Two of the Most Common Cottage Questions—That Won’t Actually Help You Buy the Right One And What to Ask Instead if You’re Serious About Finding Your Dream Muskoka Getaway
When you’re touring cottages in Lake of Bays or North Muskoka with a trusted local real estate team (hello from us at The Richardson Team 👋), you probably have a list of questions in your back pocket. Some are practical. Some come from watching too much HGTV. A few might not be doing you any favours in your property search.
In fact, we hear two questions almost every time we show a cottage. They come up so often, we thought it was time to talk about them — and why they may not be helpful at all in choosing the right waterfront property.
❌ Question 1: “How long has this property been on the market?”
This one comes up like clockwork. We get it — buyers ask this because they’re trying to gauge the seller’s motivation. Has it been sitting for months, unsold and unloved? Maybe they’ll take a deal! Is it brand new to the market? Better move fast!
But here’s the thing: the number of days on market doesn’t tell you anything useful.
- A cottage might sit on the market longer because it was overpriced initially. That doesn’t mean it’s not the perfect fit now at its adjusted price.
- Some sellers aren’t in a rush. Others are, even if the listing is only a few days old.
- It might have fallen through previously due to financing or a change of heart on the buyer’s end — not the fault of the property.
The truth is, there are dozens of reasons a listing stays on the market — none of which tell you if this is the right cottage for you.
A better question to ask:
“Are there any recent comparable sales in the area that help support this price?”
That’s a smart question. It focuses on value, not days on market.
❌ Question 2: “Why are they selling?”
This question is often asked with a slight squint of suspicion, like we’re hiding some sinister secret. We promise — if the neighbour was an axe murderer, the sellers wouldn’t put it in the listing remarks.
But more importantly — why the sellers are moving is none of your business, and it’s largely irrelevant to your decision.
- They could be moving for a job, for family, downsizing, or simply ready for a change.
- Knowing why they’re selling doesn’t change what the property offers you.
- And no, we can’t (and shouldn’t) disclose private or speculative details. Our role is to represent the property fairly — not dig into the sellers’ personal life.
Even if the sellers are “motivated,” it doesn’t guarantee a bargain. Good cottages in desirable locations tend to hold their value — regardless of the backstory.
A better question to ask:
“Have there been any major renovations or upgrades in the last few years?”
Now that’s useful. It tells you about the condition and future maintenance of the property — key for waterfront buyers.
Ask the Questions That Actually Help You Buy Smarter
If you’re seriously shopping for a Muskoka or Lake of Bays retreat, let’s shift the focus to questions that really matter. Here are some of our favourites:
- What are the topography and shoreline like? (Great for understanding swimming and boating potential)
- Is the cottage insulated and winterised? (Especially important for year-round use)
- What are the annual costs to run the property? (Think hydro, road maintenance, septic, and taxes)
- Is the lake motor-restricted or busy? (Affects your lifestyle significantly)
- How close are the nearest neighbours? (Privacy matters)
- Can I build, expand, or renovate here? (Zoning and setbacks make a big difference)
These are the kinds of questions that uncover whether a cottage truly fits your lifestyle, budget, and long-term plans.
The Bottom Line
In the world of waterfront property, curiosity is a good thing — but strategic curiosity is even better. Don’t waste your time on questions that won’t move the needle in your decision. Instead, lean into conversations that uncover the real pros, cons, and potential of a cottage.
If you’re thinking about buying a cottage in North Muskoka / Lake of Bays and want an experienced, caring team to guide you every step of the way, we’d love to help. Whether it’s your first viewing or your fiftieth, we’ll help you ask the right questions — and find a property that truly fits your lifestyle.
Contact us today for expert advice on buying smart in cottage country.