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Waterfront Homes in Holiday, FL
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35 listings
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3 bedsWith a pool

Waterfront Homes in Holiday, FL

Waterfront Homes in Holiday, FL

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24 of 35 Listings
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Waterfront Homes in Holiday, FL

24 of 35 Listings

Your Holiday agent

LR

LPT Realty

Call LPT
  1. 3207 Brewster Dr — photo69Active

    $149,900

    2 bd · 2 ba · 1,018 sqft

    3207 Brewster Dr, Holiday, FL

    Jennifer Zulian · COLDWELL BANKER REALTY

  2. 1022 Bowsprit Ln #1022 — photo10Active

    $175,000

    2 bd · 2 ba · 1,114 sqft

    1022 Bowsprit Ln #1022, Holiday, FL

    Erin Humphrey · BAY TO SHORE PROPERTY MANAGEMENT AND LEASING LLC

  3. 3211 Southport Dr — photo34Active

    $179,900

    2 bd · 2 ba · 1,329 sqft

    3211 Southport Dr, Holiday, FL

    Stella Wooster · CITY BREEZE ACTION REALTY

  4. 5410 Flora Ave — photo55Active

    $359,900

    2 bd · 2 ba · 1,356 sqft

    5410 Flora Ave, Holiday, FL

    Nadia Heinz · DENNIS REALTY & INV. CORP.

  5. 1117 Rushmore Dr — photo29Active

    $399,000

    3 bd · 2 ba · 1,502 sqft

    1117 Rushmore Dr, Holiday, FL

    Gene Morales · TMWRK BROKERAGE LLC

  6. 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

  7. 2217 Harrison Dr — photo100Active

    $245,995

    4 bd · 2 ba · 1,566 sqft

    2217 Harrison Dr, Holiday, FL

    Eddie Rivera · IMPACT REALTY TAMPA BAY

  8. 4036 Sunray Dr — photo46Active

    $300,000

    3 bd · 2 ba · 1,842 sqft

    4036 Sunray Dr, Holiday, FL

    Ekaterina Osipova · DALTON WADE INC

  9. 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.

  10. 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

  11. 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

  12. 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.

  13. 3852 Sunray Dr — photo32Active

    $239,900

    2 bd · 2 ba · 1,088 sqft

    3852 Sunray Dr, Holiday, FL

    Jakea Cates · KELLER WILLIAMS REALTY- PALM HARBOR

  14. 2578 Charlan Ct — photoPrice Reduced36Active

    $255,000

    3 bd · 3 ba · 1,634 sqft

    2578 Charlan Ct, Holiday, FL

    LORI Smith, PA · BEST OF THE GULF REALTY INC

  15. 2044 Pamela Dr — photoPrice Reduced23Active

    $219,900

    2 bd · 2 ba · 1,116 sqft

    2044 Pamela Dr, Holiday, FL

    Tony Baroni · KELLER WILLIAMS SUBURBAN TAMPA

  16. 2030 Gulfview Dr — photoPrice Reduced77Active

    $774,900

    2 bd · 2 ba · 2,280 sqft

    2030 Gulfview Dr, Holiday, FL

    STEVE DeMatos · RE/MAX ALLIANCE GROUP

  17. 3201 Brewster Dr — photo21Active

    $145,500

    2 bd · 2 ba · 864 sqft

    3201 Brewster Dr, Holiday, FL

    Stella Wooster · CITY BREEZE ACTION REALTY

  18. 4318 Tahitian Gardens Cir #F — photoPrice Reduced31Active

    $113,900

    1 bd · 1 ba · 576 sqft

    4318 Tahitian Gardens Cir #F, Holiday, FL

    Greg Blackall · VERANDA REALTY GROUP

  19. 3806 Staysail Ln — photoPrice Reduced54Active

    $114,900

    1 bd · 1 ba · 880 sqft

    3806 Staysail Ln, Holiday, FL

    Denvir Steele · REALTY EXPERTS ASSOCIATES

  20. 2228 Society Dr — photo47Active

    $240,000

    2 bd · 2 ba · 1,039 sqft

    2228 Society Dr, Holiday, FL

    Hoss Pollard · LPT REALTY, LLC

  21. 3318 Pineview Dr — photoPrice Reduced56Active

    $509,000

    2 bd · 2 ba · 1,047 sqft

    3318 Pineview Dr, Holiday, FL

    STEVE DeMatos · RE/MAX ALLIANCE GROUP

  22. 2146 Society Dr — photoPrice ReducedOpen house Sun, Oct 18 · 1:00 PM40Active

    $259,000

    2 bd · 2 ba · 1,371 sqft

    2146 Society Dr, Holiday, FL

    Traci Pearson · KELLER WILLIAMS REALTY PORTFOLIO COLLECTION

  23. 3507 Landale Dr — photoPrice Reduced19Active

    $235,000

    2 bd · 2 ba · 1,326 sqft

    3507 Landale Dr, Holiday, FL

    Brian Eades, PA · DALTON WADE INC

  24. 3011 Shadow Oaks Dr — photoPrice Reduced26Active

    $319,000

    3 bd · 2 ba · 1,480 sqft

    3011 Shadow Oaks Dr, Holiday, FL

    Kim Doukas · RE/MAX CHAMPIONS

12

About Waterfront Homes in Holiday, FL

Waterfront Homes in Holiday, FL: 35 active listings as of October 17, 2026, 18:50 UTC.

Explore Holiday 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.