Legacy Landscaping Company, 50-Year Chicagoland Residential Contractor

$1.4M

Revenue

$538K

SDE

3.7x

Multiple

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Full Editorial Writeup

Legacy Landscaping Company is a 50-plus year old residential landscaping operation serving the affluent suburbs of Cook County, Illinois, in the Chicagoland market. The core of the business is recurring lawn maintenance, supplemented by planting, grading, and general outdoor property services. The model leans on long-term client relationships, word-of-mouth referrals, and an established online presence to drive predictable, repeat revenue from homeowners who view property upkeep as non-negotiable.

The company generates roughly $1.4M in annual revenue with reported SDE exceeding $500K, a healthy 39 percent owner-earnings margin for a services business of this scale. The asset base, including crews, trucks, trailers, and landscaping equipment, transfers with the deal, allowing a buyer to service the book immediately after closing. The notable catch is the real estate: operations currently run from seller-owned property that is NOT part of the sale, so a buyer must relocate to a contractor yard or warehouse after the season.

The positioning is straightforward and durable. Demand for professional landscaping in high-home-value Chicago suburbs is sticky, and a half-century of brand recognition plus an installed recurring-maintenance base gives this business a real edge over a startup competitor. The obvious upside is reactivating higher-margin design/build, hardscape, lighting, and winter services that the current owner has let sit underutilized.

Why we like it

Earnings quality is strong for the category: $537K SDE on $1.37M revenue is a 39 percent margin, and the revenue is anchored by recurring lawn maintenance rather than one-off project work. Recurring maintenance contracts in an affluent market produce the kind of predictable, defensible cash flow you can underwrite a loan against.
The moat is real and unusual for landscaping: 50-plus years of brand recognition, a loyal referral-driven base in one of the Midwest's wealthiest zip-code clusters, and established crews and systems. New entrants cannot manufacture five decades of reputation, and affluent homeowners reward reliability over price.
Landscaping in high-home-value suburbs is recession-resistant. Busy, wealthy homeowners outsource property upkeep regardless of the cycle, and curb-appeal culture in these communities makes professional maintenance a default expense rather than a discretionary one.
The operator advantage is clear: the seller has run this seasonally and left margin on the table by neglecting design/build, hardscape, outdoor living, lighting, and winter services. A motivated owner-operator inherits brand, crews, and a customer list and can layer higher-margin offerings onto an existing relationship base with modest capital.

How to improve it

Reactivate higher-margin design/build, hardscape, and outdoor living services in the first 90 days. These carry far better margins than recurring mowing and you already have the customer relationships and brand permission to upsell them, so the cost of acquisition is effectively zero.
Add winter services such as snow and ice management to convert the seasonal model into year-round revenue. The same affluent client base needs driveways and walkways cleared, and this smooths cash flow across the slow months while improving crew utilization.
Lock in the relocation early and turn it from a risk into a fixed cost. Secure a contractor yard or warehouse lease before the season ends, ideally during diligence, so there is no operational gap and you can model the new occupancy cost into the deal.
Convert informal recurring maintenance into signed annual contracts with auto-renew and price escalators. This hardens the revenue base, raises the multiple at your eventual exit, and protects against churn during the ownership transition.
Expand into commercial and HOA accounts using the existing residential reputation as a credential. Commercial contracts are larger, multi-year, and less seasonal, and they leverage the same crews and equipment without proportional overhead.
Implement targeted digital marketing and a simple CRM to capture referral demand the business is likely leaving unmonetized. With an established online presence already in place, modest spend on local SEO and review generation should convert in an affluent, high-intent market.
Audit pricing across the maintenance book and reprice underwater accounts. Long-tenured family businesses routinely under-raise prices on loyal clients, and a disciplined 5 to 10 percent increase on a sticky base flows almost entirely to SDE.

Diligence notes

Quantify how much of the $537K SDE is genuinely recurring versus project-based. The listing leans heavily on recurring maintenance language, so pull customer-level revenue, retention, and contract terms to confirm the durability that justifies the 3.71x multiple.
Scrutinize the relocation problem hard, because the real estate is excluded and operations must move after the season. Confirm zoning, availability, lease terms, and added occupancy cost for a suitable contractor yard, and verify the business can run without disruption from a new site.
Verify the condition, age, and ownership status of the included trucks, trailers, and equipment. Landscaping is capital-intensive, so confirm assets are owned free and clear and assess near-term replacement capex that the SDE figure may not reflect.
Assess crew and key-person dependency since this is a 50-year owner-run business. Identify whether crew leads will stay post-close, what the owner personally handles in estimating and customer relationships, and how transferable those relationships are to a new owner.
Confirm the seasonality of cash flow and working capital needs through a downturn-style stress test. Pull monthly revenue to understand the off-season cash gap, and model how much working capital a buyer needs to carry crews and equipment through winter absent snow services.
Clarify the seller financing terms and structure given only limited financing is offered for strong offers. Push for a meaningful seller note and a holdback tied to customer retention through the transition to align incentives during the relocation.

Source

Originally listed on BizBuySell. View original listing →