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3 bedsNew constructionWith a pool
Homes Under $300K in Winter Haven, FL
22 listings

Homes Under $300K in Winter Haven, FL

Homes Under $300K in Winter Haven, FL

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22 Listings
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Homes Under $300K in Winter Haven, FL

22 Listings

  1. 104 13th St SE — photoNew21

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$200,000

2 bd · 2 ba · 1,776 sqft

104 13th St SE, Winter Haven, FL

Chuck Ferdinandsen · CHARLES RUTENBERG REALTY ORLANDO

  • 304 Corso Loop — photo12Active

    $220,000

    3 bd · 2 ba · — sqft

    304 Corso Loop, Winter Haven, FL

    Soreina Del Valle Gonzalez Medina PA · United Realty Group Inc.

  • 333 Lake Howard Dr NW #302B — photoPrice Reduced12Active

    $99,000

    2 bd · 2 ba · 1,030 sqft

    333 Lake Howard Dr NW #302B, Winter Haven, FL

    Karen Myers · UNITED REALTY GROUP INC

  • 276 18th St NE — photo27Active

    $279,900

    3 bd · 2 ba · 1,218 sqft

    276 18th St NE, Winter Haven, FL

    Marcelo Garrido · AGENT TRUST REALTY CORPORATION

  • 153 Browning Cir — photo48Active

    $269,000

    3 bd · 2 ba · 1,144 sqft

    153 Browning Cir, Winter Haven, FL

    Kimberly Jones · RE/MAX HERITAGE PROFESSIONALS

  • 116 Harbor Dr — photo28Active

    $289,900

    4 bd · 2 ba · 1,476 sqft

    116 Harbor Dr, Winter Haven, FL

    Allison McDaniel · XCELLENCE

  • 144 Waterside Cir — photoPrice ReducedOpen house Fri, Oct 9 · 4:00 PM37Active

    $299,000

    3 bd · 2 ba · 1,847 sqft

    144 Waterside Cir, Winter Haven, FL

    Ythamarie Rosario · KELLER WILLIAMS ADVANTAGE III

  • 3334 Avenue J NW — photoPrice Reduced45Active

    $249,765

    3 bd · 2 ba · 1,473 sqft

    3334 Avenue J NW, Winter Haven, FL

    Nicki Salas Fuentes · ELEVE REAL ESTATE LLC

  • 235 6th St NW #307 — photo55Active

    $125,000

    1 bd · 1 ba · 714 sqft

    235 6th St NW #307, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  • 2021 Oliver Pl — photoPrice Reduced45Active

    $274,989

    3 bd · 2 ba · 1,507 sqft

    2021 Oliver Pl, Winter Haven, FL

    Ray Colon · TRUE FLORIDA REALTY LLC

  • 706 Avenue I NE — photoPrice Reduced29Active

    $285,000

    3 bd · 2 ba · 1,925 sqft

    706 Avenue I NE, Winter Haven, FL

    Steve Lockhart · LOCKHART & ASSOCIATES INC

  • 3357 Timberline Rd W — photoPrice Reduced15Active

    $265,000

    4 bd · 2 ba · 1,675 sqft

    3357 Timberline Rd W, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 132 Duval Rd — photoPrice Reduced38Active

    $290,000

    2 bd · 2 ba · 1,260 sqft

    132 Duval Rd, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 136 Lake Ring Dr — photoPrice Reduced41Active

    $299,900

    3 bd · 2 ba · 1,728 sqft

    136 Lake Ring Dr, Winter Haven, FL

    Lamanda Jones · CENTURY 21 WATSON & MYERS REALTY

  • listing photoPrice Reduced28Active

    $265,000

    2 bd · 1 ba · 2,142 sqft

    Address withheld · Winter Haven, FL

    Marcia Rains - Nadal, Mrs · YELLOWFIN REALTY

  • 1450 W Lake Cannon Dr NW — photoPrice Reduced15Active

    $299,000

    5 bd · 2 ba · 4,053 sqft

    1450 W Lake Cannon Dr NW, Winter Haven, FL

    Veronica Davis · EXP REALTY LLC

  • 878 Killearn Blvd — photoPrice Reduced19Active

    $245,000

    3 bd · 2 ba · 1,467 sqft

    878 Killearn Blvd, Winter Haven, FL

    Barbi Rodriguez, LLC · SIGNATURE INTERNATIONAL REAL E

  • 3022 Hickory St NW — photoPrice Reduced40Active

    $265,000

    3 bd · 1 ba · 1,602 sqft

    3022 Hickory St NW, Winter Haven, FL

    Ashlee Morrell · THE URBAN GROUP, INC.

  • 119 Allen Ave — photo9Active

    $219,000

    4 bd · 2 ba · 1,520 sqft

    119 Allen Ave, Winter Haven, FL

    Randall Patrick · WESTBAY REAL ESTATE

  • 508 Lakeside Ranch Way — photoPrice Reduced24Active

    $79,000

    2 bd · 2 ba · 1,128 sqft

    508 Lakeside Ranch Way, Winter Haven, FL

    Jean Murphy · CENTURY 21 MYERS REALTY

  • 5850 Cypress Gardens Blvd #304 — photoPrice Reduced34Active

    $139,000

    2 bd · 2 ba · 1,332 sqft

    5850 Cypress Gardens Blvd #304, Winter Haven, FL

    Matthew Davis · FLORIDA HOMES REALTY & MTG

  • 3829 Giorgio — photoPrice Reduced9Active

    $242,000

    3 bd · 2 ba · — sqft

    3829 Giorgio, Winter Haven, FL

    Ivette Loaiza · First Pro International Rlty

  • Explore Winter Haven homes

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    MIAMI REALTORS MLS
    The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
    The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-09-17 17:50:51 UTC
    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 99.7% of asking price

    Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $270,000$207,500–$329,495 typical range
    Price per sq. ft.
    $161
    Sales
    135
    Paid in cash
    36.3%

    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
    48 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.