Matt Biggley, REALTOR®
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Which Town Fits You?

Pick the town before you pick the house.

The town decides more about your next ten years than the house does, and it's the one thing you can't renovate later. Kingsville and Leamington are twenty minutes apart and they are not the same life. Answer six questions about how you want to live and you'll get the two or three areas worth a drive, and why each one came up.

Published Updated Reviewed by Matt Biggley

Your answers stay on this page. If you send me a note at the end, only your top matches come with it.

01How often will someone drive into Windsor for work?
02How close to the water do you want to be?

Lake Erie, Lake St. Clair, or the Detroit River.

03Walking to coffee, dinner and the shops:
04What kind of house are you picturing?
05How much room outside?
06Which pace sounds most like you?

Checked against what freehold homes Sold for in six towns over the past year. A town where nothing Sold in your range drops off the list.

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Want to see them from the car?

The first outing with me is a driving tour with no houses in it. Just the towns on your list, the commute timed at the hour you'd actually be driving it, and where you'd buy groceries on a Tuesday. Most people rewrite their shortlist by the end of that afternoon. Only your top matches come with this note, never your answers.

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How to read your result

Why the town comes first

People move to Essex County for different reasons and end up happy in different places. Riverside and Amherstburg both put you near the water and feel nothing alike. Tecumseh and LaSalle both sit right next to Windsor, and only one of them has most of the county's newer construction. Scrolling listings won't tell you any of that. A Saturday in the car will.

What this looks at

Each area is rated on the things buyers here actually trade off against each other: the drive into Windsor, how close the water is, whether there's a centre you can walk to, how old the houses tend to be, how much land comes with them, and whether it feels like the city, a small town or the country. Your answers weight those, and the areas that fit best rise to the top. The ratings come from each area's own guide on this site.

The areas it compares

  • Kingsville: Canada's southernmost town, right on Lake Erie. A walkable Main Street with more breweries than a town this size has any business having, beaches at either end, and wine country all around it.
  • Leamington: Second largest centre in Windsor-Essex, with a deep-water marina, a real beach, and a national park inside its own boundaries. The water is what moves this market.
  • Tecumseh: The closest lakefront town to Windsor, twenty minutes from downtown. A hundred-year-old Stanley Thompson golf course on the shoreline, and a market that knows exactly where it is.
  • LaSalle: The second largest municipality in Essex County, on the Detroit River next door to Windsor. If you want newer construction without leaving the region, this is where most of it is.
  • Amherstburg: One of Ontario's oldest towns, where the Detroit River opens into Lake Erie. Three national historic sites, a waterfront park worth the drive on its own, and an island community you reach by ferry.
  • Lakeshore: The Muskie Capital of Canada, with 35 kilometres of Lake St. Clair shoreline, six marinas, the biggest beach on the lake, and the best rec centre in the region.
  • Essex: The geographic centre of the county, where everything is half an hour away. Acreage, horse farms, and vineyards, with a traditional main street in the middle of it.
  • Harrow and Colchester: A small country town in the middle of wine country, with the southernmost settlement on mainland Canada six kilometres down the road on Lake Erie.
  • Walkerville: Windsor's most walkable neighbourhood, and the only one that was drawn before it was built. Albert Kahn architecture, a shopping street you can walk to, and Willistead Park in the middle of it.
  • South Windsor: Established streets, mature trees, and a 1926 Donald Ross golf course in the middle of it. Everything in the city is about fifteen minutes away.
  • Riverside: A town of its own until 1966, and it still feels like one. Mature streets, the Detroit River at the end of them, and 5.3 kilometres of trail along the water.
  • Forest Glade: A master-planned east-end neighbourhood where thirty acres of park sit in the middle by design, not by accident. Arena, library, sixteen courts, and a nine-hole course.
  • West Windsor: Settled in 1748 and home to the newest bridge on the border. The oldest streets in the region, 900 acres of protected prairie, and the university in between.

Limits

A starting point, not a verdict. Every area holds more than one market: Kingsville, Cottam and Ruthven buy differently, and Belle River behaves like its own market inside Lakeshore. Wheatley isn't included yet. The budget check uses freehold homes Sold on the Windsor-Essex MLS from September 25, 2025 to September 25, 2026, for the six towns in What It Buys Here; the Windsor neighbourhoods, Essex and Harrow aren't checked against a budget.

Next: see what your budget buys in each town, work out the real monthly cost with that town's property tax, and read the Skip List before your first showing. Back to buying in Windsor-Essex