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Landscaping · Montgomery, MA

Landscaping in Montgomery, Massachusetts

Compare contractors serving Montgomery, Hampden County — call them directly, or send one request and let the ones who want the job come to you.

30 contractors serving Montgomery.

Contractors serving Montgomery

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

Landscaping in Montgomery — what to know

Site & seasonal factors

Montgomery is in Eversource territory and Mass Save eligible — the rebates target envelope and HVAC, not landscaping. The overlap point on these steeper lots is outdoor unit siting for heat-pump retrofits: finding a level, drained pad with clear airflow often requires landscape work first.

The Westfield River Wild & Scenic Committee and the Hilltown CDC are useful local resources for riparian buffer technical assistance — not direct rebates, but help understanding what's permittable along the river corridor.

Permits in Montgomery

The Montgomery Conservation Commission reviews work under the Wetlands Protection Act, with the Westfield River's 200-foot Riverfront Area covering a lot of parcels. Notice of Intent filings are routine for any grading, tree removal, or hardscape near streams or the river. The building inspector handles permits for retaining walls over 4 feet and footing-bearing structures. On steep lots, soil and erosion controls are commonly conditions of approval — not optional add-ons.

Typical project cost

Montgomery pricing reflects the grade challenge. A typical season of mowing and cleanup runs $1,800–$4,000. Retaining walls — segmental block or natural stone — are commonly $80–$200 per linear foot depending on height and material. Steep-driveway drainage upgrades with swales, catch basins, and culverts often run $5,000–$12,000. Stabilizing a small slope failure (regrade, install drainage, replant) typically lands $4,000–$15,000. Foundation regrading with a swale and gutter extension on a contemporary house is $2,500–$6,000.

About Montgomery homes

Montgomery is a small Hampden County hilltown of about 877 residents across 404 housing units, with a median home age around 47 years. The town straddles steep terrain between Russell and Huntington, and the Westfield River cuts along the southern edge. A lot of homes here are rebuilt or post-1970 contemporary builds set on wooded lots with significant grade.

The practical implication for landscape work: drainage, retaining structures, and steep-driveway access dominate the conversation. Lawn-only contracts are uncommon — most projects involve grading or stone work alongside whatever plantings the homeowner actually wanted.

Common questions — Landscaping in Montgomery

Water keeps showing up in my basement after storms — can a landscaper fix that?
Often yes, before you call a foundation contractor. Most Montgomery basement water comes from surface runoff finding the foundation. Regrading, swales, gutter extensions, and a French drain at the foundation perimeter solve a large share of cases for a fraction of waterproofing cost.
Do I need a retaining wall, or will a properly graded slope hold?
Up to roughly 3:1 (horizontal:vertical), a well-vegetated slope holds. Steeper than that, you're looking at terracing or a wall. Most Montgomery landscape contractors will model the slope and tell you honestly which approach is right.
What's involved in clearing trees along my Westfield River frontage?
Riverfront Area review through the Conservation Commission, almost always. Some selective limbing for views may be approvable; commercial-scale clearing is not. The Westfield River's Wild & Scenic status adds federal-level visibility to anything substantial.
How much does a fieldstone retaining wall actually run per foot?
Dry-stacked using on-site stone: $80–$140 per linear foot. Mortared natural stone over a poured footing: $200–$400+ per linear foot. Engineered segmental block is in between and often the most cost-effective for walls over 4 feet.
When should I plan tree work — winter or growing season?
Late winter when the ground is frozen is ideal for heavy equipment access without rutting. Late summer through early fall is the second-best window. Mud season (March–April) is the worst — you'll pay extra for ground protection or just damage your yard.

Landscaping guides for Massachusetts homeowners

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Landscaping contractors in nearby towns

RussellHuntingtonSouthamptonChesterBlandfordWestfieldWesthamptonEasthampton