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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
Pro Cut Landscape & Design
4.9(
197
)
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
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
)
Lawn & Yard Waste Clean UpLandscape - Install Landscaping for Yard or GardenLandscape - 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
44 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.

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

Many people have used old tires in gardens as raised beds, planters, tree rings, and DIY decor. However, these uses are not recommended due to the toxicity of many of the chemicals used to manufacture tires. These chemicals can leach into the soil and water as the tire breaks down, creating environmental pollution and health hazards for gardeners and their families.

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.

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.

While you can leave roots in the ground, if you don’t want the shrub to regrow again over time, it’s best not to leave any roots behind. Ensure you remove as much of the shrub as possible, including the root ball and any main roots you can see, to prevent new growth. Some gardeners opt for using a chemical treatment to prevent the stump from growing back, but this can kill beneficial microorganisms living in your soil.

In most cases, wait three to five days to repot or relocate a plant from a greenhouse or nursery. That way, your plant has time to recover from any shock during the move and adapt to the conditions in and around your home. Some hearty plants may not need as long, and delicate plants might need several weeks. You should ask the professional at your nursery for a recommended timeline. Consider asking about an initial watering schedule to help stimulate root growth and promote a healthy plant.

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.