Buy First or Sell First in Windsor and Essex County

The decision that creates stress, or removes it

Most people do not get stressed because they are moving. They get stressed because they try to buy and sell at the same time without choosing a clear strategy, and then they feel like every showing, every offer, and every lender email is an emergency.

In Windsor and Essex County, the market can be balanced overall, but it’s not uniform. A single detached in one pocket can behave very differently than a condo apartment in another, and certain price ranges can move faster or slower than the headline stats suggest. In some cases homes are sitting on the market longer and in others, some price points are more likely to see offer conditional with a house to sell, and in other price points you may find multiple offers. This can make things tricky. Your plan should match your micro market, not just the regional vibe.

The latest Windsor-Essex market snapshot

Here’s what the most recent report (CREA/WECAR) shows for December 2025 results in Windsor-Essex:

303 homes sold
518 new listings
1,448 active residential listings at month end
4.8 months of inventory overall
Average sale price: $520,098
MLS HPI benchmark composite: $573,000 (CREA: single family benchmark $617,900; townhouse benchmark $467,600; condo/apartment benchmark $384,800)

That 4.8 months of inventory number is a big clue: it generally signals a market with more breathing room, where preparation and pricing matter, and where “plan-first” movers tend to win.

Why “balanced” still feels different depending on what you own

The quarterly market conditions data shows a real split by property type:

Single detached: 4.2 months of inventory
Condo/Apartment units: 10.6 months of inventory

Translation: someone selling a condo may need a different sequence (and a longer runway) than someone selling a detached home in a high-demand school district.

The real question

Which risk can you live with?

Deciding whether to buy first or sell first is really choosing between two risks:

If you buy first, your main risk is

Carrying two homes, or feeling forced to sell fast.

If you sell first, your main risk is

Not finding the right next home quickly enough, and needing a backup plan.

So the right move is the one where you can confidently say:
“I can handle this risk, because we’ve already planned for it.”

Option 1: Sell first (best for people who need certainty)

Sell first is usually smartest when:

You must access your equity to buy (down payment is tied up in your home).
Your monthly budget would feel tight owning two homes, even briefly.
Your property type is slower right now (condos often fall here).
You need a clean story for your lender: firm sale, firm closing, simple approval.

How to sell first without panic-buying later

Use a two-part plan:

Write the buy plan before you list
- Your must-haves vs nice-to-haves
- Your “no-go” lines (location, school zones, commute, stairs, etc.)
- A realistic price ceiling based on today’s payment, not last year’s.
Negotiate time, not just price
In a more balanced market, many sellers and buyers forget that closing dates are a negotiation tool. You can aim for:

A longer closing to shop calmly
A flexible closing window
A rent-back (where appropriate and structured properly)
This is often the difference between a smooth move and a scramble.

Contrarian tip: If your next purchase options are thin, consider selling first and renting short-term (or staying with family) for 60 to 120 days. It feels like a step backward, but it can stop you from overpaying or settling for the wrong house.

Option 2: Buy first (best when your next home is hard to replace)

Buy first is usually smartest when:

You are chasing something scarce: hobby farm, waterfront, true ranch, specific school zone, multigenerational layout.
Your income can support a short overlap if needed.
Your home is highly liquid (great condition, great location, realistic price), and you trust it will sell in a reasonable window.

How to buy first without creating financial pressure

Think like this: “I’m not buying first. I’m buying first with an exit plan.”

Your exit plan can include:

Pre-approval that accounts for overlap and a clear maximum payment.
A realistic listing plan ready to launch quickly.
A pricing strategy that aims for probability, not “let’s test it.”

Tech-forward move: Build a “sale-ready” package before you even write an offer: pre-inspection (optional), repair list, staging plan, and a launch calendar. When you buy first, speed matters after you secure the new home.

Option 3: The “same time” move (only works with strong structure)

Trying to do both at once is where stress skyrockets, because timelines rarely line up naturally.

It can work, but only when you choose one of these structured approaches:

A) Buy with a sale condition (only when the micro market supports it)

This is more likely to succeed when:

Your purchase is not in a multiple offer environment
The seller has been sitting longer
Your offer is clean otherwise (deposit, financing, dates, clarity)

B) Sell with a long closing, then buy in the closing window

This is the most common “low stress” hybrid in a balanced market: you sell first, but you give yourself time.

C) Buy with a longer closing and list immediately

This is the “controlled buy-first.” You secure the next home, then launch your sale with urgency and precision.

The micro-market test (what you should be asking your REALTOR® for)

Because Windsor-Essex varies by area, price point, and property type, you want stats that match your exact situation:

Ask for:

Months of inventory for your property type and price band
Median days on market for comparable homes
Sale-to-list price ratio for true comparables
How many direct comparables have sold in the last 30 to 90 days

This is how you stop arguing with anecdotes and start planning with evidence.

A simple decision framework you can use tonight

Score each statement 1 to 5 (5 = strongly true)

Choose sell first if you score high on:

“We need our equity to comfortably buy.”
“We would lose sleep carrying two homes.”
“Our home might take longer to sell (condo, niche, fixer-upper, premium price point).”
“We want certainty and clean timelines.”

Choose buy first if you score high on:

“The home we want is hard to find.”
“We can carry overlap if needed.”
“Our current home will sell predictably if priced correctly.”
“We’d rather risk short-term overlap than risk not finding the right next home.”

If you’re split, pick a hybrid and write a Plan A, Plan B, Plan C with dates attached.

The calm move is the planned move

In a market with more choice and more negotiation room, the winners are rarely the most aggressive. They’re the most prepared.

If you are thinking of making a move in Windsor or Essex County, the best first step is not booking showings or guessing a list price. It’s building a sequence that matches your property type, your price point, and your tolerance for risk. Speak to your REALTOR® about the pros and cons of each situation.

A practical note about The Dan Gemus Real Estate Team

At The Dan Gemus Real Estate Team, we spend a lot of time on the part most people skip: building the actual move plan. That means mapping out timing, financing realities, neighbourhood-level stats, and backup options before emotions and deadlines take over. Whether you buy first, sell first, or use a hybrid strategy, a clear sequence protects your money and your peace of mind, especially when different pockets of Windsor-Essex behave differently.

Have a question? We have answers about the real estate market anywhere in Windsor and Essex County, or the buying and selling process. The professionals at The Dan Gemus Real Estate Team are here and happy to help answer your questions so you can make smart decisions with your next move.

*This blog is for educational and informational purposes only. We understand that everyone’s circumstances are unique so this blog is is no way intended to replace legal, financial, accounting or environmental advice, nor is it intended to solicit those under contract with another Brokerage.