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Homes for Sale Near Booker High in Longboat Key - 60 homes

Booker High is an High School in Sarasota County. Find homes for sale close to Booker High. Our REALTORS® can assist you in your search for Booker High, Longboat Key nearby homes.

Location: Longboat Key

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

    $389,000Listed 04/08/2026 8:34PM   MLS ID: R4911020

    For Sale R4911020 - 3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228 38 photos

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


    Estimated Monthly Payment: $2,366 (change assumption)
    Mortgage ($2,131) + Taxes in 2025 ($234)


    Taxes:$2,813

    Elementary School: None

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228

    $850,000Listed 04/08/2026 4:59PM   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


  • 706 BAYPORT WAY #706, LONGBOAT KEY, FL 34228

    $739,000Listed 04/08/2026 9:05PM   MLS ID: A4688503

    For Sale A4688503 - 706 BAYPORT WAY #706, LONGBOAT KEY, FL 34228 58 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1601
       Built: 1980
    Monthly Fee: $1,978
       Tax: $6,727 (2025)
    Community: Bayport Bch & Ten Ph C
    Condo


    Estimated Monthly Payment: $6,588 (change assumption)
    Mortgage ($4,049) + Fees ($1,978) + Taxes in 2025 ($561)


    Taxes:$6,727

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 2181 HARBOURSIDE DR #1403, LONGBOAT KEY, FL 34228

    $850,000287 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


  • 3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228

    $1,559,00034 Days on yellowkey   MLS ID: A4684840

    For Sale A4684840 - 3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228 58 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2579
       Built: 1998
    Monthly Fee: $833
       Tax: $17,916 (2025)
    Community: Bay Isles
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,868 (change assumption)
    Mortgage ($8,542) + Fees ($833) + Taxes in 2025 ($1,493)


    Taxes:$17,916

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228

    $1,200,000Listed 04/08/2026 7:32AM   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


  • 1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228

    $1,299,00056 Days on yellowkey   MLS ID: A4680710

    For Sale A4680710 - 1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228 55 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1748
       Built: 1982
    Monthly Fee: $146
       Tax: $11,598 (2025)
    Community: Fairway Bay 1
    Spa: Yes

    Townhouse


    Estimated Monthly Payment: $8,230 (change assumption)
    Mortgage ($7,118) + Fees ($146) + Taxes in 2025 ($966)


    Taxes:$11,598

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228

    $4,395,000149 Days on yellowkey   MLS ID: A4671696

    For Sale A4671696 - 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 91 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5080
       Built: 1996
    Monthly Fee: $208
       Tax: $42,201 (2024)
    Community: Bay Isles
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,806 (change assumption)
    Mortgage ($24,082) + Fees ($208) + Taxes in 2024 ($3,517)


    Taxes:$42,201

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 1005 BOGEY LN, LONGBOAT KEY, FL 34228

    $3,300,00072 Days on yellowkey   MLS ID: A4680006

    For Sale A4680006 - 1005 BOGEY LN, LONGBOAT KEY, FL 34228 69 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3624
       Built: 2017
    Monthly Fee: $21
       Tax: $19,847 (2025)
    Community: Country Club Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,757 (change assumption)
    Mortgage ($18,082) + Fees ($21) + Taxes in 2025 ($1,654)


    Taxes:$19,847

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


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

    $950,00095 Days on yellowkey   MLS ID: A4676681

    For Sale A4676681 - 100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228 34 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1492
       Built: 1966   Tax: $3,929 (2025)
    Community: Sands Point
    Condo


    Estimated Monthly Payment: $5,533 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($327)


    Taxes:$3,929

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 510 BOWSPRIT LN, LONGBOAT KEY, FL 34228

    $4,600,00013 Days on yellowkey   MLS ID: A4687207

    For Sale A4687207 - 510 BOWSPRIT LN, LONGBOAT KEY, FL 34228 80 photos

    Bed: 5   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 4389
       Built: 2013
    Monthly Fee: $21
       Tax: $35,060 (2025)
    Community: Country Club Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $28,148 (change assumption)
    Mortgage ($25,205) + Fees ($21) + Taxes in 2025 ($2,922)


    Taxes:$35,060

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 524 HALYARD LN, LONGBOAT KEY, FL 34228

    $5,495,000223 Days on yellowkey   MLS ID: A4663499

    For Sale A4663499 - 524 HALYARD LN, LONGBOAT KEY, FL 34228 91 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3737
       Built: 2025
    Monthly Fee: $21
       Tax: $17,932 (2024)
    Community: Country Club Shores Iv
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,624 (change assumption)
    Mortgage ($30,109) + Fees ($21) + Taxes in 2024 ($1,494)


    Taxes:$17,932

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Brookside Middle


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

    $425,0001 Day 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


  • 3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228

    $475,00034 Days on yellowkey   MLS ID: A4681154

    For Sale A4681154 - 3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228 45 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 740
       Built: 2026
    Monthly Fee: $290
       Tax: $2,070 (2025)
    Community: Gulfshore Of Longboat Key
    Manufactured Home


    Estimated Monthly Payment: $3,065 (change assumption)
    Mortgage ($2,603) + Fees ($290) + Taxes in 2025 ($173)


    Taxes:$2,070

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 3802 GULF OF MEXICO DR #A203, LONGBOAT KEY, FL 34228

    $399,000189 Days on yellowkey   MLS ID: A4667199

    For Sale A4667199 - 3802 GULF OF MEXICO DR #A203, LONGBOAT KEY, FL 34228 77 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1007
       Built: 1970
    Monthly Fee: $1,347
       Tax: $2,774 (2024)
    Community: Beach Harbor Club
    Condo


    Estimated Monthly Payment: $3,764 (change assumption)
    Mortgage ($2,186) + Fees ($1,347) + Taxes in 2024 ($231)


    Taxes:$2,774

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228

    $950,00044 Days on yellowkey   MLS ID: A4683180

    For Sale A4683180 - 2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228 97 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2282
       Built: 1986
    Monthly Fee: $143
       Tax: $10,215 (2025)
    Community: Harbour Oaks 2
    Villa


    Estimated Monthly Payment: $6,200 (change assumption)
    Mortgage ($5,205) + Fees ($143) + Taxes in 2025 ($851)


    Taxes:$10,215

    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

    $1,595,0003 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: 1470
       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


  • 1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228

    $1,075,000118 Days on yellowkey   MLS ID: A4674194

    For Sale A4674194 - 1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228 45 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1707
       Built: 1983   Tax: $11,336 (2025)
    Community: Players Club Iv
    Condo


    Estimated Monthly Payment: $6,835 (change assumption)
    Mortgage ($5,890) + Taxes in 2025 ($945)


    Taxes:$11,336

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 561 BIRDIE LN, LONGBOAT KEY, FL 34228

    $2,195,0007 Days on yellowkey   MLS ID: A4687002

    For Sale A4687002 - 561 BIRDIE LN, LONGBOAT KEY, FL 34228 49 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2256
       Built: 1967
    Monthly Fee: $17
       Tax: $15,946 (2025)
    Community: Country Club Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,373 (change assumption)
    Mortgage ($12,027) + Fees ($17) + Taxes in 2025 ($1,329)


    Taxes:$15,946

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


  • 2045 GULF OF MEXICO DR #M1-502, LONGBOAT KEY, FL 34228

    $469,500111 Days on yellowkey   MLS ID: A4675820

    For Sale A4675820 - 2045 GULF OF MEXICO DR #M1-502, LONGBOAT KEY, FL 34228 51 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 928
       Built: 1974   Tax: $6,201 (2025)
    Community: Seaplace Ii
    Condo


    Estimated Monthly Payment: $3,089 (change assumption)
    Mortgage ($2,573) + Taxes in 2025 ($517)


    Taxes:$6,201

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2025

    Middle School: Booker Middle


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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.