Top 5 Questions Seniors Ask Before Downsizing in San Diego

For many longtime San Diego homeowners, the idea of downsizing is both exciting and emotional. The thought of a simpler lifestyle, lower expenses, and less maintenance can be freeing—but at the same time, questions about where to go, what to do with belongings, and how to protect your hard-earned equity can feel overwhelming.

As a Certified Real Estate Planner®, I’ve guided many clients through this transition. Here are the top 5 questions seniors ask before downsizing—and what you need to know.

1. Where will I go?

San Diego offers incredible downsizing options depending on your lifestyle:
- 55+ communities with social clubs, pools, and fitness centers.
- Single-level homes or condos that eliminate stairs and reduce upkeep.
- Walkable neighborhoods near shops, restaurants, and medical offices.
- Townhomes with HOA-maintained exteriors for stress-free living.

👉 Downsizing isn’t about giving up—it’s about moving into a home that better fits your next chapter of life.

2. What do I do with all my stuff?

Sorting through decades of belongings can feel overwhelming. Here’s how my clients manage it:
- Start small: one closet, one drawer at a time.
- Use the 'Four-Box Method': Keep, Donate, Sell, Discard.
- Bring in help: professional organizers or estate sale companies can make the process much smoother.

Remember: you’re not discarding memories—you’re creating space for freedom.

3. How much will it really cost me to sell?

The true cost of selling includes:
- Commissions & closing costs (title, escrow, transfer taxes).
- Preparation expenses: minor repairs, cleaning, or light staging.
- Moving costs and possibly temporary housing.

And then there’s taxes. If you’ve lived in your home for at least 2 of the past 5 years, the IRS allows you to exclude up to $250,000 (single) or $500,000 (married filing jointly) of profit from capital gains tax. That’s a huge benefit for longtime owners in San Diego. Anything above those limits may be taxable, so it’s important to plan ahead with your tax professional.

4. Am I leaving money on the table by waiting?

Some seniors delay downsizing because they believe their home’s value will just keep climbing. While San Diego real estate has historically performed well, waiting comes with risks:
- Rising maintenance and utility costs in a larger home.
- Difficulty managing stairs, yard work, or upkeep as you age.
- Potential changes in tax laws that reduce today’s homeowner benefits.

👉 The right time to downsize is when it aligns with your lifestyle and financial goals—not just the market.

5. Who can help me through the process?

Selling the home where you built a lifetime of memories isn’t just a transaction—it’s a major life transition. The right guidance matters. A Real Estate Planner® can:
- Coordinate with your CPA or financial advisor to avoid tax surprises.
- Help you evaluate options for your next home.
- Connect you with trusted downsizing specialists (organizers, movers, estate sale pros).
- Ensure you net the most money from your sale while reducing stress.

📌 Case Study: Downsizing in La Mesa

Recently, I worked with a couple in their early 70s who had lived in their La Mesa home for over 30 years. The house was two stories, with a large yard that had become difficult to maintain. They loved the neighborhood but wanted less upkeep and more time to travel.

Their biggest questions were: Where do we go? How do we handle all our belongings? What about the taxes when we sell?

Together, we created a plan. They decided on a single-level condo in La Mesa, close to shopping, their church, and a favorite walking trail. We connected them with a professional organizer to help sort, donate, and sell items. And with the $500,000 IRS exclusion, they were able to keep all of their profits tax-free.

Today, they enjoy a simpler lifestyle, lower bills, and more time for the activities they love—all without leaving the community they’ve called home for decades.

Final Thoughts