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3 bedsNew constructionWith a pool
5 Bedroom Homes in Winter Haven, FL
56 listings

5 Bedroom Homes in Winter Haven, FL

5 Bedroom Homes in Winter Haven, FL

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24 of 56 Listings
Map

5 Bedroom Homes in Winter Haven, FL

24 of 56 Listings

  1. 1759 Vanilla St — photo1Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$364,745

5 bd · 3 ba · 2,470 sqft

1759 Vanilla St, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

  • 6245 Botticella Blvd — photo15Active

    $296,990

    5 bd · 3 ba · 2,112 sqft

    6245 Botticella Blvd, Winter Haven, FL

    Ben Goldstein · LENNAR REALTY

  • 219 Terranova Blvd — photo31Active

    $428,000

    5 bd · 3 ba · 2,549 sqft

    219 Terranova Blvd, Winter Haven, FL

    Dwight Head · ALLSTATE REALTY SERVICES

  • 2022 Kapree Ct — photo25Active

    $515,000

    5 bd · 3 ba · 2,685 sqft

    2022 Kapree Ct, Winter Haven, FL

    Jerome Baker · BAKER REAL ESTATE PRO. GR LLC

  • 4608 Ostero St — photo59Active

    $365,000

    5 bd · 3 ba · 2,616 sqft

    4608 Ostero St, Winter Haven, FL

    Sandy Music · MUSIC REALTY

  • 669 Sarner Pass Way — photo54Active

    $625,000

    5 bd · 3 ba · 3,016 sqft

    669 Sarner Pass Way, Winter Haven, FL

    Miguel Shellie · MARK SPAIN REAL ESTATE

  • 6159 Coronari Ln — photo37Active

    $336,990

    5 bd · 3 ba · 2,447 sqft

    6159 Coronari Ln, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 714 Avenue O SE — photo33Active

    $359,900

    5 bd · 2 ba · 2,104 sqft

    714 Avenue O SE, Winter Haven, FL

    Ileana Perez · HOUWZER INC

  • 2758 Adeline Ave — photo32Active

    $302,990

    5 bd · 2 ba · 1,708 sqft

    2758 Adeline Ave, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 4230 Roberta Dr — photo37Active

    $360,000

    5 bd · 3 ba · 2,616 sqft

    4230 Roberta Dr, Winter Haven, FL

    Giovanni Hernandez · FORTEX REALTY INC

  • 6055 Navona Way — photo37Active

    $336,990

    5 bd · 3 ba · 2,447 sqft

    6055 Navona Way, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 930 Cattleman St — photo16Active

    $345,000

    5 bd · 3 ba · 2,254 sqft

    930 Cattleman St, Winter Haven, FL

    Claudia Lopez · EXP REALTY LLC

  • 9504 Waterford Oaks Blvd — photo66Active

    $725,000

    5 bd · 3 ba · 2,916 sqft

    9504 Waterford Oaks Blvd, Winter Haven, FL

    Brooke Boyette · KELLER WILLIAMS TAMPA PROPERTIES

  • 306 Avenue a Wahneta E — photo33Active

    $174,500

    5 bd · 2 ba · 1,747 sqft

    306 Avenue a Wahneta E, Winter Haven, FL

    Ruben Galindo Vega · PREFERRED SHORE LLC

  • 1196 Lake Elbert Dr SE — photoPrice Reduced35Active

    $449,900

    5 bd · 3 ba · 2,242 sqft

    1196 Lake Elbert Dr SE, Winter Haven, FL

    Christopher Howard · DALTON WADE INC

  • 9513 Waterford Oaks Blvd — photo65Active

    $750,000

    5 bd · 4 ba · 3,611 sqft

    9513 Waterford Oaks Blvd, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 6183 Grey Heron Dr — photoPrice Reduced26Active

    $339,999

    5 bd · 4 ba · 1,872 sqft

    6183 Grey Heron Dr, Winter Haven, FL

    Diana Acosta · TFP FLORIDA REALTY LLC

  • 2639 San Marco Way — photo7Active

    $347,000

    5 bd · 4 ba · 2,701 sqft

    2639 San Marco Way, Winter Haven, FL

    Don Jerue · KELLER WILLIAMS REALTY SMART 1

  • 1436 Axel Cir — photoPrice Reduced7Active

    $340,000

    5 bd · 3 ba · 3,022 sqft

    1436 Axel Cir, Winter Haven, FL

    Don Jerue · KELLER WILLIAMS REALTY SMART 1

  • 2510 Cypress Gardens Blvd — photo93Active

    $865,000

    5 bd · 3 ba · 3,482 sqft

    2510 Cypress Gardens Blvd, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 1016 S Lake Mariam Dr — photoPrice Reduced92Active

    $750,000

    5 bd · 4 ba · 3,694 sqft

    1016 S Lake Mariam Dr, Winter Haven, FL

    Kelly Jones · KELLER WILLIAMS REALTY SMART 1

  • 218 5th Jpv St — photoPrice Reduced27Active

    $235,500

    5 bd · 2 ba · 820 sqft

    218 5th Jpv St, Winter Haven, FL

    Eva Hockenberry · MAINSTAY BROKERAGE LLC

  • 25 Lakewood Cswy — photo52Active

    $849,900

    5 bd · 4 ba · 4,108 sqft

    25 Lakewood Cswy, Winter Haven, FL

    Melissa Meyer · KEENE'S POINTE REALTY

  • 4162 Roberta Dr — photoPrice Reduced48Active

    $399,999

    5 bd · 4 ba · 2,905 sqft

    4162 Roberta Dr, Winter Haven, FL

    Marlon Persaud · REAL BROKER, LLC

  • 123

    Explore Winter Haven homes

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    By type

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    • New Construction Homes
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    Your local brokerage

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    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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.

    Winter Haven, FL community profile

    Population
    58,351
    Median income
    $56,564
    Housing units
    26,800
    People per sq. mi.
    605.3
    Area
    96.4 sq. mi.

    Source: HJN community data

    Winter Haven housing market

    September 2026 · This period is still settling

    Winter Haven 12-month median sale price trend

    Selling at 99.9% of asking price

    Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 30, 2026

    Median sale price
    $270,000$195,000–$332,030 typical range
    Price per sq. ft.
    $159
    Sales
    200
    Paid in cash
    38.0%

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

    Median list price
    $294,400
    Homes for sale
    762
    Median days on market
    42 days

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

    Year-over-year
    -18.2%

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

    Median home size
    1,632 sq. ft.