David Ramirez
← All of Winter Haven

Winter Haven homes $300K – $400K

230 active listings in Winter Haven, Florida

2595 SAN MARCO WAY

$329,000

2595 SAN MARCO WAY, WINTER HAVEN

4 bd · 2 ba · 2,004 sqft

2849 CATHY BOULEVARD

$325,000

2849 CATHY BOULEVARD, WINTER HAVEN

4 bd · 2 ba · 1,928 sqft

3365 COSTELLO CIRCLE

$320,000

3365 COSTELLO CIRCLE, WINTER HAVEN

5 bd · 3 ba · 2,522 sqft

709 SARNER PASS WAY

$310,000

709 SARNER PASS WAY, WINTER HAVEN

4 bd · 2.5 ba · 3,016 sqft

212 OVERLOOK DRIVE

$300,000

212 OVERLOOK DRIVE, WINTER HAVEN

3 bd · 2 ba · 1,731 sqft

4132 MARTINDALE LOOP

$399,900

4132 MARTINDALE LOOP, WINTER HAVEN

4 bd · 3 ba · 1,894 sqft

2925 E LAKE HARTRIDGE DRIVE

$399,000

2925 E LAKE HARTRIDGE DRIVE, WINTER HAVEN

4 bd · 3 ba · 2,684 sqft

1114 BRIMSTONE CIRCLE

$399,000

1114 BRIMSTONE CIRCLE, WINTER HAVEN

4 bd · 3 ba · 2,476 sqft

3964 GIORGIO DRIVE

$388,000

3964 GIORGIO DRIVE, WINTER HAVEN

4 bd · 3 ba · 2,387 sqft

210 MEADOWBROOK BOULEVARD

$380,000

210 MEADOWBROOK BOULEVARD, WINTER HAVEN

5 bd · 3 ba · 2,696 sqft

41 GREENFIELD COURT

$379,000

41 GREENFIELD COURT, WINTER HAVEN

3 bd · 2 ba · 2,054 sqft

516 ALACHUA DRIVE

$369,000

516 ALACHUA DRIVE, WINTER HAVEN

3 bd · 2 ba · 1,699 sqft

302 STERLING DRIVE

$365,000

302 STERLING DRIVE, WINTER HAVEN

4 bd · 2 ba · 2,460 sqft

1920 ELOISE COVE DRIVE

$363,500

1920 ELOISE COVE DRIVE, WINTER HAVEN

4 bd · 3 ba · 2,888 sqft

1500 AVENUE G NE

$359,000

1500 AVENUE G NE, WINTER HAVEN

3 bd · 2 ba · 2,280 sqft

270 MEADOWBROOK BOULEVARD

$355,900

270 MEADOWBROOK BOULEVARD, WINTER HAVEN

5 bd · 3 ba · 2,696 sqft

5337 HOGAN LANE

$355,000

5337 HOGAN LANE, WINTER HAVEN

3 bd · 2 ba · 1,833 sqft

3831 POMELO DRIVE

$350,490

3831 POMELO DRIVE, WINTER HAVEN

5 bd · 3 ba · 2,077 sqft

0 38TH STREET NW

$350,000

0 38TH STREET NW, WINTER HAVEN

3 bd · 2 ba · 1,322 sqft

0 38TH STREET NW

$350,000

0 38TH STREET NW, WINTER HAVEN

3 bd · 2 ba · 1,327 sqft

1218 37TH STREET NW

$350,000

1218 37TH STREET NW, WINTER HAVEN

3 bd · 2 ba · 2,431 sqft

0 38TH STREET NW

$350,000

0 38TH STREET NW, WINTER HAVEN

3 bd · 2 ba · 1,322 sqft

0 38TH STREET NW

$350,000

0 38TH STREET NW, WINTER HAVEN

3 bd · 2 ba · 1,322 sqft

1514 HAMLIN STREET

$349,900

1514 HAMLIN STREET, WINTER HAVEN

3 bd · 2 ba · 2,035 sqft

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.

CENTURY 21 Edge
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Stellar MLS / MFRMLSCopyright © MFRMLS.com. All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated July 19, 2026 at 10:52 PM UTC. The listing information on this page last changed on July 19, 2026 at 10:52 PM UTC. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of MFR MLS. Updated on July 19, 2026 at 10:52 PM UTC.

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Southeast Florida MLSCopyright Southeast Florida Multiple Listing Service © 2026. Accuracy of listing information is not guaranteed. Listing information is provided for personal consumer, non-commercial use, solely to identify potential properties for potential purchase. All other use is strictly prohibited, is a violation of the terms of use, and may violate federal and state law. Data Last Updated: July 19, 2026 at 10:52 PM UTC.

Space Coast AORThese listings are provided by the IDX Program of Brevard County, Florida. Real Estate listings held by brokerage firms other than CENTURY 21 Edge Central Florida are marked with the IDX Logo and detailed information about them includes the name of the listing brokers. IDX information is provided exclusively for consumers'' personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed.

Beaches MLSAll information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer''s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.