Annapolis MD Home Remodeling Services

Need Roof Shingles Replaced? Want Gutter protection or Enclosed Porch? Call today for all home improvement jobs! 800-564-7230


As a full-service roofing company in Crofton, MD, Chesapeake Roofing, Windows & Siding serves Annapolis, Baltimore and surrounding areas with all types of roofing services. Our experienced roofers offer new installations, repairs, and maintenance services. We specialize in shingle roofs which are ideal for most homes. Whether a storm damaged your roof or you need a tear-off and replacement, call us today!

  • Luxury Shingles
  • Premium Designer Shingles
  • Designer Shingles
  • Traditional Shingles
  • Low Slope Shingles
  • Ice & Water shield
  • Ridge Vent Systems

CertainTeed Logo    


Is it time to upgrade your siding? Our siding contractors offer low maintenance, high performance vinyl siding. Choose from a wide range of colors and styles to enhance your home's exterior. We also specialize in shutters, door surrounds, gable vents, dentil trim and mounting blocks.

  • Vinyl Siding
    – CertainTeed
    – Mastic
  • HardiePlank Siding
  • Soffits
  • Exterior Accents


We sell and install windows from Simonton and Anderson at great prices. Replacement windows can help control indoor comfort and lower your energy costs. Whatever size, shape or style window you are interested in, call our knowledgeable team at Chesapeake Roofing, Windows & Siding to learn about your options.

  • Simonton
  • Anderson
  • Bay Windows
  • Awning Windows
  • Garden Windows
  • Bow Windows
  • Casement Windows
  • Slider Windows
Simonton Andersen  


At Chesapeake Roofing, Windows & Siding, we have been serving the Greater Annapolis and Baltimore Areas with interior and exterior doors. We offer a wide selection including entry doors, storm doors, insulated patio doors, sliding doors and much more. Contact us at 800-564-7230 or 410-672-5822 to learn more!

  • ProVia Door
    (entry doors & storm doors)
  • Therma-Tru
    (entry doors & patio doors)
  • Jeld-Win
    (entry doors & patio doors)
  • Anderson
    (patio doors)


  • Interior Doors
  • Exterior Doors
ProVia ThermaTru   Jeldwin  Andersen

Gutters & Downspouts

If you need a new rain collection system, depend on us for reliable, affordable gutter and downspout solutions. We provide several gutter services including repairs, replacements and cleanings. Customer satisfaction is our top priority, so contact us today to get started!

  • Alcoa
  • Leaf Sentry
  • Leaf Relief
Alcoa Leaf Sentry Leaf Relief

Call Chesapeake Roofing, Windows & Siding, Inc. at 800-564-7230 or 410-672-5822.

Service Areas Include: Anne Arundel, Prince George's and Howard County Counties including Annapolis, Arnold, Arden on the Severn, Brooklyn Park, Cape Saint Claire, Crofton, Crownsville, Deale, Eastport, Edgewater, Ferndale, Galesville, Gambrills, Glen Burnie, Herald Harbor, Hillsmeare, Jessup, Lake Shore, Linthicolm, Maryland City, Mayo, Odenton, Parole, Pasadena, Riva, Riviera Beach, Selby-on-the-Bay, Severn, Severna Park, Shady Side, South Side, and Truxten Heights, MD.