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Highland Lakes Single Family Homes For Sale in Palm Harbor - 25 homes

Highland Lakes single family homes for sale are located in Pinellas County, Florida. Find Highland Lakes single family homes in Palm Harbor for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Highland Lakes, Palm Harbor single family houses.

Location: Highland Lakes, Palm Harbor

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  • 999 GILLESPIE DR, PALM HARBOR, FL 34684

    $479,900Listed 04/02/2026 9:07AM   MLS ID: TB8492306

    For Sale TB8492306 - 999 GILLESPIE DR, PALM HARBOR, FL 34684 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1732
       Built: 1983
    Monthly Fee: $164
       Tax: $6,872 (2025)
    Community: Highland Lakes Unit Fifteen Ph 1
    Single Family


    Estimated Monthly Payment: $3,366 (change assumption)
    Mortgage ($2,630) + Fees ($164) + Taxes in 2025 ($573)


    Taxes:$6,872

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1207 GILLESPIE DR N, PALM HARBOR, FL 34684

    $534,9006 Days on yellowkey   MLS ID: TB8491462

    For Sale TB8491462 - 1207 GILLESPIE DR N, PALM HARBOR, FL 34684 18 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 1985
    Monthly Fee: $150
       Tax: $4,394 (2025)
    Community: Highland Lakes Unit Fifteen Ph 3
    Single Family


    Estimated Monthly Payment: $3,447 (change assumption)
    Mortgage ($2,931) + Fees ($150) + Taxes in 2025 ($366)


    Taxes:$4,394

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3569 OAK LAKE DR, PALM HARBOR, FL 34684

    $399,00055 Days on yellowkey   MLS ID: TB8472815

    For Sale TB8472815 - 3569 OAK LAKE DR, PALM HARBOR, FL 34684 42 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1466
       Built: 1987
    Monthly Fee: $164
       Tax: $2,919 (2024)
    Community: Highland Lakes Unit Eighteen
    Single Family


    Estimated Monthly Payment: $2,594 (change assumption)
    Mortgage ($2,186) + Fees ($164) + Taxes in 2024 ($243)


    Taxes:$2,919

    Elementary School: Highland Lakes Elementary-PN

    High School: Palm Harbor Univ High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 3098 E DORCHESTER DR, PALM HARBOR, FL 34684

    $399,900180 Days on yellowkey   MLS ID: TB8433251

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale TB8433251 - 3098 E DORCHESTER DR, PALM HARBOR, FL 34684 95 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1567
       Built: 1980
    Monthly Fee: $164
       Tax: $3,136 (2024)
    Community: Highland Lakes Unit 14 Ph 1
    Single Family


    Estimated Monthly Payment: $2,617 (change assumption)
    Mortgage ($2,191) + Fees ($164) + Taxes in 2024 ($261)


    Taxes:$3,136

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1563 WICKLOW DR, PALM HARBOR, FL 34684

    $499,00069 Days on yellowkey   MLS ID: TB8467874

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale TB8467874 - 1563 WICKLOW DR, PALM HARBOR, FL 34684 76 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 1985
    Monthly Fee: $164
       Tax: $5,324 (2024)
    Community: Highland Lakes Unit Fifteen Ph 4
    Single Family


    Estimated Monthly Payment: $3,342 (change assumption)
    Mortgage ($2,734) + Fees ($164) + Taxes in 2024 ($444)


    Taxes:$5,324

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2938 MACALPIN DR W, PALM HARBOR, FL 34684

    $499,0005 Days on yellowkey   MLS ID: TB8491531

    For Sale TB8491531 - 2938 MACALPIN DR W, PALM HARBOR, FL 34684 64 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1944
       Built: 1979
    Monthly Fee: $164
       Tax: $2,779 (2025)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $3,130 (change assumption)
    Mortgage ($2,734) + Fees ($164) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2149 MALCOLM DR, PALM HARBOR, FL 34684

    $409,00044 Days on yellowkey   MLS ID: TB8475863

    For Sale TB8475863 - 2149 MALCOLM DR, PALM HARBOR, FL 34684 38 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1535
       Built: 1978
    Monthly Fee: $164
       Tax: $5,408 (2024)
    Community: Highland Lakes Unit Six
    Single Family


    Estimated Monthly Payment: $2,856 (change assumption)
    Mortgage ($2,241) + Fees ($164) + Taxes in 2024 ($451)


    Taxes:$5,408

    Elementary School: Highland Lakes Elementary-PN

    High School: Palm Harbor Univ High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 3529 OAK LAKE DR, PALM HARBOR, FL 34684

    $420,00049 Days on yellowkey   MLS ID: TB8474960

    For Sale TB8474960 - 3529 OAK LAKE DR, PALM HARBOR, FL 34684 34 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1671
       Built: 1987
    Monthly Fee: $164
       Tax: $2,348 (2025)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $2,661 (change assumption)
    Mortgage ($2,301) + Fees ($164) + Taxes in 2025 ($196)


    Taxes:$2,348

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1303 GLENGARRY DR, PALM HARBOR, FL 34684

    $449,50041 Days on yellowkey   MLS ID: TB8477898

    For Sale TB8477898 - 1303 GLENGARRY DR, PALM HARBOR, FL 34684 40 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1687
       Built: 1979   Tax: $6,600 (2025)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $3,013 (change assumption)
    Mortgage ($2,463) + Taxes in 2025 ($550)


    Taxes:$6,600

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2954 CURLING CT, PALM HARBOR, FL 34684

    $299,99938 Days on yellowkey   MLS ID: TB8479013

    For Sale TB8479013 - 2954 CURLING CT, PALM HARBOR, FL 34684 54 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1069
       Built: 1976
    Monthly Fee: $164
       Tax: $3,134 (2025)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $2,069 (change assumption)
    Mortgage ($1,644) + Fees ($164) + Taxes in 2025 ($261)


    Taxes:$3,134

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 984 GILLESPIE DR, PALM HARBOR, FL 34684

    $490,00015 Days on yellowkey   MLS ID: TB8487388

    For Sale TB8487388 - 984 GILLESPIE DR, PALM HARBOR, FL 34684 69 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1593
       Built: 1983
    Monthly Fee: $164
       Tax: $3,140 (2025)
    Community: Highland Lakes Unit Fifteen Ph 1
    Single Family


    Estimated Monthly Payment: $3,111 (change assumption)
    Mortgage ($2,685) + Fees ($164) + Taxes in 2025 ($262)


    Taxes:$3,140

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3400 RUGBY CT, PALM HARBOR, FL 34684

    $375,00016 Days on yellowkey   MLS ID: TB8484795

    For Sale TB8484795 - 3400 RUGBY CT, PALM HARBOR, FL 34684 68 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1420
       Built: 1981
    Monthly Fee: $164
       Tax: $4,157 (2025)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $2,565 (change assumption)
    Mortgage ($2,055) + Fees ($164) + Taxes in 2025 ($346)


    Taxes:$4,157

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1658 MACDONNELL CT, PALM HARBOR, FL 34684

    $498,00084 Days on yellowkey   MLS ID: TB8462135

    For Sale TB8462135 - 1658 MACDONNELL CT, PALM HARBOR, FL 34684 60 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1875
       Built: 1981
    Monthly Fee: $164
       Tax: $3,480 (2025)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $3,183 (change assumption)
    Mortgage ($2,729) + Fees ($164) + Taxes in 2025 ($290)


    Taxes:$3,480

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 142 STAFFORD CIR, PALM HARBOR, FL 34684

    $357,900123 Days on yellowkey   MLS ID: TB8450333

    For Sale TB8450333 - 142 STAFFORD CIR, PALM HARBOR, FL 34684 50 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1294
       Built: 1977
    Monthly Fee: $164
       Tax: $5,331 (2024)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $2,569 (change assumption)
    Mortgage ($1,961) + Fees ($164) + Taxes in 2024 ($444)


    Taxes:$5,331

    Elementary School: Highland Lakes Elementary-PN

    High School: Palm Harbor Univ High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1446 QUEEN ANNE BLVD, PALM HARBOR, FL 34684

    $350,00036 Days on yellowkey   MLS ID: TB8477938

    For Sale TB8477938 - 1446 QUEEN ANNE BLVD, PALM HARBOR, FL 34684 94 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1980
    Monthly Fee: $164
       Tax: $5,527 (2025)
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $2,542 (change assumption)
    Mortgage ($1,918) + Fees ($164) + Taxes in 2025 ($461)


    Taxes:$5,527

    Elementary School: Highland Lakes Elementary-PN

    High School: Palm Harbor Univ High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 3132 BRUNSWICK CIR, PALM HARBOR, FL 34684

    $474,90027 Days on yellowkey   MLS ID: TB8483229

    For Sale TB8483229 - 3132 BRUNSWICK CIR, PALM HARBOR, FL 34684 61 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1858
       Built: 1981
    Monthly Fee: $164
       Tax: $2,083 (2025)
    Community: Highland Lakes Unit 14 Ph 2
    Single Family


    Estimated Monthly Payment: $2,940 (change assumption)
    Mortgage ($2,602) + Fees ($164) + Taxes in 2025 ($174)


    Taxes:$2,083

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1369 GILLESPIE DR N, PALM HARBOR, FL 34684

    $589,90013 Days on yellowkey   MLS ID: TB8487483

    1 Days Off yellowkey (back on 3/24/2026)

    For Sale TB8487483 - 1369 GILLESPIE DR N, PALM HARBOR, FL 34684 66 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1706
       Built: 1984
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $3,232 (change assumption)
    Mortgage ($3,232)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 2928 MACALPIN DR S, PALM HARBOR, FL 34684

    $390,00010 Days on yellowkey   MLS ID: TB8489035

    For Sale TB8489035 - 2928 MACALPIN DR S, PALM HARBOR, FL 34684 40 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1352
       Built: 1979
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $2,137 (change assumption)
    Mortgage ($2,137)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 2869 DOONE CIR, PALM HARBOR, FL 34684

    $355,90012 Days on yellowkey   MLS ID: TB8489123

    1 Days Off yellowkey (back on 3/24/2026)

    For Sale TB8489123 - 2869 DOONE CIR, PALM HARBOR, FL 34684 57 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1284
       Built: 1978
    Community: Highland Lakes Unit Six
    Single Family


    Estimated Monthly Payment: $1,950 (change assumption)
    Mortgage ($1,950)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 102 STAFFORD DR, PALM HARBOR, FL 34684

    $379,90041 Days on yellowkey   MLS ID: TB8478206

    For Sale TB8478206 - 102 STAFFORD DR, PALM HARBOR, FL 34684 45 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1264
       Built: 1979
    Community: Highland Lakes
    Single Family


    Estimated Monthly Payment: $2,082 (change assumption)
    Mortgage ($2,082)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


12


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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.