138 Fomer Rd # A, Southampton, MA 01073
Landscaping in Chester, Massachusetts
Compare contractors serving Chester, Hampden County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Chester.
Contractors serving Chester
Claimed listings within 5 miles come first, then the rest by rating, then distance. Google ratings as of October 2026. How we list and rank contractors
- Better PathwaysServes Chester · 9.1 mi★★★★★5.0 Google rating
- Geeleher Enterprises IncServes Chester · 12.0 mi★★★★★5.0 Google rating
39 College Hwy, Southampton, MA 01073
- ElectroCutServes Chester · 12.8 mi★★★★★5.0 Google rating
259 Chesterfield Rd, Leeds, MA 01053
- Cedar HorticultureServes Chester · 13.4 mi★★★★★5.0 Google rating
2 Culdaff St, Easthampton, MA 01027
- RJM Landscaping, IncServes Chester · 13.4 mi★★★★★5.0 Google rating
13 Airport Dr, Westfield, MA 01085
- Wellnesscapes DesignServes Chester · 14.2 mi★★★★★5.0 Google rating
39 Kingsley Ave, Haydenville, MA 01039
- Plan It Green Landscape ArchitectureServes Chester · 15.9 mi★★★★★5.0 Google rating
142 Main St, Northampton, MA 01060
- Zuber LandscapingServes Chester · 16.5 mi★★★★★5.0 Google rating
642 College Hwy, Southwick, MA 01077
- Nathan T Buratto Landscaping & ExcavationServes Chester · 16.8 mi★★★★★5.0 Google rating
165 Highfield Dr, Lee, MA 01238
- Integrastone LandscapingServes Chester · 19.0 mi★★★★★5.0 Google rating
1589 East St Suite C, Pittsfield, MA 01201
- In The Green Gardens Inc.Serves Chester · 19.3 mi★★★★★5.0 Google rating
243 Russell St, Hadley, MA 01035
- Berkshire GreenscapesServes Chester · 19.9 mi★★★★★5.0 Google rating
285 Pomeroy Ave, Pittsfield, MA 01201
- Ocare Landscaping & Lawn CareServes Chester · 13.7 mi★★★★★4.9 Google rating
20 Chestnut St, Westfield, MA 01085
- CMS LandscapingServes Chester · 17.0 mi★★★★★4.9 Google rating
175 Suffolk St, Holyoke, MA 01040
- MissionGreen ServicesServes Chester · 18.1 mi★★★★★4.8 Google rating
933 Meadow St, Chicopee, MA 01013
- Pandolfi Landscape ConstructionServes Chester · 20.0 mi★★★★★4.8 Google rating
28 N Ramah Cir Rear, Agawam, MA 01001
- Kelley Brothers Tree ServiceServes Chester · 18.5 mi★★★★★4.7 Google rating
1863 East St, Pittsfield, MA 01201
- Better View LandscapesServes Chester · 18.8 mi★★★★★4.6 Google rating
49 River Dr, Hadley, MA 01035
- Dodson & Flinker, IncServes Chester · 14.3 mi★★★★★4.5 Google rating
40 Main St Suite 101, Florence, MA 01062
- The Barefoot Gardener LLCServes Chester · 19.1 mi★★★★★4.5 Google rating
36 Pittsfield Rd, Lenox, MA 01240
- Nature Works Land Care Inc.Serves Chester · 16.6 mi★★★★☆4.4 Google rating
900 Pleasant St, Lee, MA 01238
- Beyond Landscape ContractingServes Chester · 19.3 mi★★★★☆4.4 Google rating
83 State Rd, South Deerfield, MA 01373
- Greenstuff Lawncare, Inc.Serves Chester · 19.9 mi★★★★☆4.4 Google rating
211 Union St, West Springfield, MA 01089
- By Design Landscape Concepts, Inc.Serves Chester · 20.2 mi★★★★☆4.4 Google rating
50 Russo Cir, Agawam, MA 01001
- G & H Landscaping, Inc.Serves Chester · 17.2 mi★★★★☆4.2 Google rating
58 Commercial St, Holyoke, MA 01040
- Omasta LandscapingServes Chester · 19.6 mi★★★★☆4.2 Google rating
265 Bay Rd, Hadley, MA 01035
- Edge Tree Service Inc.Serves Chester · 17.7 mi★★★★☆3.7 Google rating
336 Hadley St, South Hadley, MA 01075
- Mountain View Landscapes and LawncareServes Chester · 18.3 mi★★★☆☆3.4 Google rating
67 Old James St, Chicopee, MA 01020
- Hunter Tree ServiceServes Chester · 17.1 mi★★★☆☆3.3 Google rating
33 Berkshire St, Holyoke, MA 01040
- Serves Chester · 20.1 mi
455 South St, Pittsfield, MA 01201
Landscaping in Chester — what to know
Site & seasonal factors
Chester is served by the Chester Municipal Light Plant, which makes it a Municipal Light Plant (MLP) town. With no natural gas service either, Mass Save does not apply here, a meaningful gap on energy work, though it doesn't directly affect landscaping (Mass Save doesn't fund landscape projects in any town).
What does shape Chester landscape work is the Wetlands Protection Act, administered by the Chester Conservation Commission, plus the additional protections of the Westfield River Wild and Scenic designation. Hardscape, grading, or significant clearing within 100 feet of the Westfield or its tributaries typically requires an NOI rather than just an RDA, and projects with substantial visual impact along the protected river stretch can face additional federal-level review.
Permits in Chester
Plantings and routine lawn work don't need permits. The MA thresholds apply: retaining walls over about 4 feet and meaningful grading work need a building permit. ConCom is the more common gate for near-river work. Chester doesn't have a formal historic district overlay. The Wild and Scenic designation adds a review layer for substantial projects along the protected river corridor. Plan a 4–8 week permitting front end for near-river work.
Typical project cost
Chester pricing tracks western Hampden County hill-town norms — labor a step below eastern-MA, with site complexity adding back what flat lots wouldn't have. A standard lawn-and-foundation refresh runs $3,500–$8,500. A paver or stone patio with a small wall typically lands $15,000–$32,000 depending on slope and access. Dry-laid stone walls — Chester sits near historic quarry sites, with bluestone readily available — run $300–$600 per linear foot finished.
About Chester homes
Chester is a small Hampden County hill town of about 1,403 residents and 689 housing units, set along the Westfield River. The median home is around 71 years old — an older housing stock by state standards, reflecting the town's history as a rail and stone-quarrying center. Many older houses cluster around the village center along Main Street, with newer rural builds spread across the surrounding hills.
The terrain is steep and water-dense. The Westfield River — designated a National Wild and Scenic River in stretches — runs through the heart of town, with tributary brooks like Walker Brook coming off the surrounding ridges. Landscape work here usually involves significant site work, drainage, and stone, not flat suburban lawns.
Common questions — Landscaping in Chester
- Am I eligible for Mass Save energy rebates in Chester?
- No. Chester Municipal Light Plant is the electric utility and the town has no natural gas service, so Mass Save does not apply. That doesn't affect landscaping directly, but it's important context if you're considering bundled energy and outdoor work.
- Do I need ConCom approval near the Westfield River?
- Yes for any work within 100 feet of the river or its tributary brooks. The Westfield is a National Wild and Scenic River in stretches, so the Chester Conservation Commission looks carefully at near-river projects and substantial work may face additional review. Expect an NOI.
- Is Chester bluestone really easier to source here?
- Yes. Chester sits near historic bluestone quarry sites, and local stone yards stock material readily. Sourcing native Chester bluestone for patios and walls is usually less of a logistics problem than for towns further from the quarry belt.
- How tall can a wall be before I need a permit?
- About 4 feet is the standard MA threshold. Over that, building permit and typically engineering. Walls in a wetland buffer or in the Wild and Scenic corridor need additional review regardless of height.
- Who works in Chester?
- Crews based in Huntington, Westfield, and Blandford cover Chester routinely. A handful of smaller hill-town landscapers are based locally. Confirm experience with steep grades, river-corridor work, and ConCom filings before signing.
