Hiring a landscaping company is a bigger decision than it might seem at first. You are choosing someone to work on your property, sometimes over multiple seasons. You are trusting them to execute a vision, stay on schedule, and stand behind their work. In a market like Westchester County, where the condition of your property has a direct impact on its value, that decision carries real weight.
This guide breaks down what to look for before you hire, based on the questions we hear most often from homeowners across Westchester and Fairfield Counties.
Look for Established Local Experience
Local experience matters in landscaping more than in most industries. Soil types, drainage patterns, plant hardiness zones, municipal permit requirements, and even the visual aesthetic expectations of communities like Scarsdale, Rye, or Greenwich all vary. A company that has been working in this specific region for decades has encountered every variation of these conditions and knows how to work within them.
DBI Landscape Group has been based in Westchester County since 1970. That is more than 50 years of working on properties across this exact region, building relationships with local suppliers, and developing the institutional knowledge that only comes from real time on the ground.
When evaluating a company, ask how long they have been operating in your area and ask for specific examples of projects they have completed nearby.
Understand the Full Range of Services They Offer
Not all landscaping companies offer the same scope of work. Some focus exclusively on maintenance. Others specialize in design and installation but do not offer ongoing care. A few, like DBI, handle everything from landscape design and full-service landscaping to hardscaping and masonry, irrigation, lighting, tree care, and grounds maintenance.
Working with a single company that handles multiple aspects of your property has practical advantages. Communication is simpler. Coordination between trades is handled internally. The team doing the maintenance work is the same one that installed the landscaping, which means they know the property.
Ask any company you are considering for a full list of their services before you commit.
Ask to See Their Portfolio
A company’s past work is the clearest indicator of the quality you can expect. Before signing any contract, ask to see a portfolio of completed projects. Look for variety. Do they handle small residential projects and large estate work? Do their designs feel cohesive and well-executed? DBI’s completed project portfolio spans a wide range of scope and style, from intimate backyard redesigns to sweeping multi-acre transformations. We are happy to walk prospective clients through our portfolio and connect them with homeowners who are willing to speak to their experience.
Ask the Right Questions Before You Sign
The conversation you have before hiring a landscaper tells you a lot about how the relationship will work once the project is underway. Here are three questions worth asking every company on your shortlist.
Are you licensed and insured?
This is non-negotiable. A reputable landscaping company should carry general liability insurance and workers’ compensation. Licensing requirements vary by state, but any contractor doing significant grading, hardscaping, or irrigation work in New York or Connecticut should be properly licensed for that work. Ask to see proof before signing anything.
Who will be on-site managing the project?
Large companies sometimes win the sale and then hand the project off to a crew the homeowner has never met. Ask who your point of contact will be during the project and how reachable they will be if questions come up mid-build.
Can you provide a detailed written estimate?
Verbal estimates and vague proposals create room for misunderstandings. A professional landscaping company should be able to provide a written estimate that breaks down labor, materials, and timeline clearly. If they cannot or will not, that is a reason to keep looking.
Consider Whether They Have Their Own Nursery
Plant quality matters more than most homeowners realize. A company that sources plants from a wholesale supplier at the last minute often has limited selection and limited control over the health of what goes into your yard. A company with its own nursery sources plants on their own timeline, selects for quality and climate compatibility, and can often provide a closer match if a plant needs replacing. DBI Landscape Group has operated its own plant nursery in Westchester County for decades. That means better plants, faster sourcing, and fewer delays mid-project.
The Value of a Family-Owned Business
There is something different about working with a company that has been family-owned for generations. Reputation is not just a marketing talking point. It is a direct reflection of every project they have ever completed. They cannot afford to cut corners and walk away, because they are still in the community, still taking calls from the same neighborhoods, still building the next referral from the last job done right.
DBI Landscape Group was founded in 1970 and has been family-owned and operated since. Over more than five decades, the company has built its name project by project across Westchester and Fairfield Counties. According to the National Association of Landscape Professionals, the landscaping industry employs over one million people across the United States. With that many companies in the market, reputation and longevity are among the best filters available when narrowing your list.
Getting Started With DBI Landscape Group
If you are ready to move forward on a landscaping project, or if you just want to explore what is possible for your property, our team is easy to reach. We serve communities throughout Westchester and Fairfield Counties and bring the same level of care to every project regardless of size. Start the conversation with our team today.
Frequently Asked Questions
How much does landscaping cost in Westchester County?
Landscaping costs in Westchester vary widely depending on the scope of work, the size of the property, and the materials involved. A seasonal maintenance plan operates at a very different price point than a full design-and-install project. The best way to get an accurate figure is to request a written estimate from a reputable local company after an on-site assessment.
How long does it take to complete a landscaping project?
Small projects like new planting or seasonal cleanup can often be completed in a day or two. Larger projects involving hardscaping, grading, and full landscape installation typically take anywhere from one week to several weeks depending on scope and weather. Your project team will provide a clear timeline during the estimate process.
Do landscaping companies handle permits in Westchester County?
Reputable companies handle the permit process as part of the project. This is especially important for hardscaping work, retaining walls above a certain height, and any grading that affects neighboring properties or waterways. Always confirm permit responsibilities in writing before work begins.
How do I know if a landscaping company is reputable?
Look for established local history, a real portfolio of completed work, proper licensing and insurance, and the ability to provide references from past clients in your area. Online reviews are useful, but nothing replaces a direct conversation with a homeowner who has actually worked with the company.
References
National Association of Landscape Professionals. landscapeprofessionals.org
