Hillside Landscape provides full-service landscaping in Winnetka, IL — design-build, hardscaping, weekly lawn maintenance, mulch & bed care, lighting, and snow removal — serving Winnetka and the North Shore since 2001. A local family crew based minutes away in Lincolnshire handles the whole property, from the first free estimate through seasonal care.
Winnetka's historic lots
Winnetka's historic homes and generous, mature lots ask for landscaping that reads as part of the architecture — not bolted on after the fact. Old trees, established grades, and classic homes reward stonework, plant choices, and clean edges that respect what's already there.
We design, build, and maintain Winnetka landscapes with that in mind: natural-stone hardscape in keeping with the house, gardens that work with mature shade, and maintenance that keeps a refined property looking its best in every season.
- Architecture-matched design
- Mature-tree & shade gardens
- Natural-stone hardscape
- Estate-scale maintenance
- Landscape lighting
Everything your Winnetka property needs, one local crew
On the North Shore's most established blocks, the details matter — stonework, plant choices, clean edges. That's where our family crew shines.
Landscape design
Master plans, AI previews, and full design-build for your whole property.
Explore landscape design →Hardscaping
Patios, walls, walkways, and fire features in bluestone, brick, and granite.
Explore hardscaping →Maintenance & lawn care
Weekly mowing and full-season plans that keep the property sharp April–November.
Explore maintenance & lawn care →Mulch & bed care
Premium hardwood mulch, crisp bed edging, weeding, and seasonal refreshes.
Explore mulch & bed care →Landscape lighting
Low-voltage architectural, path, and garden lighting with 25-year fixtures.
Explore landscape lighting →Snow & ice management
Plowing, salting, and 24/7 storm response for homes, HOAs, and commercial sites.
Explore snow & ice management →A local family crew, on your street since 2001
Winnetka landscaping questions
- Do you serve Winnetka?
- Yes — Winnetka is right in our service area. We're based in Lincolnshire (Cook County), so Winnetka homeowners get fast estimates and reliable, on-time service. We also serve nearby Kenilworth, Glenview, Wilmette, Northbrook.
- What landscaping services do you offer in Winnetka?
- Everything for the property: landscape design & build, hardscaping, weekly lawn maintenance and seasonal plans, mulch & bed care, landscape lighting, and snow & ice management — all from one family crew.
- Is the first estimate free?
- Yes. We walk your Winnetka property with you, talk through what you need, and give you a clear, no-obligation estimate. You only move forward if it feels right.
- Do you handle HOAs and commercial properties in Winnetka?
- We do. Alongside residential yards, we maintain HOA common areas and commercial grounds in Winnetka and across the North Shore, with a dedicated contact and documented service.
Get a free Winnetka estimate
Tell us a little about your Winnetka property and what you need. We'll set up a free on-site walk-through and put together a plan and quote — no obligation.
- Free, no-obligation on-site visit
- Honest, up-front pricing
- Every service from one local crew
- Fast response — we're based minutes away
