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Displaying: For Sale

Location: Longboat Key

Property Type(s): Single Family

Living Area Square Feet: 3500+

Longboat Key - 40 properties found

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  • 569 BAYVIEW DR, LONGBOAT KEY, FL 34228

    $4,695,000270 Days on yellowkey   MLS ID: A4661312

    REDUCED by $155,000 (3.2%) on 05/01/2026

    For Sale A4661312 - 569 BAYVIEW DR, LONGBOAT KEY, FL 34228 89 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4106
       Built: 2025   Tax: $12,064 (2024)
    Community: Bayview Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,731 (change assumption)
    Mortgage ($25,725) + Taxes in 2024 ($1,005)


    Taxes:$12,064

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 510 BOWSPRIT LN, LONGBOAT KEY, FL 34228

    $4,400,00038 Days on yellowkey   MLS ID: A4687207

    REDUCED by $200,000 (4.3%) on 04/13/2026

    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: $27,052 (change assumption)
    Mortgage ($24,109) + 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


  • 597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228

    $3,890,000441 Days on yellowkey   MLS ID: A4640902

    For Sale A4640902 - 597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228 92 photos

    Bed: 5   Bath: 6.0   Gar: 5
    Liv Area Sq Ft: 4176
       Built: 2025   Tax: $7,998 (2024)
    Community: Buttonwood Harbor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,981 (change assumption)
    Mortgage ($21,315) + Taxes in 2024 ($666)


    Taxes:$7,998

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228

    $4,695,000195 Days on yellowkey   MLS ID: A4669195

    REDUCED by $100,000 (2.1%) on 04/22/2026

    For Sale A4669195 - 530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228 100 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4106
       Built: 2025   Tax: $12,064 (2024)
    Community: Sleepy Lagoon Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,731 (change assumption)
    Mortgage ($25,725) + Taxes in 2024 ($1,005)


    Taxes:$12,064

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2024

    Middle School: Martha B. King Middle


  • 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228

    $4,395,000174 Days on yellowkey   MLS ID: A4671696

    For Sale A4671696 - 510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 90 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


  • 6001 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228

    $9,995,000208 Days on yellowkey   MLS ID: A4667111

    For Sale A4667111 - 6001 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 55 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 6959
       Built: 2013   Tax: $105,194 (2024)
    Community: Longboat Key
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $63,532 (change assumption)
    Mortgage ($54,766) + Taxes in 2024 ($8,766)


    Taxes:$105,194

    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

    $5,995,000102 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


  • 1600 HARBOR SOUND DR, LONGBOAT KEY, FL 34228

    $11,900,0004 Days on yellowkey   MLS ID: A4692027

    For Sale A4692027 - 1600 HARBOR SOUND DR, LONGBOAT KEY, FL 34228 8 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5689
       Built: 2026
    Monthly Fee: $792
       Tax: $24,527 (2025)
    Community: Bay Isles
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $68,040 (change assumption)
    Mortgage ($65,204) + Fees ($792) + Taxes in 2025 ($2,044)


    Taxes:$24,527

    Elementary School: Southside Elementary

    High School: None

    Tax Year: 2025

    Middle School: None


  • 550 YARDARM LN, LONGBOAT KEY, FL 34228

    $3,775,000165 Days on yellowkey   MLS ID: A4672604

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

    REDUCED by $20,000 (0.5%) on 04/28/2026

    For Sale A4672604 - 550 YARDARM LN, LONGBOAT KEY, FL 34228 79 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4281
       Built: 2006
    Monthly Fee: $23
       Tax: $16,615 (2024)
    Community: Country Club Shores Sec 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,092 (change assumption)
    Mortgage ($20,684) + Fees ($23) + Taxes in 2024 ($1,385)


    Taxes:$16,615

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 530 CHIPPING LN, LONGBOAT KEY, FL 34228

    $5,799,00058 Days on yellowkey   MLS ID: A4685275

    For Sale A4685275 - 530 CHIPPING LN, LONGBOAT KEY, FL 34228 49 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4216
       Built: 2026
    Monthly Fee: $21
       Tax: $16,910 (2025)
    Community: Country Club Shores Sec 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $33,205 (change assumption)
    Mortgage ($31,775) + Fees ($21) + Taxes in 2025 ($1,409)


    Taxes:$16,910

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 677 LANDS END DR, LONGBOAT KEY, FL 34228

    $2,790,00077 Days on yellowkey   MLS ID: A4682565

    REDUCED by $60,000 (2.1%) on 04/18/2026

    For Sale A4682565 - 677 LANDS END DR, LONGBOAT KEY, FL 34228 76 photos

    Bed: 3   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 4182
       Built: 1989
    Monthly Fee: $967
       Tax: $33,361 (2025)
    Community: Lands End
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,034 (change assumption)
    Mortgage ($15,287) + Fees ($967) + Taxes in 2025 ($2,780)


    Taxes:$33,361

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: W.D. Sugg Middle


  • 1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228

    $4,550,000217 Days on yellowkey   MLS ID: A4666688

    REDUCED by $200,000 (4.2%) on 04/29/2026

    For Sale A4666688 - 1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228 93 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4209
       Built: 1987   Tax: $16,980 (2024)
    Community: Bay Isles
    Single Family


    Estimated Monthly Payment: $26,346 (change assumption)
    Mortgage ($24,931) + Taxes in 2024 ($1,415)


    Taxes:$16,980

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


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

    $8,995,000215 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


  • 592 JUAN ANASCO DR, LONGBOAT KEY, FL 34228

    $4,000,0006 Days on yellowkey   MLS ID: A4691388

    For Sale A4691388 - 592 JUAN ANASCO DR, LONGBOAT KEY, FL 34228 1 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 3600
       Built: 2027   Tax: $6,949 (2025)
    Community: Sleepy Lagoon Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,496 (change assumption)
    Mortgage ($21,917) + Taxes in 2025 ($579)


    Taxes:$6,949

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 3408 FAIR OAKS LN, LONGBOAT KEY, FL 34228

    $2,595,000195 Days on yellowkey   MLS ID: A4667842

    0 Days Off yellowkey (back on 4/28/2026)

    REDUCED by $50,000 (1.9%) on 04/28/2026

    For Sale A4667842 - 3408 FAIR OAKS LN, LONGBOAT KEY, FL 34228 76 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4510
       Built: 1992   Tax: $20,206 (2024)
    Community: Coreys Landing
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $15,903 (change assumption)
    Mortgage ($14,219) + Taxes in 2024 ($1,684)


    Taxes:$20,206

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6489 GULFSIDE RD, LONGBOAT KEY, FL 34228

    $13,995,000108 Days on yellowkey   MLS ID: A4677413

    For Sale A4677413 - 6489 GULFSIDE RD, LONGBOAT KEY, FL 34228 71 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 6616
       Built: 2026   Tax: $42,641 (2025)
    Community: Sleepy Lagoon
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $80,236 (change assumption)
    Mortgage ($76,683) + Taxes in 2025 ($3,553)


    Taxes:$42,641

    Elementary School: Anna Maria Elementary

    High School: Bayshore High

    Tax Year: 2025

    Middle School: Martha B. King Middle


  • 65 LIGHTHOUSE POINT DR, LONGBOAT KEY, FL 34228

    $7,445,000140 Days on yellowkey   MLS ID: A4674851

    For Sale A4674851 - 65 LIGHTHOUSE POINT DR, LONGBOAT KEY, FL 34228 96 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4921
       Built: 2001
    Monthly Fee: $617
       Tax: $45,712 (2024)
    Community: Lighthouse Point
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $45,220 (change assumption)
    Mortgage ($40,794) + Fees ($617) + Taxes in 2024 ($3,809)


    Taxes:$45,712

    Elementary School: Southside Elementary

    High School: Booker High

    Tax Year: 2024

    Middle School: Booker Middle


  • 5005 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228

    $3,995,000262 Days on yellowkey   MLS ID: A4661988

    2 Days Off yellowkey (back on 4/23/2026)

    For Sale A4661988 - 5005 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228 82 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4044
       Built: 2018
    Monthly Fee: $766
       Tax: $49,274 (2024)
    Community: Bonaire
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,762 (change assumption)
    Mortgage ($21,890) + Fees ($766) + Taxes in 2024 ($4,106)


    Taxes:$49,274

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 573 SPINNAKER LN, LONGBOAT KEY, FL 34228

    $2,995,000185 Days on yellowkey   MLS ID: A4668083

    0 Days Off yellowkey (back on 4/23/2026)

    For Sale A4668083 - 573 SPINNAKER LN, LONGBOAT KEY, FL 34228 43 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3926
       Built: 1998
    Monthly Fee: $8
       Tax: $17,104 (2024)
    Community: Country Club Shores Sec 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $17,844 (change assumption)
    Mortgage ($16,411) + Fees ($8) + Taxes in 2024 ($1,425)


    Taxes:$17,104

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228

    $7,800,000137 Days on yellowkey   MLS ID: A4673495

    For Sale A4673495 - 5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228 60 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4630
       Built: 2018
    Monthly Fee: $572
       Tax: $30,971 (2024)
    Community: Bonaire At Longboat Key
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $45,892 (change assumption)
    Mortgage ($42,739) + Fees ($572) + Taxes in 2024 ($2,581)


    Taxes:$30,971

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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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.