Roofing in Cheshire, CT: Repair & Replacement
Reroofs, skylight replacement and leak repair for Cheshire colonials and contemporaries, with drone photos of every slope and a written price before any work.
Sunday to Friday
A Class repairs and replaces roofs across Cheshire, where many houses built since the 1950s have large, cut-up roofs, skylights and shaded lots. As a ballpark, skylight leak repair runs $400–$1,200, skylight replacement $1,500–$4,000 per skylight, and a complete asphalt roof for a typical Connecticut home $10,000–$25,000+. There is no charge for the inspection or the estimate, which you get in writing.
How Cheshire’s roofs got so big
Cheshire more than doubled in the 1950s, from about 6,300 residents in 1950 to about 13,400 in 1960, and reached about 19,000 by 1970. Building carried on for decades after that, and many of the houses it produced are colonials and contemporaries on generous, often wooded lots.
Bigger houses mean bigger, more complicated roofs: intersecting gables, several valleys, dormers, skylights over kitchens and stairwells, and sometimes a low-slope section over a sunroom. The older center around Cheshire Academy, whose Bowden Hall dates to 1796, has the town’s antique houses and their own set of issues.
Skylights: often the first thing to leak
A skylight is an opening in the roof with a window in it, and its flashing has to work with the shingles around it. In many homes the skylights are as old as the house or the last reroof, and their seals, glazing and flashing often wear out before the roof does.
If a skylight is leaking and the roof is more than about halfway through its life, consider replacing the skylight when the roof is replaced, so both get new flashing at once. Skylight leak repair runs about $400–$1,200 as a ballpark and replacement $1,500–$4,000 per skylight installed. See skylight installation and repair and skylight replacement cost for details.
If you no longer want a skylight, it can be removed during a reroof and the opening framed and decked over, which removes a leak point and a source of summer heat for good.
Roofing price check
Typical Connecticut ranges for common roofing jobs.
Leak or condensation? Reading a wet skylight
Before you assume the roof has failed, match the symptom to the likely cause.
| What you see | Likely cause | What to do |
|---|---|---|
| Drips during or right after rain, stains at the top corners of the well | Flashing or seal failure | Have the flashing checked, then repair or replace |
| Water on the inside of the glass on cold mornings, with no rain | Condensation from humid indoor air | Run bath and kitchen fans and lower the humidity; this is not a roof leak |
| Fog or moisture between the panes | Failed insulated glass seal | Replace the skylight or its glazing |
| A leak only while snow is melting | Ice or snow damming above the skylight | Check the flashing and the insulation around the well |
| Cracked or crazed plastic dome | Old acrylic broken down by sun | Replace the unit |
Shade, algae and gutters on wooded lots
Black streaks
Dark streaks running down the shingles are usually algae, Gloeocapsa magma, which thrives on shaded, damp slopes. It is mostly cosmetic. Do not pressure wash shingles, because it strips the granules; our black streaks and moss guide explains gentler options.
Moss
Moss is more serious than algae because it holds water against the roof and can lift shingle edges. It grows thickest on north-facing slopes under trees.
Gutters full of leaves
Large lots under oaks and maples fill gutters every fall, and overflowing gutters soak fascia boards and feed ice dams. Gutter guards run about $1,000–$3,000 as a ballpark; see gutter installation and repair.
Limbs over the roof
Branches that touch the roof scrape granules off and drop debris into valleys. Have a licensed arborist trim them back before a reroof.
Sunroom and porch roofs
Low-slope roofs over sunrooms and porches sit in the shade of the main house and the trees, so leaves pile up and stay wet. These sections usually need a membrane rather than shingles, and their seam with the main wall is the first place to look for a leak.
Decisions to make before a Cheshire reroof
Settle these early, so they are in the written estimate instead of decided on the day.
- Replace the skylights now or keep them, based on their age and condition
- Remove a skylight you no longer want, and have the opening framed and decked over
- Add or upgrade ridge and soffit ventilation, especially over a finished bonus room
- Choose an algae-resistant shingle if your roof is shaded
- Pick a color knowing that streaks show more on light shingles, while dark roofs absorb more summer heat
- Decide whether gutters will be replaced at the same time, because drip edge and gutter have to line up
- Confirm that chimney flashing and any cricket will be replaced, not reused
- Check with Cheshire’s building department about the permit
How A Class works on a Cheshire roof
- Reach usUse (203) 779-6787 or the callback form, and list any skylights, sunrooms or earlier leaks.
- No-cost inspectionWe look at every slope, skylight and valley, and use a drone for photos of the parts of a large roof that cannot be seen from the yard.
- Written estimateEach item, from skylights to ventilation, is listed with its price, so you can choose what to include.
- InstallationLandscaping, decks and walkways are covered before tear-off, and the new roof goes on with new flashing where it meets skylights and walls.
- Clean-upDebris is hauled off, and gutters, beds and the driveway are cleaned before we go.
Chimneys and nearby towns
Where a colonial has a brick chimney on an outside wall rising past the eaves, the flashing and cricket behind it deserve a close look whenever the roof is replaced.
For chimney flashing, caps or masonry on a Cheshire home, see our Cheshire chimney page. We also do roofing in Southington, Hamden and Wallingford.
Prefer we call you?
Three quick taps and a real person from A Class Chimney calls you back to set up a free roof inspection.
- Free roof inspection and written estimate
- Photos of everything we find
- A written price before any work starts
- Licensed and insured in Connecticut
Sunday to Friday
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Cheshire roofing questions
Roofing help in Cheshire
Free roof inspection, photos of what we find and a written price before any work. Licensed and insured in Connecticut.