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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 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

"Silvio and his crew are the absolute best. Hire them - you will be glad you did! Silvio came out the day that I called him, and I had a very fair quote from him that evening. He was very involved in the project, and I could always reach him when I needed to talk to him. They turned my small, neglected back and side yard into a place that brings me so much joy! They put up a new retaining wall, graded the back yard and put down sod, and installed a magnificent side patio. What a difference!! They also removed some old shrubs and landscaped with mulch and crushed stone. They even made a very cool rock garden out of the large boulders that they dug up from my back yard! Silvio's crew was talented and so hard-working. The guys worked very long days, and they cleaned up each night before they left. SRS Construction and Landscape is the best! I will definitely be using them again!"
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+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 am very happy with the landscape design and implementation. I showed them the area I wanted. They came up with a plan and I just trusted it would be something I would like. I love it. They did a great job and installed it in two days. Very happy"
Additional Photos
Additional Photos
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+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

Consulting your local university extension, Audubon society, or municipal urban forestry program are all good ideas when choosing a tree to plant. You can also ask an arborist or a knowledgeable landscaping company for advice on good trees to plant.

The landscaping elements that add the most value are often the basics. A well-maintained, attractive lawn can have a return on investment (ROI) of up to 217%. Routine lawn maintenance, such as edging and mulching, can provide an ROI of over 100%. Other high-value projects include upgrading your front walkway, which can offer a 100% ROI, and planting trees. Projects like adding decks, patios, outdoor lighting, irrigation systems, fire pits, and outdoor kitchens also add value and enjoyment, though their direct financial ROI may be less than 100% in some cases.

If you are xeriscaping a lawn from scratch, your best bet for preparing the lawn is to work with a xeriscaping specialist in your area. The most common first step to making the transformation, however, will be to remove the turfgrass from your lawn. The subsequent steps will often include amending the soil to support new plants and installing low-drip or drip irrigation systems.

Since the nature of the landscaping project can heavily influence the overall cost, it helps to understand what different types of landscaping projects cost on average. For example:

  • Plant a tree: $100–$2,000

  • Build a retaining wall: $3,250–$9,200

  • Reseed a lawn: $450–$1,700

  • Install a water fountain: $950–$4,800

  • Install a paver patio: $2,400–$7,000

  • Install a concrete walkway: $1,200–$2,400

  • Install a flower bed: $800–$3,000

  • Landscape lighting: $2,000–$6,000

There are some instances when you can use extra drywall in your garden. Ideally, unused scraps of new drywall are best for amending soil without the concern of additional chemicals or mold. However, drywall with paint, mold, or potential asbestos requires specialized disposal by a professional and should be kept out of your garden.

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.