What it costs to own a home in Winter Garden

Owning a single-family home at the median sale price in Winter Garden ($695,000) costs about $4,871 a month with 20% down at 6.8%: $3,625 for the mortgage, $898 property tax and $348 insurance. Homes in an HOA or CDD add about $164 a month for an HOA (93% of house listings report one) and about $177 for a CDD (8%).

Sellers in Winter Garden report a median tax bill of about 1.16% of the price. That number is low for a buyer: Florida's Save Our Homes cap holds down a long-time owner's assessment, and it resets after a sale. We budget 1.55% of the price for a new owner until the county's estimator says otherwise.

95% of recent listings report an HOA or condo association fee, median $2,460 a year. For single-family listings it's 93%, median $1,968 a year. Of listings that say whether a CDD applies, 8% have one, median $2,127 a year on the tax bill. A blank fee on a listing usually means no association but isn't confirmed, so these are shares of listings that report a fee, not of all homes. Fees vary a lot by community, so check the community pages below before you compare homes.

Homes that sold recently spent a median 35 days on the market and sold for 96% of their original asking price. There are 668 homes for sale right now.

Stellar MLS via Repliers listings and sales in Winter Garden, 2026-01 to 2026-10, one data point per address (1,428 homes, 465 of them closed sales by closing date). Prices are closed sales only; asking prices are shown separately. This covers housing costs, not utilities, upkeep or the rest of a household budget. The mortgage, tax and insurance math uses the same assumptions as every monthly estimate on this site: 20% down, 6.8% rate, 30-year loan, tax 1.55% and insurance 0.6% of the price a year. Insurance in particular varies by age, roof and flood zone, so get quotes on any home you're serious about.