Professional Painters in Windermere, Ontario
Roll On Painting provides premium painting services in Windermere, a beautiful community on Lake Rosseau. With over 25 years of experience serving Muskoka's finest properties, we deliver results that match the elegance of Windermere living.
📍 Windermere House — Muskoka's Historic Resort
Painting Services in Windermere
Windermere is one of Muskoka's most established cottage communities, sitting on the shores of Lake Rosseau between Port Carling and Rosseau. Properties here include heritage family cottages, modern lakefront homes, and prestigious estates. The community's rich history and waterfront setting require painters who respect both the architecture and the environment. We use premium products suited to lakeside conditions and take pride in maintaining Windermere's character.
Our Services in Windermere
Why We Love Working in Windermere
Windermere is steeped in Muskoka history — the iconic Windermere House has been welcoming guests since 1870, and the community still has that timeless, gracious feel. We love painting homes here because the architecture tells a story, from grand Victorian cottages to elegant modern lakefront builds. Windermere homeowners have impeccable taste and high standards, which is exactly the kind of challenge we thrive on. Working lakeside here with the gentle waves of Lake Rosseau as your soundtrack — there's nothing better.
Why Windermere Homeowners Choose Roll On Painting
25+ Years Experience
Owner Chad Gilchrist brings over 25 years of painting industry expertise to every Windermere project.
Free Touch Ups for Life
Every completed project includes our exclusive Free Touch Ups for Life guarantee — no other Windermere painter offers this.
Local to Muskoka
Based in Port Sydney, we know Windermere and the surrounding area. We're not a franchise — we're your neighbours.
Frequently Asked Questions — Windermere
Do you paint heritage cottages in Windermere?
Yes. We have extensive experience with heritage properties and understand the importance of preserving original character while providing modern protection.
What stains work best for Windermere cottages?
We recommend premium exterior stains from Sansin, Benjamin Moore, and Sikkens that are specifically formulated for Muskoka's waterfront conditions.
Do you offer deck staining in Windermere?
Yes. We provide professional deck, dock, and boathouse staining throughout Windermere using marine-grade products.
Do I need to be home for a painting estimate in Windermere?
No. We can provide estimates based on photos, video calls, or on-site visits when you're not home. Many of our Windermere clients — especially cottage owners — arrange estimates remotely. We'll work around your schedule.
How long does it take to paint a house in Windermere?
Most interior projects in Windermere take 3–5 days, while full exterior painting typically takes 5–10 days depending on size and weather. We provide a detailed timeline with every estimate so you know exactly what to expect.
What paint brands do you use in Windermere?
We use Benjamin Moore, Sherwin-Williams, and specialty coatings selected for Muskoka's climate. Our team will recommend the best products for your Windermere property based on surface type, exposure, and desired finish.
Do you offer winter painting services in Windermere?
Yes — we perform interior painting year-round in Windermere. For exterior projects, we plan around Muskoka's freeze-thaw cycles to ensure optimal adhesion and durability. We'll advise you on the best timing for your project.
What is the Free Touch Ups for Life guarantee?
Every completed project with Roll On Painting includes our exclusive Free Touch Ups for Life program. If your walls get scuffed or nicked after we've finished, we'll come back and touch them up at no charge. No other Windermere painter offers this.
Also Serving Areas Near Windermere
View all 48+ service areas →Private Client Services
For homeowners who prefer a fully managed approach, our Private Client program provides ongoing care, maintenance planning, and priority scheduling for Muskoka properties.
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Get a free, no-obligation estimate for your Windermere painting project. Most quotes delivered within 24 hours.
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