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Winter Haven, FL Homes for Sale | 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 814 Listings
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Homes for Sale in Winter Haven, FL

24 of 814 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 2037 San Marcos Dr SE #325 — photoNew9Active

    $180,000

    2 bd · 2 ba · 826 sqft

    2037 San Marcos Dr SE #325, Winter Haven, FL

    Hoover Yap · PRIMESTATE REALTY, INC.

  2. 516 McKenna Dr — photoNew18Active

    $278,000

    3 bd · 2 ba · 1,844 sqft

    516 McKenna Dr, Winter Haven, FL

    Jesse Carriedo · REALTYCITY INC

  3. 928 Sunshine Way SW — photoNew37Active

    $195,000

    2 bd · 1 ba · 915 sqft

    928 Sunshine Way SW, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  4. 926 Sunshine Way SW — photoNew29Active

    $205,000

    2 bd · 1 ba · 915 sqft

    926 Sunshine Way SW, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  5. 5780 Lakeside Landings Blvd — photoNew45Active

    $290,000

    4 bd · 3 ba · 2,526 sqft

    5780 Lakeside Landings Blvd, Winter Haven, FL

    Monica Hawkinson · LIVE FLORIDA REALTY

  6. 384 Holly Ridge Rd — photoNew68Active

    $339,975

    3 bd · 2 ba · 2,066 sqft

    384 Holly Ridge Rd, Winter Haven, FL

    Vivian Ortiz · OAK AVENUE REAL ESTATE LLC

  7. 9457 Waterford Oaks Dr — photo24Active

    $710,000

    3 bd · 3 ba · 3,292 sqft

    9457 Waterford Oaks Dr, Winter Haven, FL

    Amy Riggleman · SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

  8. 1501 N Lake Howard Dr — photoNew65Active

    $375,000

    3 bd · 2 ba · 2,200 sqft

    1501 N Lake Howard Dr, Winter Haven, FL

    Kennedy Matthews · JULIE MATTHEWS GROUP LLC

  9. 3937 Giorgio Dr — photoNew6Active

    $344,720

    4 bd · 2 ba · 1,840 sqft

    3937 Giorgio Dr, Winter Haven, FL

    Bryan Sumner · MERITAGE HOMES OF FL REALTY

  10. 1688 Teagan Ln — photo21Active

    $250,000

    3 bd · 2 ba · 1,432 sqft

    1688 Teagan Ln, Winter Haven, FL

    Luana Oliveira · ORANGE SLICE PROPERTIES

  11. 235 6th St NW #507 — photo44Active

    $140,000

    1 bd · 1 ba · 714 sqft

    235 6th St NW #507, Winter Haven, FL

    Blake Denz · KELLER WILLIAMS REALTY

  12. 1140 Tyler Loop — photoNew36Active

    $308,000

    3 bd · 3 ba · 1,933 sqft

    1140 Tyler Loop, Winter Haven, FL

    Darcy Aguilera · REALTY OF AMERICA

  13. 1643 Linz Ct — photo19Active

    $197,000

    2 bd · 2 ba · 1,369 sqft

    1643 Linz Ct, Winter Haven, FL

    Jesse Carriedo · REALTYCITY INC

  14. 1151 Carefree Cove Dr — photo24Active

    $399,000

    3 bd · 2 ba · 1,734 sqft

    1151 Carefree Cove Dr, Winter Haven, FL

    Jonathan Minerick · HOMECOIN.COM

  15. 230 Shore Dr — photo72Active

    $415,000

    3 bd · 2 ba · 1,502 sqft

    230 Shore Dr, Winter Haven, FL

    Perry Kemp · LPT REALTY, LLC

  16. 138 Saint Kitts Cir — photo32Active

    $259,000

    3 bd · 2 ba · 1,248 sqft

    138 Saint Kitts Cir, Winter Haven, FL

    Erik McGinnis · HOMEVEST REALTY

  17. 1010 Edgewater Dr — photoOpen house Sun, Nov 8 · 11:00 AM48Active

    $795,000

    4 bd · 3 ba · 2,346 sqft

    1010 Edgewater Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  18. 3429 Sherry Ave — photo38Active

    $319,999

    5 bd · 2 ba · 1,744 sqft

    3429 Sherry Ave, Winter Haven, FL

    Sandra Canales · LA ROSA REALTY PRESTIGE

  19. 3115 Captain Jax Way — photo21Active

    $201,790

    3 bd · 3 ba · 1,386 sqft

    3115 Captain Jax Way, Winter Haven, FL

    Ben Goldstein · LENNAR REALTY

  20. 1606 Eagle Pond Dr — photo41Active

    $155,000

    2 bd · 2 ba · 1,017 sqft

    1606 Eagle Pond Dr, Winter Haven, FL

    Lienyvette Grimaldo · MAZELG REALTY

  21. 6052 Kaley Dr — photoOpen house Sat, Nov 7 · 11:00 AM56Active

    $375,000

    4 bd · 3 ba · 2,200 sqft

    6052 Kaley Dr, Winter Haven, FL

    Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

  22. 3223 Avenue S NW — photo33Active

    $182,900

    2 bd · 1 ba · 728 sqft

    3223 Avenue S NW, Winter Haven, FL

    Carrie Sanchez · THE BARNETT GROUP, INC.

  23. 4462 Emerald Palms Ln — photo47Active

    $975,000

    4 bd · 3 ba · 2,825 sqft

    4462 Emerald Palms Ln, Winter Haven, FL

    Stephen Hachey · FLAT FEE MLS REALTY

  24. 1828 Avenue O SW — photo6Active

    $215,000

    3 bd · 2 ba · 1,354 sqft

    1828 Avenue O SW, Winter Haven, FL

    Cliff Glansen · FLATFEE.COM

12…34

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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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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.

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

October 2026 · This period is still settling

Winter Haven 12-month median sale price trend

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 126 sales · as of Oct 30, 2026

Homes that sold · County records, as of Oct 15, 2026

Median sale price
$300,000$242,000–$1,281,875 typical range
Price per sq. ft.
$167
Sales
146
Paid in cash
44.5%

Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

Median list price
$295,000
Homes for sale
713
Median days on market
52 days

Price trend · Assessor repeat sales, as of Oct 31, 2026

Year-over-year
1.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size
1,632 sq. ft.
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  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

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