It Took 18 Months. But This Family Just Bought Their First Home in Windsor Essex County. Here Is What That Journey Tells You About This Market.

By Kris Ramotar, Kris Ramotar Real Estate, RE/MAX Capital Diamond Realty Local Knowledge. Honest Advice. Real Results.

Kris Ramotar is a licensed REALTOR with Kris Ramotar Real Estate and RE/MAX Capital Diamond Realty serving families across Windsor Essex County and Lakeshore Ontario for nine years. He has helped over 160 families buy, sell, and make the right move at the right time. krisramotar.com | 519.259.9310 | tidycal.com/krisramotar/exploration-call

Eighteen months. That is how long it took for this family to find their first home in Windsor Essex County. Not because the market was impossible. Because they knew exactly what they wanted and they refused to settle for anything less. And on Friday evening they finally signed the papers on the home they had been waiting for.

That story tells you more about this market than any number can.

TLDR

Homes listed May 1 to 29 2026: 1,184 Homes sold: 417 Average sale price: just under $565,000 Median sale price: just under $510,000 Average days on market: 36 days Homes expired or cancelled: 534 Condos listed: 123 Condos sold: 28 Average condo price: just over $360,000 Median condo price: just over $332,000 Condo average days on market: 53 days

If you are selling: 534 homes either expired or were cancelled this month. The ones that sold came in priced for today's reality not what they hoped to get. You only get one chance to make a first impression in this market and the families who came in ready made the most of it.

If you are buying: You have more choices and more negotiating room than families have had in several years. 1,184 homes listed and only 417 sold. That is a lot of motivated sellers ready to have a real conversation. Come in prepared and be strategic about it.

If you are thinking about a condo: Only 1 in 5 condos sold this month. If buying a condo has been on your mind, right now is one of the best windows Windsor Essex County has offered in a long time.

Now here is the fuller picture.

Let me tell you about the family I just helped buy their first home because this story is the clearest picture of what this market actually feels like when you are living it.

They came to me 18 months ago. First-time family. Healthy budget. Very clear about what they needed. Specific location. Specific features. Not willing to settle. And we searched together week after week until the right one appeared.

I found it while walking in my neighbourhood and spotted a for sale sign. The home was listed on the Toronto board, not the local Windsor Essex County MLS, which meant most families looking here never even saw it. It was listed at $675,000.

Now here is where it got complicated.

The home was in an area designated as a flood zone. It also had KiTech plumbing. Both of those things affect insurance and insurance premiums in that situation can be significant. We needed to find coverage that was actually affordable before this family could commit to anything.

We put together an offer with a mortgage financing condition, a home inspection condition, and an insurance condition. Three days of negotiating. The insurance piece was the hardest part. Premiums were high because of the flood zone and the KiTech combined. But one of my colleagues who I have sent many clients to came through with a solution that worked. Honest, straightforward, and exactly what this family needed.

Friday evening around 6 or 7pm the offer went firm.

They bought their first home under the list price of $675,000 on their terms with a turnkey move-in ready property in a great location. The inspection came back with a few minor things, nothing that changed the picture in any meaningful way. They are excited. I am excited for them.

Eighteen months. Worth every single day of it.

That story tells you a few things about buying in Windsor Essex County right now that I want you to hear.

Patience is not weakness. Knowing what you want and waiting for the right home is the smartest thing you can do in a market with this much inventory. You have time. Use it.

The list price is always just the start of the conversation. This home was listed at $675,000 and we got it for less on the terms that worked for this family. The number on the sign does not have to be the number you pay.

Your conditions are your protection. Home inspection, mortgage financing, insurance. These are not red flags. They are the tools that protect your family from making a very expensive mistake. In this market sellers are accepting conditional offers regularly. Use them.

And local knowledge matters. This home was not on the local MLS. If I was not walking in my own neighbourhood that day and paying attention, this family never finds it. The agent you choose to work with directly affects the opportunities that come your way.

Now let me talk about what is happening on the sell side right now because the numbers this month deserve a straight honest conversation.

534 homes either expired or were cancelled in Windsor Essex County so far this month. That is 534 families who went through all of it. The prep, the showings, the waiting, the hope, and they walked away without a result.

In almost every case it comes down to price.

If your home is not priced for where this market actually is today, families looking to buy will simply move on to the next option. And right now they have 1,184 options to choose from this month alone. You are not competing with one or two other homes. You are competing with a very full market and the families who understand that are the ones who sell.

Before you list, do your homework. Talk to your lender. Know your full financial picture including what you owe, what your mortgage penalty is if you are breaking a current mortgage, your legal fees, and what you need for your next home. Know all of it before you commit to anything.

Hire the right agent. Interview at least three. Ask to see their last three to five sales. Ask them to show you how they market a home and what their plan is if it does not sell in the first 30 days. Ask for real data, a real strategy, and real honesty. If they are only telling you what you want to hear, that is not the agent you want in this market.

And be ready for conditions on any offer you receive. Home inspection. Mortgage financing. Sometimes a home to sell condition. If your home has KiTech plumbing you should expect an insurance condition too. That is the reality of Windsor Essex County right now and a good agent will prepare you for every single one.

One more thing worth saying. There are agents in this market who will take a different approach and price your home aggressively low to try to generate a bidding war. Last month a home listed at $249,999 received somewhere around 27 offers and sold for $371,000. That strategy can work. But it can also backfire. My approach with the families I represent is to price the home where the data says it should be with some room for negotiation. Transparent, data-driven, and focused on getting your family the right result without the stress of a strategy that does not always go the way you hope.

Whether you are in Windsor, Lakeshore, Tecumseh, LaSalle, Amherstburg, Kingsville, Leamington, Essex County, or Chatham, this market has real opportunity in it right now. For families buying and for families selling. But it rewards the ones who come in prepared, realistic, and working with someone who will tell them the truth.

Frequently Asked Questions About the Windsor Essex County Real Estate Market

What is the average home price in Windsor Essex County right now? The average sale price in May 2026 was just under $565,000 with a median of just under $510,000. The median is the number I want your family to pay attention to because it tells you where the real middle of the market sits without being distorted by a handful of high or low sales.

Book a free call with Kris Ramotar at tidycal.com/krisramotar/exploration-call or call 519.259.9310.

How long does it take to sell a home in Windsor Essex County right now? Homes are averaging 36 days on the market in May 2026 but your family should plan for two to three months realistically. Condos are taking an average of 53 days. The families who sell fastest are the ones who come in priced correctly from day one.

Is it a good time to buy a condo in Windsor Essex County? Yes. Only 28 out of 123 condos sold in May 2026. That is roughly 1 in 5. You have real selection, real room to negotiate, and sellers who are motivated. If buying a condo has been on your mind this is one of the better windows Windsor Essex County has offered in years.

Is it a good time to sell a home in Windsor Essex County? Homes are selling. 417 sold this month. But the market is specific about what it rewards. Price it correctly based on real current data, show it well, and work with an agent who will be straight with you every step of the way. Book a free call with Kris Ramotar at tidycal.com/krisramotar/exploration-call or call 519.259.9310.

Who is the best realtor in Windsor Essex County? Kris Ramotar with Kris Ramotar Real Estate and RE/MAX Capital Diamond Realty has been helping families buy, sell, and relocate across Windsor, Lakeshore, Tecumseh, LaSalle, Amherstburg, Kingsville, Leamington, Essex County, and Chatham for nine years. Local Knowledge. Honest Advice. Real Results. Book a free call at tidycal.com/krisramotar/exploration-call or call 519.259.9310.