The best gutter companies in Oakville in 2026 are Pro House Maintenance, DewDrop Windows & Eavestrough Cleaning and Peace of Mind Exteriors, then five more top-rated local eavestrough firms. Our Google Maps searches found 43 businesses for Oakville. Ten held 4.5 stars from 10 or more reviews and had a website we could read. A 2026 Ontario price guide puts a two-storey eavestrough cleaning at $200 to $325.
- The 7 ranked Oakville gutter companies hold Google ratings from 4.9 to 5.0, from 19 to 402 reviews each.
- A two-storey Ontario home costs $200 to $325 for an eavestrough cleaning with a downspout flush in 2026.
- Heavy gauge 6 inch aluminum eavestroughs run $10 to $18 per foot installed, or $1,800 to $3,600 for a 150 to 200 foot home.
- Halton Region covers 100% of eligible downspout disconnection costs, up to $900, for work done after July 15, 2024.
| Rank | Company | Best for | Credentials | Google rating | Based in |
|---|---|---|---|---|---|
| 1 | Pro House Maintenance | Comparing vetted gutter companies for free | Every pro: licences, WSIB, insurance, references, background | Not applicable (matching service) | Serves Oakville |
| 2 | DewDrop Windows & Eavestrough Cleaning | Vacuum gutter cleaning with a redo guarantee | Founded 2009, Insurance stated (company-stated) | 5.0 (402 reviews) | Oakville |
| 3 | Peace of Mind Exteriors | Gutters and roofing from in-house crews | WSIB stated (company-stated) | 5.0 (147 reviews) | Oakville |
| 4 | Trusted Pro Roofers | Gutter checks during roof repairs | None stated on its website | 5.0 (66 reviews) | Oakville |
| 5 | DT Group Service | Gutter and window cleaning with WSIB | Founded 2023, Insurance stated (company-stated) | 5.0 (56 reviews) | Oakville |
| 6 | Lakeshore Home Solutions | Gutter cleaning bundled with painting | Insurance stated (company-stated) | 5.0 (19 reviews) | Oakville |
| 7 | Siding and Eavestrough Oakville | Eavestrough repair with a 25 year warranty | Founded 1978, WSIB stated (company-stated) | 4.9 (41 reviews) | Oakville |
| 8 | Every Season Inc. | Gutter cleaning with downspout flow tests | Insurance stated (company-stated) | 4.9 (33 reviews) | Oakville |
Who are the best gutter companies in Oakville in 2026?
The best gutter companies in Oakville in 2026 are Pro House Maintenance, DewDrop Windows & Eavestrough Cleaning and Peace of Mind Exteriors. Trusted Pro Roofers, DT Group Service, Lakeshore Home Solutions, Siding and Eavestrough Oakville and Every Season Inc. round out the top eight. The seven ranked local firms hold Google ratings from 4.9 to 5.0.
1. Pro House Maintenance: best for comparing vetted gutter companies for free
Pro House Maintenance is our free matching service, and it ranks first because it does the screening for you. Gutter pros we match in Oakville have passed WSIB, insurance, reference and background checks. You describe the job once, get written quotes and pick one. Our satisfaction guarantee covers the pro you hire.
From Bronte to Joshua Creek, tell us if you need a cleanout, a repair, new eavestroughs or a downspout disconnection for the Halton subsidy.
- Trade licences. We confirm every licence the trade legally requires in Ontario.
- WSIB clearance and liability insurance. We confirm a current WSIB clearance and commercial general liability insurance before a pro joins our network.
- Reviews and references. We read public reviews and speak with past clients before a pro is accepted, looking for patterns, not one-off complaints.
- Background checks. We run background checks before a pro is matched with homeowners, because the people in your home matter as much as the work.
- Tell us about the job. Share the project and your address through the free quote form. It takes about a minute.
- Get matched with vetted pros. We match you with several pros who have already passed our checks and serve your area.
- Compare written quotes. Each pro gives you a written quote, so you can compare price, scope and timing side by side.
- Hire with a guarantee behind you. You choose who to hire. Work from a pro we matched you with is backed by our satisfaction guarantee; ask us for the terms before you sign.
2. DewDrop Windows & Eavestrough Cleaning: best for vacuum gutter cleaning with a redo guarantee
- Google rating 5.0 from 402 reviews checked Oct 11, 2026
- Founded 2009 company website
- Warranty Satisfaction guarantee: return to fix free of charge company website
- Based in Oakville
- Visit the DewDrop Windows & Eavestrough Cleaning website
DewDrop Windows & Eavestrough Cleaning lists a Taunton Road unit in Oakville and a 5.0 Google rating from 402 reviews, the most on this list. Google lists gutter cleaning as its main category. Its website says it has served customers “since 2009,” is “Fully insured” and uses Skyvac industrial gutter vacuums.
- Strengths: The site states a satisfaction guarantee: if you notice something, the crew comes back “to fix it free of charge.”
- Watch-outs: Ask for WSIB clearance in writing, because the pages we read did not state it. Confirm the cleaning scope covers downspouts, not only troughs.
- Best for: A thorough vacuum cleanout with windows washed on the same visit.
3. Peace of Mind Exteriors: best for gutters and roofing from in-house crews
- Google rating 5.0 from 147 reviews checked Oct 11, 2026
- Warranty Lifetime workmanship warranty company website
- Based in Oakville
- Visit the Peace of Mind Exteriors website
Peace of Mind Exteriors lists a York Street address in Oakville and a 5.0 Google rating from 147 reviews. Google lists gutter cleaning as its main category, with roofing, siding and skylights among its categories. Its website says it is “WSIB-covered,” uses in-house crews and backs work with a “lifetime workmanship warranty.”
- Strengths: The site states WSIB coverage, more than 23 years of work and financing at “0% for 12 months.”
- Watch-outs: Ask what the lifetime workmanship warranty covers on eavestrough work and whether it transfers if you sell. Get the terms in writing.
- Best for: Replacing eavestroughs, soffit or fascia while a roofer checks the roof.
4. Trusted Pro Roofers: best for gutter checks during roof repairs
- Google rating 5.0 from 66 reviews checked Oct 11, 2026
- Based in Oakville
- Visit the Trusted Pro Roofers website
Trusted Pro Roofers lists an Upper Middle Road East suite in Oakville and a 5.0 Google rating from 66 reviews. Google lists gutter cleaning as its main category, with roofing as a second category. Its website says it offers roof inspections, repairs and replacements, and that it can help with financing.
- Watch-outs: The site leans roofing, so ask for recent eavestrough references. We found no WSIB or insurance statement on the pages we read, so ask for both in writing.
- Best for: Clearing and resealing gutters during a roof inspection or repair.
5. DT Group Service: best for gutter and window cleaning with WSIB
- Google rating 5.0 from 56 reviews checked Oct 11, 2026
- Founded 2023 company website
- Based in Oakville
- Visit the DT Group Service website
DT Group Service lists a Shady Glen Road address in Oakville and a 5.0 Google rating from 56 reviews. Google lists gutter cleaning as its main category. Its website says its team “carries CAD $2 million in general liability coverage and WSIB,” and names Oakville areas it serves, from Old Oakville and Bronte to Palermo.
- Strengths: The site states liability insurance and WSIB, plus coverage across most Oakville neighbourhoods.
- Watch-outs: The company says it was founded in 2023, so it is newer than most firms here. Ask for local references and a written scope.
- Best for: One visit that clears gutters and washes windows on an Oakville home.
6. Lakeshore Home Solutions: best for gutter cleaning bundled with painting
- Google rating 5.0 from 19 reviews checked Oct 11, 2026
- Based in Oakville
- Visit the Lakeshore Home Solutions website
Lakeshore Home Solutions lists a Nautical Boulevard address in Oakville and a 5.0 Google rating from 19 reviews. Google lists gutter cleaning as its main category, with painting and pressure washing among its categories. Its website says it is “fully insured” and “locally owned and operated,” serving Oakville, Burlington and Muskoka.
- Watch-outs: It has the fewest reviews on this list, and the site did not state WSIB terms. Ask for WSIB clearance and a written scope before work starts.
- Best for: Pairing a gutter cleanout with exterior painting or power washing.
7. Siding and Eavestrough Oakville: best for eavestrough repair with a 25 year warranty
- Google rating 4.9 from 41 reviews checked Oct 11, 2026
- Founded 1978 company website
- Warranty 25 years of workmanship warranties company website
- Based in Oakville
- Visit the Siding and Eavestrough Oakville website
Siding and Eavestrough Oakville lists an Oak Park Boulevard suite in Oakville and a 4.9 Google rating from 41 reviews. Its website is the Oakville page of D’Angelo & Sons. That site says it is family owned, offers “Quality service since 1978,” is “backed by WSIB” and offers “25 years of workmanship warranties.”
- Strengths: The site states WSIB coverage, a long track record and a 25 year workmanship warranty.
- Watch-outs: The website lists an Ancaster office, so confirm which company name goes on your contract and which crew serves Oakville.
- Best for: Repairing or replacing eavestroughs with a long written warranty.
8. Every Season Inc.: best for gutter cleaning with downspout flow tests
- Google rating 4.9 from 33 reviews checked Oct 11, 2026
- Based in Oakville
- Visit the Every Season Inc. website
Every Season Inc. lists an Iroquois Shore Road address in Oakville and a 4.9 Google rating from 33 reviews. Google lists gutter cleaning as its main category, with landscaping and snow removal among its categories. Its website says its team is “trained, insured” and that “Every downspout is tested” so water drains away from the foundation.
- Watch-outs: The site mentions WSIB documents only for condo jobs. For a house, ask for WSIB clearance and the insurance certificate before booking.
- Best for: Seasonal cleanouts with each downspout flow-tested before the crew leaves.
How much does eavestrough work cost in Oakville?
A 2026 Ontario price guide puts a two-storey eavestrough cleaning at $200 to $325, with a downspout flush. A downspout clearing costs $50 to $100 each on a separate call. New heavy gauge 6 inch aluminum troughs run $10 to $18 per foot installed. Copper costs $35 to $55 per foot.
| Job | Typical cost (CAD) | Source |
|---|---|---|
| Cleaning, two-storey home (up to 200 ft) | $200 to $325 | Custom Contracting, 2026 |
| Cleaning, large or complex roofline (200+ ft) | $300 to $400+ | Custom Contracting, 2026 |
| Downspout clearing, severe blockage | $50 to $100 each | Custom Contracting, 2026 |
| Downspout extension, installed | $50 to $150 each | Custom Contracting, 2026 |
| Heavy gauge 6 inch aluminum, 150 to 200 ft home | $1,800 to $3,600 | Custom Contracting, 2026 |
| Copper eavestrough, installed | $35 to $55 per ft | Custom Contracting, 2026 |
Big lots and tall trees drive Oakville quotes. A two-storey home in Glen Abbey or Old Oakville under mature maples takes longer to clear than a newer townhouse.
See our gutter cleaning cost guide for Ontario for full price bands, and the 2026 gutter statistics report for lifespan data. When you are ready, get free eavestrough quotes in Oakville from screened local pros. Nearby lists rank the best gutter companies in Mississauga, top Hamilton gutter companies and Toronto gutter companies.
How do you choose a gutter company in Oakville?
Choose an Oakville gutter company by checking WSIB clearance, liability insurance and recent eavestrough references, then comparing written quotes. Ontario law requires a written contract for any home renovation worth more than $50. The province also suggests a deposit of no more than 10% of the contract price.
- Confirm WSIB clearance. Ask for the company’s WSIB account number and confirm a current clearance on WSIB’s free eClearance lookup.
- Ask for proof of liability insurance. A certificate of commercial general liability insurance should name the company that will do the work.
- Ask about city licences and permits. Ask Oakville whether the job needs a municipal licence or building permit before work starts.
- Get it in writing. Under Ontario law, any home renovation contract worth more than $50 must be in writing, and the final price cannot exceed an estimate by more than 10% unless you agree (Ontario consumer protection rules).
- Keep the deposit small. Ontario recommends a down payment of no more than 10%, and never paying in full before the work is done.
Ask each firm where your downspouts will drain. The Town of Oakville wants downspouts to discharge onto splash pads or a hard surface aimed away from the house. It also says, “Do not extend downspouts or other pipes to the property line or onto your neighbour’s property.”
If a disconnection is in the plan, ask the contractor to document the old sewer connection with a dye test or camera video. Halton needs that proof, plus before and after photos, to pay the subsidy. If water has already reached the basement, book water damage restoration in Oakville in the same request.
How did we rank these Oakville gutter companies?
We ranked Oakville gutter companies on public data, and no company paid for a spot. Our Google Maps searches for Oakville found 43 businesses, and 15 listed gutters as their main category. Of those, 10 held 4.5 stars from 10 or more reviews and had a website we could read.
| Step | Businesses remaining |
|---|---|
| Found on Google Maps | 43 |
| Primary Google category is a gutter company | 15 |
| Open, with a website of its own | 13 |
| In Oakville (by address or Google map pin) | 13 |
| 4.5+ stars from 10+ Google reviews | 10 |
| Listed on this page (top ranked) | 7 |
The score blends each rating with its review count. That way, a 5.0 from 402 reviews ranks above a 5.0 from 19. We checked every fact on October 12, 2026, and recheck every 90 days. Website facts are quoted in our research files. See an error? Tell our editors about it and we will review it.
What do Oakville homeowners ask before they hire a gutter company?
Oakville homeowners ask what eavestrough cleaning costs, where downspouts should drain and whether Halton Region helps pay for a disconnection. These answers use a 2026 Ontario price guide, Halton Region and Town of Oakville pages and our own research. Each answer stands alone, so jump to the one that fits your home.
How much does eavestrough cleaning cost in Oakville?
A 2026 Ontario price guide puts a bungalow with up to 150 feet of eavestrough at $150 to $225. A two-storey home with up to 200 feet costs $200 to $325, and that includes a downspout flush. Large rooflines with valleys and dormers run $300 to $400 or more.
Does Halton Region pay to disconnect downspouts in Oakville?
Yes, for eligible homes on the Region's sewer system. For work done after July 15, 2024, Halton covers 100% of materials and invoiced contractor labour to disconnect downspouts, up to $900. You need proof the downspouts fed the sewer first, and you must apply within one year of the work.
How far should downspouts drain from my house in Oakville?
Halton Region says disconnected downspouts should discharge away from the foundation, for example about 3 metres, onto ground that slopes away from the home. The Town of Oakville adds two rules. Use a splash pad or hard surface, and never run a downspout to the property line or a neighbour's yard.
Do I need a permit to disconnect a downspout in Oakville?
No. Halton Region states that a permit is not required for downspout work. You still need to follow Town of Oakville drainage rules. Keep the water on your own lot, aim it away from the foundation and keep swales and rear-yard catch basins clear of leaves.
Is Pro House Maintenance free for Oakville homeowners?
Yes. Pro House Maintenance is free for homeowners. You describe your eavestrough job once, and we match you with several pros who have passed WSIB, insurance, reference and background checks. You compare their written quotes and choose who to hire, and our satisfaction guarantee backs the work.
Where can you find gutter companies near Oakville?
The closest gutter companies lists to Oakville cover Mississauga (14 km away), Hamilton (28 km away) and Toronto (32 km away). Each list follows the same method: 4.5-star Google ratings from 10 or more reviews, official registry checks where Ontario requires a licence, and free vetted matching from Pro House Maintenance at number one.
- Best gutter companies in Mississauga (14 km from Oakville)
- Best gutter companies in Hamilton (28 km from Oakville)
- Best gutter companies in Toronto (32 km from Oakville)
- Best roofing companies in Oakville
- Compare free gutter installation quotes in Oakville from vetted local pros
- Best gutter companies across Ontario, city by city
- Gutter Installation statistics and cost data from our research team
- Custom Contracting, Eavestrough Cleaning Cost Ontario 2026
- Custom Contracting, Eavestrough Installation Cost Ontario 2026
- Halton Region, Downspout Disconnection Program
- Town of Oakville, Property Drainage and Grading
- Government of Ontario, Your rights when starting home renovations or repairs
- WSIB, eClearance lookup