Easy Payment Options For Your Home Improvement Project

Chesapeake Roofing, Windows & Siding Inc. has been in business for more than 30 years. We have a reputation throughout the Annapolis region as one of the most trusted and easiest to work with companies. We offer Free Estimates for home improvement projects with upfront, all-inclusive pricing – so there are no surprises at the end of the job.

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Our Process

Once you’ve decided to hire us for your replacement roof or siding, we will schedule your job. Work generally begins in about 1 1/2 to 3 weeks from signing your contract. Most jobs are completed in 1 to 4 days.


We require 1/3 payment upfront at the time the contract is signed. Once you are satisfied, the remaining 2/3 balance is due when the job is complete.


Payment can be made online here. Please note that our servicer adds a 3% credit card fee.


We accept cash, checks, and credit cards for home improvement work. Many homeowners like the convenience of financing their projects. You can work with your bank or mortgage company to take out a home equity loan. In addition, we offer attractive financing options through GreenSky.

Why Choose GreenSky Financing

We are excited to offer GreenSky Financing with same-day financing up to $55,000 for approved customers. How it works:
Greensky
  1. Apply: Easy to apply by mobile app, online or by phone
  2. Get Approved: GreenSky provides quick approvals with same-day financing
  3. Get Funding: GreenSky works like a credit card; you can use it instantly

GreenSky is one of the only providers in the United States to offer no interest and no payment options for home improvement projects. With 0%, low APR plans, and flexible terms, you can pay over time and easily manage your budget. GreenSky offers a wide range of credit plans, all without prepayment penalties. The best part? GreenSky offers a simple, paperless application process with same-day approval.

Apply Now