Providing Roofing and Painting Services to Southeast Missouri

One Team for Your Home’s Complete Exterior

Old Town Roofing & Paint handles your entire exterior from start to finish. Roofing, window replacement, siding, and paint from one local crew you can trust.

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Roofing

Replacement, repair, storm damage, and insurance help.

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Painting & Siding

Exterior, interior, siding, and trim. Sherwin-Williams products.

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Window Replacement

Energy-efficient VinylKraft windows installed by the same team you trust.

One Company. One Crew. One Person to Call.

Most homeowners in Southeast Missouri end up juggling a roofer, a painter, and a window company just to take care of their home’s exterior. Old Town Roofing & Paint is the only contractor in Cape Girardeau that handles all of it under one brand. You get one estimate, one timeline, and one team that’s accountable for the finished result. That means no juggling schedules. No gaps in accountability. And an exterior that looks like it was planned together, because it was.

Roofing

Whether it’s time for a full roof replacement or you need storm damage repaired before it gets worse, Old Town has you covered. We’re a GAF Certified Plus™ contractor, which means your new roof comes backed by one of the strongest warranties in the industry. What we handle:

  • Roof replacement and new roof installation
  • Roof repair and leak fixes
  • Storm, wind, and hail damage repair
  • Insurance claim assistance from inspection to completion
  • Free roof inspections

If a storm came through your neighborhood, call us. We’ll inspect your roof, document everything, and walk you through the insurance process so you’re not doing it alone.

Old Town Roofing and Paint uses GAF’s #1 selling shingle. High Definition® - Timberline HDZ® Shingles
Painted trim on house corner

Painting & Siding

A great paint job starts long before anyone picks up a brush. We scrape, caulk, sand, and prep every surface so the finish holds up and looks right for years. We use Sherwin-Williams paints and professional-grade equipment on every job. What we handle:

  • Exterior painting
  • Interior painting
  • Siding painting and restoration
  • Trim, fascia, and detail work
  • Surface prep, caulking, and repair

Painting is where Old Town started, and it’s the reason we think about your home’s exterior as a complete system, not just a collection of separate projects.

Window Replacement

Old windows do more than let drafts in. They drive up your energy bills, make your home harder to heat and cool, and quietly drag down your curb appeal. Replacing them is one of the smartest investments you can make in your home’s comfort and value. We install Vinyl Kraft windows, custom-built, energy-efficient, and backed by a manufacturer warranty. They’re installed by the same team that handles your roof and paint. That means if you’re already getting exterior work done, your windows can be part of the same project, with the same crew, on the same timeline.

What we handle:

  • Full residential window replacement
  • Energy efficient VinylKraft window installation
  • Window upgrades during roof or paint projects
  • Free window evaluation as part of any exterior inspection

Not sure if your windows need replacing or just some attention? We’ll take a look and give you an honest answer. No pressure, no upsell. Just a straight recommendation based on what we see.

Vinyl Kraft windows installed in house

Common Exterior Combinations

Not every homeowner needs all three services at once. Here are the combinations we see most often, and when each one makes sense:

  • Roof + Paint. Common after a storm-driven roof replacement, when the paint has aged and a fresh exterior makes the whole house feel new. Often the right call for homes 12 to 20 years old.
  • Roof + Windows. An energy efficiency upgrade. Replacing both at once means one round of crew mobilization, less disruption, and a sealed exterior that performs from top to bottom.
  • Paint + Windows. A curb appeal refresh with a comfort and value upgrade built in. New windows change how the trim sits; fresh paint frames them properly.
  • Complete Exterior. Roof, paint, and windows together. Typically homes 15+ years old, or a post-storm rebuild. The cleanest version of the project, with a single coordinated finish.

Not sure which combination is right for your home? We’ll walk your exterior and give you an honest recommendation — including which services can wait if they don’t need attention yet.

Take Care of Everything at Once

When you combine two or more services with Old Town, the whole project runs smoother. One schedule, one crew, one point of contact. No waiting on a second contractor to finish before the next one can start.

Here’s what that looks like in practice:

one team on site

One team on-site means less disruption to your daily routine

coordinated timeline

A coordinated timeline so your project finishes faster

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One warranty covering the work, not three separate agreements

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A finished exterior that actually looks cohesive because it was planned together

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Financing available across all services to make the full project manageable

Getting a new roof? Ask us about your windows and paint while we’re there. Most homeowners are surprised at how much easier it is to handle everything at once.

Why Old Town Roofing & Paint

Locally owned. We live and work here. Your home’s exterior is our reputation.

Craftsmanship-focused. We came up through painting, where prep and detail make the difference. We bring that same mindset to roofing.

Roof + exterior under one brand. Damaged fascia or peeling trim after a replacement? We handle that too.

Honest communication. Clear proposals, real numbers, no pressure.

Quality materials. GAF Certified Plus™. Sherwin-Williams products. Manufacturer warranties backed by proper installation.

Financing available to those who qualify. A new roof is a big investment. We offer options to make it work for your budget.

Old Town Roofing and Paint uses GAF’s #1 selling shingle. High Definition® - Timberline HDZ® Shingles

Complete Exterior FAQs

What is "complete exterior" home renovation?
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Complete exterior home renovation means handling every outside surface of your home — roof, siding, paint, trim, and windows — as one coordinated project rather than three separate jobs. Old Town is the only contractor in Cape Girardeau that handles all of it under one brand, with one team, one timeline, and one point of contact.

Can you do my roof, paint, and windows all at once?
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Yes, we can do your roof, paint, and windows as one coordinated project. We're the only contractor in Southeast Missouri that handles all three services under one brand. Combining the work means one schedule, one crew, and a finished exterior that looks like it was planned together — because it was.

Does bundling exterior services save money?
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Bundling exterior services often saves money compared to hiring three separate contractors, mostly through shared mobilization, single project management, and reduced rework where one trade affects another. The exact savings depend on the project scope. We'll quote each service clearly so you can see the full picture before deciding what to bundle.

How long does a complete exterior project take?
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A complete exterior project typically takes two to four weeks, depending on the scope of work, the size of your home, and the weather. Roof replacement is usually three to five days, exterior painting is three to five days, and window replacement varies based on the order timeline. We coordinate the work so it runs in the right sequence with minimum downtime.

Can you handle the insurance claim for storm damage on a complete exterior project?
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Yes, we handle insurance claims for storm damage on complete exterior projects. We'll inspect every affected surface — roof, siding, windows, and trim — document the damage with photos, and work directly with your insurance company through the claim. Having one contractor document the full scope of damage often results in a more accurate claim than piecing it together across multiple companies.

Do you offer financing for a complete exterior renovation?
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Yes, we offer financing for complete exterior renovations to qualifying homeowners through GreenSky. Terms and conditions apply. Bundling services into one financed project is often more manageable than financing each piece separately. Ask us for details when you request your free estimate.

Will my complete exterior project come with one warranty or three?
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Your complete exterior project comes with the manufacturer warranties on each product (GAF for roofing, Sherwin-Williams for paint, VinylKraft for windows) plus a workmanship warranty from Old Town covering the installation across all services. You get one point of contact for any warranty issue, not three separate companies pointing at each other.

Service Areas

We currently serve the following cities and their surrounding communities:

Cape Girardeau

Jackson

Perryville

Scott City

Sikeston

Don’t see your town? Give us a call. If you’re in the area, we can probably help.

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Get Your Free Estimate

“They are very professional and fast at responding to any questions you have. I will definitely use them again. They also did an amazing job. You will not regret calling them. They also have very reasonable rates.” – Peggy R.

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Ask us about our financing options that fit with your budget.*

*Loans for the GreenSky® consumer loan program are offered and made by federally insured, federal or state chartered financial institutions providing credit without regard to age, race, color, religion, national origin, gender, disability, or familial status. A list of financial institutions currently providing loans through the GreenSky® Program is available at www.greensky.com/bank-partners. GreenSky Servicing, LLC services the loans on behalf of your lender, NMLS #1416362. www.nmlsconsumeraccess.org. GreenSky® is a registered trademark of GreenSky, LLC and is licensed to banks and other financial institutions for their use in connection with that consumer loan program. GreenSky Servicing, LLC is a financial technology company that manages the GreenSky® consumer loan program by providing origination and servicing support to banks and other financial institutions that make or hold program loans. GreenSky, LLC and GreenSky Servicing, LLC are not lenders. All credit decisions and loan terms are determined by program lenders.