Why Upsizing Feels So Complicated
If you’re thinking about upsizing in the Worcester, Massachusetts area market, you’ve probably asked yourself:
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What if my home sells before I find the right next one?
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What if I buy first and my current home doesn’t sell fast enough?
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Do I really need to move into temporary housing?
These are valid concerns but they’re also solvable. The key is understanding your options before you list or start house hunting.
Strategy #1: Sell With a Home Sale Contingency
One common approach is writing an offer on your next home that’s contingent on selling your current one. This strategy can work well when:
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Your home is likely to sell quickly
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Your pricing strategy is strong
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You’re working with clear timelines
In competitive situations, the details matter. Clean terms, strong earnest money, and realistic deadlines can make your offer far more attractive, even with a contingency.
Strategy #2: Use a Rent-Back to Buy Yourself Time
A rent-back allows you to sell your home and then stay in it for a short period after closing. This gives you:
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Access to your sale proceeds
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Time to close on your next home
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One single, well-timed move
This is one of the most effective ways to avoid moving twice, especially if you already have your next home under contract.
Strategy #3: Coordinate Extended or Flexible Closings
Another option is aligning the closing dates on both properties as closely as possible. This works best when:
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You’re buying new construction or a vacant home
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Both sides are open to flexible timelines
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You’re planning well in advance
When done right, this creates a near-simultaneous sale and purchase.
Strategy #4: Know When Buying First Makes Sense
In some cases, buying before you sell can be the right move, but only with careful planning. This often depends on:
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Your financial comfort level
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Market conditions
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Your risk tolerance
The goal isn’t to rush. It’s to choose the strategy that protects your flexibility and peace of mind.
The Biggest Mistake to Avoid
Trying to “wing it” without a plan is what leads to double moves, rushed decisions, and unnecessary stress. When you start with a clear roadmap, upsizing becomes far more manageable.
Final Takeaway
You don’t have to choose between missing out on your next home or living out of boxes. With the right approach, you can sell and buy at the same time; smoothly, strategically, and on your terms.
If you’re considering selling and upsizing in the Worcester, Massachusetts area, preparation makes all the difference.
👉 Download my free Home Seller Guide here:
https://annieoakman.myflodesk.com/ec5upmelag
This guide walks you through timelines, preparation steps, and common mistakes so you can move forward with confidence.
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This post was written by Annie Oakman, REALTOR®, and is intended for educational and informational purposes only. It does not constitute legal, financial, or real estate advice.
