Chimney Services in Middlebury, CT

Are you looking for chimney services in Middlebury, CT? Four Seasons Chimney & Roofing provides complete chimney services and residential roofing to homeowners in Middlebury and across Litchfield, Hartford, and New Haven Counties. Celebrating 20 years strong, we are a local, family-built Connecticut company known for honest recommendations, quality workmanship, and fully licensed and insured crews.

From established neighborhoods near the Green to newer construction, Middlebury homes span every era — and every type of chimney and roofing system. From annual sweeps to complete masonry restoration and new roofs, one trusted contractor handles it all.

Chimney fires, storm damage, and sudden leaks don’t wait for business hours — our 24/7 emergency callout service covers Middlebury and neighboring towns including Woodbury, Southbury, and Watertown. Call 866-794-9830 any time, day or night.

What We Do in Middlebury

Middlebury homeowners call us for every stage of chimney and roof care:

Why Choose Four Seasons

Why Middlebury Homeowners Choose Us

20 Years Strong

Celebrating two decades of chimney and roofing service in Middlebury and across Connecticut — family-built, local, and still growing.

Licensed & Insured

Every technician and mason on our team is fully licensed and insured, so your home and family are always protected.

Chimney & Roof, One Call

We’re one of the few CT contractors handling both trades — we catch flashing and leak issues single-trade companies miss.

24/7 Emergency Service

Storm damage or chimney emergency in Middlebury? Call 866-794-9830 any time — day, night, weekends, and holidays.

5 year Warranty On chimney workmanship

10yr Warranty On
roofing Workmanship

Lifetime Warranty
on Materials

Emergency
Storm Work

Frequent Questions

Chimney Questions From Middlebury Homeowners

How often should I have my chimney cleaned in Middlebury?

Once a year, at minimum. NFPA 211, the national fire safety standard, requires chimneys, fireplaces, and vents to be inspected annually and cleaned as needed. Creosote — the flammable byproduct of burning wood — is the leading cause of chimney fires. An annual sweep and inspection keeps your Middlebury home safe.

Do you handle both chimney and roofing work in Middlebury in one visit?

In many cases, yes. Because we’re one of the few Connecticut contractors that specializes in both, we can inspect your roof, flashing, and chimney together — which matters, since chimney leaks are often actually flashing or roofing problems in disguise.

How long has Four Seasons Chimney & Roofing been in business?

We’re celebrating 20 years strong. Four Seasons Chimney & Roofing was built by a local family who saw the need for an honest, customer-focused chimney and roofing company in Connecticut. Two decades later, we’re still family-run, still local, and still standing behind every job we complete in Middlebury and across New Haven County.

Do you offer roofing services in Middlebury too?

Yes — roofing is half of what we do. Our Middlebury customers rely on us for roof repair, roof maintenance, new roof installation, and storm damage repair. Because we handle chimneys and roofs together, we catch problems — like failing flashing around the chimney — that single-trade contractors often miss.

What areas do you serve near Middlebury?

Our crews cover Middlebury and nearby towns including Woodbury, Southbury, and Watertown, plus communities throughout Litchfield, Hartford, and New Haven Counties. See the full list of areas we serve below, or call 866-794-9830 to confirm coverage for your address.

Areas We Serve

For 20 years strong, Four Seasons Chimney & Roofing has provided expert chimney and roofing services across Litchfield, Hartford, and New Haven Counties in Connecticut. Find your town below.

Bristol, CT

Goshen, CT

Harwinton, CT

Litchfield, CT

Middlebury, CT

Morris, CT

Northfield, CT

Plymouth, CT

Southbury, CT

Southington, CT

Terryville, CT

Thomaston, CT