Should You Buy and Sell a Home This Winter as a Move-Up Buyer?

Is winter a smart time to buy and sell a home if you're upgrading to your next one?

Yes — winter can offer unique advantages for move-up buyers, especially if you’re working with a local Realtor who understands how to navigate timing, negotiations, and inventory.

Why Move-Up Buyers Shouldn’t Dismiss the Winter Market

When most people think of buying or selling a home, spring and summer often come to mind. But winter can be a surprisingly strategic season — especially if you’re looking to sell your current home and buy a new one at the same time.

Here’s why:

• Less competition means more negotiating power on both sides of your transaction.
• Motivated buyers and sellers tend to dominate the winter market, which can lead to quicker decisions.
• Service providers are more available, including inspectors, appraisers, movers, and even contractors if your next home needs work.

If you're upgrading your home — more space, a better layout, or that dream kitchen — winter might actually give you an edge.

What to Know About Selling in the Winter

Don’t worry — winter doesn’t mean your home won’t sell. In fact, it can work to your advantage:

• Fewer listings mean less competition. Your home has a better chance of standing out in the market.
• Buyers who shop in winter are typically serious. You're less likely to deal with “just looking” types.
• Homes feel cozier during the holidays. With the right staging and lighting, your home can really shine.

The key is pricing it correctly, preparing it well, and marketing it effectively — and that’s where having a local Realtor makes all the difference.

What to Consider When Buying During the Winter

On the flip side, you’ll also be buying in a winter market — and that can benefit you as a move-up buyer:

• You might find better deals. With fewer buyers competing, sellers may be more flexible on price or concessions.
• You can move faster. With less transactional traffic, your offer, inspection, and closing might progress more smoothly.
• Interest rates fluctuate year-round. Working with a trusted lender can help you lock in a favorable rate.

That said, inventory can be a little tighter, so it’s smart to work with someone who knows how to find listings before they hit the broader market.

Juggling Both: Selling First or Buying First?

This is one of the biggest questions for move-up buyers:
Do you sell first or buy first?

There’s no one-size-fits-all answer — it depends on your finances, local market timing, and your risk tolerance. But here are a few tips:

• Sell first if you need the equity from your current home to buy the next one. You can negotiate a lease-back or extended closing to give yourself time.
• Buy first if you can comfortably carry two mortgages or have temporary housing options. This lets you shop without pressure.

Let’s talk through the pros and cons of each strategy — a quick coffee chat can go a long way in helping you feel confident and clear about your options.

Final Thoughts for Winter Move-Up Buyers

Winter can be a smart — and even strategic — time to make your move. Whether you’re selling, buying, or doing both, the right timing and guidance make all the difference. As your local Realtor in Wadsworth, Beach Park, Winthrop Harbor, Zion, and Kenosha, I’m here to help you navigate every step..

Let’s Chat Over Coffee

Thinking about buying or selling a home this winter? Whether you’re ready to take the next step or just want to explore your options, give me a call and let’s meet for coffee. No pressure — just real answers from someone who knows the local market.

 

Chris Varsek 

Realtor - Illinois & Wisconsin

847-445-2283