Windmill Point
Homes for Sale in Kissimmee, FL

Windmill Point market snapshot (as of August 2, 2026): the median sale price is about $345K ($197 per sq ft over the trailing 12 months of closed sales), and a median 22 days on market for closed sales. The trailing-12-month median is down 1% from the prior 12 months, computed from record-level Stellar MLS closed sales (5 closings in the current window).

In ZIP 34746 (KISSIMMEE), 1,623 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.3% year over year, with a median 67 days on market. Right now 435 active and 80 pending listings put supply at about 6.7 months — a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.

Windmill Point is a community of 324 homes in Kissimmee, Osceola County, built between 1981 and 2017 (median 1999.0), with a median living area of about 2,093 square feet. 77% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

This is a compact, fully built-out enclave of late-1990s homes where the housing stock is uniform enough that updates and upkeep — not layout — set the tone. With roughly three-quarters of homes carrying a homestead exemption, turnover tends to be light.

Homes here date to a five-year build span ending in the late 1990s, which means most are approaching or past the point where original roofs, HVAC systems, and water heaters have needed attention. Buyers should treat the inspection as the main event: two homes with the same footprint can be very different purchases depending on what's been replaced. Sellers who have documented major-system updates hold a real, defensible advantage.

The homestead share — about 73% — points to a neighborhood held largely by long-term owners rather than churned by investors. That typically means fewer listings at any given moment and a stock that reflects owner-occupant maintenance. It also means a seller here isn't competing against a wall of inventory, but a buyer may need to wait for the right home to surface.

With no recent in-community closing to point to, pricing this neighborhood takes real judgment — reading condition, major-system age, and the wider Osceola market rather than copying a comp. We do that homework so sellers price to defend and buyers pay for what a home actually is, not what its vintage suggests.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.