A roof replacement is the biggest exterior job most homeowners ever pay for, and it is almost impossible to compare two quotes for it. This page explains exactly what we install, what drives the price up or down in Massachusetts, and how to tell whether you actually need one yet.
If a company has told you that you need a full replacement and you have not had a second opinion, get one. We do repairs as well as replacements, so we have no reason to push you toward the bigger job. Here is how to tell the difference yourself.
What we actually install
Most estimates you receive will say “tear off and install architectural shingles” and stop there. That sentence hides about $9,000 of possible variation. A DeSouza replacement is specified layer by layer, and every line below appears on your written estimate before anything starts.
Full tear-off, down to the deck
We strip the roof back to bare wood. We do not lay new shingles over an old roof to save a day of labor. An overlay hides rotted sheathing, adds weight the frame was not designed for, traps heat that shortens shingle life, and makes the next replacement more expensive than it needed to be. It also makes it impossible to install ice & water shield properly, which on a Massachusetts roof is the layer that matters most.
Decking inspected and repaired
Once the old roof is off we walk the entire deck. Soft, delaminated or water-stained sheathing gets replaced, not covered up. This is the single most common place where a roofing quote changes mid-job, so we handle it two ways: we check the attic before quoting so we already know roughly what to expect, and if we do find more than we allowed for, you hear about it the same hour with a price — not at the end in an invoice.
Ice & water shield
A self-adhering rubberised membrane that bonds directly to the decking and seals around every nail driven through it. It goes along the eaves, up the valleys, and around every penetration — chimneys, vents, skylights, pipe boots. In New England this is not an upgrade. It is the layer that stops meltwater from an ice dam getting into your ceiling, and it is the first thing a cheap quote quietly reduces.
Synthetic underlayment
Across the full deck, over the ice & water shield. It is the secondary water barrier for the life of the roof, and it keeps the structure dry during the install itself.
New drip edge and new flashing
Metal drip edge along every eave and rake. New step flashing where the roof meets a wall, new counterflashing at the chimney, new valley metal, new pipe boots. Reusing old flashing is where leaks come back two winters later on an otherwise perfect roof — and it is a very easy line for a competitor to save money on, because you cannot see it from the ground.
Architectural asphalt shingles
Laminated architectural shingles rather than the old three-tab type. They are heavier, carry far better wind ratings for coastal and nor’easter exposure, last considerably longer, and they give the roof actual depth and shadow line instead of looking flat.
Ridge vent and intake ventilation
The part almost nobody talks about at the estimate, and the part that decides whether you get ice dams next winter. A roof needs balanced airflow — intake low at the soffits, exhaust high at the ridge. If the intake is blocked by insulation, a ridge vent alone does nothing. We check this in your attic, not from the driveway.
What a roof replacement costs around Boston
Anyone who gives you a firm price before seeing the roof is guessing. That said, homeowners deserve a real range rather than “it depends,” so here is what actually moves the number on a typical single-family home in our service area.
| What drives the price | Why it moves the number |
|---|---|
| Roof size and number of squares | The base of every estimate. Measured in 100 sq ft “squares” of actual roof surface, not floor area. |
| Pitch and height | A steep or third-storey roof needs staging, more fall protection and slower work. A walkable ranch roof is the cheapest surface there is. |
| Number of layers coming off | Two or three old layers means more labor and a bigger dumpster. |
| Decking condition | The genuine unknown until the roof is open. We inspect the attic first to narrow it. |
| Complexity | Dormers, valleys, skylights, chimneys and multiple roof planes all add flashing work — and flashing is where leaks start. |
| Ventilation corrections | Adding proper intake or a continuous ridge vent where none exists. |
| Access | A narrow Somerville two-family with no driveway is a different job from a Wilmington colonial with a wide-open yard. |
For a detailed breakdown with real Massachusetts ranges, read how much a roof replacement costs in Massachusetts.
When a roof actually needs replacing
Age alone is not the answer. An asphalt roof in New England typically gives you somewhere in the region of 20 to 30 years depending on the shingle, the ventilation and how much direct weather it takes. What matters more is what it is doing now.
- Shingles curling, cupping or losing granules. Granules in the gutters and bald patches on the shingle mean the mat is exposed and UV is finishing it off.
- Multiple leaks in different places. One leak is a repair. Leaks appearing in three unrelated spots usually means the roof surface itself is done.
- Widespread nail pops or lifted tabs after wind. If a nor’easter takes shingles off in several areas rather than one, the field is brittle.
- Daylight or damp sheathing visible in the attic. Look up at the underside of the deck with a torch on a bright day.
- Repeated ice dam damage. Sometimes a ventilation fix. Sometimes the roof.
- A sagging roof line. Structural. Get this looked at promptly.
If you recognize one or two of these, you may well be looking at a repair. If you recognize most of them, the roof is telling you it is finished. Either way we will look and tell you which.
How the job runs
- We look at it properly. On the roof, in the attic, at the flashing and the ventilation — not a drive-by from the curb.
- You get it in writing. The full specification, the price, and what happens if we find bad decking. Free, and with no obligation.
- We protect the property. Landscaping, walkways, deck and driveway covered before a single shingle comes off.
- Tear-off and deck check. The old roof comes off and the deck is inspected in front of you if you want to see it.
- The system goes on. Ice & water shield, underlayment, drip edge, flashing, shingles, ventilation — in that order, properly.
- We clean up. Magnet sweep for nails, debris gone the same day, and a walk-round with you before we leave the street.
Most single-family roofs in our area are a one to two day job once we start. Weather is the only thing that reliably moves that, and we will not open a roof we cannot dry in.
Roof replacement questions we get asked
How long does a roof replacement take?
Most single-family homes in the Boston area are one to two days once we start. Larger, steeper or more complex roofs — multiple dormers, several valleys, three storeys — can run to three. We will not tear off more roof than we can make watertight the same day, so a forecast with heavy rain in it will move the start date rather than stretch the job.
Can you just put new shingles over the old roof?
It is physically possible and we do not do it. An overlay hides any rot in the decking, adds significant weight, traps heat that shortens the life of the new shingles, and makes it impossible to install ice & water shield at the eaves — which is the layer that protects a Massachusetts roof from ice dam damage. It saves money on day one and costs more over the life of the roof.
What happens if you find rotted decking once the roof is off?
We tell you the same hour, with a price, before we replace anything. We also check your attic before quoting so we usually have a good idea of what is under there in advance. What we will not do is discover “unexpected rot” halfway through and hand you a much larger invoice at the end.
What time of year is best for a roof replacement in Massachusetts?
Late spring through autumn is easiest — the shingles seal down properly in warmer temperatures and the weather windows are more reliable. That said, roofs get replaced here year-round, and if you have active water coming into the house in February we are not going to tell you to wait until May. Cold-weather installs need the sealant strips handled correctly, which is a technique question rather than a reason to postpone.
Do I need to be home while you work?
No. Plenty of our replacements happen while people are at work. We will want access to the attic at the estimate stage and a quick word before we start, but the job itself does not need you there. We will walk the finished roof with you afterwards whenever suits.
How long will a new asphalt roof last here?
Architectural asphalt shingles in this climate generally give somewhere in the region of 20 to 30 years. The spread comes down to three things: how well the attic is ventilated, how much direct sun and weather that particular roof plane takes, and whether the flashing was done properly. Ventilation is the one most often got wrong, and it is the one that shortens a roof fastest.
Is a roof replacement covered by homeowners insurance?
Sudden, identifiable damage — a nor’easter tearing shingles off, a tree limb coming through — is often covered. Age, ordinary wear and long-term neglect are generally not. We are roofers rather than public adjusters, so we will document what we find and give you a written assessment you can hand to your insurer, but we will not tell you your worn-out roof is storm damage, and we would be wary of any contractor who offers to.
Roof replacement across the north-of-Boston corridor
We replace roofs in Boston, Somerville, Medford, Melrose, Stoneham, Woburn, Wakefield, Burlington and Wilmington.