WINDSOR HILLS, VENTURA AT WINDSOR HILLS
Homes for Sale in KISSIMMEE, FL

Ventura at Windsor Hills is a gated, guard-staffed community of 84 homes built in a single year (2005), with a median living area of 1,246 square feet — a compact footprint consistent with a community built for turnkey use rather than long-term customization.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

WINDSOR HILLS, VENTURA AT WINDSOR HILLS is a small community — 10 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.

In ZIP 34747, 1,240 homes are on the market and 12% are under contract — a slower corner of KISSIMMEE.

Across Osceola County, 4,437 homes are active and 1,149 pending (21% under contract).

Homes here are condominium.

ZIP and county figures describe the wider market, not WINDSOR HILLS, VENTURA AT WINDSOR HILLS specifically. Momentum Research analysis of MLS records.

Every home in Ventura at Windsor Hills was built in 2005, so there is no older-versus-newer-section dynamic to navigate. What you are evaluating instead is how well each individual unit has been maintained and updated over roughly two decades, since the shell, layout, and original finish level were largely standardized across the community.

The 0% homestead share is the structural fact to plan around. A community built almost entirely around non-primary-residence use tends to see different turnover patterns, different maintenance discipline from one owner to the next, and a buyer pool that is thinking about rental performance or a secondary property rather than a full-time move-in. The amenity set — clubhouse, pool, tennis courts, dog park, and a guard-gated entry — supports that use case directly; confirm current access and any rental restrictions with the HOA before assuming how a given unit can be used.

With active inventory this thin, timing and access matter more than usual — we track new listings here as they hit and can walk you through condition and update history unit by unit, since the community's uniform build year means that detail is where the real differences live. We will also give you a straight read on the non-homestead concentration and what it means for your specific goal, whether that is a rental play, a secondary property, or a resale exit.

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