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Winter Haven, FL Homes for Sale — Page 17 | Realty.com
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3 bedsNew constructionWith a pool

Homes for Sale in Winter Haven, FL

Homes for Sale in Winter Haven, FL

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24 of 778 Listings
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Homes for Sale in Winter Haven, FL

24 of 778 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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  1. 4919 St James Dr — photoPrice Reduced31Active

    $299,900

    3 bd · 2 ba · 1,577 sqft

    4919 St James Dr, Winter Haven, FL

    Crystal Taylor · LIVE FLORIDA REALTY

  2. 1015 Robin Ln — photoPrice Reduced43Active

    $359,900

    3 bd · 2 ba · 1,632 sqft

    1015 Robin Ln, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  3. 315 Lanceolate Dr — photoPrice Reduced71Active

    $469,000

    3 bd · 2 ba · 2,153 sqft

    315 Lanceolate Dr, Winter Haven, FL

    Veronica Bard · LA ROSA REALTY PRESTIGE

  4. 362 Holly Ridge Rd — photoPrice Reduced23Active

    $249,900

    3 bd · 2 ba · 1,355 sqft

    362 Holly Ridge Rd, Winter Haven, FL

    Katrina Asher · MILLSHIRE REALTY

  5. 1700 6th St NW #a38 — photo33Active

    $78,800

    2 bd · 1 ba · 840 sqft

    1700 6th St NW #a38, Winter Haven, FL

    Shelby Beasley · S & D REAL ESTATE SERVICE LLC

  6. 1500 Avenue G NE — photo60Active

    $359,000

    3 bd · 2 ba · 2,280 sqft

    1500 Avenue G NE, Winter Haven, FL

    Suzie Rudd · KELLER WILLIAMS REALTY SMART 1

  7. 139 Avenue G SE — photoPrice Reduced18Active

    $170,000

    2 bd · 1 ba · 896 sqft

    139 Avenue G SE, Winter Haven, FL

    Paola Arias · MBA REALTY GROUP, INC

  8. 221 Avenue C NE — photoPrice Reduced14Active

    $215,000

    3 bd · 2 ba · 720 sqft

    221 Avenue C NE, Winter Haven, FL

    Paola Arias · MBA REALTY GROUP, INC

  9. 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

  10. 709 Sarner Pass Way — photoPrice Reduced16Active

    $279,900

    4 bd · 3 ba · 3,016 sqft

    709 Sarner Pass Way, Winter Haven, FL

    Jesse Carriedo · REALTYCITY INC

  11. 1776 6th St NW #807 — photo35Active

    $162,000

    2 bd · 2 ba · 1,347 sqft

    1776 6th St NW #807, Winter Haven, FL

    Lisa Simpson · KELLER WILLIAMS REALTY SMART 1

  12. 41 Greenfield Ct — photoPrice Reduced28Active

    $350,000

    3 bd · 2 ba · 2,054 sqft

    41 Greenfield Ct, Winter Haven, FL

    Steven Smith, PA · LOCKHART & ASSOCIATES INC

  13. 2390 29th St NW — photoPrice Reduced40Active

    $199,900

    4 bd · 2 ba · 1,048 sqft

    2390 29th St NW, Winter Haven, FL

    John Scalia · EXP REALTY LLC

  14. 1404 Axel Cir — photoPrice Reduced22Active

    $359,000

    5 bd · 3 ba · 2,523 sqft

    1404 Axel Cir, Winter Haven, FL

    Carlos DeJesus · EXIT REALTY 4CORNERS

  15. 1328 3rd St NE — photoPrice Reduced11Active

    $199,999

    3 bd · 2 ba · 1,118 sqft

    1328 3rd St NE, Winter Haven, FL

    Dewayne Smith · CHARLES RUTENBERG REALTY ORLANDO

  16. 333 Lake Howard Dr NW #211B — photo29Active

    $149,900

    3 bd · 2 ba · 1,218 sqft

    333 Lake Howard Dr NW #211B, Winter Haven, FL

    Steven Smith, PA · LOCKHART & ASSOCIATES INC

  17. 1802 White Elephant Loop — photo20Active

    $314,900

    4 bd · 2 ba · 1,863 sqft

    1802 White Elephant Loop, Winter Haven, FL

    Chris Courtney · PREFERRED REAL ESTATE BROKERS

  18. 444 Avenue B NE — photoPrice Reduced15Active

    $179,000

    4 bd · 2 ba · 1,464 sqft

    444 Avenue B NE, Winter Haven, FL

    Malak Hassani Benbachir · KELLER WILLIAMS REALTY SMART 1

  19. 6666 Briarhill Dr NE — photo34Active

    $140,000

    2 bd · 2 ba · 1,144 sqft

    6666 Briarhill Dr NE, Winter Haven, FL

    EJ Jimenez · KELLER WILLIAMS ADVANTAGE III

  20. 308 Vaniman Ave — photoPrice Reduced20Active

    $229,900

    3 bd · 2 ba · 1,228 sqft

    308 Vaniman Ave, Winter Haven, FL

    Robert Salmons · ENTERA REALTY LLC

  21. 611 Morgan Rd — photoPrice Reduced86Active

    $695,000

    3 bd · 3 ba · 2,077 sqft

    611 Morgan Rd, Winter Haven, FL

    Brittanee Brossart · KELLER WILLIAMS REALTY SMART

  22. 372 Lake Daisy Cir — photoPrice Reduced62Active

    $299,000

    4 bd · 2 ba · 1,907 sqft

    372 Lake Daisy Cir, Winter Haven, FL

    Chrissi Jasso · ASSOCIATE REALTY

  23. 233 Kensington View Blvd — photoPrice Reduced18Active

    $270,000

    3 bd · 2 ba · 1,491 sqft

    233 Kensington View Blvd, Winter Haven, FL

    Christopher Gallon, PA · EXP REALTY LLC

  24. 1475 S Lake Howard Dr — photoPrice Reduced79Active

    $520,000

    4 bd · 4 ba · 2,118 sqft

    1475 S Lake Howard Dr, Winter Haven, FL

    Deanna Stone · THE STONES REAL ESTATE FIRM

1…161718…33

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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 99.7% 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.
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    TO

    Thomas O'Leary

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    Lic. #BK3453168

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