
exterior renovation order of operations: what to replace first
When a house needs more than one thing on the outside, the order you do them in decides whether each job protects the next or damages it. New siding before new windows means cutting into the siding a year later. New gutters before a new roof means taking the gutters down again. A deck built before the siding means a ledger you can never flash properly. This guide gives the order we recommend on a Massachusetts home, why each step comes where it does, when to break the order, and how to phase and budget the work when it cannot all happen at once.
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The logic is water: the roof sheds it, the windows and doors are flashed into the wall, the siding covers the wall and the flashing, the gutters hang on the finished fascia, and the deck attaches to a wall that is already finished and sealed. Outside before inside, because there is no point finishing a room under a roof or behind a wall that leaks. Any single project can be done alone; it is when two are close together that the order matters, and when the roof and the siding are both due, doing them together is the best outcome of all.

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Pick the service you are planning, answer a few quick questions and see a standard, premium and deluxe range for siding, roofing, windows, doors, decks or gutters. Every project is quoted after we visit the house, and financing is available on all six services.
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the order and why
Six steps, and the reason each one comes where it does. Scroll through.

1. Roof
The roof keeps everything below it dry, and a roof replacement is messy: tear-off debris slides down the walls, crews walk the eaves, and the drip edge and fascia get handled. Do it before new siding and before new gutters so nothing gets scraped or dented. A roof also sets the drip edge, which the gutters hang against. If the roof has a few years left, it can wait, but then protect the new siding and gutters when the roof day comes.
2. Windows and doors
Windows and doors are flashed into the wall's weather barrier, which sits under the siding. Full-frame replacements and new openings should happen before the siding so each unit is taped and flashed into a continuous barrier and the siding and trim are cut to fit it once. If the siding is new and the windows are old, insert windows can be installed later without disturbing the siding, at the cost of a little glass area.
3. Siding and trim
With the roof done and the windows in, the walls can be stripped, the sheathing repaired, the weather barrier and flashing installed, and the siding and trim put on. This is also the point to replace the fascia and soffit, insulate the walls from outside if you are doing that, and run the trim around the new windows and doors. See our siding installation cost guide.
4. Gutters
Gutters hang on the finished fascia and tuck under the new drip edge, so they come after the roof and the siding. Doing them earlier means removing them for the roof or the fascia and rehanging them, which loosens hangers and bends gutters. Size them for the new roof and add guards if trees overhang. See our gutter installation cost guide.
5. Deck or porch
The deck ledger bolts to the house through the wall, and the flashing over it has to tuck behind the weather barrier and the siding. Build the deck after the siding so the ledger is flashed into a finished wall; if the deck is already there when the siding is replaced, we pull the ledger flashing and redo it as part of the siding job. The deck also benefits from being last because it is where the crews and the debris would otherwise land. See our deck cost guide.
6. Paint, finish and landscaping
Anything site-painted, such as cedar siding, trim or a wood door, is finished last, after the dust is gone, and the beds and lawn along the house are repaired after the last crew leaves.
When siding comes before the roof
The order above assumes both are due. There are three reasons to do the siding first. If the walls are actively rotting, water is getting into the house through the siding and the sheathing is failing, that outranks a roof with life left in it; a wall problem does not wait. If the roof has ten or more years left and the siding is done, the roofer can protect the new siding and fascia when the day comes. And if the fascia, soffit and rake trim are being replaced as part of the siding, that work ties into the roof edge, which is the strongest argument of all for doing both together.
Roof and siding together
When both are due, one project is better than two. The drip edge, fascia, soffit, rake trim, step flashing where the roof meets a wall, and the kick-out flashing at the bottom of every roof-to-wall joint all sit exactly where the roof and the siding meet, and the only way to get every one of them right is to have the same crew do both sides of the joint. It also means one set of staging, one permit visit, one cleanup, and no new siding scraped by a later tear-off. We quote the combination often, and it is the job that shows what one crew for the whole exterior is for.
projects that pair well, and phasing over several years
Roof and siding: every piece of flashing where they meet done once, by one crew. Roof and gutters: one set of staging, and the drip edge and gutters set right once. Windows and siding: each window flashed into the new barrier and the trim done once. Siding and doors: same reason, and the brickmould matches the new trim. Deck and patio door: the door is replaced while the wall behind the ledger is open. Siding and gutters: the fascia is replaced under the siding job and the gutters go on at the end. Most families do the exterior in two or three phases. A common sequence: roof and gutters in year one, windows and doors in year two, siding and deck in year three. The rule is to keep the order within each phase and to do the thing that is failing first. A leaking roof outranks everything; a rotted ledger outranks tired siding. A free estimate with the whole exterior in mind lets us plan the phases so no job undoes an earlier one.

what each project costs
Roofing
Per square foot; asphalt shingles
- Standard
- $7.20
- Premium
- $8.90
- Deluxe
- $9.30
Siding
Per square foot of wall; vinyl, with James Hardie from $20.20
- Standard
- $11.30
- Premium
- $12.40
- Deluxe
- $18.10
Windows
Per window; vinyl, with fiberglass from $1,210
- Standard
- $998
- Premium
- $1,130
- Deluxe
- $1,285
Entry doors
Per door; single entry, sidelights from $6,280
- Standard
- $4,830
- Premium
- $5,445
- Deluxe
- $6,312
Gutters
Per linear foot; seamless aluminum, copper from $96
- Standard
- $28.50
- Premium
- $31.50
- Deluxe
- $36.50
Composite decks
Per square foot; wood from $141
- Standard
- $183
- Premium
- $233
- Deluxe
- $298
Six services, one crew, one estimate
Plum ProExteriors prices every service per unit installed, in standard, premium and deluxe tiers. Use the calculator above to price any of the six, then book a free estimate for the whole house. See our cost guides for roofing, siding, windows, doors, gutters and decks. Financing is available on every project.
how plum proexteriors plans a whole exterior
We look at the whole house, not the one thing you called about: the roof from the attic, the walls at the sills and the corners, the windows, the gutters and the deck ledger. You get a written plan that says what is failing first, what pairs with it, and what can wait, with a quote for each phase so no job undoes an earlier one. One crew and one point of contact across roofing, siding, windows and doors, gutters and decks. Financing is available.


what our clients say
The owner is on site for every project, and when the job is done he asks every client the same question on camera: what do you think? These are their answers, at their own homes.
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frequently asked questions
Should I replace the roof or the siding first?
Roof first if both are due and they cannot be done together, because the tear-off and the crews on the eaves will damage new siding. Siding first if the walls are actively rotting. Together is best.
Should I renovate the inside or the outside first?
Outside. A roof or a wall that leaks will undo interior work, and the exterior is where the water is stopped.
Windows before or after siding?
Before, for full-frame replacements, so each window is flashed into the new weather barrier. Insert windows can go in after siding without disturbing it.
Do gutters go before or after siding?
After. Gutters hang on the finished fascia, which is replaced under the siding job.
Can gutters go on before the roof?
They can, but they will have to come down for the roof. Do the roof first.
Can I build a deck before residing?
You can, but the ledger flashing will have to be redone when the siding is replaced. Build it after, or plan both together.
Do roofers do siding?
Some do, most do not, and the joint between the two is where a roofing-only or siding-only crew leaves the other side's flashing for someone else. Plum ProExteriors does both.
What if only one thing is failing?
Fix that one. The order matters when two projects are close together; a single project can be done on its own at any time.
Do you do all six services?
Yes. Roofing, siding, windows, doors, gutters and decks, with one crew and one point of contact, which is what makes the sequencing easy.
plan the whole exterior with one estimate
Call us or send the estimate form. We will look at the whole house, tell you what is failing first, and give you a written quote for each phase.
Call (508) 266-5411 Send the estimate form