Should You Buy Before You Sell in Downtown Chicago Real Estate?
In most cases, it depends on your financial flexibility, risk tolerance, and how competitive the current downtown Chicago real estate market is. The right move isn’t universal, it’s strategic.
Understanding the Trade-Off in Downtown Chicago Real Estate
If you buy before you sell, you gain control. You can shop confidently, move once, and avoid temporary housing. In a fast-moving downtown Chicago real estate market, that can be a major advantage.
But there’s a catch.
Buying first means you may carry two mortgages temporarily. Even if you qualify financially, that overlap can create stress if your current home takes longer to sell than expected.
On the flip side, selling before buying gives you clarity. You know exactly how much equity you’re working with. You eliminate financial overlap. But you may need:
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A rent-back agreement
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Short-term housing
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Or a flexible moving timeline
In competitive segments of downtown Chicago real estate, selling first can sometimes leave you scrambling to secure your next property.
When Buying First Makes Sense
You might consider buying before selling if:
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You have strong savings or equity reserves
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Inventory is tight and desirable properties move quickly
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You’ve found a home that checks all your boxes
This approach works best when you have a clear pricing and marketing strategy for your current home. If you're unsure whether your property would sell quickly in today’s downtown Chicago real estate environment, that’s where a strategy call becomes valuable.
When Selling First Is the Smarter Move
Selling first may be better if:
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You need your equity for the next purchase
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You prefer financial certainty
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The market is shifting and timing matters
This route reduces risk. You’ll negotiate your purchase from a stronger financial position because you’re not contingent on selling.
The Strategic Middle Ground
There are also hybrid strategies:
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Contingent offers
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Extended closings
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Bridge financing
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Negotiated possession timelines
The key is building a plan before you list or start touring homes. In downtown Chicago real estate, timing and negotiation structure can matter just as much as price.
Final Takeaway
There’s no one-size-fits-all answer to whether you should buy before you sell. The right decision depends on your goals, financial position, and the current dynamics of downtown Chicago real estate.
If you're even considering making a move, the smartest first step isn’t guessing — it’s building a clear plan.
Let’s Map Out Your Next Move
If you’re debating whether to buy before you sell, schedule a call with me. We’ll look at your equity position, current market conditions, and your ideal timeline so you can move forward with confidence, not uncertainty.
Contact Us to schedule your call and start building your strategy today.
THE HANCOCK GROUP
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