⭐⭐⭐⭐⭐ “Vent Wise cleaned our gutters, flushed the downspouts, and sealed a leak in one visit. The before/after photos were great!”
— Rebecca Doe
Gutter Cleaning Services
Vent Wise delivers full-service gutter care in Chestertown: debris removal, downspout flushing, gutter guard installation, minor repairs, leak sealing, fascia inspection, and seasonal maintenance programs. We service single-family homes, multi-units, HOAs, and commercial properties.
Gutter cleaning • Downspout flushing • Guard installs • Minor repairs • Roof & siding rinses
See the Difference
Our before-and-after gutter projects show spotless troughs, cleared downspouts, resealed seams, and water flowing freely away from foundations in Chestertown. We share photos and notes with every customer so you know the job is done right.
Before & after results from real jobs
Why Choose Us
We combine safety-certified crews, modern gutter tools, and clear communication. Every visit includes a photo inspection, debris removal, flow testing, and recommendations tailored to Chestertown’s rainy seasons.
Trusted by homeowners & property managers across the Peninsula
Eco-friendly disposal
Same-day service
Licensed & insured
25+ years family owned
Upfront pricing
Debris haul away
Satisfaction guarantee
Local storm expertise
24/7 emergency calls
Book Your Preferred Time
Share gutter issues, overflow areas, or downspout concerns when booking. We confirm arrival windows, send reminders, and provide photo proof after every cleaning in Chestertown.
Pick a date and time. We'll confirm and dispatch a technician for a free estimate.
Limited-Time Coupons
Use these offers for gutter cleaning, guard installation, roof rinse add-ons, and multi-property maintenance packages in Chestertown.
Grab a deal before the clock runs out
$30 OFF
on gutter cleaning & flushing
CODE:
--:--:-- until 7 PM
$75 OFF
with guard installation or repair
CODE:
--:--:-- until 7 AM
How It Works
Our gutter cleaning workflow covers scheduling, inspection, cleaning/repairs, and final verification with photos. We keep you informed at every step.
1. Schedule
Choose your date & window.
2. Inspect
Assess gutters, fascia & downspouts.
3. Clean & Repair
Remove debris, flush, seal & adjust.
4. Verify
Photo report & maintenance tips.
Testimonials
Homeowners in Chestertown trust Vent Wise for dependable gutter maintenance, clear communication, and spotless clean-up.
Recent Work
Browse recent gutter projects across Chestertown: debris removal, guard installs, fascia repairs, and drainage improvements.
Frequently Asked Questions
Get quick answers about gutter cleaning frequency, guard options, and what to expect from our service.
Most homes in Chestertown benefit from cleaning twice per year (spring and fall), more often if surrounded by heavy trees or storms.
Yes, we flush downspouts and can hydro-jet underground drainage lines to ensure proper water flow.
We install mesh, screen, or stainless gutter guards and will recommend the best option based on roof type and tree coverage.
Yes, Vent Wise is fully licensed & insured. We use ladder stabilizers and fall protection on every job.
Yes—call early and we’ll prioritize same-day service for overflow, leaks, or storm damage.
Our Expertise
With 25+ years in exterior maintenance, our gutter crews in Chestertown handle multi-story homes, HOA communities, and commercial properties safely.
Family business serving the Chestertown area for over 25 years
We use ladder stabilizers, fall protection, and gutter vacuums to remove debris without damaging landscaping. Our crews seal leaks, secure hangers, replace elbows, and install guards in a single visit whenever possible.
As a family-owned company, we value punctual arrivals, tidy clean-up, and detailed photo reports. Expect transparent pricing, honest recommendations, and proactive maintenance reminders.
Proudly Serving
We clean gutters throughout Chestertown and neighboring Peninsula communities, coordinating with homeowners, HOAs, and property managers.
Chestertown • San Mateo • Palo Alto • Menlo Park • Mountain View • San Carlos • Belmont
Why Gutter Cleaning Matters
Clogged gutters cause foundation erosion, flooded basements, roof leaks, and fascia rot. Routine cleaning keeps water moving safely away from your home.
- Prevents overflow that undermines foundations and landscaping.
- Stops roof leaks, fascia rot, and soffit staining.
- Reduces pest nesting, mosquitoes, and mold growth.
- Extends gutter lifespan and preserves siding and paint.
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