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Longboat Key Homes For Sale & Real Estate - 362 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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  • 815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228

    $850,0006 Days on yellowkey   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


  • 765 SAINT JUDES DR N, LONGBOAT KEY, FL 34228

    $1,499,90053 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

    $699,00095 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

    $850,000292 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

    $8,999,00039 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

    $3,980,000167 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


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

    $338,90088 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


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

    $795,0006 Days on yellowkey   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

    $1,200,0006 Days on yellowkey   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


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

    $2,950,000123 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


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

    $675,00051 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


  • 1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228

    $6,750,00035 Days on yellowkey   MLS ID: A4685503

    For Sale A4685503 - 1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228 52 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2347
       Built: 2024   Tax: $50,055 (2025)
    Community: St. Regis
    Spa: No

    Condo


    Estimated Monthly Payment: $41,157 (change assumption)
    Mortgage ($36,985) + Taxes in 2025 ($4,171)


    Taxes:$50,055

    Elementary School: Southside Elementary

    High School: Sarasota High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $13,000,00034 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


  • 1591 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228

    $3,950,00084 Days on yellowkey   MLS ID: A4679040

    3 Days Off yellowkey (back on 3/24/2026)

    For Sale A4679040 - 1591 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228 88 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2154
       Built: 2024   Tax: $34,330 (2025)
    Community: St. Regis Longboat Key
    Spa: No

    Condo


    Estimated Monthly Payment: $24,504 (change assumption)
    Mortgage ($21,643) + Taxes in 2025 ($2,861)


    Taxes:$34,330

    Elementary School: Southside Elementary

    High School: Sarasota High

    Tax Year: 2025

    Middle School: Booker Middle


  • 1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228

    $2,750,000208 Days on yellowkey   MLS ID: A4665247

    For Sale A4665247 - 1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228 69 photos

    Bed: 1   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1556
       Built: 2025   Tax: $25,560 (2025)
    Community: St. Regis Longboat Key
    Spa: No

    Condo


    Estimated Monthly Payment: $17,198 (change assumption)
    Mortgage ($15,068) + Taxes in 2025 ($2,130)


    Taxes:$25,560

    Elementary School: Southside Elementary

    High School: Sarasota High

    Tax Year: 2025

    Middle School: Booker Middle


  • 6161 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228

    $8,995,000195 Days on yellowkey   MLS ID: A4665992

    1 Days Off yellowkey (back on 4/8/2026)

    For Sale A4665992 - 6161 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 83 photos

    Bed: 4   Bath: 4.5   Gar: 5
    Liv Area Sq Ft: 4224
       Built: 1997   Tax: $77,915 (2024)
    Community: Sleepy Lagoon
    Spa: No

    Single Family


    Estimated Monthly Payment: $55,779 (change assumption)
    Mortgage ($49,286) + Taxes in 2024 ($6,493)


    Taxes:$77,915

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: W.D. Sugg Middle


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

    $2,195,00013 Days on yellowkey   MLS ID: A4686984

    For Sale A4686984 - 455 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228 50 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: $13,546 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($1,519)


    Taxes:$18,228

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7105 GULF OF MEXICO DR #21, LONGBOAT KEY, FL 34228

    $895,000211 Days on yellowkey   MLS ID: A4665082

    For Sale A4665082 - 7105 GULF OF MEXICO DR #21, LONGBOAT KEY, FL 34228 61 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1170
       Built: 1974   Tax: $10,071 (2024)
    Community: Longbeach
    Spa: No

    Condo


    Estimated Monthly Payment: $5,743 (change assumption)
    Mortgage ($4,904) + Taxes in 2024 ($839)


    Taxes:$10,071

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


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

    $995,00073 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

    $6,100,00011 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




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.