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TRUSTED BY WINCHESTER, MA HOMEOWNERS

  • Average homeowner rating star icon4.4
    Average homeowner rating
  • Verified reviews icon819
    Verified landscaping services reviews

Top-Rated Landscapers in Winchester - Updated Nov 2026

Avatar for Madison Floral & Landscape Solutions
Madison Floral & Landscape Solutions
5.0(
22
)
Landscape - Install Landscaping for Yard or GardenLandscape - Minor Grading or ReslopingLandscape - Minor Grading or Resloping - For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 2000

Free estimates

Small jobs welcome

"I hired Edison for a small 1,000 sq ft backyard landscaping project in South Boston. He did a great job of listening to what I wanted, making recommendations, explaining different aspects of the project and completing it quickly. He neither oversold nor undersold and responded quickly to my questions with detailed suggestions, but always deferring to my decisions in the end. The finished product was very well-done and an amazing newly landscaped backyard."
Madison Floral
Madison Floral
Madison Floral
Madison Floral
Madison Floral

+10

Response time12 hrs
Recommended by100%of homeowners
Avatar for Deangele Landscape & Construction Corp.
Deangele Landscape & Construction Corp.
4.3(
218
)
Sod - Install - For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 2006

Free estimates

Emergency services offered

"Moving into our new house, we were excited to design our landscape. We immediately contacted the DeAngele Landscape & Construction Company to install sod. They completed the installation quickly and offered us valuable suggestions. We are thankful to be working with this company."
Outdoor Living Space
Outdoor Kitchen
Stainless Steel Sink
Single Side Burner
Stair

+12

Response time2 days
47 neighbors recently requested a quote
Recommended by86%of homeowners
Mendoza Landscaping
4.9(
21
)
Lawn & Yard Waste Clean UpLawn Care - Maintain and Mow a LawnSod - Install+1 more

Serving Winchester, MA and surrounding areas

Approved

In business since 2000

Free estimates

Offers commercial services

"We called Scott Mendoza from Mendoza landscaping and he responded very quickly which was great. He came out gave us an estimate on the spot and we hired him right away because we could tell that he knew his business! He started yesterday and finished today with a total clean up and cut he did a fantastic job and we highly recommend his company to anyone looking for lawn care needs you won't be disappointed !"
Response time2 hrs
Response rate91%
Recommended by95%of homeowners
Avatar for Pro Cut Landscape & Design
Pro Cut Landscape & Design
4.9(
191
)
Landscape - Install Landscaping for Yard or GardenLawn & Yard Waste Clean UpLandscape - Minor Grading or Resloping+2 more

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2001

Free estimates

Small jobs welcome

"Yes, Bob Assarian (Pro Cut Landscape & Design) and his assistant, Manuel, were punctual, communicative and thorough clearing our spacious yard of leaves & small sticks in just 1.5 hours, living up to the high standards of our former landscaper. We also look forward to engaging Bob's landscape design services to beautify our front, back and side yards."
My work
My work
My work
My work
My work

+1

Response time11 hrs
35 neighbors recently requested a quote
Recommended by74%of homeowners
Avatar for SRS Construction & Landscape
SRS Construction & Landscape
5.0(
20
)
Retaining Wall - Install

Serving Winchester, MA and surrounding areas

Approved

In business since 2007

Free estimates

Warranties offered

"I’m very impressed while working with the SRS Contruction & Landscape team. They showed up right away to assess my needs, listened carefully to my ideas, and offered helpful suggestions. Throughout the process, the team was friendly, flexible, and ready to accommodate my requests. To top it off, their pricing was more competitive than any other contractor I contacted. I highly recommend SRS Construction & Landscape for this smooth, professional and pleasant experience."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+124

Response time1 day
Response rate100%
Recommended by100%of homeowners
M & L LANDSCAPING & CONSTRUCTION, LLC
4.9(
97
)
Retaining Wall - Install

Serving Winchester, MA and surrounding areas

Approved

In business since 2020

Free estimates

Credit card accepted

Locally owned business with over 12 years of experience. Custom Paver Patios, walkways, retaining walls, and driveways. We also offer full clean up landscaping, hardscaping, and stone work. \nPassionate about serving our local community and continuing to deliver great customer service. Feel free to call or text with questions regarding your projects. Look forward to working with you on all your home endeavors.

1 neighbors recently requested a quote
Recommended by88%of homeowners
Avatar for John's Landscape Services Inc
John's Landscape Services Inc
4.3(
138
)
Architect - LandscapeDesigner - LandscapeDrywell - Construct or Rebuild+10 more

Serving Winchester, MA and surrounding areas

Approved

In business since 1986

Free estimates

Credit card accepted

"I contacted four landscapers through Angie's List. Two never responded; one got back to me but couldn't do the work for weeks. John's responded quickly, popped by to survey the job (without me even knowing!) and was able to schedule it within the week. Two men came by and worked for three or four hours on the bed. It was too tough for a tiller, so in the end they used an industrial aerator to loosen the dirt/roots, then raked it out. They did a great job, were very careful of the surrounding garden decorations, and thoroughly cleaned up after themselves. The job came in right on estimate, despite it being harder than they thought."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+17

Recommended by83%of homeowners
Pro Cut Landscape & Design
4.9(
198
)
Lawn & Yard Waste Clean UpLandscape - Minor Grading or ReslopingLandscape - Soil, Sand, Mulch and Rock Delivery+2 more

Serving Winchester, MA and surrounding areas

Approved

In business since 2001

Free estimates

Credit card accepted

"Bob Assarian?s Pro Cut Landscape & Design took on a big job in the back of our property ? lawn & yard waste clean up, and also trimmed back overgrown bushes. Bob was super communicative in scheduling the work at a convenient time for us. He and his team performed the work professionally, efficiently, and to our specification and utmost satisfaction; and for a very fair price. We would not hesitate to engage Pro Cut again for further work to be done our property to keep it looking tidy and well groomed."
14 neighbors recently requested a quote
Recommended by72%of homeowners
Avatar for Martinez Landscaping & Construction
Martinez Landscaping & Construction
5.0(
15
)
Lawn & Yard Waste Clean Up

Serving Winchester, MA and surrounding areas

Approved

In business since 2020

Free estimates

Offers commercial services

"They work so hard, and I really love all the jobs they do. I really recommend this Landscaping & Construction company because they do fantastic job and they are very hard working. Also they finish the jobs on time and leave it as new. I really love their job and how professional they are. And it?s also amazing how the woman works too they help each other on everything. They have a very strong group and I recommend this company 100%."
Landscaping
Landscaping
Landscaping
3 neighbors recently requested a quote
Recommended by66%of homeowners
Avatar for Elmer's Landscaping and Construction
Elmer's Landscaping and Construction
4.9(
76
)
Landscape - Install Landscaping for Yard or GardenRetaining Wall - InstallLandscape - Minor Grading or Resloping+2 more

Serving Winchester, MA and surrounding areas

Approved

In business since 2013

Free estimates

Offers commercial services

As experts in residential lawn care and ground maintenance, Elmer's Landscaping and Construction, will exceed your expectations. With years of experience manicuring lawns and power washing exterior surfaces, we understand the value of quality, professionalism and responsiveness. We offer competitive pricing and look forward to serving you.

Profile Picture
57 neighbors recently requested a quote
Recommended by85%of homeowners
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Landscaping FAQs, answered by experts

Landscape design can be a simple service that includes a drawing or visual representation of how your yard can be set up and optimized for your intended purposes. But it can also include all of the manual labor to make your vision a reality. When you speak with your landscape designer, ensure everyone understands the specific services you want. Some add-on services may include the following:

  • Sourcing and delivery of raw materials

  • Professional installation of features, including pergolas, decks, and pathways

  • Drainage system design

  • Recommendations for specific plants and trees

There are many factors to consider when building an in-ground concrete pool. This includes the pool’s primary purpose (relaxation or exercise) if you live in a warm or cold climate (how often it’ll be used), and if you have the budget for chemical treatments and pool maintenance. In-ground pools are often more costly than aboveground pools, but they’re considered more luxurious and hold more value.

A green home is one that focuses on conservation, with the goal often being net-zero carbon emissions and self-sustainability. It will often include some kind of self-generation equipment, like solar panels or a small wind turbine, high-efficiency electrical components and mechanicals, and high-quality insulation and air sealing to reduce the loss of conditioned air. Many green homes also include xeriscaping or rainwater collection to cut down on drainage and water consumption.

A half inch above ground level is ideal for metal edging. This provides enough depth for the edging to hold in place and enough height to keep in most landscaping materials (like mulch or gravel). If you install edging too high off the ground, it will stand out from your landscaping and pose a tripping risk. If you install it too low, your ground cover won’t stay in place.

You should plant trees at least 15 to 20 feet away from your house, and more if the tree will grow large and spread its limbs. Trees pose several dangers to houses when planted too close. They can litter the roof with leaves and branches, create fire hazards, make a ladder for larger pests, and even damage the foundation as their roots grow.

The Winchester, MA homeowners’ guide to landscaping services

From average costs to expert advice, get all the answers you need to get your job done.