When Should I Sell My House?

How to Move Up with Ease Series

When should I sell my house?

We all love our first home but eventually there comes a point when it’s time to move on. Life changes and so do our needs and wants in a home.

When you are ready for a new home but also have one to sell or rent-out, the stakes are much higher. This time around, you’ve got more to think about, plan, and “get right” than when you bought your first home.

This 5-part weekly series is a “how-to” guide for moving up to your next home with as little stress as possible. Whether it’s your first time moving up or you’ve done it before, this series is a great resource.

First up… How do you decide if you should move or stay in your current home?

Maybe your cozy home now feels cramped, your hip neighborhood now feels noisy, or your job and commute have changed. Or …maybe your oldest kid starts school next year, or your youngest kid graduated from college. All of the sudden you start thinking “Should I Stay or Should I Go?”. (With apologies to The Clash.)

YOU change. LIFE changes. Your needs and wants evolve. Whatever the situation, your home just isn’t a good fit for your family’s needs and lifestyle anymore. It’s easy to put up with your current situation, but what if you should consider a new home?

Moving can be a hard decision, both financially and personally, so determine if you’re truly ready for it. Here’s what to consider before you start packing:

Your $$$ Situation

  • Equity in your home. If you have owned your home for five or more years, then you should have substantial equity. This is when your investment pays off and you can use this equity toward the purchase of your next home.
  • Financial Outlook. If your employment is steady, your income is improving, and your entire financial situation looks good now and down the road, this is a good sign. This means three things: 1) You will get approved for a mortgage; 2) you can afford higher mortgage payments; and 3) you can own a more expensive, larger home. (If you want)
  • Healthy Housing Market. If the market is stable or flourishing, then it’s a good time to sell your current home and buy a new one. Homes priced right will move and that’s good if you’re a seller. It’s better to avoid a sluggish time in the market. Your home could take a while to sell and who wants to drag it out and not get the price you were hoping for.
  • Low Interest Rates. While interest rates ARE starting to rise a little, they are still low compared to many other times in history. This can still be a good deal for you. 

Your Needs & Wants

  • Location, Location, Location.  When you bought your current home, it probably felt like the perfect location for you, but maybe not now. So many variables go into what makes a good neighborhood for you and your family at this specific time.

It might not be a kid-friendly neighborhood and you want a better school district, or you changed jobs and now spend more time in the car, or maybe the neighborhood itself has changed. Maybe your quiet street is now too busy. Perhaps you want a stronger community feel or a more walkable neighborhood. Or you want a larger yard and more space between neighbors.

It all comes down to what you want now and where you picture yourself living. Plan to stay at your next home at least five years, and picture what your life is going to be like then.

  • Can’t or Won’t Remodel.  You love HGTV and can just imagine your home remodeled and updated with larger rooms, gleaming kitchen. But you realize it’s only a fixer-upper dream. Your yard is too small for an addition, you’re not zoned for it, or you just can’t live through the mess or cost. Plus, you never want to be the nicest house on the block. Moving can provide you with more sanity, more room, and you can ditch the rejiggering of the floor plan.
  • Space is Changing. You want to increase your home’s size since your family is growing OR you want to downsize since your kids are gone. Whatever the direction, you’ve realized the size and space of your home doesn’t work for you and your family anymore.

You want space for toys (yours and theirs!) and to say good-bye to cluttered, cramped rooms. Or, you don’t need 4 bedrooms anymore and want a more manageable home and yard. Space needs can change dramatically in a short period of time so plan accordingly for down the road.

  • Green Acres. Homeowners either love big yards or hate them. Have you figured out what you like? Yard space can be a wonderful addition to your home — for entertaining friends, for kids, for dogs, for gardening, for just getting some fresh air. Even a small patio or deck or even a nearby park may be what you are looking for next.

If you don’t want to mow every Saturday or don’t have enough privacy between you and your neighbor’s yard, and it’s nagging you Every. Single. Day … then it’s time to move.

  • Life Changes You.  Where you live impacts your life and vice versa … your life will affect where you should live. If you’re a growing family, a newly single mom, or empty nesters, you want a home that reflects you and your new needs.

A condo unit and all of its amenities were perfect for you when you were on the go with travel and work. But maybe you’re more settled now and ready for a townhome or single-family home to take care of and spend time with family and friends.

Or maybe you weren’t “ready” for a single-family home and its responsibilities a few years back as a first-time buyer. Now you’re a confident homeowner and you want your own space and yard and to not deal with your condo’s rules anymore.

Sometimes you can anticipate upcoming life changes that will happen in the next few years. It’s good to be prepared and perhaps plan an earlier move, especially if the housing market is good and rates are low. Timing can make or break the affordability of certain homes.

Making the decision about whether it’s time to go or if you should stay is sometimes the hardest part. I’d be happy to help you with how to think through what’s best.

And…no, the answer isn’t always to sell just because I’m a real estate agent.  

Sometimes the answer is not yet or wait until X time when it makes more sense. Think of me as your real estate counselor, helping you talk through these types of big real estate decisions. 

Whether you move now or later doesn’t matter to me, I just want to help you when the time is right for you, not rush you into something that isn’t in your best interest too early!

If you want more articles all about homeownership and selling your Chicago Northwest Suburb home, click here.

Or, if you’re thinking about buying a new home in Chicago’s Northwest Suburbs, here they are!

Don’t forget to check out my YouTube Channel – Chicago to the ‘Burbs!

Hi, there!

I'm Mike and I love helping buyers discover what's really important in their forever home, then working to find that in Chicago's 

Northwest Suburbs. I also have a soft spot in my heart for teachers and love giving back to them whenever I can. Let me know how I can help you make your real estate dreams come true. 




NorthWest Suburbs

schedule your free consultation

or email me!

Hi there!

I'm Mike and I love helping buyers discover what's really important in their forever home, and working to find that in 

Chicago's Northwest Suburbs. I also have a soft spot in my heart for teachers and love giving back to them whenever I can. Let me know how I can help you make your real estate dreams come true. 

schedule your free consultation




NW suburbs