Business Details
9 Years
experience
Professional Roofing Services in Orangeville & Area
Established in 2017, Jesse James Roofing is a family-owned and operated business serving Orangeville and surrounding areas. Our founders, Jesse and James, boast over 50 years of combined experience, having worked closely with roofing consultants and architects to master industry best practices. As licensed sheet metal workers and members of the Ontario College of Trades, we specialize in comprehensive roofing solutions, including flat roofs, shingle roofs, metal roofs, and historical cornice work. Our commitment to quality is underscored by a 10-year workmanship warranty and 100% satisfaction guarantee, ensuring clients receive durable, precision-crafted installations using premium materials. We offer tailored maintenance programs to extend roof longevity, emphasizing proactive care over reactive repairs.Our expertise in custom sheet metal fabrication, including chimney flashing, roof penetration covers, and seamless eavestroughs, sets us apart from conventional roofing contractors. By treating every home as our own investment, we uphold rigorous standards of craftsmanship, transparency, and client communication. Recognizing regional climate challenges, we educate homeowners on seasonal maintenancefrom fall inspections to winter snow managementto prevent costly damage. With service areas spanning Orangeville, Caledon, Brampton, and beyond, we blend local knowledge with technical proficiency to deliver trusted, results-driven roofing solutions.
Services
Roof Installation
Metal Roofing
Flat Roof Systems
Roof Maintenance
Custom Sheet Metal Work
Details
- Year established: 2017
Highlights and features
- We combine 50+ years of combined experience with technical certifications.
- Our team are licensed sheet metal workers with specialized fabrication skills.
- 10-year workmanship warranty and 100% satisfaction guarantee on all installations.
- Seasonal maintenance programs prevent costly emergency repairs.
- Use of premium materials ensures long-term performance and durability.
Associations and certifications
- Ontario College of Trades
What people say
Expert craftsmanship
Reliable service
Detailed work
Long-term warranty
Professional team
Services
Roof Installation
We specialize in residential and commercial roof installations, including asphalt shingles, metal roofing, and flat roofing systems. Our licensed team uses premium materials and advanced techniques to ensure watertight, energy-efficient results. Backed by a 10-year workmanship warranty, our installations protect properties while enhancing curb appeal.
Metal Roofing
Custom metal roofing solutions for durability and aesthetic appeal. We work with steel, copper, aluminum, and Corten Steel, crafting standing seam, metal shingles, and historical cornice systems. Our expertise includes seamless eavestroughs and snow guards to suit modern and heritage properties.
Flat Roof Systems
Comprehensive flat roofing services using TPO, EPDM rubber, modified BUR, and heat-applied asphalt. Our systems prioritize waterproofing and energy efficiency, with proper drainage solutions to prevent ponding. Ideal for commercial buildings and modern homes requiring low-slope solutions.
Roof Maintenance
Preventative maintenance programs to extend roof lifespan. We offer seasonal inspections, gutter cleaning, flashing repairs, and ice dam prevention. Regular maintenance reduces emergency repair risks and helps clients avoid costly structural damage from undetected leaks.
Custom Sheet Metal Work
Precision-crafted sheet metal components including chimney flashing, roof cones, wall coping, and historical cornices. Our licensed tradespeople solder and fabricate custom solutions for unique roof penetrations, flashings, and architectural details that standard contractors cannot handle.
People
Jesse
Owner / Licensed Sheet Metal Worker
With 25+ years of experience, Jesse specializes in roof installation and custom sheet metal fabrication. He ensures every project meets rigorous quality standards, combining technical expertise with hands-on craftsmanship.
James
Owner / Licensed Sheet Metal Worker
James brings 25+ years of roofing and sheet metal expertise, focusing on problem-solving for complex installations. His attention to detail guarantees precise execution of historical and modern roofing systems.
Questions
Do you offer a warranty on roofing installations?
Yes, all installations come with a 10-year workmanship warranty against defects.
What types of roofs do you specialize in?
We handle asphalt shingle, metal, flat roofing systems, and custom sheet metal work for residential and commercial properties.
Is seasonal roof maintenance necessary?
Yes—fall inspections, winter snow removal, and spring checks prevent leaks and extend roof lifespan.
Can you handle historical or custom roof details?
Yes, our licensed sheet metal workers specialize in historical cornices, soldered copper, and custom flashing solutions.
Do you service properties outside Orangeville?
Yes, we serve Caledon, Brampton, Guelph, Milton, and surrounding areas within a 60km radius.
