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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
50 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
)
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
41 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.

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 and his crew were very professional and did an excellent job creating new garden beds, transplanting shrubs and cutting down the tree. Bob’s communication was prompt and clear. I would highly recommend this company for design and yard work."
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
54 neighbors recently requested a quote
Recommended by85%of homeowners
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Landscaping FAQs, answered by experts

Plant a peach tree right at the end of your local dormancy period, likely at the very end of winter after the last frost when you can dig into the soft soil. Plan your backyard gardening season, including when planting peach trees, based on the frost schedule predicted in your local hardiness zone.

Costs for lakefront landscaping are influenced by project size, choice of plants and materials, labor, and any additional features or structures desired. Projects can range from a few thousand dollars to extensive transformations costing much more.

You'll likely need more than great home staging to sell your home. Now is a great time to get to work on the curb appeal of your home . Hire local exterior painters and landscapers to coat the exterior of your home and bring it new life with some sprucing up.

You should avoid planting grass, shrubs, plants, and trees in freezing temperatures, as the ground can get frozen and become too hard for proper root growth. It’s best to plant in the fall to allow your plants to establish root systems before the first frost. Landscaping when the average temperature in your area is between 50 and 60 degrees will usually deliver the best results.

The best time to plant a privet hedge is autumn, ideally October or early November. Fall is the best time to plant privet hedges because young plants need plenty of water to jump-start their growth, and it typically rains more during this season. However, you can also successfully plant privets in the spring.

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.