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Winter Garden homes: prices, market and costs

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$610,00011.9% up over the year, May 2026
Months of supply3.6May 2026
Listing age80Median days on market, active listings, September 2026
Active listings62637% with a price cut, September 2026

Winter Garden is about 20.7 road miles from Disney World, measured from the center of town. Compare other towns.

Market balance, my own reading

67 of 100. This market leans to sellers.

  • Months of supply7330 of 100 points. 2 months or less scores 100, 8 or more scores 0, straight line between.
  • Listing age (median days on market, active listings)4020 of 100 points. 20 days or less scores 100, 120 or more scores 0, straight line between.
  • Sale-to-list ratio8220 of 100 points. 100% or more scores 100, 92% or less scores 0, straight line between.
  • One-year change in median sale price10015 of 100 points. +8% or more scores 100, -8% or less scores 0, straight line between.
  • Share of listings with a price cut3715 of 100 points. 15% or less scores 100, 50% or more scores 0, straight line between.

This is my own descriptive model, not an industry index and not a forecast. It turns five published figures into one 0 to 100 reading, weighted as shown, and higher favors sellers. Above 65 leans to sellers, 45 to 65 is balanced, below 45 leans to buyers. Months of supply, sale-to-list and the price change are Redfin closed sales for May 2026; listing age and price cuts are Realtor.com listings for September 2026. It describes those months and says nothing about where prices go next.

What it means

The numbers, in plain words.

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 value

Buying in Winter Garden

37% of active listings carried a price cut in September 2026. A home listed longer than the 80-day median listing age is often where the conversation about price, credits and repairs starts.

Talk to me

New 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, scanned November 2, 2026. Published homes, availability changes daily. Builder prices change without notice, so confirm before relying on any figure.

Cost to own

The price is only the first number.

Total millage, 202517.41Orange County-wide, not the rate for every address
Tax on the median home$9,896Per year, with homestead, estimated below
Citizens HO3 average$2,692Per year, 2026
Homestead exemption$51,411Maximum, 2026

How the tax estimate works

  1. Price: the Winter Garden median sale price, May 2026, $610,000. A new owner is assessed at about market value, so this uses the price as the assessed value.
  2. School taxes: $610,000 less the $25,000 exemption that applies to school taxes is $585,000. At 6.4490 school mills (2025), that is $3,773.
  3. Every other tax: $610,000 less the full $51,411 homestead exemption (2026) is $558,589. At 10.9610 non-school mills (the 17.4100 county-wide total less the school rate), that is $6,123.
  4. Estimated total: $9,896 a year, before non-ad valorem assessments such as CDD or solid waste fees, which are billed separately.

School taxes get only the first $25,000 of the homestead exemption; the rest of it applies to non-school taxes only. The millage is a Orange County-wide figure, not the rate for every address: city and district levies differ, so get an estimate for the exact home.

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 my market balance reading (my own descriptive model, not a forecast), 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 have current Winter Garden listings been on the market?

In September 2026, the median active listing in Winter Garden had been on the market 80 days, and 37% of listings carried a price cut (Realtor.com). That is the age of homes still for sale, not how long a sale takes from listing to closing. A listing that has sat longer than that 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

Sources

Your next chapter, by the numbers.

Search the market, read the data, or talk to me. The numbers are the same either way.

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