What it costs to own a home in Winter Park

Owning a single-family home at the median sale price in Winter Park ($610,000) costs about $4,274 a month with 20% down at 6.8%: $3,181 for the mortgage, $788 property tax and $305 insurance. Homes in an HOA or CDD add about $81 a month for an HOA (15% of house listings report one).

Sellers in Winter Park report a median tax bill of about 0.93% 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.

40% of recent listings report an HOA or condo association fee, median $4,452 a year. For single-family listings it's 15%, median $977 a year. Of listings that say whether a CDD applies, 0% have one. 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 20 days on the market and sold for 96% of their original asking price. There are 340 homes for sale right now.

Stellar MLS via Repliers listings and sales in Winter Park, 2026-01 to 2026-10, one data point per address (718 homes, 290 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.