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.

Stellar MLS sales records identify 15 homes in Windsor Hills Ventura At Windsor Hills that have changed hands since 2008, built between 2005 and 2006 (median 2005), with a median living area of about 1,246 sq ft and a typical 3-bedroom, 2-bath layout; 93% are condominiums. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

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 too small for its own price trend, so here is the market around it.

In ZIP 34747, 1,258 homes are on the market and 12% are under contract — a slower corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

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.

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.

Listings in this community report association dues of about $330 per month ($3,960 a year) - the median AssociationFee across 4 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

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