REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Longboat Key Homes For Sale & Real Estate - 418 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

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

    $1,000,00010 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


  • 3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228

    $4,999,0003 Days on yellowkey   MLS ID: A4694394

    For Sale A4694394 - 3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228 83 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3842
       Built: 2000
    Monthly Fee: $833
       Tax: $29,486 (2025)
    Community: Queens Harbor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $30,681 (change assumption)
    Mortgage ($27,391) + Fees ($833) + Taxes in 2025 ($2,457)


    Taxes:$29,486

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 311 FIREHOUSE CT, LONGBOAT KEY, FL 34228

    $2,399,000248 Days on yellowkey   MLS ID: A4665445

    For Sale A4665445 - 311 FIREHOUSE CT, LONGBOAT KEY, FL 34228 100 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2352
       Built: 2005
    Monthly Fee: $467
       Tax: $29,195 (2025)
    Community: Conrad Beach
    Single Family


    Estimated Monthly Payment: $16,045 (change assumption)
    Mortgage ($13,145) + Fees ($467) + Taxes in 2025 ($2,433)


    Taxes:$29,195

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 2185 GULF OF MEXICO DR #212, LONGBOAT KEY, FL 34228

    $1,995,000Listed 05/29/2026 10:51AM   MLS ID: A4694656

    For Sale A4694656 - 2185 GULF OF MEXICO DR #212, LONGBOAT KEY, FL 34228 54 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2448
       Built: 1996   Tax: $15,129 (2025)
    Community: Villa Di Lancia Ph 1
    Spa: No

    Condo


    Estimated Monthly Payment: $12,192 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($1,261)


    Taxes:$15,129

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228

    $389,00051 Days on yellowkey   MLS ID: R4911020

    For Sale R4911020 - 3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228 77 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1046
       Built: 1970
    Monthly Fee: $1,457
       Tax: $2,813 (2025)
    Community: Beach Harbor Club
    Condo


    Estimated Monthly Payment: $3,823 (change assumption)
    Mortgage ($2,131) + Fees ($1,457) + Taxes in 2025 ($234)


    Taxes:$2,813

    Elementary School: None

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 3427 WINDING OAKS DR #14, LONGBOAT KEY, FL 34228

    $1,150,00067 Days on yellowkey   MLS ID: A4686623

    For Sale A4686623 - 3427 WINDING OAKS DR #14, LONGBOAT KEY, FL 34228 49 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2555
       Built: 1988   Tax: $13,850 (2025)
    Community: Winding Oaks
    Spa: No

    Condo


    Estimated Monthly Payment: $7,455 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($1,154)


    Taxes:$13,850

    Elementary School: Southside Elementary

    High School: None

    Tax Year: 2025

    Middle School: None


  • 552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228

    $999,999113 Days on yellowkey   MLS ID: A4680786

    For Sale A4680786 - 552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 46 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 1960   Tax: $17,419 (2024)
    Community: Sleepy Lagoon Park
    Single Family


    Estimated Monthly Payment: $6,931 (change assumption)
    Mortgage ($5,479) + Taxes in 2024 ($1,452)


    Taxes:$17,419

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 548 GUNWALE LN, LONGBOAT KEY, FL 34228

    $2,200,000116 Days on yellowkey   MLS ID: A4680965

    For Sale A4680965 - 548 GUNWALE LN, LONGBOAT KEY, FL 34228 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 1967
    Monthly Fee: $17
       Tax: $9,801 (2025)
    Community: Country Club Shores Sec 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,888 (change assumption)
    Mortgage ($12,054) + Fees ($17) + Taxes in 2025 ($817)


    Taxes:$9,801

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $320,000133 Days on yellowkey   MLS ID: A4678390

    REDUCED by $18,900 (5.6%) on 05/29/2026

    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: $2,141 (change assumption)
    Mortgage ($1,753) + Taxes in 2024 ($388)


    Taxes:$4,654

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228

    $530,000144 Days on yellowkey   MLS ID: A4676925

    For Sale A4676925 - 4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228 60 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1969   Tax: $6,041 (2024)
    Community: Longboat Harbour
    Condo


    Estimated Monthly Payment: $3,407 (change assumption)
    Mortgage ($2,904) + Taxes in 2024 ($503)


    Taxes:$6,041

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 4370 CHATHAM DR #104, LONGBOAT KEY, FL 34228

    $470,000175 Days on yellowkey   MLS ID: A4674307

    For Sale A4674307 - 4370 CHATHAM DR #104, LONGBOAT KEY, FL 34228 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1969   Tax: $5,334 (2024)
    Community: Longboat Harbour
    Spa: No

    Condo


    Estimated Monthly Payment: $3,020 (change assumption)
    Mortgage ($2,575) + Taxes in 2024 ($445)


    Taxes:$5,334

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 595 BOWSPRIT LN, LONGBOAT KEY, FL 34228

    $3,140,000224 Days on yellowkey   MLS ID: A4668868

    REDUCED by $35,000 (1.1%) on 05/29/2026

    For Sale A4668868 - 595 BOWSPRIT LN, LONGBOAT KEY, FL 34228 49 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2550
       Built: 1966
    Monthly Fee: $21
       Tax: $26,814 (2025)
    Community: Country Club Shores
    Single Family


    Estimated Monthly Payment: $19,461 (change assumption)
    Mortgage ($17,205) + Fees ($21) + Taxes in 2025 ($2,235)


    Taxes:$26,814

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 2109 GULF OF MEXICO DR #1303, LONGBOAT KEY, FL 34228

    $1,049,000137 Days on yellowkey   MLS ID: A4677817

    REDUCED by $26,000 (2.4%) on 05/11/2026

    For Sale A4677817 - 2109 GULF OF MEXICO DR #1303, LONGBOAT KEY, FL 34228 44 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1463
       Built: 1984   Tax: $9,654 (2025)
    Community: Sunset Beach
    Spa: Yes

    Condo


    Estimated Monthly Payment: $6,552 (change assumption)
    Mortgage ($5,748) + Taxes in 2025 ($805)


    Taxes:$9,654

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 761 NORTON ST, LONGBOAT KEY, FL 34228

    $4,390,000127 Days on yellowkey   MLS ID: A4677200

    For Sale A4677200 - 761 NORTON ST, LONGBOAT KEY, FL 34228 66 photos

    Bed: 4   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4674
       Built: 2004   Tax: $14,281 (2024)
    Community: Sleepy Lagoon Park 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $25,244 (change assumption)
    Mortgage ($24,054) + Taxes in 2024 ($1,190)


    Taxes:$14,281

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 6381 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228

    $5,995,000127 Days on yellowkey   MLS ID: A4678978

    For Sale A4678978 - 6381 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 60 photos

    Bed: 4   Bath: 5.0   Gar: 9
    Liv Area Sq Ft: 4224
       Built: 2021   Tax: $94,565 (2025)
    Community: Sleepy Lagoon
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $40,729 (change assumption)
    Mortgage ($32,848) + Taxes in 2025 ($7,880)


    Taxes:$94,565

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6664 & 6660 & 6670 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228

    $18,500,0008 Days on yellowkey   MLS ID: A4694502

    For Sale A4694502 - 6664 & 6660 & 6670 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 23 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 10298
       Built: 1955   Tax: $34,371 (2025)
    Community: Robert Lennox
    Single Family


    Estimated Monthly Payment: $104,232 (change assumption)
    Mortgage ($101,367) + Taxes in 2025 ($2,864)


    Taxes:$34,371

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 3804 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228

    $389,00064 Days on yellowkey   MLS ID: TB8490120

    1 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $8,000 (2.0%) on 05/24/2026

    For Sale TB8490120 - 3804 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1133
       Built: 1970   Tax: $3,764 (2025)
    Community: Beach Harbor Club
    Condo


    Estimated Monthly Payment: $2,445 (change assumption)
    Mortgage ($2,131) + Taxes in 2025 ($314)


    Taxes:$3,764

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2945 PYRULA DR, LONGBOAT KEY, FL 34228

    $3,125,00014 Days on yellowkey   MLS ID: O6408404

    For Sale O6408404 - 2945 PYRULA DR, LONGBOAT KEY, FL 34228 50 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3815
       Built: 2024   Tax: $36,325 (2025)
    Community: Coquina Beach
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,150 (change assumption)
    Mortgage ($17,123) + Taxes in 2025 ($3,027)


    Taxes:$36,325

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 500 HALYARD LN, LONGBOAT KEY, FL 34228

    $2,149,00080 Days on yellowkey   MLS ID: A4683571

    REDUCED by $50,000 (2.3%) on 05/04/2026

    For Sale A4683571 - 500 HALYARD LN, LONGBOAT KEY, FL 34228 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2311
       Built: 1967
    Monthly Fee: $21
       Tax: $23,973 (2025)
    Community: Country Club Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,794 (change assumption)
    Mortgage ($11,775) + Fees ($21) + Taxes in 2025 ($1,998)


    Taxes:$23,973

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 545 SANCTUARY DR #B506, LONGBOAT KEY, FL 34228

    $1,828,000161 Days on yellowkey   MLS ID: A4675800

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale A4675800 - 545 SANCTUARY DR #B506, LONGBOAT KEY, FL 34228 55 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2375
       Built: 1991   Tax: $19,482 (2025)
    Community: Sanctuary Iii
    Condo


    Estimated Monthly Payment: $11,640 (change assumption)
    Mortgage ($10,016) + Taxes in 2025 ($1,624)


    Taxes:$19,482

    Elementary School: Southside Elementary

    High School: Riverview High

    Tax Year: 2025

    Middle School: Booker 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.