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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
)
Sod - InstallSod - Install - For Business

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 GardenLandscape - Minor Grading or ReslopingLandscape - Soil, Sand, Mulch and Rock Delivery+1 more

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2001

Free estimates

Small jobs welcome

"The service Bob and his associate provided was exceptional. They arrived as promised and delivered service in the utmost manner of professionalism. I still have a smile on my face as I look at my perfectly landscaped yard.. Pro Cut Landscape & Design will not disappoint you ð"
My work
My work
My work
My work
My work

+1

Response time11 hrs
37 neighbors recently requested a quote
Recommended by74%of homeowners
Pro Cut Landscape & Design
4.9(
198
)
Landscape - Minor Grading or ReslopingLandscape - Soil, Sand, Mulch and Rock DeliverySod - Install+1 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 Elmer's Landscaping and Construction
Elmer's Landscaping and Construction
4.9(
76
)
Landscape - Install Landscaping for Yard or GardenLandscape - Minor Grading or ReslopingLandscape - Install Landscaping for Yard or Garden - For Business+1 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
Avatar for Roberto's Affordable Landscaping
Roberto's Affordable Landscaping
4.0(
815
)
Landscape - Soil, Sand, Mulch and Rock DeliveryLandscape - Install Synthetic Grass for Putting Greens, Play Areas, etc.Drywell - Construct or Rebuild+8 more

Serving Winchester, MA and surrounding areas

Approved

In business since 2007

Free estimates

Warranties offered

"Roberto and his team were great. We hired them to install Sod on our property. We got a fair proposal quickly and they were able to complete the work in record time. The work is great and the neighbors said we must have hired great landscapers because it looks awesome."
Additional Photos
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+76

Response time2 days
Response rate100%
13 neighbors recently requested a quote
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