FL 34228 50 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2298
       Built: 1991   Tax: $12,180 (2024)
    Community: Tangerine Bay Club
    Spa: Yes

    Condo


    Estimated Monthly Payment: $10,741 (change assumption)
    Mortgage ($9,726) + Taxes in 2024 ($1,015)


    Taxes:$12,180

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5970 EMERALD HARBOR DR, LONGBOAT KEY, FL 34228

    $2,795,000130 Days on yellowkey   MLS ID: A4681905

    For Sale A4681905 - 5970 EMERALD HARBOR DR, LONGBOAT KEY, FL 34228 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3098
       Built: 1977
    Monthly Fee: $63
       Tax: $12,915 (2024)
    Community: Emerald Harbor Unit 1 Rev
    Spa: No

    Single Family


    Estimated Monthly Payment: $16,454 (change assumption)
    Mortgage ($15,315) + Fees ($63) + Taxes in 2024 ($1,076)


    Taxes:$12,915

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2089 GULF OF MEXICO DR #G1-108, LONGBOAT KEY, FL 34228

    $675,000124 Days on yellowkey   MLS ID: A4683552

    REDUCED by $24,000 (3.4%) on 04/08/2026

    For Sale A4683552 - 2089 GULF OF MEXICO DR #G1-108, LONGBOAT KEY, FL 34228 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 933
       Built: 1974
    Monthly Fee: $1,250
       Tax: $6,817 (2025)
    Community: Seaplace I
    Condo


    Estimated Monthly Payment: $5,517 (change assumption)
    Mortgage ($3,699) + Fees ($1,250) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1561 GULF OF MEXICO DR #304, LONGBOAT KEY, FL 34228

    $13,000,000107 Days on yellowkey   MLS ID: A4685495

    For Sale A4685495 - 1561 GULF OF MEXICO DR #304, LONGBOAT KEY, FL 34228 69 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4891
       Built: 2024   Tax: $94,589 (2025)
    Community: St. Regis Longboat Key
    Spa: No

    Condo


    Estimated Monthly Payment: $79,114 (change assumption)
    Mortgage ($71,231) + Taxes in 2025 ($7,882)


    Taxes:$94,589

    Elementary School: Southside Elementary

    High School: Sarasota High

    Tax Year: 2025

    Middle School: Booker Middle


  • 4401 GULF OF MEXICO DR #601, LONGBOAT KEY, FL 34228

    $995,000146 Days on yellowkey   MLS ID: A4679728

    For Sale A4679728 - 4401 GULF OF MEXICO DR #601, LONGBOAT KEY, FL 34228 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1524
       Built: 1972   Tax: $14,214 (2024)
    Community: Longboat Harbour Towers
    Condo


    Estimated Monthly Payment: $6,636 (change assumption)
    Mortgage ($5,452) + Taxes in 2024 ($1,185)


    Taxes:$14,214

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 415 L AMBIANCE DR #A301, LONGBOAT KEY, FL 34228

    $6,100,00084 Days on yellowkey   MLS ID: A4688759

    For Sale A4688759 - 415 L AMBIANCE DR #A301, LONGBOAT KEY, FL 34228 70 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3380
       Built: 1992   Tax: $46,418 (2025)
    Community: L Ambiance 1
    Spa: Yes

    Condo


    Estimated Monthly Payment: $37,292 (change assumption)
    Mortgage ($33,424) + Taxes in 2025 ($3,868)


    Taxes:$46,418

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2600 HARBOURSIDE DR #L-11, LONGBOAT KEY, FL 34228

    $425,00080 Days on yellowkey   MLS ID: A4689192

    For Sale A4689192 - 2600 HARBOURSIDE DR #L-11, LONGBOAT KEY, FL 34228 19 photos

    Bed:    Bath: 0.0
    Built: 1985

    Monthly Fee: $459
       Tax: $3,077 (2025)
    Community: Bay Isles
    Dock-Rackominium


    Estimated Monthly Payment: $3,044 (change assumption)
    Mortgage ($2,329) + Fees ($459) + Taxes in 2025 ($256)


    Taxes:$3,077

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 96 TWIN SHORES BLVD, LONGBOAT KEY, FL 34228

    $425,00081 Days on yellowkey   MLS ID: A4688151

    For Sale A4688151 - 96 TWIN SHORES BLVD, LONGBOAT KEY, FL 34228 9 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 758
       Built: 2026
    Monthly Fee: $280
       Tax: $815 (2025)
    Community: Twin Shores Mobile Home
    Manufactured Home


    Estimated Monthly Payment: $2,677 (change assumption)
    Mortgage ($2,329) + Fees ($280) + Taxes in 2025 ($68)


    Taxes:$815

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 100 SANDS POINT RD #114, LONGBOAT KEY, FL 34228

    $2,100,000112 Days on yellowkey   MLS ID: A4685212

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

    For Sale A4685212 - 100 SANDS POINT RD #114, LONGBOAT KEY, FL 34228 40 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2094
       Built: 1966   Tax: $14,826 (2025)
    Community: Sands Point
    Spa: Yes

    Condo


    Estimated Monthly Payment: $12,742 (change assumption)
    Mortgage ($11,507) + Taxes in 2025 ($1,236)


    Taxes:$14,826

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3010 GRAND BAY BLVD #482, LONGBOAT KEY, FL 34228

    $1,845,000492 Days on yellowkey   MLS ID: A4640667

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

    For Sale A4640667 - 3010 GRAND BAY BLVD #482, LONGBOAT KEY, FL 34228 71 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2250
       Built: 1999   Tax: $15,440 (2024)
    Community: Grand Bay 4
    Condo


    Estimated Monthly Payment: $11,396 (change assumption)
    Mortgage ($10,109) + Taxes in 2024 ($1,287)


    Taxes:$15,440

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Pine View School


  • 2800 HARBOURSIDE DR #E-07, LONGBOAT KEY, FL 34228

    $300,00085 Days on yellowkey   MLS ID: A4688599

    For Sale A4688599 - 2800 HARBOURSIDE DR #E-07, LONGBOAT KEY, FL 34228 17 photos

    Bed:    Bath: 0.0
    Built: 1985

    Monthly Fee: $372
       Tax: $2,230 (2025)
    Community: Longboat Key Moorings Marina
    Dock-Rackominium


    Estimated Monthly Payment: $2,202 (change assumption)
    Mortgage ($1,644) + Fees ($372) + Taxes in 2025 ($186)


    Taxes:$2,230

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 2295 GULF OF MEXICO DR #64S, LONGBOAT KEY, FL 34228

    $625,000188 Days on yellowkey   MLS ID: A4675582

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

    For Sale A4675582 - 2295 GULF OF MEXICO DR #64S, LONGBOAT KEY, FL 34228 58 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1235
       Built: 1970   Tax: $6,088 (2025)
    Community: Islander Club Of Longboat
    Condo


    Estimated Monthly Payment: $3,932 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($507)


    Taxes:$6,088

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.