Roland Contracting LLC — Roofing, siding and gutters in Pittsburgh, PA

Free inspections and written estimates in Allegheny County

Roofs built for Pittsburgh weather.

Quality You Can See. Work You Can Trust. At Roland Contracting LLC, we provide professional roofing, siding, gutter, and home improvement services. We are committed to quality workmanship, reliable service, and making sure every project is completed with care and attention to detail. Your home deserves work done right

  • Licensed and insured

    PA 217875, with liability coverage on every job we take.

  • Warrantied materials

    GAF, Owens Corning and ATLAS products installed to the manufacturer's spec.

  • Our own crew

    The person who quotes your roof is on the roof when the work starts.

Complete protection for the outside of your home

Roofing, siding and gutters for houses, row homes and small commercial buildings across Pittsburgh. One contractor, one crew, and one number to call for the whole exterior.

Newly installed asphalt shingle roof

Roofing

Inspections, leak and storm repairs, and full tear-off replacements with new flashing and ventilation.

  • Inspection
  • Repair
  • Replacement
  • Storm damage
How we do roofing
Vinyl siding on a house exterior

Siding

New siding, panel repairs and full replacements that seal the walls and refresh how the house looks from the street.

  • Vinyl
  • Cedar shake
  • Fiber cement
  • Soffit & fascia
How we do siding
Aluminium gutter being installed along a roof edge

Gutters

Seamless gutters, downspouts and guards sized to your roof, so rain and meltwater end up away from the foundation.

  • Installation
  • Replacement
  • Repair
  • Guards
How we do gutters
Rolled membrane being torched onto a flat roof

Flat & roll roofing

Torch-down and rolled membrane for the flat and low-slope roofs on porches, garages and row-house backs.

  • Torch-down
  • Roll roofing
  • Coatings
How we do flat roofs
Debris being cleared out of a gutter by hand

Gutter cleaning

Spring and fall clear-outs, downspout flushing and a condition check. The cheapest way to avoid an ice dam in January.

  • Clear-out
  • Flush test
  • Seasonal
How we do cleaning

Something else?

Chimney flashing, skylights, a leak you can't trace. Tell us what you're seeing and we'll tell you honestly if it's a job for us.

Ask us

Storm damage? Call us before the next rain.

High wind, hail and fallen branches can lift shingles, crack flashing and open the roof to water in places you can't see from the ground. The sooner it's looked at, the smaller the repair.

  • Fast assessment. Send photos and we'll tell you how urgent it looks, usually the same day.
  • Insurance-ready documentation. Photos and measurements of the damage you can hand straight to your adjuster.
  • We meet the adjuster. On site, if it helps your claim go smoother.
  • Repair or replace. Whatever the roof actually needs, explained in writing.

Emergencies are answered on Sundays too.

Roof deck dried in with synthetic underlayment during repairs

From first call to clean yard in four steps

No pressure, no surprise charges. You know what's being done, what it costs and how long we'll be there before any work starts.

  1. Tell us what's wrong

    Call, text or send a photo on WhatsApp. Many times we can tell right away if it's a repair or a replacement.

  2. Free inspection

    We get on the roof where it's safe, check the attic from underneath and photograph everything we find.

  3. Written estimate

    Scope, materials, price and days on site, usually within a day of the visit. The price doesn't move once we start.

  4. Work and clean-up

    Landscaping protected, the job done properly, and a magnetic sweep of every nail before we leave.

Signs your home needs a closer look

Most roof and siding problems start small and quiet. If you notice any of these, a free inspection now costs a lot less than a rotten deck later.

Book a free inspection
  • Missing or curling shingles

    Wind and age lift the edges, and every gap is a path for water.

  • Stains on ceilings or walls

    By the time it shows inside, water has usually been getting in for a while.

  • Granules in the gutters

    Shingles shedding their grit are near the end of their life.

  • Overflowing gutters

    Clogged or undersized gutters soak the fascia and feed ice dams in winter.

  • Sagging or soft spots

    A dip in the roof line often means the deck underneath is rotting.

  • Cracked or loose siding

    Water gets behind the wall and works quietly for months before you see it.

Recent jobs

Tear-offs, gutter runs, cedar shake and flat-roof work, photographed on the day the crew finished.

Finished shingle roof with a ridge vent
New gutter run along a roof edge
House exterior finished in cedar shake siding
Synthetic underlayment laid across a roof deck
Roll membrane being torched down on a flat roof
Cedar shakes fitted under an eave
Shingle roof seen across a Pittsburgh neighbourhood

Walk a finished roof with us

Straight lines, sealed pipe boots, clean valleys and ridge caps that sit flat. This is what a finished Roland roof looks like up close, before we pack up and sweep the yard.

We use materials that last

Shingles, underlayment and accessories from manufacturers that back their products with a real warranty, installed the way they specify.

  • GAF
  • Owens Corning
  • ATLAS

Your local partner for roofing and exteriors

Roland Contracting LLC is a Pittsburgh roofing and exterior contractor. For ten years we've worked on houses, row homes and small commercial buildings across the city and the surrounding boroughs, and we know exactly what a Western Pennsylvania winter does to flashing, valleys and gutters.

We keep things simple: free inspections, honest advice, a written price that doesn't change, and a crew that treats your property like its own. Whether you need a small repair or a complete new roof, you get the same care and the same straight answers.

Roland Contracting branded work truck
You'll know us when we pull up.

How we work

Every job runs on three things we don't negotiate on:

  • Honest assessments, including when you don't need the work
  • Materials and fasteners rated for the pitch and the climate
  • A site left cleaner than we found it, nails included

Where we're going

We want to be the contractor Pittsburgh homeowners call first and recommend without being asked, known for doing what we said we'd do, at the price we quoted.

Durable work, straight answers, and relationships that outlast any single project.

Where we work

Based in Pittsburgh, serving homes and businesses throughout Allegheny County. Don't see your neighbourhood? Ask us — if we can get there, we will.

  • Pittsburgh
  • Penn Hills
  • Monroeville
  • Plum
  • Wilkinsburg
  • Churchill
  • Forest Hills
  • Verona
  • Oakmont
  • Fox Chapel
  • O'Hara
  • Shaler

Common questions

The things homeowners ask us most. If yours isn't here, send it on WhatsApp and we'll answer the same day.

Is the inspection really free?

Yes. We come out, look at the roof, siding or gutters, and give you a written estimate at no cost and with no obligation to book the work.

How quickly can you give me a price?

Usually within a day of seeing the job. For smaller repairs, a couple of clear photos on WhatsApp is often enough for us to give you a good idea straight away.

Do I need a repair or a full replacement?

It depends on the age of the roof, how many layers it has and where it's failing. Isolated wind damage or one bad flashing is a repair. If your roof still has good years left, we'll tell you so.

Do you help with insurance claims?

Yes. After storm damage we document the roof with photos and measurements you can give your adjuster, and we'll meet them on site if that helps.

Are you licensed and insured?

Yes. Roland Contracting LLC is registered in Pennsylvania under PA 217875 and carries liability insurance on every job.

How long does a new roof take?

Most single-family homes take one to three days, depending on size, pitch and how many layers are coming off. You'll have the number before we start.

Do you work on commercial buildings?

Yes, small commercial buildings as well as houses and row homes, including the flat and low-slope roofs common on them.

Get your free estimate

Call, text or send photos. We answer through the working day and reply to evening messages first thing the next morning.

Hours

Monday to Friday
7:00 AM — 6:00 PM
Saturday
8:00 AM — 2:00 PM
Sunday
Emergencies only