“Should I buy a second home now or wait until retirement?”
It’s one of the most common questions I hear from clients. It’s a big decision, and it usually comes with many other questions trailing behind it:
- What if we can’t afford both properties?
- What if my parents need me closer?
- Is it better to invest the money instead?
- Does this property actually fit how we want to spend our time?
Over the past few months, I’ve had three conversations with couples navigating exactly this decision. Each came to the table with different circumstances, different dreams, and different questions about timing. After helping them review all their information, one couple decided to wait, another walked away from what seemed like the perfect property, and the third pulled the trigger immediately.
What they all discovered is that “should I buy a second home?” isn’t really a yes-or-no question; it’s a conversation about whether the timing works for your whole life, not just your bank account.
Story 1: When “Yes” Was Possible, But “Not Yet” Was Better
Mark and Sarah are about a year away from retirement. They’ve always dreamed of living near the ocean—not just visiting, but actually waking up to the sound of the waves every day. Throughout his successful career as an attorney, Mark had been slowly designing their coastal dream home, exactly the way they want it.
When we sat down with Mark and Sarah to discuss this beachy dream home, the numbers told an interesting story:
- The good news: They could technically afford to own and maintain both their existing property and the new home, at least for the foreseeable future.
- The complication: Buying now would significantly deplete their liquid assets. With retirement quickly approaching, that could impact Mark and Sarah’s flexibility in regards to travel or other major expenses during the transition.
And that’s when other factors started surfacing.
Both Mark and Sarah have elderly parents who need active support with day-to-day needs, and moving to the coast right now would mean being farther away during a time when their presence really matters.
Mark will also likely receive an inheritance in the coming years. As we talked, a different path started to make more sense: timing this purchase to coincide with that inheritance could ease a lot of the financial pressure and give them more flexibility to design and build exactly what they want without depleting their savings.
– What We Can Do: Run Multiple Scenarios Before Deciding
When Mark and Sarah came in, we didn’t just answer “can they afford it?” We built out five different scenarios based on them purchasing the second home:
- Buy at $2M now vs. $2.5M after inheritance
- Impact on liquid assets at ages 70, 80, 90
- What happens if elder care costs spike in year three
- Financial flexibility if one parent needs to move in with them
- The difference between financing vs. cash purchase
This is what scenario planning looks like in practice. We show you exactly how each choice impacts your financial picture at different ages and life stages. You get to see the trade-offs in real numbers, not just gut feelings.
For Mark and Sarah, the planning revealed that, yes, they can buy now, but waiting might mean they can buy better. The decision isn’t “no.” It’s “not yet.” And that’s actually a really empowering place to be.
Story 2: The Dream Property That Didn’t Match Real Life
Jim and Tammy are retired and already own two properties, one home and one rental. When a beachside condo caught their eye, it looked perfect on paper.
Scenario planning made it clear that to move forward, they’d need to sell both existing properties. That was a big decision, but one they were willing to consider—if the condo truly fit their vision.
That’s where the story shifted.
As we talked through how they’d actually use the property, it became clear they wouldn’t live there full-time. Most of the year, it would be rented out. Once that reality set in, the emotional appeal faded, because the “dream” wasn’t something they’d be enjoying day to day.
Then came the risks:
- The building concerns: The condo was in an older building with the real possibility of large special assessments.
- The financial reality: Tens of thousands of dollars in surprise costs would be very much on the table.
- The lifestyle mismatch: They’d be managing a rental property instead of enjoying a second home.
In the end, they passed. Jim and Tammy sold one property, held the proceeds in cash, and kept looking, with clearer priorities and fewer compromises. Sometimes the most valuable thing planning can do is help you see when something isn’t the right fit, before you’re locked in.
– What We Can Do: Take Your New Life Out for a Test Drive
Before you commit to any second home purchase, let’s make sure you’re buying the right property for the right reasons. Here’s what I always recommend:
- Experience the location first. If you’re buying somewhere new, rent an Airbnb for a week or two. See if you can actually picture yourself living that life.
- Get honest about how you’ll use it. Are you buying this property for you, or for some theoretical future version of yourself that might not even materialize? Will you live here, or will you rent it out?
- Do your homework on HOAs and hidden costs. If this is a condo or HOA property, what’s the building’s condition and financial health? Request meeting minutes, reserve studies, and assessment history. A cheap HOA fee can turn into an expensive surprise.
Related: How to Prepare for Home Buying When Your Income Fluctuates
Story 3: When the Decision Was an Easy Yes
Now let’s talk about Ken and Carrie, because their story shows what it looks like when both the finances and the lifestyle align beautifully.
They’re in their 40s with two young kids, and they wanted to buy a vacation home in a small Central Coast beach town. If you live in California, you know the type. It’s one of those classic beach towns where families go to unwind, and it holds a lot of nostalgia for people who grew up here.
For Ken and Carrie, this purchase checks every box.
- Financially comfortable: They can carry the costs of both their primary residence and this vacation home without straining their long-term plan.
- Actually using it: It’s not just a rental property or an investment they’re hoping appreciates. It’s a place where they can build family memories right now with their kids.
- Family logistics: Carrie’s parents live in Southern California, so Central Coast beach town is roughly halfway between their primary home and her parents’ place. It gives them a natural spot to meet up, making it easier to stay connected with extended family.
When we looked at their overall financial picture, including estate planning considerations down the road, this property made sense on every level. It fits their current lifestyle, it supports their family dynamics, and it’s something they can afford without sacrificing other goals.
So, we said: pull the trigger. This is exactly the kind of decision that financial planning is meant to support. Not just “can you afford it,” but “does this enhance the life you want to live?”
– What We Can Do: Create Your Decision Framework
Every situation is different, but we often use these questions to help clients decide whether they’re in a good position to move forward:
- Can we carry both properties without depleting emergency saving or retirement accounts?
- Does the location serve our family’s needs and logistics right now?
- Are we buying this for us, not as an investment we’re hoping pays off?
- Does this purchase feel exciting rather than anxiety-inducing when we talk about it?
- Have we stress-tested the scenarios and still feel comfortable with the numbers?
When the financial capacity, lifestyle fit, and family dynamics all line up, that’s when “should I buy a second home?” becomes a clear, confident yes.
Your Home, Your Life, Your Path
Financial planning can tell you whether something is possible, but only you can decide whether it’s right.
We can model different scenarios and show you what happens at different price points, timelines, and financing options. That’s the technical side, and it matters. But we know that the lifestyle side matters even more, which is why we want to know about your vision for yourself and your family.
Does this property actually serve how you want to live? Does the timing work with everything else happening in your life? Do you feel excited about this decision, or does it make you anxious?
That’s where our scenario planning becomes so valuable, because you get to see the real impact of each choice, not just guess at it.
If you’re weighing this decision and want to talk through your specific situation, let’s set up time to walk through the scenarios together. We’ll look at your full financial picture, discuss what matters most to you, and help you move forward with clarity.
Ready to see what buying (or waiting) would actually look like for your situation?
We’d be happy to map out your second home scenarios together, so you can move forward knowing this decision works for both your finances and your life.
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Team Hewins, LLC (“Team Hewins”) is an SEC-registered investment adviser; however, such registration does not imply a certain level of skill or training, and no inference to the contrary should be made. We provide this information with the understanding that we are not engaged in rendering legal, accounting, or tax services. We recommend that all investors seek out the services of competent professionals in any of the aforementioned areas. Certain information provided herein is based on third-party sources, which information, although believed to be accurate, has not been independently verified by Team Hewins. Team Hewins assumes no liability for errors and omissions in the information contained herein.