The cross-border economy's influence
Windsor's economy is closely tied to the Detroit border crossing and the auto and manufacturing sector on both sides of it, which historically has made local housing demand more sensitive to that industry's cycles than markets without that concentration. That connection doesn't make every house in the region behave the same way, but it's part of the backdrop worth understanding for anyone comparing Windsor-Essex to a more diversified market elsewhere in Ontario.
The smaller towns further from Windsor proper — Essex, Kingsville, Leamington — carry more of an agricultural economic base, which shapes their housing stock and demand differently again, including more larger rural lots and farmhouse-style properties than the city itself has.
Why housing stock varies so much town to town
LaSalle and Tecumseh have grown as newer, family-oriented suburbs with a lot of relatively recent construction. Amherstburg carries a genuinely older, heritage-heavy core near the waterfront. Leamington's economy around greenhouse agriculture has shaped its housing and rental stock in ways distinct from the rest of the region. This isn't a single market with one price curve — it's several sub-markets that happen to share a county boundary.
What this means for a specific house
Because the region varies this much town to town, general regional statistics are a weak substitute for a buyer who actually knows the specific town a house sits in — its typical housing age, its economic base, and what's actually sold nearby recently. That's the more useful question to ask than "what's the Windsor-Essex market doing" in the abstract.