Homes for Sale in Winter Haven, FL Under $500K

Looking at homes under $500K for sale in Winter Haven, FL? This page brings together current listings, local market numbers and answers to common questions. One of the FL communities we know and serve. Andi Gamble | LPT Realty can help you tour homes and make a confident offer.

Market snapshot

• Active listings: 35+
• Median list price: $294,997
• Median days on market: 1
• Updated: 2026-10-15

Current listings

• 668 REGGIE ROAD, WINTER HAVEN — $285,000 (3 bd, 2 ba, 1,432 sqft)
• 240 WESTWOOD AVENUE, WINTER HAVEN — $249,900 (3 bd, 2 ba, 1,140 sqft)
• 125 WHITTIER LANE, WINTER HAVEN — $225,000 (3 bd, 2 ba, 1,245 sqft)
• 6733 KENSINGTON DRIVE NE, WINTER HAVEN — $165,500 (2 bd, 2 ba, 1,176 sqft)
• 1767 VANILLA STREET, WINTER HAVEN — $333,090 (4 bd, 3 ba, 2,039 sqft)
• 1764 VANILLA STREET, WINTER HAVEN — $410,620 (4 bd, 3 ba, 2,292 sqft)
• 6245 BOTTICELLA BOULEVARD, WINTER HAVEN — $294,990 (5 bd, 3 ba, 2,112 sqft)
• 219 TERRANOVA BOULEVARD, WINTER HAVEN — $428,000 (5 bd, 3 ba, 2,549 sqft)
• 703 AVENUE L SE, WINTER HAVEN — $278,000 (4 bd, 2 ba, 1,830 sqft)
• 5365 SAN PIETRO DRIVE, WINTER HAVEN — $319,999 (4 bd, 3 ba, 2,039 sqft)
• 138 GROVE BRANCH ROAD, WINTER HAVEN — $289,000 (4 bd, 2 ba, 1,851 sqft)
• 1759 VANILLA STREET, WINTER HAVEN — $364,745 (5 bd, 3 ba, 2,470 sqft)

Listing information courtesy of Stellar MLS.

Frequently asked questions

How many homes under $500K are for sale in Winter Haven, FL?

There are at least 35 active homes under $500K for sale in Winter Haven, FL as of 2026-10-15, based on listing data from the local MLS.

What is the median list price of homes under $500K in Winter Haven, FL?

The median list price of active homes under $500K in Winter Haven, FL is $294,997, based on a sample of 35 current listings.

How long have homes under $500K in Winter Haven, FL been on the market?

Active homes under $500K in Winter Haven, FL have been listed for a median of 1 day.

How can I see every home for sale in Winter Haven, FL?

Use the full home search to browse every active listing in Winter Haven, FL, save favorites and get alerts when new homes come on the market. Andi Gamble | LPT Realty can also help you schedule showings.

Explore more

• About Winter Haven
• Homes for Sale in Winter Haven, FL
• Single-Family Homes for Sale in Winter Haven, FL
• Homes for Sale in Winter Haven, FL Under $1M
• Homes for Sale in Winter Haven, FL Under $300K
• Homes for Sale in Winter Haven, FL Under $400K
• Homes for Sale in Winter Haven, FL Under $750K

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