Ventura at Windsor Hills Condo
Condos for Sale in Kissimmee, FL

Ventura at Windsor Hills Condo market snapshot (as of August 2, 2026): the median sale price is about $325K ($241 per sq ft over the trailing 12 months of closed sales), and a median 161 days on market for closed sales. The trailing-12-month median is up 0% from the prior 12 months, computed from record-level Stellar MLS closed sales (23 closings in the current window).

In ZIP 34747 (KISSIMMEE), 2,598 homes closed in the last 12 months at a median of $458K ($220/sq ft), down 3.9% year over year, with a median 74 days on market. Right now 552 active and 96 pending listings put supply at about 7.3 months — a buyer's market. See the live ZIP 34747 housing market and the Osceola County market.

Ventura at Windsor Hills Condo is a community of 262 homes in Kissimmee, Osceola County, built between 2005 and 2005 (median 2005.0), with a median living area of about 1,246 square feet. 2% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

Ventura at Windsor Hills is a compact, all-2005 condo enclave of about 90 units in Kissimmee's Windsor Hills area, close to the Osceola County tourism corridor. The homestead share is very low, so most of these units trade as second homes or rentals rather than primary residences.

With every unit built in 2005 and a median footprint near 1,246 square feet, there is little to separate one listing from another on paper. That makes condition and presentation the whole game. Two units at the same $325,000 median can be very different buys depending on updates, furnishings, and floor — and because the inventory is so consistent, an informed buyer can comp a target unit against its neighbors quickly.

The low homestead share tells you this is largely an investment and second-home market, which matters for financing, HOA rules, and resale timing. Buyers should read the condo association's budget, reserves, and rental policies as carefully as the unit itself; those documents can affect value and carrying cost more than a coat of paint. The long days-on-market figure reinforces that patience — on both sides of the table — is the operative skill here.

In a small, uniform condo community with slow turnover, the edge is knowing which specific units have shown well, what the association documents actually say, and how to price against a thin comp set. We read the reserves and rental rules before you fall for a floor plan, and we set expectations honestly on how long a sale — buy or sell — is likely to take.

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