Regal Oaks At Old Town

It's a gated, resort-style community in Kissimmee's tourism corridor, which appeals to both full-time residents and second-home buyers. You're about 22 minutes from Walt Disney World and 32 from Orlando International Airport, and assigned schools include Westside K-8 and Celebration High School. The compact townhome layouts suit anyone who wants low-maintenance living near the parks.

Not by area standards — the median list price is $299,000, with active listings ranging from $264,900 to $364,900. That's a comparatively accessible way into a gated community this close to the theme parks, and it stacks up well against pricier options like Storey Lake.

Homes here average about $210 per square foot, and with a median size around 1,350 square feet, most list near the $299,000 median. Over the past 12 months, 26 homes sold at a median price of $294,000, so buyers can expect to pay close to current asking prices.

It's balanced and steady. There are 29 active listings with a median of 66 days on market, and sellers have been getting about 97% of asking over the past year. That combination gives buyers room to negotiate without the frenzy you'll find in tighter segments.

The median HOA runs about $621 a month, which is typical for a gated, amenity-focused community like this and often covers exterior upkeep and shared facilities. Property taxes come in around $4,062 a year at the median. Factor both into your monthly budget alongside the purchase price.