West Michigan Real Estate
Born here. Selling yours.Finding your next.
Move-up specialist serving Plainwell, Kalamazoo, Gun Lake, and Southwest Michigan.
Just looking? Browse homes →
Jason O'Brien · REALTOR®
I'm a Plainwell native who does both sides of your move.
I grew up here. My family's been in Southwest Michigan for three generations.
I sell your home and find your next one in parallel — so you never have a “now what?” moment in the middle of a move.
#2 in Michigan · #32 in the nation
Homes for Heroes affiliates, by closings in the last 12 months (Homes for Heroes affiliate dashboard, October 2026)
How a move-up works with me
Selling and buying in parallel — without the gap in between.
01
We figure out what your home is worth
I run a real CMA on your current home so we know your budget before we start.
02
We find your next one
I search on your behalf, set up showings around your schedule, and write offers ready to win.
03
I coordinate the close
Your sale and your purchase happen in parallel. You don't end up homeless between them. Backup plans in place if timing wobbles.
Currently on the market
IDXA snapshot of active listings in West Michigan.
Where I work
Click any town to browse current listings.
Lake Homes
Every lake, with its own sale record.
I track thirty-four lakes across Barry, Allegan, Kalamazoo, Calhoun, St. Joseph and Van Buren counties. What sold, what it asked, how long it sat, and how much frontage came with it — pulled from the MLS every morning.
Organized by lake, because that is how people who live on one think about it. If you own on the water, your lake has a page.
See every lakeWhat clients say
Jason helped us navigate the Homes for Heroes® program and made both our sale and purchase seamless.
“Incredibly helpful answering our questions and guiding us through the process of selling our home and purchasing our next one.”
“Jason's strategic approach to listing our home resulted in multiple offers and a quick sale.”
“Efficient, communicative, informative, and friendly. Jason helped us sell multiple properties over the years.”
Move-up questions, answered
The things people ask me before they list.
No. Most of my move-up clients close on both within days of each other. I run your sale and your search in parallel — by the time you find the next home, your current one is usually already under contract.
We price it right from day one and present it like a luxury listing regardless of price point. Most of my listings move in under 30 days. If something stalls, I have a tested process for adjusting strategy fast — and I'll tell you exactly what's working and what isn't.
We build the timing into both contracts from the start. Either the dates line up exactly, or we negotiate a short post-close occupancy with the buyer of your current home. I've never had a client end up without a roof.
Yes. There are a few ways — sale-of-home contingencies that are friendlier than buyers think, bridge financing, or in some cases a non-contingent offer once we know your home will sell. I'll talk you through what fits your situation.
Have a question I didn't answer? Text me
Let's talk
Tell me a bit about what you're thinking — I'll get back personally, usually same day.