Selling in Winter Garden
Winter Garden had 3.6 months of supply in May 2026, and sellers collected 98.5% of asking. The median sale price is up 11.9% over the year, so the comparable sales that count are the recent ones.
Get my home valueHomes for sale in Winter Garden
An old downtown with a new story. Winter Garden has a historic downtown on the National Register of Historic Places, with the West Orange Trail running through it.
Winter Garden by the numbers
Know the town before you fall for a house.
Median sale price$610,000
Months of supply3.6
Days on market80
Active listings626
Winter Garden is about 20.7 road miles from Disney World, measured from the center of town. Compare other towns.
Market balance
67 of 100. This market leans to sellers.
- Supply7330 points of the reading
- Speed4020 points of the reading
- Pricing8220 points of the reading
- Price trend10015 points of the reading
- Demand3715 points of the reading
A 0 to 100 reading built from five published inputs: months of supply, days on market, sale-to-list ratio, one-year price change and the share of listings without a price cut. Higher scores favor sellers.
What it means
The numbers, in plain words.
Buying in Winter Garden
37% of active listings carried a price cut in September 2026. A home listed past the 80-day median is often where the conversation about price, credits and repairs starts.
Talk to meNew construction
New homes in Winter Garden, as of this week.
- Homes available124
- Median asking price$723,332
- Price cuts, last 30 days47 of 122
- Communities15
Counted from builders' published homes on November 2026. Builder prices change without notice, so confirm before relying on any figure.
Cost to own
The price is only the first number.
Total millage, 202517.41
Tax on the median home$9,725
Citizens HO3 average$2,692
Homestead exemption$51,411
Many newer communities add HOA dues and a CDD assessment. Read how those fees work.
What sold
Homes sold in Winter Garden, by type.
- Single-family82%
- Townhome12%
- Condo6%
590 closed sales, June 2025 to May 2026.
Common questions about Winter Garden
Should I buy a home in Winter Garden right now?
The market is leaning toward sellers, at 67 of 100 on the market balance reading, with 3.6 months of supply in May 2026. Nothing here predicts prices. The right time for you depends on the whole monthly cost: price, deposit, rate, term, taxes, insurance and any HOA or CDD.
How does Winter Garden compare to Orange County?
The median sale price is 35.6% above the county median, at $610,000 against $449,900.
How long does it take to sell a home in Winter Garden?
In September 2026, the median active listing had been on the market 80 days, and 37% of listings carried a price cut. A home that passes the median without an offer often needs a fresh look at recent closed sales.
How much is homeowners insurance in Winter Garden?
Citizens Property Insurance reports an average HO3 premium of $2,692 a year in Orange County for 2026. Private carriers price each home on its roof age, construction year and wind features, so get a quote for the specific address.
What should I check before I make an offer?
Four things decide the real monthly cost: an insurance quote for that address, the FEMA flood map and the seller's flood disclosure, the HOA and CDD assessments, and a tax estimate at the price you'd pay. My guide on HOA and CDD fees explains the fee side.
Guides for buying in Winter Garden
- Property tax and homestead in Florida
- Home insurance and flood zones near Disney World
- HOA and CDD fees near Disney World
- Tolls and commuting around Disney World
- Can a home near Disney World be rented short term?
Sources
- City of Winter Garden, history, checked November 2, 2026
- Redfin Data Center, closed sales, data through May 2026
- Realtor.com listing data, data through September 2026
- Citizens Property Insurance policies in force, 2026 figures
- Florida Department of Revenue data book, 2025 millage
- Section 196.031, Florida Statutes, homestead exemption, 2026 amount
- Road distance from OpenStreetMap data, OSRM routing, measured November 2, 2026
- Builder websites, count of published homes, scanned November 2, 2026
Your next chapter, by the numbers.
Search the market, read the data, or talk to me. The numbers are the same either way.