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Homes for Sale in Winter Park, FL

There are 19 homes for sale in Winter Park, FL on Path Explore right now, from $245,000 to $3,890,000, with a median asking price of $669,000. They run from 2 to 6 bedrooms.

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Winter Park market snapshot

• 19For sale
• $669,000Median ask
• $245K to $3.9MPrice range
• 2 to 6Bedrooms

Figures are asking prices for listings currently on the Path Explore map, not sold comps.

Current Winter Park listings

• 620 Virginia Dr $3,890,000 · 6 bd
• 609 S Phelps Ave $2,800,000 · 5 bd
• 948 Poinciana Ln $2,750,000 · 4 bd
• 648 Worthington Dr $2,700,000 · 5 bd
• 2343 Versailles Ave $1,865,000 · 4 bd
• 150 E Reading Way $1,495,000
• 1431 Palm Ave $850,000 · 2 bd
• 950 S Kentucky Ave $799,000 · 4 bd
• 2286 Marsh Sedge Ln $770,000 · 4 bd
• 1409 Sunset Dr $669,000 · 2 bd
• 2627 Ambergate Rd $575,000 · 4 bd
• 1652 Berkshire Ave $549,900 · 3 bd
• 7384 Grand Ave $450,000 · 3 bd
• 1955 Eland Ave $439,000 · 3 bd
• 4963 Tangerine Ave $375,000 · 4 bd
• 1915 Carrigan Ave $299,900 · 3 bd
• 1333 S Denning Dr $299,000 · 2 bd
• 2477 Tahoe Cir Unit 2477 $254,000 · 2 bd

See all 19 Winter Park listings on the interactive map ›

What Winter Park buyers should actually check

Most portals stopped showing the numbers that decide a deal. On Path Explore you can ask the AI concierge, for any Winter Park listing, the things that actually matter:

• Flood zone, read from FEMA's National Flood Hazard Layer.
• Condo special-assessment risk, estimated from the building's age under Florida's 2025 SIRS reserve law.
• True monthly cost, a rough all-in estimate covering mortgage, taxes, HOA and Florida's insurance premiums.

Ask the map about a Winter Park home ›

Winter Park buyer FAQ

How much does a home in Winter Park cost?

Across the 19 priced Winter Park listings on Path Explore right now, the median is $669,000 and the range runs from $245,000 to $3,890,000. That is what is on the map today, not a historical average.

Is Winter Park in a flood zone?

Parts of Winter Park sit in FEMA high-risk flood zones and parts do not. On the Path Explore map you can ask the AI for the flood zone on any specific Winter Park listing, read from FEMA's National Flood Hazard Layer.

Do condos in Winter Park have special assessment risk?

Older three-plus-story Florida condos can, and the 2025 SIRS reserve law made those reserve studies mandatory. Path Explore flags likely assessment exposure from a building's year built. Always verify with the association's own documents.

What will a Winter Park home really cost per month?

Path Explore gives a rough all-in monthly estimate per listing, mortgage plus taxes plus HOA plus insurance, so the asking price is not the only number you see. Confirm it with a lender and a real insurance quote before you rely on it.