Downsizing in Retirement: Real Stories, Smart Moves & What You Need to Know

Retirement looks different for everyone. For some, it means a new adventure in a different city. For others, it’s about staying rooted in a community they love—just with a little less to manage. One thing that’s consistent? After decades of homeownership, many people are ready to simplify life and unlock the equity they’ve built.

Whether you're looking to stay close to family, travel more, or just trade in stairs and yard work for something easier, downsizing doesn’t have to mean downgrading. It’s about finding the right fit for this next season of life.

Here are three real examples of clients we helped through that transition—and how thoughtful planning (and the right team) made all the difference. Scroll down for important tax resources.

🌿 Example 1: Selling a Bernal Heights Home – Simplifying Life After 30+ Years

After more than three decades in their cherished Bernal Heights home close to Holly Park, these longtime owners were ready for a change — but not a big move. Their goal was to stay in San Francisco and trade in the responsibilities of homeownership for the ease of renting a turnkey space.

We helped them secure a Concierge loan to prep the home for market — including fresh paint, refinished floors, and professional staging to highlight its potential. With 4 bedrooms, 2 baths, and 1,750 square feet, the home offered more space than they needed as empty nesters.

With the right pricing strategy and professional photography, including drone shots, the home drew strong interest and ultimately sold over $2M. The sellers transitioned to a low-maintenance lifestyle — still rooted in the city they love — with financial flexibility for retirement ahead.

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🏠 Example 2: Selling a Home in Sunnyside  – A Family Home Moves to Its Next Chapter

A beloved family home in Sunnyside, ideally located within walking distance to BART and with sweeping City views, was ready for its next chapter as the longtime owners prepared to move into a retirement center. The transition marked a major life moment — and Jennifer Burden & Carren Shagley, Legacy Real Estate Founders, were honored to help guide it with care and strategy.

By leaning into the home’s original charm and family-friendly floor plan, we were able to market it to a new generation of buyers seeking space and character. The property ultimately sold for $1,375,000, allowing the sellers to move forward with peace of mind and a well-funded retirement plan.

🌊 Example 3: Buying a Turnkey Condo in Emeryville

Retirement downsizing doesn’t always mean compromise — sometimes, it’s a lifestyle upgrade. That was the case for our buyer who found their ideal home, a bright 1-bed, 1-bath corner unit in Emeryville’s desirable Watergate community.

Thanks to swift decisions, our client secured a winning offer after the property had been on the market for just 14 days. The amenities sealed the deal: four year-round heated pools, hot tub, tennis courts, a clubhouse, gym, waterfront trails, and a private balcony — all in a walkable, vibrant community ideal for low-maintenance living.

Understanding the Tax Implications of Downsizing

Before making a move, it’s important to understand how selling your longtime home might affect your financial picture. Here are two key things to consider:

Capital Gains Tax Exemption 🧾 

When selling your primary residence, you may qualify for a capital gains exclusion:

• Up to $250,000 in profit (if you're single)
  
  

• Up to $500,000 (if you're married filing jointly)
  You must have owned and lived in the home for at least 2 of the past 5 years.
  
  

Prop 19: Property Tax Portability

If you’re 55+, severely disabled, or a wildfire victim, Prop 19 allows you to transfer your current property tax base to a new home anywhere in California (up to 3 times). This can be a huge financial benefit when downsizing or moving closer to family. Learn more about Prop 19 in our in-depth post here.

Resources to Make Downsizing Easier 🧰

Whether you're a year out or thinking about it "someday," here are some tools we offer to help:

1. Concierge Prep Services (painting, staging, repairs—upfront costs covered)
   
   

2. Trusted Vendors (organizers, financial planners, lenders, licensed tradespeople, movers)
   
   

3. Home Buying Services (Buy Before You Sell, All-Cash Offers, and custom home searches, data-driven purchase offers, inspections and guidance around contingencies)

Your Next Chapter, Your Way ✨

There’s no one-size-fits-all approach to retirement—and that’s the beauty of it. Whether you’re staying local or making a fresh start elsewhere, downsizing can open the door to new possibilities.

Whatever your situation, Jennifer Burden and Carren Shagley are here to help you navigate each step with care, strategy, and zero pressure. If you’re curious about your options, or just want to talk through next steps, we’d love to chat.

Links & Resources

Prop 19

https://legacysfhomes.com/blog/how-to-take-advantage-of-prop19

https://www.sf.gov/transfer-your-property-tax-base-replacement-home

CA Capital Gains Exemption

https://www.ftb.ca.gov/file/personal/income-types/income-from-the-sale-of-your-home.html

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