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

Homes Under $300K in Winter Haven, FL

Homes Under $300K in Winter Haven, FL

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24 of 464 Listings
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Homes Under $300K in Winter Haven, FL

24 of 464 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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  1. 6066 SE Southern Oaks Dr — photo36Active

    $129,900

    2 bd · 2 ba · 828 sqft

    6066 SE Southern Oaks Dr, Winter Haven, FL

    Ryan Odenweller, LLC · RE/MAX HERITAGE PROFESSIONALS

  2. 213 Lakeside Ranch Cir — photoNew10Active

    $54,900

    2 bd · 1 ba · 672 sqft

    213 Lakeside Ranch Cir, Winter Haven, FL

    Nadia Aguilar · EXIT REALTY 4CORNERS

  3. 1358 Buckeye Trace Blvd — photoNew10Active

    $270,000

    3 bd · 2 ba · 1,820 sqft

    1358 Buckeye Trace Blvd, Winter Haven, FL

    Don Jerue · KELLER WILLIAMS REALTY SMART 1

  4. 4956 Jackson St — photoNew38Active

    $295,000

    4 bd · 2 ba · 1,876 sqft

    4956 Jackson St, Winter Haven, FL

    Anthony Medina · KELLER WILLIAMS REALTY SMART 1

  5. 395 San Jose Dr — photoNew24Active

    $170,000

    2 bd · 2 ba · 1,093 sqft

    395 San Jose Dr, Winter Haven, FL

    Chrissi Jasso · ASSOCIATE REALTY

  6. 3944 Giorgio Dr — photoNew7Active

    $275,000

    4 bd · 2 ba · 1,607 sqft

    3944 Giorgio Dr, Winter Haven, FL

    Bryan Sumner · MERITAGE HOMES OF FL REALTY

  7. 503 William Ave — photoNew25Active

    $269,900

    3 bd · 2 ba · 1,372 sqft

    503 William Ave, Winter Haven, FL

    Miriam Adame · OAKSTRAND REALTY

  8. 7060 Fairview Village Cir — photo44Active

    $134,990

    1 bd · 1 ba · 481 sqft

    7060 Fairview Village Cir, Winter Haven, FL

    AJ Alvarez · LPT REALTY, LLC

  9. 1354 Haines Dr — photo21Active

    $295,000

    3 bd · 2 ba · 1,292 sqft

    1354 Haines Dr, Winter Haven, FL

    Aizat Tuleeva · LPT REALTY, LLC

  10. 306 Eagle Pond Drive #306 — photoNew27Active

    $211,000

    2 bd · 2 ba · 1,017 sqft

    306 Eagle Pond Drive #306, Winter Haven, FL

    Amy Sullivan · FLORIDA HOME REALTY GROUP, LLC

  11. 668 Reggie Rd — photoNew42Active

    $285,000

    3 bd · 2 ba · 1,432 sqft

    668 Reggie Rd, Winter Haven, FL

    Kenny Medina · LPT REALTY, LLC

  12. 6733 Kensington Dr NE — photoNew71Active

    $165,500

    2 bd · 2 ba · 1,224 sqft

    6733 Kensington Dr NE, Winter Haven, FL

    Cynthia Cole · FLORIDA REALTY MARKETPLACE

  13. 997 Harold Pass — photoNew34Active

    $299,999

    4 bd · 3 ba · 1,933 sqft

    997 Harold Pass, Winter Haven, FL

    Andrea Heck · KELLER WILLIAMS TAMPA CENTRAL

  14. 222 Cloverdale Rd — photoNewOpen house Sat, Oct 17 · 9:00 AM22Active

    $300,000

    3 bd · 3 ba · 1,867 sqft

    222 Cloverdale Rd, Winter Haven, FL

    Karen Albright · OPENDOOR BROKERAGE LLC

  15. 125 Whittier Ln — photoNew33Active

    $225,000

    3 bd · 2 ba · 1,245 sqft

    125 Whittier Ln, Winter Haven, FL

    Lori Roberts · GOLD HEART REALTY LLC

  16. 240 Westwood Ave — photoNew64Active

    $249,900

    3 bd · 2 ba · 1,140 sqft

    240 Westwood Ave, Winter Haven, FL

    Nicole Silva · RE/MAX COLLECTIVE

  17. 6245 Botticella Blvd — photo15Active

    $294,990

    5 bd · 3 ba · 2,112 sqft

    6245 Botticella Blvd, Winter Haven, FL

    Ben Goldstein · LENNAR REALTY

  18. 703 Avenue L SE — photo21Active

    $278,000

    4 bd · 2 ba · 1,830 sqft

    703 Avenue L SE, Winter Haven, FL

    Sandra Wyhnanskyj, PA · OLYMPUS EXECUTIVE REALTY INC

  19. 420 Hillcrest Dr SE — photo42Active

    $279,900

    3 bd · 2 ba · 1,556 sqft

    420 Hillcrest Dr SE, Winter Haven, FL

    Raymond Thomas · STAR BAY REALTY CORP.

  20. 1406 Meadow Dr NE — photo21Active

    $130,000

    3 bd · 2 ba · 1,678 sqft

    1406 Meadow Dr NE, Winter Haven, FL

    Cesar Estrada, PA · EXP REALTY LLC

  21. 2771 Adeline Ave — photo1Active

    $296,990

    4 bd · 2 ba · 1,574 sqft

    2771 Adeline Ave, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  22. 86 Lake Daisy Blvd — photo27Active

    $269,999

    2 bd · 2 ba · 1,826 sqft

    86 Lake Daisy Blvd, Winter Haven, FL

    Steven Torres · DALTON WADE INC

  23. 2767 Adeline Ave — photo1Active

    $298,990

    4 bd · 2 ba · 1,574 sqft

    2767 Adeline Ave, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  24. 609 Maggie Cir — photo23Active

    $224,900

    3 bd · 2 ba · 1,430 sqft

    609 Maggie Cir, Winter Haven, FL

    Lynne Powers · POWERS REAL ESTATE SOLUTIONS LLC

12…20

About Homes Under $300K in Winter Haven, FL

Homes Under $300K in Winter Haven, FL: 464 active listings as of October 17, 2026, 22:12 UTC.

Property types among these 464 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence29363.1%
Condominium6213.4%
Manufactured Home6113.1%
Townhouse224.7%
Mobile Home51.1%

Homes Under $300K in nearby cities

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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.
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  • Explore Winter Haven homes

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    Thomas O'Leary

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    Lic. #BK3453168

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    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 28, 2026

    Median sale price
    $270,000$196,000–$334,500 typical range
    Price per sq. ft.
    $160
    Sales
    175
    Paid in cash
    37.7%

    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.