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

Waterfront Homes in Holiday, FL

Waterfront Homes in Holiday, FL

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24 of 35 Listings
Map

Waterfront Homes in Holiday, FL

24 of 35 Listings

  1. 3087 Jackson Dr — photoOpen house Sun, Nov 1 · 12:00 AM35

Your Holiday agent

LR

LPT Realty

Call LPT
Active

$549,000

4 bd · 2 ba · 1,787 sqft

3087 Jackson Dr, Holiday, FL

Tymofiy Pyshnyuk · LOKATION

  • 2529 San Luis Rd — photo48Active

    $324,900

    3 bd · 2 ba · 1,836 sqft

    2529 San Luis Rd, Holiday, FL

    Bradley Uline · RE/MAX REALTEC GROUP INC

  • 3138 Bluff Blvd — photo83Active

    $649,000

    2 bd · 3 ba · 1,956 sqft

    3138 Bluff Blvd, Holiday, FL

    STEVE DeMatos · RE/MAX ALLIANCE GROUP

  • 3207 Brewster Dr — photo69Active

    $149,900

    2 bd · 2 ba · 1,018 sqft

    3207 Brewster Dr, Holiday, FL

    Jennifer Zulian · COLDWELL BANKER REALTY

  • 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

  • 3211 Southport Dr — photo34Active

    $179,900

    2 bd · 2 ba · 1,329 sqft

    3211 Southport Dr, Holiday, FL

    Stella Wooster · CITY BREEZE ACTION REALTY

  • 5410 Flora Ave — photoPrice Reduced55Active

    $359,000

    2 bd · 2 ba · 1,356 sqft

    5410 Flora Ave, Holiday, FL

    Nadia Heinz · DENNIS REALTY & INV. CORP.

  • 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

  • 3532 Overland Dr — photoPrice Reduced17Active

    $275,000

    2 bd · 2 ba · 1,334 sqft

    3532 Overland Dr, Holiday, FL

    Jason Duraj PA · FUTURE HOME REALTY INC

  • 2217 Harrison Dr — photo100Active

    $245,995

    4 bd · 2 ba · 1,566 sqft

    2217 Harrison Dr, Holiday, FL

    Eddie Rivera · IMPACT REALTY TAMPA BAY

  • 4036 Sunray Dr — photoPrice Reduced46Active

    $290,000

    3 bd · 2 ba · 1,842 sqft

    4036 Sunray Dr, Holiday, FL

    Ekaterina Osipova · DALTON WADE INC

  • 2203 Riomar Dr — photoPrice Reduced34Active

    $275,000

    2 bd · 2 ba · 1,112 sqft

    2203 Riomar Dr, Holiday, FL

    Elaine Hope · LIPPLY REAL ESTATE

  • 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

  • 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

  • 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.

  • 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

  • 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

  • 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

  • 3201 Brewster Dr — photo21Active

    $145,500

    2 bd · 2 ba · 864 sqft

    3201 Brewster Dr, Holiday, FL

    Stella Wooster · CITY BREEZE ACTION REALTY

  • 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

  • 3806 Staysail Ln — photoPrice Reduced54Active

    $114,900

    1 bd · 1 ba · 880 sqft

    3806 Staysail Ln, Holiday, FL

    Denvir Steele · REALTY EXPERTS ASSOCIATES

  • 2228 Society Dr — photo47Active

    $240,000

    2 bd · 2 ba · 1,039 sqft

    2228 Society Dr, Holiday, FL

    Hoss Pollard · LPT REALTY, LLC

  • 3318 Pineview Dr — photoPrice Reduced56Active

    $499,000

    2 bd · 2 ba · 1,047 sqft

    3318 Pineview Dr, Holiday, FL

    STEVE DeMatos · RE/MAX ALLIANCE GROUP

  • 2146 Society Dr — photoPrice Reduced40Active

    $259,000

    2 bd · 2 ba · 1,371 sqft

    2146 Society Dr, Holiday, FL

    Traci Pearson · KELLER WILLIAMS REALTY PORTFOLIO COLLECTION

  • 12

    Explore Holiday homes

    By price

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

    By bedrooms

    • 2 Bedroom Homes
    • 3 Bedroom Homes

    By type

    • Single-Family Homes
    • Condos
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    By feature

    • Homes with a Pool
    • Waterfront Homes
    • 55+ Community Homes
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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Your Holiday agent

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    LPT Realty

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    Listing data & MLS disclosures

    Stellar MLS
    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.

    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 30, 2026

    Median sale price
    $228,900$149,000–$300,000 typical range
    Price per sq. ft.
    $164
    Sales
    85
    Paid in cash
    27.1%

    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
    0.5%

    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.