Winchester homeowners researching landscaping services have access to a mix of established local companies and well-regarded firms from neighboring towns. But a meaningful, side-by-side comparison is hard to come by. This guide profiles 7 landscaping companies serving Winchester, MA, comparing their services, service areas, pricing, ratings, and credentials so you can make an informed decision. Data was compiled by Moodscapes LLC, a landscape design firm based in Arlington with over 30 years of experience serving Winchester and surrounding communities. Last reviewed: July 2026.
| # | Company | Address | Services Offered | Google Rating | Pricing |
|---|---|---|---|---|---|
| 1 | Moodscapes LLC OUR PICK | 216 Hillside Ave, Arlington, MA 02476 | Ecological Landscape Design, Build & Maintenance | 4.8 (23) | View full pricing — $850–$2,000+/month maintenance; $5K–$200K+ design/build |
| 2 | Clipco Landscaping | 972R Main St, Winchester, MA 01890 | Landscape Management, Lawn Care, Mowing, Pruning, Planting, Patios, Walkways, Snow Removal | 5.0 (9) | Free estimates; no rates published |
| 3 | MC Landscaping | Winchester, MA 01890 | Lawn Maintenance, Renewals, Plantings, Patios, Walkways, Cleanups, Snow Plowing | 5.0 (25) | Free estimates; no rates published |
| 4 | Chestnut Grove Design Group | 48 Mount Vernon St, Winchester, MA 01890 | Full-Service Landscape Design & Architecture, Interior Design | 4.9 (16) | Luxury-tier; no rates published |
| 5 | Eldco, Inc. | 2 Kirk St, Winchester, MA 01890 | Lawn Care, Tree & Shrub Care, Irrigation, Nightscaping, Snow Removal | No profile | No rates published; "reasonable and fair rates" |
| 6 | Perennial Landscape Corporation | Woburn, MA (serves Winchester) | Landscape Design & Installation, Maintenance, Hardscaping, Masonry, Irrigation, Lighting | 5.0 (25) | Free estimates; no rates published |
| 7 | Crugnale Associates LLC | 73 Dartmouth St, Belmont, MA 02478 | Landscape Design, Installation, Maintenance, Lawn Care, Hardscapes, Snow Removal | 5.0 (3) | No mention of pricing |
Four of the seven companies on this list — Clipco Landscaping, MC Landscaping, Chestnut Grove Design Group, and Eldco, Inc. — are based directly in Winchester. Moodscapes is based in neighboring Arlington, and has been serving Winchester homeowners for over 30 years. Perennial Landscape Corporation is based in Woburn, which borders Winchester to the north, and has maintained a dedicated focus on Winchester since 1995. Crugnale Associates is based in Belmont and explicitly includes Winchester in its service area.
Before contacting any company on this list, it helps to know what you actually need. Here are six questions to guide your decision.
Landscape designers create plans and build new outdoor spaces. Maintenance companies keep existing ones tidy. Full-service firms do both — but that doesn't always mean they're best at both. Start by identifying which category describes your project.
A "mow and blow" lawn service and a landscape design firm are fundamentally different businesses. If you want to transform your outdoor space, a lawn maintenance company is likely the wrong call — and vice versa.
A long service list can be a warning sign. Companies that do everything often do none of them exceptionally well. Look for companies with a clear specialty that matches your project.
A company serving 30+ towns has a very different operational model than one focused on 3–5 communities. Tighter service areas often mean faster response times, better local plant knowledge, and crews that aren't spread thin.
Look at the number of reviews, not just the star rating. A 5.0 with 3 reviews tells a different story than a 4.9 with 25. Read the one- and two-star reviews carefully — patterns in complaints are more telling than the average score.
Ask: Are you licensed and insured in Massachusetts? Can you provide references from Winchester projects? What does a typical project timeline look like? Do you provide a written contract and detailed estimate? How do you handle changes mid-project?
A boutique ecological landscape design and build firm serving Winchester, Arlington, Belmont, Lexington, Newton, and Watertown. Moodscapes believes that landscapes are not just places where you do things, but places that provide the opportunity for people to leave their everyday worries and improve their mood.
A full-service landscape management company based in Winchester, owned and operated by Cliff Cunningham since 2000. Clipco is one of Winchester's most established local landscapers, with a strong reputation for attention to detail across lawn care, maintenance, plantings, and snow removal.
A full-service landscaping company owned and operated by Mike Costello out of Winchester. MC Landscaping has built a strong local following through word-of-mouth, with consistently high ratings and a wide service range that includes lawn care, plantings, hardscaping, and snow removal.
A luxury residential interior design and landscape architecture firm based in Winchester, founded by husband-and-wife team Ryan and Christina Wikman. Chestnut Grove offers a rare, streamlined experience: simultaneous design of both the interior and exterior of your home within a single firm. Winner of Best of Boston 2021 for Interior Design.
A family-owned and operated landscape maintenance and installation company that has been serving Winchester and surrounding communities for over 40 years — now spanning three generations. Eldco employs both Massachusetts and Maine certified arborists and specializes in comprehensive lawn, shrub, tree, and irrigation care.
A full-service, award-winning landscape design and construction company that has been serving Winchester since 1995. Founded by Scott Carzo, Perennial is a family-owned business with a dedicated Winchester page, strong local reviews, and a portfolio of complex projects including patios, outdoor kitchens, stone walls, and lighting installations.
A full-service landscaping and snow removal company founded by brothers Mike and Chris Crugnale. Started as a neighborhood snow-shoveling operation and grown into a professional landscape and hardscape firm serving Belmont, Winchester, Lexington, Concord, and surrounding communities. Known for a strong emphasis on reliability and quality customer service.
These are the questions Winchester homeowners most commonly ask about landscaping. Answers reflect conditions specific to eastern Massachusetts.
When should I aerate my lawn in Winchester, MA?
Fall is the best time — specifically late August through mid-October. Winchester's cool-season grasses (bluegrass, fescue, ryegrass) recover most aggressively in fall when soil temperatures are still warm but air temperatures have dropped. Pair aeration with overseeding in early September for the best results. Aerating in spring is a secondary option but less effective since grass must compete with weed germination for recovery nutrients.
How much does a patio cost in Winchester, MA?
A basic patio in Winchester typically runs $15,000–$25,000 installed, depending on size, material (concrete pavers vs. natural stone), and site prep. More complex projects — retaining walls, drainage, steps, or regrading — commonly reach $25,000–$50,000. Larger outdoor living spaces typically fall in the $50,000–$100,000 range. These figures reflect 2026 Greater Boston labor and material costs.
When do landscapers typically start spring work in Winchester?
Most Winchester landscapers begin spring cleanups and soil preparation in late March to early April, depending on frost depth and ground conditions. Planting typically starts mid-April through May. Popular companies fill their spring schedules quickly — book in February or early March to secure your spot for the season.
What plants work best in Winchester's climate and soil?
Winchester falls in USDA Hardiness Zone 6b. Native plants that perform well here include mountain laurel, native azalea, switchgrass, coneflower, and New England aster. Winchester's hilly terrain and proximity to Horn Pond and the Aberjona River mean many properties have slopes and varied drainage conditions — assessing your site before planting significantly improves long-term results. Native and drought-tolerant plantings are particularly well-suited to Winchester's hillside properties.
Do I need a permit for hardscaping in Winchester, MA?
It depends on the scope. In Winchester, retaining walls over 4 feet typically require a building permit. Projects near Horn Pond, the Aberjona River, or other water resources may require Conservation Commission review under the Massachusetts Wetlands Protection Act. Check with the Winchester Building Department before starting any significant hardscaping — requirements vary by project and proximity to protected areas.
How much does landscape design cost in Winchester, MA?
Landscape design fees in Winchester typically range from $1,500 to $5,000 for a residential design plan, depending on property size and project complexity. Design-build firms like Moodscapes often apply the design fee toward construction if you hire them for installation. Most offer a free initial consultation before proposing a design agreement.
What is the difference between a landscape designer and a landscaper?
A landscape designer creates a detailed plan for your outdoor space — assessing site conditions, specifying plants and materials, and producing drawings or renderings. A landscaper typically executes maintenance or installation work. Some companies do both (design-build). If you're starting from scratch or want a cohesive vision for your property, begin with a designer before hiring for installation.
What should I know about Winchester's terrain and conservation areas?
Winchester has more topographic variety than most surrounding towns — the hilly western sections near Horn Pond and the Aberjona River watershed present real site challenges around drainage, erosion, and grading. Properties in these areas may fall under Conservation Commission jurisdiction. If your yard slopes significantly, drainage and erosion control should be part of any landscape plan. Horn Pond itself is a town conservation area, and landscaping near its shores requires particular care with runoff and native plantings.
How do I verify a landscaper is licensed in Massachusetts?
Massachusetts requires a Home Improvement Contractor (HIC) registration for residential work over $1,000. You can verify a contractor's registration at mass.gov/hic. For pesticide application, look for a Massachusetts Commercial Pesticide Applicator license issued by the Department of Agricultural Resources. Always ask for proof of general liability and workers' compensation insurance before signing a contract.
Zach Rubin is the owner of Moodscapes LLC, an ecological landscape design firm based in Arlington, MA serving Winchester, Arlington, Belmont, Lexington, Newton, and Watertown. Company data in this guide was gathered from Google Maps, BBB.org, Angi, Houzz, Yelp, and individual company websites in July 2026. Ratings and details are accurate at time of research and may have changed. Last reviewed: July 2026. Also see our Belmont, Arlington, Lexington, Newton, and Watertown landscaping guides.
Moodscapes LLC has been transforming outdoor spaces in Winchester and surrounding communities for over 30 years. We believe your landscape should be more than a place where you do things — it should be a place where you can leave your everyday worries behind. We offer a free initial consultation to discuss your project, your property, and what's possible.
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