(203) 271-2926 CT HIC #0565252 · Licensed & Insured · In Business Since 1986
Mon–Sat 7AM–6PM · Free Estimates →

Roofing, Siding & Gutter Services in New Haven County, CT

One company, every exterior need — 40 years of proven residential craftsmanship. One call: (203) 271-2926.

40 Years in Business (Est. 1986)
Owens Corning Preferred Contractor
BBB A+ Rating · CT HIC #0565252
★ 4.9 Stars · [OWNER] Google Reviews
BBB A+ BBB Rating
OC Owens Corning Preferred
CT Licensed & Insured · HIC.0565252

Professional Residential Services

Every service is performed by our dedicated crew, using proper Connecticut cold-climate building practices, manufacturer-certified materials, and full property protection.

#1 Most Requested

Roof Replacement

Tear-off and replacement with architectural shingles rated 110–130 mph — most homes finished in 1–2 days, yard left spotless.

  • Owens Corning Duration® shingles with SureNail® technology
  • Self-propelled Equipter Roofers Buggy protects flower beds
  • Ice & water shield at eaves, valleys, rakes & chimneys
Fast Diagnostic

Roof Repair & Inspections

Leaks, storm damage, missing shingles — free inspections with photos, honest answers, and repairs done right the first time.

  • Digital photo report of roof deck, flashing & penetrations
  • Chimney step flashing, pipe boots, skylight seals & missing tabs
  • Storm damage documentation & insurance adjuster on-site meetings
High Search Demand

Gutter Cleaning

Full cleanout, downspout flush, and a condition check — the cheap insurance your roof deserves.

  • 100% hand cleanout with all leaves & mud bagged and removed
  • High-pressure downspout flushing to clear clogs at elbows & outlets
  • Free inspection of roof edge, drip edge & fascia rot
Custom On-Site

Gutter Replacement

Seamless aluminum gutters sized for New England downpours, installed with proper pitch and secure hangers.

  • Seamless continuous runs custom-extruded on our truck to exact fit
  • Heavy-gauge 0.032" aluminum with baked-on enamel finish
  • Heavy-duty hidden screw hangers spaced 24" on center
Permanent Shield

Gutter Guards

Keep leaves out for good — quality guard systems that end the twice-a-year cleaning cycle.

  • Surgical-grade stainless micro-mesh keeps out pine needles & grit
  • Low-profile profile preserves roof warranty & roofline aesthetics
  • Proven performance through heavy New England torrential rains
Whole Home Exterior

Vinyl Siding

Durable, low-maintenance vinyl siding in styles and colors that lift the whole look of your home.

  • Clapboard, Dutch lap, and cedar impression shake styles
  • Contoured insulating foam backer to lower winter heating costs
  • Custom aluminum window casing & soffit ventilation wrapping
New Construction

New Roof Installation

New construction and additions, installed to Connecticut code including ice & water shield at every eave and valley.

  • Collaboration with general contractors, architects & homebuilders
  • Engineered ridge and soffit intake balance for long shingle life
  • Flawless roof tie-ins on additions and garage expansions
Natural Light

Skylight Installation

Bring in the light — professionally flashed skylights that brighten rooms without inviting leaks.

  • Triple-layer weather-tight flashing kits engineered for CT winters
  • Energy-efficient Low-E glass reduces solar heat gain in summer
  • Seamless replacements during roof jobs or custom new cuts

Not sure what you need?

Schedule a free inspection — we'll tell you straight what's wrong and what it costs. No pressure.

We take high-resolution photos of your roof deck & flashing so you see what we see before spending a dime.

Why Cheshire & New Haven County Choose One Trusted Contractor

Handling roofing, gutters, and siding together ensures seamless water runoff and single-source accountability.

Single-Contractor Accountability

When the same crew handles your roof replacement and gutters, the drip edge, ice barrier, and gutter pitch align with precision. No finger-pointing between separate subcontractors.

The Roofers Buggy Clean-Yard Guarantee

Every tear-off uses our specialized Equipter debris container. Debris goes straight from roof to container, keeping flower beds, siding, and driveways completely safe.

40 Years Standing Behind Every Job

In business under the same family name since 1986. Most contractors close their doors within 5 years. With Kelley, you know exactly who to call tomorrow, next year, or a decade from now.

Ready for a Worry-Free Exterior?

Tell us what your home needs and we'll reach out within one business day with an honest, straight quote. Or call us directly — we answer.

Call (203) 271-2926

Direct assistance from our Cheshire team

Licensed & Insured
CT HIC #0565252
40 Years
A+ BBB

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Licensed & Insured · CT HIC #0565252 · 40 Years · A+ BBB
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