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Longboat Key Homes For Sale & Real Estate - 366 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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  • 3435 WINDING OAKS DR #18, LONGBOAT KEY, FL 34228

    $949,000161 Days on yellowkey   MLS ID: A4680403

    REDUCED by $101,000 (9.6%) on 05/20/2026

    For Sale A4680403 - 3435 WINDING OAKS DR #18, LONGBOAT KEY, FL 34228 83 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2555
       Built: 1988   Tax: $8,565 (2025)
    Community: Winding Oaks
    Spa: No

    Condo


    Estimated Monthly Payment: $5,914 (change assumption)
    Mortgage ($5,200) + Taxes in 2025 ($714)


    Taxes:$8,565

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $6,600,000126 Days on yellowkey   MLS ID: A4685503

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

    REDUCED by $150,000 (2.2%) on 04/30/2026

    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: $40,335 (change assumption)
    Mortgage ($36,163) + Taxes in 2025 ($4,171)


    Taxes:$50,055

    Elementary School: Southside Elementary

    High School: Sarasota High

    Tax Year: 2025

    Middle School: Booker Middle


  • 541 SPANISH DR N, LONGBOAT KEY, FL 34228

    $349,00095 Days on yellowkey   MLS ID: TB8496387

    For Sale TB8496387 - 541 SPANISH DR N, LONGBOAT KEY, FL 34228 40 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1100
       Built: 1968   Tax: $871 (2025)
    Community: Spanish Main Yacht Club Condo
    Villa


    Estimated Monthly Payment: $1,985 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($73)


    Taxes:$871

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 408 GULF OF MEXICO DR #2112, LONGBOAT KEY, FL 34228

    $39,50043 Days on yellowkey   MLS ID: A4695317

    For Sale A4695317 - 408 GULF OF MEXICO DR #2112, LONGBOAT KEY, FL 34228 5 photos

    Bed:    Bath: 0.0    Tax: $381 (2024)
    Community: Boathouse On Longboat
    Dock-Rackominium


    Estimated Monthly Payment: $248 (change assumption)
    Mortgage ($216) + Taxes in 2024 ($32)


    Taxes:$381

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1050 LONGBOAT CLUB RD #901, LONGBOAT KEY, FL 34228

    $1,400,00052 Days on yellowkey   MLS ID: A4694717

    For Sale A4694717 - 1050 LONGBOAT CLUB RD #901, LONGBOAT KEY, FL 34228 37 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1409
       Built: 1974   Tax: $12,907 (2025)
    Community: Privateer North
    Spa: Yes

    Condo


    Estimated Monthly Payment: $8,747 (change assumption)
    Mortgage ($7,671) + Taxes in 2025 ($1,076)


    Taxes:$12,907

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3481 BAYOU SOUND, LONGBOAT KEY, FL 34228

    $1,950,000112 Days on yellowkey   MLS ID: A4687106

    REDUCED by $450,000 (18.8%) on 05/27/2026

    For Sale A4687106 - 3481 BAYOU SOUND, LONGBOAT KEY, FL 34228 79 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3391
       Built: 1986
    Monthly Fee: $104
       Tax: $21,359 (2025)
    Community: Bay Isles
    Single Family


    Estimated Monthly Payment: $12,569 (change assumption)
    Mortgage ($10,685) + Fees ($104) + Taxes in 2025 ($1,780)


    Taxes:$21,359

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1065 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228

    $749,000662 Days on yellowkey   MLS ID: A4624142

    INCREASED by $130,000 (21.0%) on 06/01/2026

    For Sale A4624142 - 1065 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228 13 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1392
       Built: 1981   Tax: $4,571 (2023)
    Community: Beachplace Iii
    Condo


    Estimated Monthly Payment: $4,485 (change assumption)
    Mortgage ($4,104) + Taxes in 2023 ($381)


    Taxes:$4,571

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 435 L AMBIANCE DR #L707, LONGBOAT KEY, FL 34228

    $2,890,000312 Days on yellowkey   MLS ID: A4663998

    For Sale A4663998 - 435 L AMBIANCE DR #L707, LONGBOAT KEY, FL 34228 67 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2525
       Built: 1994   Tax: $32,005 (2025)
    Community: L Ambiance At Longboat Key Club Ph 02
    Condo


    Estimated Monthly Payment: $18,502 (change assumption)
    Mortgage ($15,835) + Taxes in 2025 ($2,667)


    Taxes:$32,005

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 536 KETCH LN, LONGBOAT KEY, FL 34228

    $2,599,000118 Days on yellowkey   MLS ID: A4686553

    REDUCED by $96,000 (3.6%) on 04/25/2026

    For Sale A4686553 - 536 KETCH LN, LONGBOAT KEY, FL 34228 80 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2960
       Built: 2012
    Monthly Fee: $10
       Tax: $13,360 (2025)
    Community: Country Club Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $15,364 (change assumption)
    Mortgage ($14,241) + Fees ($10) + Taxes in 2025 ($1,113)


    Taxes:$13,360

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228

    $649,900173 Days on yellowkey   MLS ID: A4679160

    0 Days Off yellowkey (back on 5/30/2026)

    REDUCED by $10,000 (1.5%) on 04/01/2026

    For Sale A4679160 - 4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228 75 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1523
       Built: 1975   Tax: $7,738 (2025)
    Community: Windward Bay Amd
    Condo


    Estimated Monthly Payment: $4,206 (change assumption)
    Mortgage ($3,561) + Taxes in 2025 ($645)


    Taxes:$7,738

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 4390 EXETER DR #206, LONGBOAT KEY, FL 34228

    $529,000257 Days on yellowkey   MLS ID: A4670032

    0 Days Off yellowkey (back on 5/30/2026)

    For Sale A4670032 - 4390 EXETER DR #206, LONGBOAT KEY, FL 34228 53 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1152
       Built: 1970   Tax: $7,775 (2024)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $3,546 (change assumption)
    Mortgage ($2,899) + Taxes in 2024 ($648)


    Taxes:$7,775

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4440 EXETER DR #106, LONGBOAT KEY, FL 34228

    $649,000137 Days on yellowkey   MLS ID: D6146366

    For Sale D6146366 - 4440 EXETER DR #106, LONGBOAT KEY, FL 34228 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1376
       Built: 1970   Tax: $9,714 (2024)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $4,366 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($810)


    Taxes:$9,714

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1055 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228

    $1,299,000308 Days on yellowkey   MLS ID: A4663883

    For Sale A4663883 - 1055 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228 35 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1503
       Built: 1981   Tax: $14,051 (2024)
    Community: Beachplace Iii
    Spa: Yes

    Condo


    Estimated Monthly Payment: $8,289 (change assumption)
    Mortgage ($7,118) + Taxes in 2024 ($1,171)


    Taxes:$14,051

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6330 LAGUNA DR, LONGBOAT KEY, FL 34228

    $1,999,979238 Days on yellowkey   MLS ID: A4672554

    REDUCED by $10 (0.0%) on 05/28/2026

    For Sale A4672554 - 6330 LAGUNA DR, LONGBOAT KEY, FL 34228 62 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2856
       Built: 2002
    Monthly Fee: $542
       Tax: $18,656 (2023)
    Community: Laguna Yacht Village
    Single Family


    Estimated Monthly Payment: $13,055 (change assumption)
    Mortgage ($10,959) + Fees ($542) + Taxes in 2023 ($1,555)


    Taxes:$18,656

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 1926 HARBOURSIDE DR #1302, LONGBOAT KEY, FL 34228

    $769,000315 Days on yellowkey   MLS ID: TB8422578

    REDUCED by $20,000 (2.5%) on 05/27/2026

    For Sale TB8422578 - 1926 HARBOURSIDE DR #1302, LONGBOAT KEY, FL 34228 31 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2606
       Built: 1982
    Monthly Fee: $1,832
       Tax: $8,181 (2024)
    Community: Fairway Bay 1
    Spa: No

    Townhouse


    Estimated Monthly Payment: $6,727 (change assumption)
    Mortgage ($4,214) + Fees ($1,832) + Taxes in 2024 ($682)


    Taxes:$8,181

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1211 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228

    $1,648,00049 Days on yellowkey   MLS ID: A4694733

    For Sale A4694733 - 1211 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228 53 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1598
       Built: 1985   Tax: $9,234 (2025)
    Community: Promenade
    Condo


    Estimated Monthly Payment: $9,799 (change assumption)
    Mortgage ($9,030) + Taxes in 2025 ($770)


    Taxes:$9,234

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228

    $1,595,00099 Days on yellowkey   MLS ID: A4688987

    For Sale A4688987 - 2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228 44 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1513
       Built: 1973   Tax: $9,602 (2025)
    Community: Sea Gate Club
    Spa: No

    Condo


    Estimated Monthly Payment: $9,540 (change assumption)
    Mortgage ($8,740) + Taxes in 2025 ($800)


    Taxes:$9,602

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228

    $3,699,999263 Days on yellowkey   MLS ID: A4669533

    REDUCED by $100,000 (2.6%) on 05/26/2026

    For Sale A4669533 - 2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1173
       Built: 1955   Tax: $36,688 (2024)
    Community: Coquina Beach
    Spa: No

    Single Family


    Estimated Monthly Payment: $23,331 (change assumption)
    Mortgage ($20,273) + Taxes in 2024 ($3,057)


    Taxes:$36,688

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


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

    $2,750,000299 Days on yellowkey   MLS ID: A4665247

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

    Bed: 1   Bath: 1.5   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


  • 3060 GRAND BAY BLVD #195, LONGBOAT KEY, FL 34228

    $1,595,000182 Days on yellowkey   MLS ID: A4677880

    5 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $100,000 (5.9%) on 05/11/2026

    For Sale A4677880 - 3060 GRAND BAY BLVD #195, LONGBOAT KEY, FL 34228 49 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1994   Tax: $10,399 (2025)
    Community: Grand Bay 1
    Spa: Yes

    Condo


    Estimated Monthly Payment: $9,606 (change assumption)
    Mortgage ($8,740) + Taxes in 2025 ($867)


    Taxes:$10,399

    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.