Windsor at Westside

It's a gated, pool-oriented community close to the theme parks, with Walt Disney World about 18 minutes away and Universal Orlando roughly 32 minutes out. Assigned schools include Westside K-8 School, Celebration High School, and Osceola County School for the Arts. It leans heavily toward resort-style and vacation-home living, so it suits buyers who value amenities and proximity to Orlando's attractions.

The median list price is $518,000, with active homes ranging from $37,500 all the way to $1,100,000, so there's a wide spread depending on size and finishes. Only two current listings are priced above $1 million, meaning most inventory sits in the mid-$500s and below. Compared with other resort-style Kissimmee homes for sale, it's competitively positioned for the amenities you get.

Expect a median list price around $518,000 and a median sold price near $495,000 over the past year. That works out to roughly $185 per square foot on a median home of about 2,492 square feet. Nearby communities like Solara offer useful price comparisons if you're weighing options.

There are 97 active listings and 95 homes sold in the last 12 months, so supply and demand are fairly balanced. Homes take a median of 55 days to sell, and sellers are getting about 96% of their asking price on average. That gives buyers reasonable negotiating room without the frenzy of a red-hot market.

The median HOA runs about $584 a month, which reflects the gated access and resort-style amenities common here. Median property taxes come in around $8,350 a year. Both are worth factoring into your monthly budget alongside the mortgage, especially if you're comparing against Storey Lake or other amenity-rich communities.