Downsizing a house that made perfect sense when your kids were home — the extra bedrooms, the big backyard, the second living room nobody uses anymore — can start to feel like a lot once they’re gone. If you’re an empty nester (someone whose grown kids have moved out) in Woodland Hills, West Hills, Calabasas, Agoura Hills, Oak Park, Westlake Village, or Thousand Oaks and finding yourself rattling around a house built for a bigger season of life, you’re not alone. Here’s how to think through downsizing the right way.
1. Get honest about what you’re actually using
Walk through your home room by room and ask: when’s the last time this space earned its keep? For many empty nesters, it’s the guest room that hosts guests twice a year, the formal dining room that’s seen three dinners since 2020, or the yard that costs more in upkeep than it delivers in enjoyment. This isn’t about giving anything up — it’s about matching your home to your actual life instead of the one you were living five or ten years ago.
2. Understand what your equity can do for you
Many homeowners in this area have built substantial equity over the years, and downsizing is often less about “settling for less” and more about converting that equity into flexibility — lower monthly costs, less maintenance, and cash freed up for travel, retirement, or helping the next generation. Before you get attached to a number, talk to your accountant about how a sale would affect your taxes, including the capital gains exclusion on a primary residence — the specifics depend on your situation, so this is worth a real conversation with a CPA, not a guess. This is the real financial upside of downsizing.
3. Decide what “smaller” actually means for you
Downsizing doesn’t have to mean downgrading. Some empty nesters want a low-maintenance single-story in the same neighborhood so they can stay close to friends and routines. Others want a condo or townhome with lock-and-leave convenience for travel. Others are ready to leave the area altogether. Get specific about what you’re solving for — less yard work, less square footage to clean, one story instead of two, lower property taxes — before you start touring homes, so you’re not shopping blind.
4. Start decluttering earlier than you think you need to
This is the step people underestimate most. Twenty-plus years of a family home means twenty-plus years of stuff, and sorting through it under a moving deadline is stressful. Start now, even if you’re not selling for six months: donate, sell, or pass down what you can, and give sentimental items time to find the right home rather than making rushed decisions during a move.
5. Time it around the market, not just your calendar
Fall and winter get an undeserved reputation as bad times to sell. In practice, serious buyers shop year-round, and a well-priced, well-presented home in this area can move in any season — sometimes with less competition than the spring rush. If you’ve been waiting for “the right time,” it’s worth a real conversation about current conditions in your specific neighborhood rather than defaulting to a rule of thumb.
Frequently asked questions
When is the best time to downsize a family home? There’s no single right age or year — the better signal is when the home’s upkeep (cost, cleaning, maintenance) outweighs how much of it you actually use. Market timing matters less than most people assume; a well-priced home in this area can sell in any season.
Do I have to sell before I find a new place? Not necessarily. Some sellers buy first and carry two homes briefly; others sell first and rent short-term while they look. The right order depends on your equity, the current inventory in the neighborhoods you want, and how much flexibility you need — worth a specific conversation rather than a general rule.
Will I owe taxes on the sale of my home? Possibly, depending on your gain and how long you’ve owned and lived in the home — the primary residence capital gains exclusion may cover some or all of it. This varies by situation, so confirm the specifics with your CPA before deciding based on assumed numbers.
If you’re weighing this downsizing decision
This is a big one, and it deserves more than a generic checklist. If you’re an empty nester in Woodland Hills, West Hills, Calabasas, Agoura Hills, Oak Park, Westlake Village, or Thousand Oaks and you’re wondering whether now’s the time, reach out — happy to walk through your specific home, your equity position, and what a realistic timeline could look like, no pressure attached.
— Ashkan Shirinkar
