Should You Buy Before You Sell? How to Bridge the Gap Safely

For many homeowners, deciding when to buy their next home comes with a tricky question: Should you buy before you sell? It’s one of the most common dilemmas in real estate — especially in markets where inventory is limited and homes move fast.

The right answer depends on your financial situation, local market conditions, and your comfort with risk. Buying first offers flexibility, but it also requires a strategy to avoid getting caught juggling two homes or missing out on the one you love.

The Pros of Buying First

The biggest advantage of buying before selling is control. You can search for your ideal home without the stress of being on a deadline or worrying about where you’ll live between closings. You also have more freedom to prepare and stage your current home once it’s empty, helping it show its best.

In a slower or balanced market, buying first can make sense — you can take your time, make thoughtful decisions, and transition smoothly.

The Challenges and Financial Realities

However, buying before selling can create financial strain. Without proceeds from your current home, you may need to qualify for two mortgages, which isn’t feasible for everyone. There’s also the risk of timing — if your current home takes longer to sell than expected, carrying two sets of expenses can become stressful.

Another challenge arises in competitive markets like Chicago’s most sought-after neighborhoods. When multiple offers are common, sellers rarely accept home sale contingencies because they add uncertainty and delay.

A contingency means your offer depends on selling your existing home first, and in fast-moving markets, sellers almost always choose buyers who can close without those strings attached. That’s why serious buyers often need a financial plan in place before shopping — one that allows them to make a strong, non-contingent offer when the right property appears.

Bridging the Gap Safely

If you’re considering buying first, here are a few ways to make it work:

1. Bridge Loans: A short-term bridge loan uses the equity in your current home to fund your new purchase. It’s convenient but comes with higher rates and fees, so it’s best for buyers who are confident their home will sell quickly.

   
   

2. Home Equity Line of Credit (HELOC): If you plan ahead, open a HELOC before listing your home. This lets you tap into your home’s equity for a down payment — often at lower cost than a bridge loan.

   
   

3. Temporary Housing or Lease-Backs: Another approach is to sell first, then negotiate a short lease-back with your buyer or find short-term housing. It keeps your finances safe while giving you time to find your next home.

   
   

Final Thoughts

Whether you decide to buy or sell first, the most important thing is to plan carefully and stay realistic about timing. Every situation is unique — what works for one buyer or seller might not fit another. The right approach depends on your financial situation, market conditions, and the level of flexibility you need for your move.

If you’re considering a transition this year and aren’t sure where to start, I’d be happy to walk you through your options — from understanding your home’s market position to exploring ways to bridge the gap smoothly. A clear plan can make the process far less stressful and help you move forward with confidence.

Photo Credit: Architectural Digest