Expert Landscaping in Ossining, NY

Landscaping Services in Ossining, NY

At Hilltop Landscaping, we know every yard is different. That’s why we offer landscaping services designed specifically for Ossining homeowners. We understand Westchester’s seasonal weather, native plants, and soil conditions—so your landscape doesn’t just look good, it stays healthy year-round.
We design with both beauty and function in mind. That might mean blending colorful garden beds with smooth stone walkways, or choosing trees that offer shade in summer and color in fall. Whether you want to boost your home’s value or simply enjoy your outdoor space more, we’ll make it happen with care and precision.
We specialize in combining hardscape and softscape elements to create a landscape that feels balanced, natural, and livable. From a small backyard refresh to a full property transformation, we handle every project with professionalism.


Our Landscaping Services in Ossining
Trust your local landscaper expert
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Transform Your Outdoor Space With Hilltop Masonry & Landscaping
Are you looking for a reliable and experienced landscaping company in Cortlandt, NY? Look no further than Hilltop Masonry & Landscaping! We are a family-owned business that has been serving both residential and commercial customers since 1985.

Why Ossining Homeowners Choose Hilltop Landscaping
Choosing the right residential landscaper is a big decision—and we don’t take your trust lightly. Here’s what sets Hilltop Masonry & Landscaping apart

Local Expertise
We’ve been working in Ossining and nearby towns for 40+ years. That kind of local knowledge means we know what grows well, what lasts, and what to avoid.

Proven Experience
From modest front yard upgrades to large backyard redesigns, we’ve handled thousands of successful projects across Westchester.

Custom Solutions
No two homes—or homeowners—are the same. We work closely with you to design something that fits your space, style, and budget.
Skilled Team & Materials
Our crews are trained, professional, and friendly. We use top-quality materials, from plant stock to pavers, to ensure every job holds up over time.

Our Process
Getting started is easy. Here’s how we work, step-by-step
Free Consultation
We’ll walk your yard with you, listen to your goals, and share smart, realistic ideas.
Custom Design
You’ll get a clear plan that includes layout, materials, costs, and an estimated timeline.
Professional Installation
Our team handles planting, building, and cleanup—paying attention to every detail.
Final Walkthrough
We go over the finished project with you and make sure you’re completely happy.
Our Gallery
See Our Work in Ossining
Client's Reviews
What Ossining Clients Are Saying
George Riggs2025-02-08Trustindex verifies that the original source of the review is Google. Glenn just finished a small project that involved clearing out several trees, regrading a driveway, and building a small retaining wall. Before starting, Glenn spent a lot of time with me going over various approaches and outcomes for this project. The end result has worked out great. In spite of weather challenges, he was able to kept the project moving. He was always available for questions. The friendly workers always cleaned up the site after each day. I couldn’t be any happier with the process and end result. Raymond Sturz2024-12-30Trustindex verifies that the original source of the review is Google. I found this company by accident as they were doing work at my neighbor's house. They seemed to be doing a fine job so I asked for a quote to do tree work on my property. I couldn't be happier with the work they performed. The workers spent the day climbing trees and cutting off branches. They cleaned up so well that if you didn't see where the branches were cut, you'd never know that they were there. After they finished, they asked me to walk around with them to be sure that I was satisfied. I dealt with Bruce and Anthony. They have a business model that harkens back to the days when you could do work on a handshake and know you could trust them to do the work well. I will use them again and highly recommend them. Laura Lynch2024-12-19Trustindex verifies that the original source of the review is Google. I had several trees cut down with Hilltop and I am very, very satisfied with the work and the process! Hilltop Masonry & Landscaping was recommended to me. We had a number of trees to cut down, in fact I initially thought we would get a few more trees, but Glenn clearly has expertise in this and was honest in his recommendations. He suggested holding off on one big tree for another time and instead of cutting down some small trees, to rather just do pruning. His suggestions and honesty helped me understand the structure/roots of trees on my property more, but it also showed me he was not trying to just get a big job (big price). Glenn was fair with price and was efficient in getting the work done. Workers were very kind, too. It definitely makes me want to work with the company in the future. Cathy Burress2024-11-13Trustindex verifies that the original source of the review is Google. We had Hilltop come to plant mums and clean up yard and leaves. They did a really good job. Have recommended them to friends. Anthony Annunziata2024-11-06Trustindex verifies that the original source of the review is Google. My experience with Glenn from Hilltop was fantastic his man are professional neat and very organized. I would recommend that if you need landscaping and or a fence use his company. Bobby Budhu2024-11-05Trustindex verifies that the original source of the review is Google. Hilltop is friendly, professional and easy to work with. We find them to be very honest, reliable and reasonable in terms of prices on various projects such as, building wall, preparing backyard, blacktop and removal of debris, etc compared to many other similar contractors who have very much deceived us in so many ways. We recommend them highly! Stephen Damin2024-11-02Trustindex verifies that the original source of the review is Google. This was our first landscape project with Hilltop and they exceeded our expectations. Glenn was very knowledgeable and helped make our vision a reality. We loved how it came out and are already looking forward to the next project. Highly recommend Hilltop! Jacques DiCroce2024-10-30Trustindex verifies that the original source of the review is Google. I contacted Hilltop Masonry & Landscaping to inquire about replacing a decaying retaining wall on my property. I received a call back from Glenn within 5 minutes and 30 minutes later he came to look at the condition of the wall and discuss hardscape options. After consultation, I decided to replace the existing wall with a new railroad tie wall. He gave me a ball park estimate on the spot and followed up with a formal estimate within a few days. The estimate was very competitive and after confirming a few details, I accepted the proposal. A week later, a crew was onsite to start the demolition of the old wall. The crew was very professional, respectful of the property, used high quality materials, cleaned up after each workday, and minimized any inconvenience during the construction of the new wall. They made suggestions during the course of the construction that we hadn’t considered to enhance the outcome. The project was completed in 4 days, the work and attention to detail was exceptional and we couldn’t be happier with the end result. I highly recommend working with Glenn and his team. huguette Antoine2024-10-29Trustindex verifies that the original source of the review is Google. You did a great job with planting my tree..Your Staff was exceptional . I will recommend Hilltop Landscaping to Anyone thanks Alex Cannon2024-10-08Trustindex verifies that the original source of the review is Google. They did an amazing job installing my fence.Showing our latest reviews
Frequently Asked Questions
Most jobs take 1–2 weeks, depending on the size and scope.
Yes. Every consultation includes a detailed quote—no pressure, no hidden costs.
Absolutely. Every design is tailored to your preferences, property shape, and budget.
Yes. We offer seasonal maintenance, mowing, and lawn care services to keep your yard thriving.
We offer a wide selection of shrubs, trees, perennials, and seasonal flowers—all suited to Ossining’s growing conditions.
Yes. We specialize in masonry work like patios, walkways, and retaining walls.
We offer sustainable landscaping solutions using native plants, proper drainage systems, and low-chemical practices.
Just move personal items out of the way—we’ll take care of everything else, including the cleanup.
Get In Touch
Ready to get started?
We’re quick to respond, easy to talk to, and take pride in every job we do. If you’re ready to improve your outdoor space, we’re here to help.