Roofing, Siding, Windows & Gutters in Chester, CT

Welcome to A Plus Exterior, your trusted local team for roofing, siding, window replacement, and gutter services in Chester, Connecticut. We’re committed to high-quality workmanship, clear communication, and competitive pricing—so your home stays protected and looks great through every season.

Chester’s shoreline-region weather (wind, heavy rain, snow, and freeze/thaw cycles) can be tough on roofs and drainage systems. Whether you need a small repair or a full replacement, we focus on durable materials, proper installation, and clean finishes that last.

Exterior Home Improvement Services in Chester, Connecticut

Roofing Services in Chester, CT

  • Roof inspections and leak troubleshooting

  • Roof repairs (shingles, flashing, vents, skylight areas)

  • Full roof replacements

  • Storm and wind damage support

Siding Services in Chester, CT

  • Siding repair and full siding replacement

  • Trim and fascia repairs

  • Weatherproofing to help prevent moisture intrusion and drafts

  • Options that match your home’s style and budget

Window Installation & Replacement in Chester, CT

  • Window replacement and new window installation

  • Energy-efficiency upgrades for comfort and lower utility costs

  • Proper sealing and flashing to help prevent leaks and drafts

Gutter Services in Chester, CT

  • Gutter cleaning and routine maintenance

  • Gutter repairs (leaks, loose gutters, poor pitch)

  • New gutter installation and downspout upgrades

  • Drainage improvements to help protect foundations and landscaping

Why Chester Homeowners Choose A Plus Exterior

  • Skilled, detail-focused craftsmanship

  • Reliable scheduling and responsive communication

  • Respectful crews and thorough cleanup

  • 100% satisfaction guarantee on our work

Fun Facts About Chester, Connecticut

  • Incorporated in 1836: Chester became an independent town in 1836 after separating from Saybrook.

  • Chester Museum at the Mill: The Chester Historical Society operates the Chester Museum at The Mill, located at a historic mill site near the center of town.

  • Chester Sunday Market: A popular seasonal market that runs Sundays (typically mid-June through mid-October) and brings the community together around local vendors.

  • Arts + culture: Chester is known for its small-town charm and a strong arts scene, drawing visitors for galleries, shops, and events. (Great for “day-trip” traffic that also searches for local contractors.)

Get a Free Estimate in Chester, CT

If you need roofing, siding, windows, or gutters in Chester, call 203-693-2225 to schedule your free consultation and estimate. You can also visit our contact page to send us a message.

Call now: 203-693-2225