R Dillon Roofing | Roofing Services in Chesapeake, VA 23323

Chesapeake, VA 23323

(757) 530-3741

Local Business Overview

R Dillon Roofing is a Chesapeake-based contractor with deep roots in the Tidewater area. With decades of hands-on experience that began in childhood, owner R Dillon brings a practical, expert-level understanding of construction and roofing to every job. The company provides a comprehensive suite of services for local homeowners, from essential roof repairs, inspections, and skylight installations to full-scale home additions, bathroom remodels, and deck construction. This blend of specialized roofing knowledge and general contracting skill means Chesapeake residents can rely on one trusted team for both protecting their home from the top down and enhancing its livability and value. R Dillon Roofing is built on a foundation of hard work, local knowledge, and a commitment to clear communication, ensuring every project in the Chesapeake community is handled with care and professionalism.

Main Services

  • Landscaping building construction
  • Remodeling
  • Gutter replacement
  • Roof inspection
  • Deck construction
  • Patio, porch, or terrace construction or installation
  • Gutter installation
  • New structure construction

Common Questions

As a Chesapeake homeowner, how do you handle common local roofing leaks, like around skylights or in roof valleys?

Roof valley and skylight leaks are frequent issues in our area due to weather exposure and settling. We start with a thorough inspection to pinpoint the exact source—often failed flashing or sealant. For skylights, we ensure the curb and flashing are properly integrated with the roof system. For valleys, we repair or replace the underlying metal or shingle lining. Our approach is to fix the root cause to prevent recurrence, using materials suited for Chesapeake's climate, and we always clean up thoroughly afterward.

If I need both a new roof and a deck or porch addition, can R Dillon Roofing handle both projects?

Absolutely. Our unique combination of specialized roofing services and general contracting allows us to manage coordinated projects efficiently. We can schedule the work to ensure your new roof is complete and watertight before beginning construction on your deck, porch, or patio. This single-point-of-contact approach streamlines the process, ensures consistent quality, and can often be more cost-effective than hiring separate roofing and carpentry crews for your Chesapeake home.

What is your process for a bathroom remodeling project?

Our bathroom remodels begin with a detailed consultation to understand your vision, needs, and budget. We then handle all aspects, from initial demolition and plumbing/electrical rough-ins to installing new fixtures, tile, and finishes. With our background in structural work and roofing, we're particularly adept at managing any related issues, like ensuring proper ventilation to prevent moisture damage. We focus on clear timelines, keeping the worksite organized, and delivering a functional, durable remodel that adds value to your home.

Business Location & Hours



Mon:8:00 AM - 6:00 PM
Tue:8:00 AM - 6:00 PM
Wed:8:00 AM - 6:00 PM
Thu:8:00 AM - 6:00 PM
Fri:8:00 AM - 6:00 PM
Sat:8:00 AM - 6:00 PM
Sun:Closed


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