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Business Details
37 Years
experience
Trusted Roofing, Siding & Window Replacement in Naperville, IL
Hollingsworth Home Improvement has served homeowners in the Chicago area for over 35 years, specializing in roof replacement, siding replacement, and window installation. Our family-owned business prioritizes attention to detail, superior warranty protection, and personalized service. With two generations of experience, we ensure every project receives expert craftsmanship and thorough client communication.

Our team of trained professionals delivers industry-leading 20-year warranties and maintains a commitment to quality that extends from project coordination to final inspection. We work throughout Western and Southwestern Chicago suburbs, offering trusted solutions for roofing, siding, windows, and gutter systems.
Services
Roof Replacement Window Replacement Siding Replacement James Hardie Siding Vinyl Siding Stone Veneer Celect Cellular Siding
Details
  • Year established: 1989
Highlights and features
  • 35 years of specialized experience in roofing and home exterior solutions
  • Family-owned business with multi-generational expertise and accountability
  • Industry-leading 20-year warranty on workmanship and materials
  • Expert crews trained in latest installation techniques and safety standards
  • Personalized project guidance with transparent communication throughout
Associations and certifications
  • IL Roofing License #104015426
What people say
Professional crews Trustworthy management Attention to detail Timely completion Satisfaction with warranties
Services
Roof Replacement
Full roof replacement services using premium materials with superior protection during and after installation. Our expert crews ensure proper ventilation and waterproofing while maintaining strict safety standards. We provide comprehensive warranty coverage and handle all aspects from permits to final inspections.
James Hardie Siding
Durable fiber cement siding installation that combines wood-like aesthetics with low maintenance requirements. Our certified installers ensure proper flashing and moisture protection while offering multiple color and texture options to enhance home curb appeal and value.
Window Replacement
Custom window replacement solutions featuring energy-efficient vinyl and wood options. We provide precise measurements, professional installation, and guidance on selecting styles that improve insulation and home aesthetics while maintaining structural integrity.
Vinyl Siding Replacement
Premium vinyl siding replacement with reduced seam visibility and enhanced durability. Our installation process ensures proper alignment, weatherproofing, and compatibility with existing home architecture while offering long-term color retention and easy maintenance.
Stone Veneer
Aesthetic stone veneer installation that combines natural appearance with lightweight durability. We offer multiple profiles and colors that install faster than traditional masonry while providing moisture resistance and lifetime warranty protection options.
People
Phil Hollingsworth
Owner
Third-generation home improvement expert with 35+ years in exterior remodeling. Leads project coordination and client consultations, emphasizing transparency and quality craftsmanship.
Questions
What areas do you serve?
We serve Western and Southwestern Chicago suburbs including Naperville, Wheaton, Bolingbrook, and Aurora.
What roofing warranties do you offer?
We provide industry-leading 20-year warranties covering both materials and workmanship for all roof replacements.
Do you handle insurance claims for storm damage?
Yes, we assist with insurance claims and documentation for storm-related roof and siding damage repairs.
What siding options are available?
We offer James Hardie fiber cement, vinyl, Celect cellular composite, and manufactured stone veneer options.
How long does a typical roof replacement take?
Most residential roof replacements complete within 1-2 days, depending on home size and weather conditions.