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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
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
28 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
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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 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
Additional Photos
Additional Photos
Additional Photos

+17

Recommended by83%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
Pro Cut Landscape & Design
4.9(
199
)
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."
24 neighbors recently requested a quote
Recommended by72%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
58 neighbors recently requested a quote
Recommended by85%of homeowners
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Landscaping FAQs, answered by experts

Yes, you can absolutely transplant bushes instead of removing them completely. The success depends on the size of the bushes, their age, and the transplanting season. Ideally, transplant during the dormant season (late fall or winter). Dig out the entire root system in one piece, fill the new hole with fresh soil and mulch, and water thoroughly after planting.

Landscaping prices are sometimes negotiable, but it depends on the professional with whom you’re working. In most cases, you’ll have a better chance of negotiating prices down the more work you have done. Your pro might be willing to discount labor if they’re guaranteed a large job. You can also ask your landscaper to recommend more affordable materials that will still bring your vision to life to save.

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.

If you choose to leave gaps between your pavers, you can grow some ground cover plants between them for an organic feel. Look for plants such as creeping thyme, dymondia, jewel mint of Corsica, or clover.

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.

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.