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Northern Westchester · Ossining, NY

Landscaping for Ossining's Hills, Hollows and Woods

Downtown Ossining is built on a bluff, and the roads that fall from it toward the river, the Sing Sing Kill and Route 9 carry a lot of water in a storm. Yards here need grading that works with that, plus help with the leaves and deer that come with the woods.

Landscaping in Ossining, NY

Between the riverfront at Louis Engel Park and the ridge along Route 133, Ossining covers a lot of ground. The village has older homes on short, steep lots near the Double Arch where the Old Croton Aqueduct crosses the Sing Sing Kill. Out in Crotonville and toward the Croton River the houses spread out under tall trees. In neighboring Briarcliff Manor, including Scarborough and Chilmark, lots are larger, more wooded and often set well back from the road.

That range shapes what we do. In the village we spend a lot of time controlling runoff before it reaches a foundation or a neighbor's yard. Further out, it is about keeping up with wooded edges: thorough spring and fall cleanups, hedges trimmed and protected from browsing, and fresh mulch in beds each year. We have been working in Westchester since 2009 and carry a 4.9-star rating on Google.

Problems Ossining homeowners call us about

01

Storm water on a steep village lot

Heavy rain on the hilly streets downtown runs fast and finds the lowest point, which is too often a basement door or a back patio. We regrade around the house, cut swales across the slope, install catch basins and dry wells, and build short walls where the ground needs a step down.

02

Woodland edges full of leaves and debris

Homes in Crotonville and along the Briarcliff line back onto stands of oak, maple and tulip trees. Every spring we clear what the winter left behind, and every fall we work through leaf drop in more than one visit, cleaning out beds and keeping drains and swales open so they function when the rain comes.

03

Hedges and shrubs under deer pressure

Deer move freely through the wooded parts of town and strip arborvitae and yews from the ground up. We prune what remains to encourage regrowth, mulch beds to protect roots, and when a hedge is beyond saving, suggest more deer-resistant shrubs that will still give you privacy along the road.

Most-requested services in Ossining

🚧 Drainage & Grading

Standing water, soggy lawns and runoff toward the house usually come down to grade and soil. We find where the water is going and give it a better path.

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🍂 Spring & Fall Cleanups

A thorough reset of the yard twice a year: clearing winter damage and old growth in spring, and getting leaves, beds and plants ready for winter in fall.

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🌿 Shrub, Hedge & Mulch

Pruning that keeps shrubs healthy and in proportion, hedges trimmed clean and even, and beds finished with fresh mulch and sharp edges.

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Recent work by our crews

Mulched shrub bed along a driveway
Mulched shrub bed along a driveway
Hydrangeas in full bloom beside a home
Hydrangeas in full bloom beside a home
Walkway border planted with new shrubs and stone
Walkway border planted with new shrubs and stone

Photos from Roman Design & Landscaping projects in Westchester County.

What clients say

“Roman and his crew did an amazing job, reviving a neglected lawn and grounds on our new home. They even removed a small dead tree and cleared the way for more improvements!”

— Jeff Porper · Google review · Oct 2024

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Ossining landscaping questions

Water runs from the street into my yard in Ossining. Is that something you can fix?

In many cases, yes. We look at where the water enters and where it needs to leave, then use grading, a berm, a swale or a drain line to steer it around the house. We work within your property and can point out if part of the problem is on the village side.

Do you cover Briarcliff Manor and Scarborough as well as the village?

Yes. Our northern Westchester crews work throughout the Ossining area, including Briarcliff Manor, Scarborough, Chilmark and Crotonville. Wooded lots out there usually call for a bit more cleanup time each season, and we plan the schedule with that in mind.

The deer ate the bottom of my arborvitae. Will it grow back?

Usually not on the bare lower trunk. Arborvitae rarely refills from old wood, so we often trim the top to balance it, then plant lower, deer-resistant shrubs in front to fill the gap. If the hedge is mostly gone, we can lay out a replacement planting that holds up better.

Get a free estimate in Ossining

Call, text or WhatsApp — the owner walks the property with you and you get a written estimate. Most visits are scheduled within 1–3 days.