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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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  • 1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228

    $2,125,00024 Days on yellowkey   MLS ID: A4694983

    For Sale A4694983 - 1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228 70 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2100
       Built: 1985   Tax: $17,857 (2025)
    Community: Promenade
    Spa: Yes

    Condo


    Estimated Monthly Payment: $13,132 (change assumption)
    Mortgage ($11,644) + Taxes in 2025 ($1,488)


    Taxes:$17,857

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 1115 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228

    $899,000225 Days on yellowkey   MLS ID: A4671664

    For Sale A4671664 - 1115 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228 60 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1172
       Built: 1979   Tax: $7,815 (2024)
    Community: Beachplace I
    Spa: Yes

    Condo


    Estimated Monthly Payment: $5,577 (change assumption)
    Mortgage ($4,926) + Taxes in 2024 ($651)


    Taxes:$7,815

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3240 GULF OF MEXICO DR #B104, LONGBOAT KEY, FL 34228

    $450,00077 Days on yellowkey   MLS ID: A4688243

    REDUCED by $25,000 (5.3%) on 06/05/2026

    For Sale A4688243 - 3240 GULF OF MEXICO DR #B104, LONGBOAT KEY, FL 34228 58 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1260
       Built: 1975   Tax: $4,538 (2025)
    Community: Portobello
    Condo


    Estimated Monthly Payment: $2,844 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($378)


    Taxes:$4,538

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $320,000161 Days on yellowkey   MLS ID: A4678390

    0 Days Off yellowkey (back on 6/5/2026)

    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


  • 5320 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228

    $999,00045 Days on yellowkey   MLS ID: A4693334

    For Sale A4693334 - 5320 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1323
       Built: 1981   Tax: $3,942 (2025)
    Community: Longboat Landing
    Spa: No

    Condo


    Estimated Monthly Payment: $5,802 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($329)


    Taxes:$3,942

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2301 GULF OF MEXICO DR #11N, LONGBOAT KEY, FL 34228

    $1,225,27723 Days on yellowkey   MLS ID: A4695843

    For Sale A4695843 - 2301 GULF OF MEXICO DR #11N, LONGBOAT KEY, FL 34228 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1235
       Built: 1970   Tax: $4,043 (2025)
    Community: Islander Club Of Longboat
    Condo


    Estimated Monthly Payment: $7,051 (change assumption)
    Mortgage ($6,714) + Taxes in 2025 ($337)


    Taxes:$4,043

    Elementary School: None

    High School: Pine View School

    Tax Year: 2025

    Middle School: None


  • 548 HORNBLOWER LN, LONGBOAT KEY, FL 34228

    $4,950,000255 Days on yellowkey   MLS ID: A4668463

    1 Days Off yellowkey (back on 6/5/2026)

    For Sale A4668463 - 548 HORNBLOWER LN, LONGBOAT KEY, FL 34228 98 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3976
       Built: 2015
    Monthly Fee: $8
       Tax: $47,046 (2024)
    Community: Country Club Shores Sec 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,051 (change assumption)
    Mortgage ($27,123) + Fees ($8) + Taxes in 2024 ($3,920)


    Taxes:$47,046

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 5125 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228

    $725,000459 Days on yellowkey   MLS ID: A4645905

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

    For Sale A4645905 - 5125 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228 54 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 961
       Built: 1983   Tax: $3,448 (2025)
    Community: Seagrape Inn
    Condo


    Estimated Monthly Payment: $4,260 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($287)


    Taxes:$3,448

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 225 SANDS POINT RD #6201, LONGBOAT KEY, FL 34228

    $675,000178 Days on yellowkey   MLS ID: A4676042

    REDUCED by $115,000 (14.6%) on 06/04/2026

    For Sale A4676042 - 225 SANDS POINT RD #6201, LONGBOAT KEY, FL 34228 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 642
       Built: 1983   Tax: $7,304 (2025)
    Community: Inn On The Beach Ph Iii
    Condo


    Estimated Monthly Payment: $4,307 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($609)


    Taxes:$7,304

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 225 SANDS POINT RD #7205, LONGBOAT KEY, FL 34228

    $675,000178 Days on yellowkey   MLS ID: A4676041

    REDUCED by $24,000 (3.4%) on 06/04/2026

    For Sale A4676041 - 225 SANDS POINT RD #7205, LONGBOAT KEY, FL 34228 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 642
       Built: 1983   Tax: $7,183 (2025)
    Community: Inn On The Beach Ph Iii
    Spa: Yes

    Condo


    Estimated Monthly Payment: $4,297 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($599)


    Taxes:$7,183

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3060 GRAND BAY BLVD #155, LONGBOAT KEY, FL 34228

    $1,145,00094 Days on yellowkey   MLS ID: A4685023

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

    REDUCED by $50,000 (4.2%) on 05/11/2026

    For Sale A4685023 - 3060 GRAND BAY BLVD #155, LONGBOAT KEY, FL 34228 67 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2250
       Built: 1994   Tax: $14,345 (2025)
    Community: Grand Bay 1
    Spa: Yes

    Condo


    Estimated Monthly Payment: $7,469 (change assumption)
    Mortgage ($6,274) + Taxes in 2025 ($1,195)


    Taxes:$14,345

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 250 SANDS POINT RD #5203, LONGBOAT KEY, FL 34228

    $899,900147 Days on yellowkey   MLS ID: A4680085

    For Sale A4680085 - 250 SANDS POINT RD #5203, LONGBOAT KEY, FL 34228 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 640
       Built: 1982   Tax: $8,720 (2025)
    Community: Inn On The Beach Ph Ii
    Spa: No

    Condo


    Estimated Monthly Payment: $5,658 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($727)


    Taxes:$8,720

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 4420 EXETER DR #303, LONGBOAT KEY, FL 34228

    $599,000151 Days on yellowkey   MLS ID: TB8455704

    REDUCED by $26,000 (4.2%) on 05/13/2026

    For Sale TB8455704 - 4420 EXETER DR #303, LONGBOAT KEY, FL 34228 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1152
       Built: 1970
    Monthly Fee: $1,412
       Tax: $3,678 (2025)
    Community: Longboat Harbour
    Spa: No

    Condo


    Estimated Monthly Payment: $5,001 (change assumption)
    Mortgage ($3,282) + Fees ($1,412) + Taxes in 2025 ($306)


    Taxes:$3,678

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 741 OLD COMPASS RD, LONGBOAT KEY, FL 34228

    $1,795,000112 Days on yellowkey   MLS ID: A4684578

    REDUCED by $100,000 (5.3%) on 06/04/2026

    For Sale A4684578 - 741 OLD COMPASS RD, LONGBOAT KEY, FL 34228 51 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2173
       Built: 1969
    Monthly Fee: $63
       Tax: $11,776 (2024)
    Community: Emerald Harbor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,880 (change assumption)
    Mortgage ($9,835) + Fees ($63) + Taxes in 2024 ($981)


    Taxes:$11,776

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: W.D. Sugg Middle


  • 2301 GULF OF MEXICO DR #33N, LONGBOAT KEY, FL 34228

    $1,199,00023 Days on yellowkey   MLS ID: A4695318

    For Sale A4695318 - 2301 GULF OF MEXICO DR #33N, LONGBOAT KEY, FL 34228 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1235
       Built: 1970   Tax: $9,383 (2025)
    Community: Islander Club Of Longboat
    Spa: No

    Condo


    Estimated Monthly Payment: $7,352 (change assumption)
    Mortgage ($6,570) + Taxes in 2025 ($782)


    Taxes:$9,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6322 LAGUNA DR #1, LONGBOAT KEY, FL 34228

    $2,499,900245 Days on yellowkey   MLS ID: A4669170

    For Sale A4669170 - 6322 LAGUNA DR #1, LONGBOAT KEY, FL 34228 70 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2886
       Built: 2001   Tax: $12,100 (2024)
    Community: Laguna Yacht Village A Condo
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,706 (change assumption)
    Mortgage ($13,698) + Taxes in 2024 ($1,008)


    Taxes:$12,100

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL 34228

    $1,225,27723 Days on yellowkey   MLS ID: A4695851

    For Sale A4695851 - 2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL 34228 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1235
       Built: 1970   Tax: $9,496 (2025)
    Community: Islander Club Of Longboat
    Spa: No

    Condo


    Estimated Monthly Payment: $7,505 (change assumption)
    Mortgage ($6,714) + Taxes in 2025 ($791)


    Taxes:$9,496

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $529,000172 Days on yellowkey   MLS ID: A4676925

    REDUCED by $1,000 (0.2%) on 06/03/2026

    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: $3,402 (change assumption)
    Mortgage ($2,899) + 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


  • 2110 HARBOURSIDE DR #523, LONGBOAT KEY, FL 34228

    $659,000121 Days on yellowkey   MLS ID: A4682869

    REDUCED by $40,000 (5.7%) on 06/03/2026

    For Sale A4682869 - 2110 HARBOURSIDE DR #523, LONGBOAT KEY, FL 34228 69 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2031
       Built: 1988   Tax: $5,680 (2025)
    Community: Fairway Bay
    Spa: No

    Condo


    Estimated Monthly Payment: $4,084 (change assumption)
    Mortgage ($3,611) + Taxes in 2025 ($473)


    Taxes:$5,680

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1045 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228

    $950,00034 Days on yellowkey   MLS ID: A4694202

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

    For Sale A4694202 - 1045 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228 68 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1172
       Built: 1981   Tax: $12,005 (2025)
    Community: Beachplace Iii
    Spa: Yes

    Condo


    Estimated Monthly Payment: $6,206 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($1,000)


    Taxes:$12,005

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle




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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.