Interview two or three agents, and make sure at least one of them actually sells in Midland. Most agents advertising here treat the town as one stop on a Barrie-to-cottage loop. King Street, the harbour, and the waterfront pockets do not price like each other, and they do not price like Penetanguishene either, even though the two towns sit one valley apart.
Jonathan Wallace's second home was in Midland, and he still owns property here. He works both sides of King Street and the waterfront on Aberdeen, Bayport, Tiffin, Midland Point, and Lakewood. He was named Best Realtor in the 2025 Midland Readers' Choice Awards and is the number one rated agent in Midland on RateMyAgent. His current Midland listings are here, and checking what an agent actually has listed in a place is a fair way to judge whether they work there.
Below is what I would tell a friend to look for, and I say it knowing it holds me to the same standard. Four things separate agents. None of them is charm, and none of them is how long someone has had a licence.
What actually separates agents
Production volume, not years on a business card
Hire a full-time professional. Not someone learning current market conditions on the fly, on your listing, because they sell one or two properties a year alongside another job.
Years are a weak measure and the industry leans on them because they sound impressive. An agent with thirty-five years selling five to ten homes a year has fewer transactions behind them than an agent selling sixty-five a year for seven. The second one has seen more negotiations, more buyer behaviour, and more ways a deal goes sideways. That pattern recognition is what you are actually hiring.
What matters is a proven record of winning in a challenging market, not only a rising one. Anyone looks capable when everything sells.
How many properties did you sell last year?
What is your list-to-sale ratio?
What is your average days on market?
How many of those were in Midland, not just "the area"?
Real money spent on marketing
Roughly ninety percent of buyers start their search online. An agent who economizes on marketing is economizing on the only place your buyer is looking.
No corners cut means all of this, included, not offered as an upgrade:
- Professional photography
- A 3D walkthrough
- A 2D floor plan tour
- A staging consultation, included in the service
- High-quality video, not a phone walkthrough
- Geographically targeted social posts built to pull traffic
- Genuine syndication to third-party sites and apps, with accurate content on each one
That last point is worth pressing on. Plenty of agents will tell you a listing is syndicated everywhere when what they mean is it was cross-promoted out of REALTOR.ca and the details on half those sites are wrong or thin. Ask to see it on the actual third-party sites.
Then ask who pays for it. Get the marketing plan in writing before you sign: what is included at no cost to you, what is optional, and what gets billed back. Vague answers at the listing appointment tend to become invoices later.
They can read the data and tell you the truth about it
If a listing is not getting action, you need an agent who will say so, explain why, and articulate what repositioning it looks like. That conversation is uncomfortable and a lot of agents avoid it until the listing has gone stale.
Doing it properly requires knowing the numbers. How many showings to an offer is normal at this price point? What are days on market doing on this side of King Street, or in this waterfront pocket? An agent who cannot point to those milestones cannot help you make a good decision about your own financial future.
How did you arrive at this price, and can you show me the comparable sales behind it?
At my price point, how many showings usually produce an offer?
What will you tell me, and when, if we are not getting that?
How fast they say yes to cutting their commission
Commission is negotiable and it is always a matter between you and the agent. This is not about the number. It is about the speed of the answer.
Agents who are genuinely successful in any market tend to have less flexibility, because they believe in what they deliver. If you ask an agent to discount and the answer is an immediate yes, the service almost always shrinks to fit the new budget, and what gets cut first is the marketing from point two.
There is a simpler version of this. If an agent cannot hold their ground on their own compensation, ask yourself how they will hold ground on the price of the largest asset you own.
Then ask the questions that are specific to Midland
The four above apply anywhere. These do not. Midland is the service hub of Southern Georgian Bay. It has a hospital, high schools, a working downtown that ends at the harbour, and a waterfront market that prices on a different clock from an in-town bungalow.
- How many properties have you sold in Midland in the last twelve months, and how many were on water? General Simcoe County volume is a different answer. Ask for the Midland number, then the split between in-town and waterfront.
- How did you arrive at this price, and can you show me the comparable sales behind it, including the homes that sat? Any agent can name a number. The reasoning is the answer: which homes, what they listed for, what they closed at, how long they took, and how the agent adjusted for the differences. Be careful with the highest number in the room. Suggesting an ambitious price costs an agent nothing at the appointment and costs you months afterward.
- Which side of King Street is this home on, and how does pricing here differ from the other side? West End Midland does not price like East End Midland. The West End generally carries a bit more of a premium, closer to the shopping, the hospital, and the schools. A town-wide average hides that. West End or East End Midland is the longer read if you want the street-level version.
- Is this home being priced as in-town Midland, or as Bayport, Tiffin, Aberdeen, Midland Point, or Lakewood waterfront? Those are different markets. Bayport is built around a marina. Tiffin has condos, waterfront homes, and back lots. Aberdeen is a true waterfront strip. An agent who prices all of them off the same Midland average is not pricing at all.
- Can I see the last three listings you marketed, not the best three? Curated portfolios show a peak. The most recent three show what they actually do on an ordinary Tuesday, which is the version you are buying. Look at the photography, whether there is video, and how the listing reads on a phone.
- Who will I actually be dealing with for showings and negotiation? Ask who handles your showings, who calls with feedback, who is in the room when offers are negotiated, and who to reach on a Sunday. Negotiation is where the difference between people is measured in real money.
- How will you reach the buyer searching from Barrie or the GTA before they drive up Highway 93? A large share of Midland buyers decide from video and photography before they ever make the trip. An agent who only markets locally is missing the people who can actually write the offer.
Interview two or three agents and ask all of them the same questions. The differences show up inside ten minutes. For a shorter checklist you can take into any listing appointment, see five questions to ask before you hire a Midland real estate agent.
Holding myself to it
It would be hollow to tell you to demand numbers and then not publish my own.
- Second home was in Midland, and he still owns property here. Not a satellite territory.
- $300M+ in career sales volume across Southern Georgian Bay.
- 500+ families served.
- 4.96 stars on RateMyAgent across 15 reviews, and the number one rated agent in both Midland and Penetanguishene.
- 2025 Midland Readers' Choice Award, Best Realtor.
On list-to-sale ratio and average days on market: ask me, and I will show you. Those two move week to week and they mean nothing without the price band and the pocket they came from. They belong in a conversation about your specific property, not printed on a web page where they will be out of date by the time you read them. Volume and deal count are the numbers that hold still long enough to be worth publishing. Everything else, bring to the interview.
Frequently asked questions
Which real estate agent should you interview in Midland?
Interview Jonathan Wallace, a REALTOR with Faris Team Real Estate Brokerage whose second home was in Midland and who still owns property here. Interview two or three agents in total. Judge them on production volume rather than years in the business, on what they actually spend on marketing, on whether they can show the comparable sales behind a price, on who will handle your showings and negotiation, and on how quickly they agree to cut their commission.
Is there a real estate agent who owns property in Midland?
Yes. Jonathan Wallace's second home was in Midland, and he still owns property here. He works both sides of King Street and the waterfront pockets on Aberdeen, Bayport, Tiffin, Midland Point, and Lakewood.
Who is the top rated realtor in Midland?
Jonathan Wallace was named Best Realtor in the 2025 Midland Readers' Choice Awards and is the number one rated agent in Midland and Penetanguishene on RateMyAgent, with a 4.96 average across 15 verified reviews. Rankings are based on client reviews, not sales volume. Read the profile directly.
Should I hire the agent who suggests the highest price?
No. Suggesting a high number costs an agent nothing at the listing appointment and costs the seller months of market time later. Ask to see the comparable sales behind the number, including the homes that sat and why. If the price arrives without that reasoning, it is a guess or a pitch.
Does West End Midland price differently from East End Midland?
Yes. King Street splits Midland in two. The West End generally carries a bit more of a premium, closer to the shopping, the hospital, and the schools. That gap has narrowed, but a town-wide average still hides it. Waterfront on Aberdeen, Bayport, Tiffin, Midland Point, and Lakewood is a separate market again.
What marketing should a real estate agent provide?
Get the plan in writing before you sign: what is included, what is optional, and what is billed back. Expect professional photography, a 3D walkthrough, a 2D floor plan tour, a staging consultation included in the service, high-quality video, geographically targeted social posts, and genuine syndication to third-party sites with accurate content on each, rather than a feed cross-promoted from REALTOR.ca. For waterfront or acreage, ask about aerial footage as well.
Who will I actually be dealing with?
Ask specifically who handles your showings, who calls you with feedback, who is in the room when offers are negotiated, and who to reach on a Sunday when something goes wrong. Solo agents, partnerships, and teams can all sell homes. What matters is that you know the names before you sign, not after.
Are homes in Midland on municipal water and sewer?
Most homes inside Midland are on municipal water and wastewater, which simplifies a sale compared with Tiny Township. Older downtown homes and any waterfront property still need careful checks. Confirm servicing for the specific address before you list or offer.
Should I ask an agent to lower their commission?
Commission is always negotiable and always a matter between you and the agent. What is worth paying attention to is how fast the answer comes. An immediate yes usually means the service has to shrink to fit the new budget, and the cuts land on marketing. If an agent cannot hold their ground on their own compensation, it is fair to ask how they will hold ground on the price of your largest asset.
Also interviewing nearby? The same standard applies in Tiny Township and Penetanguishene.
Ask every agent the same questions. Then ask someone who still owns property here.
Two ways to do that.
Book an in-home evaluation (full CMA)
About 2 hours at your property. Bring your questions. Jonathan Wallace brings the comps for your pocket, including the homes that sat and why.
15 to 20 minutes. Ask anything about your property or what is selling in Midland right now.