As life evolves, so do your housing needs. Maybe your starter home feels a little cramped now that the kids are growing up, or perhaps you’re ready for that backyard you’ve always dreamed of. Whatever the reason, transitioning to a larger property is an exciting step—and Windsor-Essex is the perfect place to find your next home. With over 17 years of experience in the local market, I’ve helped many families make this leap seamlessly. Here’s how you can do it too.
Why Upsizing Makes Sense in Windsor-Essex
The Windsor-Essex market offers plenty of opportunities to upgrade without breaking the bank. Compared to cities like Toronto or Ottawa, you’ll find more spacious homes at a fraction of the cost. Plus, with rising home values, your current property might be worth more than you think, making it the perfect time to sell and move up.
Here are some common reasons why my clients decide to upsize:
- Growing Families: Extra bedrooms, larger kitchens, and bigger yards become a priority as families expand.
- Lifestyle Upgrades: A move to a home with a pool, a finished basement, or proximity to great schools.
- Investment Potential: Buying a larger property can be a smart long-term investment in Windsor-Essex’s appreciating market.
Step 1: Evaluate Your Current Home’s Value
Before you start shopping for a larger property, it’s important to understand how much your current home is worth. Windsor-Essex has experienced steady home price growth in recent years, which could mean you have more equity than you realize.
- Get a Market Evaluation: I can provide a free, detailed assessment of your home’s value.
- Consider Timing: Selling in a seller’s market can maximize your return, giving you more flexibility for your next purchase.
Step 2: Determine What You Need in a Larger Home
Upsizing isn’t just about buying a bigger house—it’s about finding a home that fits your lifestyle. Think about the features that matter most to you:
- Number of Bedrooms and Bathrooms
- Open-Concept Living Areas
- Outdoor Space for Kids or Entertaining
- Proximity to Work, Schools, and Amenities
Do you need a home office? Extra storage? A larger garage? Make a list of your must-haves and nice-to-haves to guide your search.
Step 3: Secure Financing for Your Next Home
While you may have equity in your current home, upsizing often means taking on a larger mortgage. Here’s how to prepare:
- Meet with a Mortgage Advisor: They’ll help you understand your borrowing power and options.
- Plan for a Down Payment: Depending on the sale of your current home, you may have a substantial down payment ready to go.
- Factor in Closing Costs: These can include legal fees, land transfer taxes, and moving expenses.
I work closely with local mortgage experts to ensure my clients get the best advice and rates.
Step 4: Explore Windsor-Essex’s Best Neighborhoods for Upsizing
Windsor-Essex is home to many neighborhoods ideal for upsizing. Here are a few popular options:
- South Windsor: Known for its larger homes, excellent schools, and family-friendly atmosphere.
- Tecumseh: Offers a mix of spacious suburban properties and proximity to amenities.
- LaSalle: Perfect for those seeking upscale homes and access to nature trails and parks.
- Kingsville: If you’re looking for more land or a quieter lifestyle, Kingsville offers plenty of charm.
Step 5: Buy Before You Sell—or Vice Versa?
One of the biggest questions my clients face is whether to buy their new home before selling their current one. Here’s what to consider:
- Selling First: This approach gives you a clear budget and avoids carrying two mortgages. However, you’ll need a temporary place to stay if you haven’t found your new home.
- Buying First: This can be less stressful if you find your dream home quickly, but it may require bridge financing.
I’ll help you weigh the pros and cons to make the best decision for your situation.
Step 6: Prepare for the Transition
Moving to a larger home can be a bit overwhelming, but with the right plan, it’s manageable.
- Declutter Before Listing: Start packing and purging items you won’t need in your new home.
- Work with a Professional Stager: A well-staged home sells faster and often for more money.
- Hire Reliable Movers: Choose a company with experience in handling larger moves.
Why Now Is the Right Time to Upsize in Windsor-Essex
The real estate market in 2025 is in a unique position. Rising home values mean you can get a great return on your current home, while the Windsor-Essex market still offers plenty of larger properties at competitive prices. Add in historically low inventory in major markets, and Windsor-Essex becomes an attractive option for buyers seeking more space and value.

