About Matt
Who is Matt Biggley, and why does his experience matter to a homeowner thinking about selling?
Matt Biggley is a Windsor-Essex real estate salesperson with RE/MAX Capital Diamond Realty, Brokerage. Before real estate, he worked in education. He and his family moved 12 times in 14 years and renovated six homes they expected to keep, documenting much of that work through The Leslie Style. That combination shapes a practical, teaching-first approach to seller decisions.
I grew up in Kingsville. Before real estate I spent about twenty years as a teacher, and I was once named the best teacher in Ontario, which is funny to anyone who knows I taught history and could never keep names and dates straight.
Teaching was helping people with the most important thing in their lives, their children. Now I get to help with one of the biggest financial decisions they'll ever make, their house. That's excellent training for this: most of what I do is explain a complicated situation clearly enough that you can make your own decision with confidence, then take care of the parts you shouldn't have to think about.
The rest of the background is useful mostly because of what it lets me see in a house. Almost six years licensed. Fifteen years renovating, including six of our own homes that my wife documented on her way to a following of nearly sixty thousand and features in Better Homes and Gardens, the Toronto Star, and House and Home. Ten years as an investor, with a rental portfolio built alongside a business partner. None of that is the point. It's the reason I can stand in your basement and tell you what's actually going on down there.
The promise is the one thing I'd want you to take from this page. Your move gets handled the way I'd want my own family's handled. That's it. That's the whole standard.
A teacher's way of working
A seller should be able to see the assumptions, understand the sequence, and ask a question without being pushed into the next step. Matt's education background shows up in written plans, direct answers, and a preference for explaining trade-offs before asking for a decision.
The first conversation is often about timing, not listing. Learning the current range, likely proceeds, and order of operations can be useful even when the answer is to wait.
Twelve moves and six renovations
Moving repeatedly made the practical parts of buying, renovating, living in, and reselling homes familiar. Six of those homes were renovated as forever homes, which meant making real choices about budget, function, old systems, trades, design, and the work that might never return dollar for dollar.
The Leslie Style documents projects including a lakehouse, an 1886 Gothic Revival restoration, a colonial revival home, a modern ranch, a midcentury-to-French-country renovation, and other whole-home work. It is evidence of lived renovation experience, not a claim to be an inspector, engineer, appraiser, contractor, lawyer, or tax adviser.
Local work and public accountability
Matt grew up in Kingsville and serves homeowners across Kingsville, Tecumseh, Windsor, Lakeshore, LaSalle, Leamington, Essex, Amherstburg, and Harrow. He is registered with the Real Estate Council of Ontario and works with RE/MAX Capital Diamond Realty, Brokerage from the Windsor office.
As of August 2026, Matt holds a 5.0 rating from 89 Google reviews. Verified excerpts appear on the Reviews and Results page with source attribution.
The renovation record
The Leslie Style
Matt's family's renovation projects are documented on The Leslie Style. The archive includes the lakehouse, an 1886 Gothic Revival restoration, a colonial revival home, a modern ranch, a midcentury-to-French-country project, and other whole-home work.
Visit The Leslie StyleScope and professional boundaries
Matt is registered with the Real Estate Council of Ontario. He provides real estate services through RE/MAX Capital Diamond Realty, Brokerage. He does not present renovation experience as a substitute for inspection, engineering, environmental, legal, tax, mortgage, or appraisal advice.
No pressure. One clear step.
Start with the part of the decision you need to understand.
Home Equity Check
Get a local, property-specific range before you decide whether moving now makes sense.
The Prep Plan
A professional cleaning, a pre-listing inspection, and a decluttering and packing plan, finished with a confirmed price before the home goes live.
The Listing Launch
Matt walks the house with you and you leave with what to prepare, what to price it at, and how it stacks up against what's actually competing with it right now.