CENTURY 21 Edge
← All of Winter Haven

Winter Haven homes $400K – $500K

50 active listings in Winter Haven, Florida

119 SUNFISH DRIVE

$419,000

119 SUNFISH DRIVE, WINTER HAVEN

3 bd · 2.5 ba · 2,613 sqft

154 2ND STREET SW Unit 7

$495,000

154 2ND STREET SW Unit 7, WINTER HAVEN

2 bd · 2.5 ba · 1,640 sqft

2734 ROCHELLE DRIVE

$450,000

2734 ROCHELLE DRIVE, WINTER HAVEN

4 bd · 2.5 ba · 2,829 sqft

464 FISH HAWK DRIVE

$449,489

464 FISH HAWK DRIVE, WINTER HAVEN

6 bd · 4.5 ba · 3,920 sqft

1755 BETH LANE

$435,000

1755 BETH LANE, WINTER HAVEN

3 bd · 2 ba · 2,702 sqft

139 WODEN WAY

$429,500

139 WODEN WAY, WINTER HAVEN

4 bd · 3.5 ba · 2,766 sqft

5009 STRADA DRIVE

$425,000

5009 STRADA DRIVE, WINTER HAVEN

4 bd · 2.5 ba · 2,434 sqft

204 LAKE MARIAM COURT

$420,000

204 LAKE MARIAM COURT, WINTER HAVEN

3 bd · 2 ba · 2,117 sqft

742 SANTA MARIA DRIVE

$409,900

742 SANTA MARIA DRIVE, WINTER HAVEN

3 bd · 3 ba · 2,592 sqft

4123 ISLAND LAKES DRIVE

$470,000

4123 ISLAND LAKES DRIVE, WINTER HAVEN

4 bd · 2 ba · 1,990 sqft

1061 SAWGRASS DRIVE

$449,900

1061 SAWGRASS DRIVE, WINTER HAVEN

3 bd · 2 ba · 2,069 sqft

795 CROSSTOWER DRIVE

$435,000

795 CROSSTOWER DRIVE, WINTER HAVEN

3 bd · 2 ba · 1,572 sqft

300 GREENFIELD ROAD

$425,000

300 GREENFIELD ROAD, WINTER HAVEN

4 bd · 2.5 ba · 2,350 sqft

1108 SAWGRASS DRIVE

$422,999

1108 SAWGRASS DRIVE, WINTER HAVEN

2 bd · 2 ba · 1,533 sqft

44 BREVARD DRIVE

$495,500

44 BREVARD DRIVE, WINTER HAVEN

3 bd · 2 ba · 2,269 sqft

120 LAKE MARIAM WAY

$415,000

120 LAKE MARIAM WAY, WINTER HAVEN

4 bd · 2.5 ba · 2,308 sqft

2011 RECKER HIGHWAY

$405,000

2011 RECKER HIGHWAY, WINTER HAVEN

4 bd · 2 ba · 2,000 sqft

405 VALLEY COURT

$465,000

405 VALLEY COURT, WINTER HAVEN

4 bd · 2 ba · 2,463 sqft

4162 ROBERTA DRIVE

$424,999

4162 ROBERTA DRIVE, WINTER HAVEN

5 bd · 3.5 ba · 2,905 sqft

344 RUBY LAKE LOOP

$409,000

344 RUBY LAKE LOOP, WINTER HAVEN

4 bd · 2 ba · 2,215 sqft

280 SANTA ROSA DRIVE

$430,000

280 SANTA ROSA DRIVE, WINTER HAVEN

3 bd · 2 ba · 2,251 sqft

75 SUNSET VIEW DRIVE UNIT 75

$405,000

75 SUNSET VIEW DRIVE UNIT 75, WINTER HAVEN

2 bd · 2 ba · 2,249 sqft

6704 WINTERSET GARDENS ROAD

$425,000

6704 WINTERSET GARDENS ROAD, WINTER HAVEN

3 bd · 2 ba · 2,418 sqft

205 THOMAS COURT

$440,000

205 THOMAS COURT, WINTER HAVEN

3 bd · 2.5 ba · 2,352 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
© 2026 CENTURY 21® and the CENTURY 21 Logo are registered service marks owned by Century 21 Real Estate LLC. Sunseria Real Estate Group LLC d/b/a CENTURY 21 Edge fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with, or related to Century 21 Real Estate LLC nor any of its affiliated companies.

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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 September 20, 2026 at 5:52 PM UTC. The listing information on this page last changed on September 20, 2026 at 5:52 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 September 20, 2026 at 5:52 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: September 20, 2026 at 5:52 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.