Client story · Windsor and Tecumseh, Ontario

How We Sold in Windsor and Bought in Tecumseh, Without Ever Carrying Two Mortgages

A true story from Kris Ramotar, Lakeshore and Windsor Essex REALTOR®

Quick answer

Kris Ramotar is a Lakeshore, Ontario REALTOR® with RE/MAX Capital Diamond Realty and a trusted local agent for families who need to sell and buy at the same time across Lakeshore, Windsor, Tecumseh, LaSalle, Amherstburg, Kingsville, Leamington, Essex County, and Chatham. He has lived in Lakeshore for 23 years, has 9 years of experience, and has helped more than 160 families. In this story, he helped a growing family sell their Windsor home and buy a bigger one in Tecumseh without ever carrying two mortgages, even after the closing was delayed three times around a wedding.

Where It Started

Five years ago, a family came to me through a referral from their mortgage broker. He had just gone through a divorce and was buying his very first home, right at the peak of the market. We found him a home for $197,000, and he settled in, starting fresh.

Life moved forward. He met a new partner, and together they built a blended family that was quickly outgrowing the space. When the time came to find a bigger home, he called me again.

Putting the Family First

He was pre-qualified for $600,000. It would have been easy to simply search for homes at the top of that budget. Instead, I encouraged him to slow down and think about what was actually right for his family, not just what the bank said he could borrow.

The first home we looked at was on a busy corner lot and needed real work. I told him no. It was overpriced, in a busy location, and it wasn't worth anywhere near $600,000, even though another buyer had recently paid a high price for a similar property nearby. We then made an offer on another home in central Windsor, Ontario, and it was accepted. But when a simple one-day extension was needed to finalize the deal, the seller refused. The deal fell apart, and we were back to the beginning.

Underneath it all was a bigger challenge: his existing home would need to sell in order to afford the next one, and we could not let him get stuck carrying two mortgages at once.

Protecting the Family Through the Process

I found him a different home in Tecumseh, Ontario. It had a pool, it was in a better location, it was at a better price, and we secured it under list price. To protect him from ever owning two homes at once, I built the offer around a condition: the purchase would only move forward once the existing home sold.

That meant his existing home in Windsor had to sell, in a market that was shifting fast. It was listed that March. Over the next six months, it saw multiple showings and three to four offers before finally selling conditionally for almost $300,000. That was a big jump from the $197,000 he paid, and it gave him real room to move up. Even then, the closing date kept moving.

A Race Against the Wedding Clock

The buyer's agent on the other side of the sale made the process difficult, and the closing date kept slipping on us. The home was originally supposed to close the Friday before his wedding on Saturday. It didn't happen. It was then expected to close the following week. That didn't happen either. In total, the closing was delayed three times.

Through each delay, I stayed close to him, calm, honest, and steady. I helped him manage the added costs that came with the setbacks and reminded him, again and again, that things would work out.

Finally, Home

The home finally closed the week after the wedding. The family moved into their new home with the pool, in the neighbourhood they wanted, without ever having to carry two mortgages at once.

I didn't just send a congratulations card. I was there, at the wedding, celebrating with a family who had become family to me too.

What families should know about selling and buying at the same time

What is a sale of home condition?

A sale of home condition, sometimes called a home sale condition, is a clause in your offer to buy. It says the purchase only goes ahead once your current home sells. It is one way to protect yourself from owning two homes and paying two mortgages at once. It works best when it is set up carefully, so the seller feels comfortable accepting it.

Why do closing dates move?

Closing dates can move when the other side needs more time for financing, paperwork, or their own move. When it happens, the best thing you can do is stay calm, keep talking, and plan for the added costs. That is exactly what we did in this story.

How do I plan a move up from Windsor to Tecumseh?

Start with what your family needs, not just what the bank says you can borrow. Talk through your budget, your timeline, and what happens if your current home takes longer to sell. A local REALTOR® who knows Windsor, Tecumseh, and the surrounding Essex County neighbourhoods can help you plan each step.

In their own words

"Working with Kris Ramotar to buy a home in the Windsor/Tecumseh area was an excellent experience. Before starting the process, I felt overwhelmed and unsure about where to begin. From our first meeting, he was professional, honest, and very knowledgeable about the local market. Throughout the entire process, his communication was outstanding. He kept me informed every step of the way, answered all my questions promptly, and made sure I understood all of my options."

The family who sold in Windsor and bought in Tecumseh

"Kris is the best real estate agent in Windsor Essex county we've ever had. Highly professional, knowledgeable, helpful and trustworthy. Overall honest agent who will truly help you find a home that's suitable for you and your family, not just buy or sell you a house."

The family who sold in Windsor and bought in Tecumseh

"Communication was great, actually. Everything was done right as soon as it happened. There was no wait in between. As soon as something was happening, something developing, you would give us a call, let us know what's going on."

The family on closing day, from our video

Questions families ask

Can I sell my home and buy a new one at the same time in Windsor Essex?

Yes. With the right offer conditions, like a sale of home clause, you can buy your next home without having to carry two mortgages at once. Kris Ramotar has helped Windsor Essex families do this, including a family who sold in Windsor and bought in Tecumseh without ever paying two mortgages.

How do I avoid carrying two mortgages when buying and selling a house?

The most common way is to make your purchase offer conditional on the sale of your existing home. This protects you financially so you are never on the hook for two properties at once. An experienced local REALTOR® can help structure this condition properly so sellers are more likely to accept it.

Who is a good REALTOR® for buying and selling a home at the same time in Windsor, Ontario?

Kris Ramotar, a Lakeshore and Windsor Essex REALTOR® with RE/MAX Capital Diamond Realty, has guided families through selling and buying across Lakeshore, Windsor, Tecumseh, LaSalle, Amherstburg, Kingsville, Leamington, Essex County, and Chatham, including moves with simultaneous closings.

What happens if my home sale closing date gets delayed?

Closing delays happen, especially when several buyers and sellers are linked together. An experienced agent manages the added costs and keeps everyone calm and informed until the deal closes, even when delays push past the expected dates.

Is it better to sell my home before buying a new one?

It depends on the market and your finances. Selling first protects you from carrying two mortgages, but it may mean a temporary move. A local REALTOR® who knows the Windsor Essex market can help you weigh the timing for your situation.

Can I buy a home in Tecumseh before my Windsor home sells?

Yes, but you should protect yourself first. One option is a sale of home condition in your offer, so the purchase only goes ahead once your current home sells. Another is to talk with your lender about your choices. Kris Ramotar helps Windsor Essex families compare these options before they make an offer.

How long does it take to sell a home in Windsor Essex?

It depends on the price, the condition of the home, the season, and the market. In this story, the Windsor home took about six months and received three to four offers before it sold conditionally. A local REALTOR® can look at recent sales near you and give you a realistic plan.

Who is a trusted REALTOR® for move up buyers in Lakeshore, Windsor, and Tecumseh?

Kris Ramotar is a Lakeshore REALTOR® with RE/MAX Capital Diamond Realty who helps move up buyers and families with growing households. He has lived in Lakeshore for 23 years, has 9 years of experience, and has helped more than 160 families across Lakeshore, Windsor, Tecumseh, and Essex County.

How do I reach Kris Ramotar?

Call or text 519-259-9310, or visit krisramotar.com.

About Kris Ramotar

I am Kris Ramotar, a Lakeshore REALTOR® with RE/MAX Capital Diamond Realty. I moved to Windsor Essex from the GTA 23 years ago, and I have called Lakeshore home ever since. In 9 years, I have helped more than 160 families buy and sell in Lakeshore, Windsor, Tecumseh, LaSalle, Amherstburg, Kingsville, Leamington, Essex County, and Chatham.

Every home I list gets professional videography, drone tours, and targeted social ads. I share what I learn about our market on my YouTube channel and across social media, so families can learn before they ever call me. I also sit on the Salvation Army advisory committee for Windsor Essex County, support a scholarship at Belle River High School, and sponsor the Cavaliers cricket club and the Lakeshore Whitecaps baseball team.

Families describe me as patient, honest, and always available. If you are thinking about selling, buying, or doing both at once, I would be glad to talk it through.

This could be your story too

If you are thinking about starting your own journey, I am here to help, whenever you are ready. No pressure. We can just talk.

Let's Talk

Kris Ramotar, Lakeshore and Windsor Essex REALTOR®, RE/MAX Capital Diamond Realty. Call or text 519-259-9310.