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Homes with a Pool in Holiday, FL
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28 listings
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3 bedsWith a pool

Homes with a Pool in Holiday, FL

Homes with a Pool in Holiday, FL

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24 of 28 Listings
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Homes with a Pool in Holiday, FL

24 of 28 Listings

Your Holiday agent

LR

LPT Realty

Call LPT
  1. 3024 Pineview Dr — photoNew46Active

    $485,000

    3 bd · 2 ba · 1,884 sqft

    3024 Pineview Dr, Holiday, FL

    Tina Shank · WIKLE INCORPORATED

  2. 1419 Blue Marlin Blvd — photoOpen house Sun, Oct 18 · 2:00 PM59Active

    $525,000

    4 bd · 3 ba · 2,480 sqft

    1419 Blue Marlin Blvd, Holiday, FL

    Amanda Lebiszczak · CHARLES RUTENBERG REALTY INC

  3. 1539 Dartmouth Dr — photo69Active

    $330,000

    3 bd · 2 ba · 1,388 sqft

    1539 Dartmouth Dr, Holiday, FL

    Yanelis Orozco Rosabal · AVENUE HOMES LLC

  4. 3708 Holiday Lake Dr — photo33Active

    $379,900

    3 bd · 3 ba · 1,726 sqft

    3708 Holiday Lake Dr, Holiday, FL

    Dianna Desboyaux · DOUGLAS ELLIMAN

  5. 2831 Blossom Lk — photo27Active

    $379,900

    3 bd · 2 ba · 1,613 sqft

    2831 Blossom Lk, Holiday, FL

    Rob Jones · OFFERPAD BROKERAGE FL, LLC

  6. 1117 Rushmore Dr — photo29Active

    $399,000

    3 bd · 2 ba · 1,502 sqft

    1117 Rushmore Dr, Holiday, FL

    Gene Morales · TMWRK BROKERAGE LLC

  7. 3143 Pineview Dr — photo57Active

    $1,299,999

    4 bd · 4 ba · 4,204 sqft

    3143 Pineview Dr, Holiday, FL

    Jennifer Tobey, PA · RE/MAX CHAMPIONS

  8. 5657 Oceanic Rd — photoPrice Reduced44Active

    $549,900

    4 bd · 4 ba · 3,553 sqft

    5657 Oceanic Rd, Holiday, FL

    Nicole Volentine · DALTON WADE INC

  9. 2530 Arrowpointe Dr — photoPrice Reduced35Active

    $479,900

    3 bd · 2 ba · 1,758 sqft

    2530 Arrowpointe Dr, Holiday, FL

    Jeffrey Borham, PA · EXP REALTY LLC

  10. 3748 Redwood Dr — photo42Active

    $244,900

    2 bd · 2 ba · 948 sqft

    3748 Redwood Dr, Holiday, FL

    April Nyemah · REALTY ONE GROUP BEYOND

  11. 2144 Harrison Dr — photo1Active

    $229,000

    2 bd · 2 ba · 1,383 sqft

    2144 Harrison Dr, Holiday, FL

    Thomas Ambrose-emundi · SUNCOAST GROUP REALTORS LLC

  12. 1324 Chancellor Dr — photoPrice Reduced50Active

    $448,900

    3 bd · 3 ba · 1,762 sqft

    1324 Chancellor Dr, Holiday, FL

    Beth Belloise · TROPICAL LIFE REALTY, INC.

  13. 2641 Flintwood Dr — photo15Active

    $284,900

    3 bd · 2 ba · 1,354 sqft

    2641 Flintwood Dr, Holiday, FL

    Robert Salmons · ENTERA REALTY LLC

  14. 1238 Flotilla Dr — photoPrice Reduced34Active

    $549,900

    5 bd · 6 ba · 5,360 sqft

    1238 Flotilla Dr, Holiday, FL

    Theresa Legatti · CHARLES RUTENBERG REALTY INC

  15. 3225 Hearthstone Ct — photo34Active

    $459,500

    3 bd · 2 ba · 2,151 sqft

    3225 Hearthstone Ct, Holiday, FL

    Bobbie Coleman · SUNCOAST GROUP REALTORS LLC

  16. 1332 Flotilla Dr — photoPrice Reduced33Active

    $289,000

    2 bd · 2 ba · 1,386 sqft

    1332 Flotilla Dr, Holiday, FL

    Harris Gruman · REALNET FLORIDA REAL ESTATE

  17. 3349 Overland Dr — photoPrice Reduced19Active

    $249,999

    3 bd · 2 ba · 1,326 sqft

    3349 Overland Dr, Holiday, FL

    Joseph Buchi · DENNIS REALTY & INV. CORP.

  18. 2309 Swordfish Ave — photoPrice ReducedOpen house Sun, Oct 18 · 2:00 PM57Active

    $545,000

    4 bd · 3 ba · 2,462 sqft

    2309 Swordfish Ave, Holiday, FL

    Greg Palumbo · KELLER WILLIAMS REALTY- PALM HARBOR

  19. 3153 Moog Rd — photoPrice Reduced36Active

    $199,000

    2 bd · 2 ba · 1,125 sqft

    3153 Moog Rd, Holiday, FL

    Rose Parsons · DALTON WADE INC

  20. 3225 Glenwood Cir — photoPrice Reduced60Active

    $525,000

    4 bd · 3 ba · 2,857 sqft

    3225 Glenwood Cir, Holiday, FL

    Jocelyn Carbonelli · VANDERLEELIE & ASSOC.RE ESTATE

  21. 2811 Ravendale Ln — photoPrice Reduced35Active

    $460,000

    4 bd · 2 ba · 2,366 sqft

    2811 Ravendale Ln, Holiday, FL

    Alissa Caputo · FUTURE HOME REALTY INC

  22. 3020 Sheppards Crook Ct — photoPrice Reduced63Active

    $559,000

    3 bd · 4 ba · 2,367 sqft

    3020 Sheppards Crook Ct, Holiday, FL

    STEVE DeMatos · RE/MAX ALLIANCE GROUP

  23. 2210 Bayou Dr — photoPrice Reduced43Active

    $499,999

    4 bd · 3 ba · 2,861 sqft

    2210 Bayou Dr, Holiday, FL

    Peter Ingrasselino · DEAL HOUSE REALTY LLC

  24. 3645 Overland — photoPrice Reduced37Active

    $349,999

    3 bd · 3 ba · 1,416 sqft

    3645 Overland, Holiday, FL

    Taylor Sparling · SELECT PROPERTIES INC

12

About Homes with a Pool in Holiday, FL

Homes with a Pool in Holiday, FL: 28 active listings as of October 17, 2026, 11:24 UTC.

Explore Holiday homes

By price

  • Homes Under $200K
  • Homes Under $300K

By bedrooms

  • 2 Bedroom Homes
  • 3 Bedroom Homes

By type

  • Single-Family Homes
  • Manufactured Homes

By feature

  • Homes with a Pool
  • Waterfront Homes
  • 55+ Community Homes
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Listing data & MLS disclosures

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Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.
  • Your Holiday agent

    LR

    LPT Realty

    Call LPT

    Holiday, FL community profile

    Area
    21.2 sq. mi.

    Source: HJN community data

    Holiday housing market

    September 2026

    Holiday 12-month median sale price trend

    Selling at 98.3% of asking price

    Buyers here are paying below asking. MLS · 59 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 28, 2026

    Median sale price
    $229,450$151,250–$311,250 typical range
    Price per sq. ft.
    $167
    Sales
    78
    Paid in cash
    25.6%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $239,900
    Homes for sale
    265
    Median days on market
    23 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    1.0%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,246 sq. ft.