A Practical Guide to Upsizing Your Home

Once you’ve finished this guide, check out our entire Upsizer’s playbook at the links below!

How do I prepare my home
Should I buy first or sell first?
How can I time a buy and sell?
What costs should I expect when selling?
Should I upsize or renovate?
How can I avoid common seller mistakes?

A Practical Guide to Upsizing Your Home

Upsizing is an exciting step, but it is also one of the more complex real estate decisions people make. It often involves coordinating two transactions, managing timing risk, and making financial decisions in changing market conditions. Because of that, planning matters just as much, if not more, than price alone.

This guide outlines the key considerations upsizers should understand before making decisions, with a focus on clarity, sequencing, and risk management.

What upsizing really involves

Upsizing is not just about buying a bigger home. It often means:

• Coordinating a sale and a purchase
• Managing equity and financing
• Navigating timing and market risk
• Making decisions under changing conditions

Because two transactions are involved, the process is less forgiving of rushed or emotional decisions. Clear planning reduces pressure and helps protect flexibility.

Why people choose to upsize

Common reasons include:

• Growing families or changing space needs
• Remote or hybrid work requirements
• Desire for a different layout or location
• Long term lifestyle planning

Upsizing is often driven by necessity rather than impulse, which makes thoughtful preparation especially important.

Using equity wisely

Many upsizers rely on equity from their current home to fund their next purchase. Understanding how that equity works is critical.

Key considerations include:

• How much equity is realistically available after selling costs
• Whether funds are needed before or after the sale
• If bridge financing may be required
• How changes in pricing could affect the final budget

Understanding equity early helps avoid pressure later and allows decisions to be made calmly rather than reactively.

Key financial considerations

Upsizing usually introduces new financial variables that should be reviewed early in the process.

Important factors include:

• Mortgage qualification at higher price points
• Increased monthly carrying costs
• Down payment structure and liquidity
• Closing costs on both the sale and the purchase

Being approved does not always mean being comfortable. Planning around realistic monthly costs is just as important as purchase price.

Buy first or sell first when upsizing

This is one of the most important decisions upsizers face, and it often carries more risk than for other buyers.

Rather than asking which option is better, it is often more helpful to consider which side of the transaction is more uncertain under current market conditions.

In a buyer’s market:
• Buying may feel easier due to selection and leverage
• Selling may take longer or require pricing adjustments

In a seller’s market:
• Selling is often quicker and more predictable
• Buying can be competitive and stressful

Many upsizers benefit from addressing the more uncertain side of the transaction first, rather than defaulting to comfort or convenience.

Timing and transition planning

Upsizing often overlaps with other life changes, which adds another layer of complexity.

Considerations include:

• School year timing
• Commute and lifestyle impacts
• Renovation versus move decisions
• Temporary housing or overlap periods

A flexible, realistic timeline reduces rushed decisions and unnecessary stress.

Common upsizer mistakes

Some challenges come up repeatedly:

• Falling in love with a home before being fully prepared
• Underestimating total monthly costs
• Poor sequencing between sale and purchase
• Getting anchored to list prices rather than market value

Most of these issues can be avoided with proper planning and clear expectations.

Final thoughts

Upsizing should support your life, not complicate it. A clear plan, realistic financial framework, and thoughtful sequencing go a long way in reducing stress and improving outcomes.

Getting Started

If you’re considering selling, the first step is often understanding your options. We’re happy to walk through your situation, discuss timing and strategy, and help you determine what makes sense based on your goals.

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