Investera Holdings is a Michigan family-operated company that buys established landscaping and grounds-maintenance businesses in Chicago and keeps them running. We are operators and buyers, not brokers and not a passive fund. When we acquire a company, we install strong systems and a professional management layer — route scheduling, crew leadership, account management, and a dedicated general manager — so the business runs without the owner riding every truck and bidding every property. We already operate service companies, so we understand seasonal crews, equipment, and the reality of a Midwest calendar. If you have built a book of commercial and residential grounds accounts across the Chicago area, we want to keep your name, your crews, and your reputation intact while giving you a confidential way to step back.
Why Chicago owners are thinking about selling now
Chicago’s seasons practically design a landscaping business’s revenue for it. Spring cleanups and plantings kick off after a long winter, the growing season drives weekly mowing and maintenance across the metro’s parkways, corporate campuses, and HOA properties, fall brings leaf and cleanup work, and then winter flips the whole operation into snow and ice management for parking lots and sidewalks. That snow-and-ice season is the quiet advantage of a Chicago grounds company: it turns a seasonal mowing crew into a nearly year-round operation with recurring commercial contracts that property managers cannot afford to skip when lake-effect storms roll in.
The commercial demand base is deep and durable. The office parks and corporate campuses ringing the city, the retail centers, the industrial corridors near O’Hare and the southwest suburbs, and the endless residential neighborhoods of greystones and bungalows all need grounds kept up. Meanwhile many Chicago landscaping companies are run by founders who have spent 20 or 30 seasons building crews and accounts and are now thinking about slowing down, often with no obvious successor and no systems that let the business run without them. Selling to operators who will keep the crews, honor the contracts, and add professional management is a far better path than a broker’s listing or a roll-up that treats your accounts as line items.
Who we buy in the Chicago area
We are looking for a specific kind of Chicago landscaping or grounds company — an established operation with real recurring revenue, not a seasonal side hustle. The strongest fits share these traits:
- Recurring revenue from maintenance contracts and, ideally, snow-and-ice accounts
- Around $500K or more in annual revenue or owner earnings (SDE) — close counts
- A capable team of crew leaders who can run routes without the owner on site
- A solid local reputation with commercial property managers and repeat clients
- An owner open to a clean handoff or staying on through a transition season
If most of that describes your business, it is worth a conversation even if you are still a season or two from deciding. We would rather build a relationship early than meet you the week you are ready to hang it up.
What makes selling to Investera different
No broker fees, ever. We buy directly, so you keep what a broker’s commission would have taken, and you are never left waiting on a listing that stalls while your accounts drift.
A confidential process from the first call. Your crews, your commercial accounts, and your competitors learn nothing until you decide. We sign an NDA before reviewing a single contract or financial statement.
Creative, flexible deal structures. Full buyout, partial sale, seller financing, or an earnout tied to retained maintenance and snow contracts — we shape the deal around your goals and tax picture.
Operators, not a fund. A family that runs service businesses is buying yours and plans to keep running it season after season, not a fund looking to consolidate and flip.
How the process works
The process is simple and unhurried. It begins with a confidential conversation about your company — your account mix, your seasonal revenue, your equipment, and what you want out of a transition. If there is a fit, we sign an NDA, review your financials and contracts, and bring you a clear, direct offer. From there we work through a focused diligence period to close. You deal with the family that will own the business, and we move at a pace that fits your season and your life.
We will take care of what you built
When we buy a Chicago landscaping company, we protect what makes it work: the crews, the maintenance and snow contracts, and the reputation that keeps property managers renewing. We keep your crew leaders and honor the accounts your clients rely on through every season, including the winters that matter most. What we add is structure — route and dispatch systems, standardized account management, hiring and training pipelines, and a dedicated general manager — so the company keeps its quality and its schedule after you step back. The name you built stays strong, and your people get a steadier, better-run employer.
Learn more about what we buy, see how we acquire landscaping & grounds businesses, or read about Investera Holdings.
Frequently asked questions
How much is my landscaping business worth in Chicago?
Most established landscaping and grounds companies trade in a range of roughly 2.5 to 4 times SDE (seller’s discretionary earnings). Recurring maintenance and snow contracts, crew stability, equipment, and margins move you within that band. It is a typical range, not a guarantee — we give you a real number after a confidential look at your financials.
Will you keep the sale confidential?
Yes. Confidentiality is the default. We sign an NDA before reviewing any contracts or financials, and your crews, clients, and competitors hear nothing until you decide the timing is right.
Are there broker or commission fees?
No. We are the direct buyer, not a broker, so no commission or success fee comes out of your proceeds. The price we agree on is the price that governs the deal.
Can I stay involved after selling?
You can. Many owners stay through a season to hand off accounts and mentor crew leaders; others move to a consulting role or a clean exit. We build the deal around what works for you.
How long does a deal take?
Most transactions run about 60 to 90 days from first conversation to close, depending on how organized your records are. We can adjust to your seasonal timeline.
What areas around Chicago do you buy in?
We buy across Chicago and the surrounding Cook County suburbs, including Evanston, Oak Park, Cicero, Skokie, and Berwyn. Routes spread across the metro are a strength, not a problem.
Start a confidential conversation
If you own a landscaping or grounds business in the Chicago area and are starting to think about what comes next, let’s talk before the next season locks you in. The conversation is completely confidential and carries no obligation — just a straight discussion with the family that would own and run your company after you. Contact Investera Holdings, and we will listen before we ever talk numbers.