Upsizing Your Home in Metro Detroit
How to sell your starter home and buy the bigger one without moving twice, guessing at the timing, or living in a rental in between.
Your family did not shrink. The house did. The bedrooms that felt fine three years ago are now storage for things nobody uses, one kid is sleeping in what was supposed to be an office, and you are having the same conversation with your partner every few weeks and never finishing it.
You are not confused about what you want. You are stuck on how it all lines up.
Founder & Principal Associate Broker
I am Ashley Oshinsky, founder and Principal Associate Broker of Higher Living Real Estate. Almost everything I do is this exact move: helping families in Oakland, Macomb, and Wayne County sell a home they have outgrown and buy the one they actually need.
Not investors. Not flips. Families who are out of room in a house they still like, in a neighborhood they may not want to leave.
Who This Page Is For
You have probably been at this longer than you would admit. Scrolling Zillow at midnight. Running your own numbers in a spreadsheet. Asking ChatGPT what happens if your house does not sell in time. Saving listings you will never tour.
The families I work with usually sound like this.
- We have equity in this house but we do not know how to use it.
- We cannot buy until we sell, but we do not want to sell and have nowhere to go.
- We are not sure if we should renovate this house instead.
- Our budget looks fine on paper but we do not know what it feels like at the higher payment.
- We have been about to start for over a year.
If any of that sounds like your kitchen table, you are in the right place.
The Real Problem Is Sequencing
Here is the thing almost nobody tells you. Upsizing is not hard because homes are hard to find. It is hard because two transactions have to line up, and most people try to solve them one at a time.
Sell first and you might be without a home for six weeks. Buy first and you might carry two payments. Try to do both on the same day and the whole thing depends on a chain of people you have never met.
Every stuck upsizer I talk to is stuck at the same spot. Not what do I want. Not can we afford it. It is in what order does this happen, and what do we do if one piece slips.
That is a solvable problem. It just has to be solved on purpose, before you list anything.
The Three Ways to Sequence an Upsize
There is no universally right answer. There is a right answer for your equity, your income, your risk tolerance, and how much upheaval your family can absorb. Here is the honest version of each.
Sell First, Then Buy
You list, you sell, you know your exact number, and you shop with real money and real leverage. Sellers take your offer seriously.
The tradeoff The gap. You may need a rental, a family member's basement, or a leaseback from your buyer. This is the strongest financial position and the hardest one on your daily life.
Buy First, Then Sell
You find the house, you move on your own timeline, and you sell your old home empty and staged, which usually sells faster and for more.
The tradeoff Qualifying to carry both, or using a bridge loan or a home equity line to get there. Best for families with strong income or significant equity.
Sell and Buy the Same Day
The one everybody asks for. It is possible and I do it regularly, but it takes a cooperative buyer, a cooperative seller, and a lender and title company who talk to each other.
The tradeoff The least margin for error. When it works it is seamless. When one link slips, everything slips.
Part of my job is telling you which of these three you actually qualify for before you fall in love with the wrong plan.
What Upsizing Really Costs
Not the purchase price. The parts people forget.
- The difference in your monthly payment, at today's rate, not the rate you have now
- Closing costs on the sale and closing costs on the purchase
- What you will spend to get your current home market ready
- Moving costs, twice, if there is a gap
- The furniture and window treatments a bigger house quietly demands
- Higher taxes, higher utilities, and in some neighborhoods an association fee
I put all of this in front of you in the first conversation. Not on closing day. Some families look at the full picture and decide to go. Some decide to wait a year and go stronger. Both are good outcomes. Being surprised is not.
Metro Detroit Specifics Most People Miss
Local rules matter here more than people expect, and they are not the same from one city to the next.
Many Metro Detroit municipalities require a certificate of occupancy, a pre sale inspection, or both before a home can transfer. Some require repairs to be completed and reinspected first. Requirements and timelines vary by city and township across Oakland, Wayne, Macomb, Genesee, and Livingston County. If your home is on septic or well, several communities require testing at the time of sale.
How I Work: The Curated Method
Three parts, in this order. The order is the whole point.
Calm
We take the panic out first. You cannot make a good decision about a house while you are afraid of the timing. Before we look at a single listing, we get clear on what actually happens if a piece slips, so the fear stops driving.
Clarity
We map the real sequence. What your home is likely to sell for, what you qualify for, which of the three paths fits you, what happens on which day, and what the backup plan is. You leave with a plan on paper, not a feeling.
Curation
I bring you the short list. Not every home that matches a filter. The handful that fit your family, your commute, your schools, and the way you actually live. I would rather send you four houses than forty.
More on the Curated Method, or read what past clients say.
What the Process Looks Like
- A conversationNo pressure, no listing agreement. We talk about your house, your equity, your timing, and what is making you hesitate.
- A numbers sessionWhat your home sells for, what you net, what you can carry, and what the payment feels like.
- A pathWe pick one of the three sequences and build the calendar around it, backward from the date you want to be in the new house.
- PreparationWe get your current home ready to sell, and I handle inspections and municipal requirements early instead of at the last minute.
- The searchCurated, not endless.
- Two closings, coordinatedTimed against the path we chose, with the backup plan already in place.
Common Questions About Upsizing in Metro Detroit
Should I sell before I buy?
It depends on your equity and whether you can qualify to carry two payments. Sell first is the safest financially and the hardest logistically. Buy first is more comfortable and takes more cash or borrowing power. We decide this before you list, not during.
Can I make an offer with a home sale contingency?
Yes, and whether a seller accepts it depends on the price point, the neighborhood, and how strong the rest of your offer is. In competitive segments it is a real disadvantage. There are ways to strengthen it, and there are situations where a different path is simply the better move.
How much equity do I need to upsize?
There is no single number. What matters is what you net after closing costs and payoff, what that covers on the new purchase, and what the resulting payment does to your monthly life. We run this in the first numbers session.
What if my house does not sell?
This is the fear underneath most of it. The answer is that we build the backup plan before we list, so if the market is slower than expected you already know what happens next and you are not making a panicked decision in week six.
Should I renovate instead?
Sometimes yes. If the layout can work and you love the location, renovating can beat moving. I will tell you honestly when I think that is the case, even though it means I do not get a transaction.
How long does it take to upsize?
From first conversation to keys, most upsizes run a few months, and the preparation phase is usually the longest part. Starting early costs you nothing and gives you options. Starting late costs you leverage.
Do Metro Detroit cities require an inspection before I can sell?
Many of them do. Requirements vary by city and township, but a certificate of occupancy, a pre sale inspection, or both are common across Oakland, Wayne, and Macomb County, and some municipalities require repairs to be completed and reinspected before transfer. Homes on septic or well may also need testing at the time of sale. I handle these early rather than at the last minute, because a missed inspection is one of the most common reasons a closing date moves.
Where I Work
I serve Metro Detroit, including Oakland County, Macomb County, and Wayne County. Communities I work in often include these and the surrounding areas.
- Bloomfield Hills
- West Bloomfield
- Rochester
- Ferndale
- Huntington Woods
- Royal Oak
- Berkley
- Clawson
- Troy
- Birmingham
- Waterford
Do not see your community? It is not a boundary. Ask me about your area.
Let's Talk Before You Are in a Hurry
You do not need to be ready to list. You do not need a plan. You just need to be tired of having the same conversation and not finishing it.
Fill out the form below and tell me where you are stuck. I will tell you what I would do in your position, whether that means listing this spring, waiting a year, or staying put and renovating.
Ashley Oshinsky, Founder & Principal Associate Broker, Higher Living Real Estate
Call or text 248-410-7940