Ashley Cove
Homes for Sale in Kissimmee, FL

Ashley Cove market snapshot (as of August 2, 2026): the median sale price is about $577K ($224 per sq ft over the trailing 12 months of closed sales), and a median 15 days on market for closed sales. The trailing-12-month median is up 10% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).

In ZIP 34744 (KISSIMMEE), 785 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.8% year over year, with a median 34 days on market. Right now 126 active and 26 pending listings put supply at about 6.6 months — a balanced market. See the live ZIP 34744 housing market and the Osceola County market.

Ashley Cove is a community of 94 homes in Kissimmee, Osceola County, built between 1981 and 2005 (median 2002.0), with a median living area of about 3,391 square feet. 79% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

Ashley Cove is a 94-home community in Kissimmee, Osceola County, built out mostly between the early 1980s and mid-2000s, with a median home size well above typical for the surrounding market.

The defining trait of this community is square footage. At a median of 3,391 living square feet, homes here run considerably larger than a typical resale listing, which changes how buyers should evaluate price. Larger homes carry more variables — additions, updated systems across a wider footprint, differing floor plans from one construction year to the next — so a walkthrough matters more here than a spreadsheet comparison.

The year-built range, 1981 to 2005, spans roughly a quarter century, with the median landing at 2002. That means most of the inventory is early-2000s construction, but a meaningful share predates it by two decades. Buyers should ask directly about roof age, HVAC vintage, and any system replacements rather than assuming a single build era. No community amenities are identified from current MLS listings, so amenity value, if any, is not part of what the resale data captures here — confirm directly with any specific listing or HOA documentation before assuming a feature is included.

In a small, mixed-vintage community like Ashley Cove, the difference between a fair offer and an overpay comes down to reading each home on its own terms — square footage, era, and condition rarely line up neatly. We pull the comparable history property by property, flag what the MLS record does not show, and help you price or negotiate around actual condition rather than a community-wide assumption.

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