Windsor at Westside

It's best understood as a resort-style, gated community geared toward vacation homes and short-term rentals rather than traditional year-round living. With 80 of 82 active listings offering private pools and roughly 49 behind gates, it appeals to buyers who want amenities and rental potential close to the parks. Families who want a quieter setting might also look at nearby Kissimmee homes for sale.

It sits in the mid-to-upper range for the area, with a median list price of about $526,500 and prices spanning from $37,500 to $1,100,000. Only one active listing crosses the $1M mark, so most inventory clusters well below that ceiling. At an average of $183 per square foot, you're paying for pool homes and resort amenities.

Over the last 12 months, 79 homes sold at a median price of $495,000, while today's active listings carry a median of $526,500. The typical home runs around 3,142 square feet at about $183 per square foot. For comparison shopping, communities like Solara offer a similar vacation-home profile.

It's steady and buyer-friendly on time: homes are taking a median of 57 days to sell, and sellers are netting about 97% of their asking price. With 82 active listings and 79 sales in the past year, supply and demand are fairly balanced, giving buyers room to negotiate.

Budget carefully here — the median HOA runs about $584 per month, which typically covers the resort amenities and gated access, and the median property tax is roughly $8,764 per year. If you plan to rent, the median rent of about $3,250 per month helps offset those carrying costs. Lower-fee alternatives exist across other Kissimmee homes for sale.