Roofing, Siding, Windows & Gutters in Middlebury, CT

Welcome to A Plus Exterior, your trusted local team for roofing, siding, window replacement, and gutter services in Middlebury, Connecticut. We deliver high-quality workmanship, clear communication, and competitive pricing—backed by a 100% satisfaction guarantee.

Middlebury’s four-season weather (wind, heavy rain, snow loads, and freeze/thaw cycles) plus mature trees throughout town can be tough on roofs and drainage systems. Whether you need a quick repair or a full exterior upgrade, we focus on durable materials and long-lasting installs.

Exterior Home Improvement Services in Middlebury, Connecticut

Roofing Services in Middlebury, CT

  • Roof inspections and leak troubleshooting

  • Roof repairs (shingles, flashing, vents, skylight areas)

  • Full roof replacements

  • Storm and wind damage support

Siding Services in Middlebury, CT

  • Siding repair and full siding replacement

  • Trim and fascia repairs

  • Weatherproofing to help prevent moisture intrusion and drafts

Window Installation & Replacement in Middlebury, CT

  • Window replacement and new window installation

  • Energy-efficiency upgrades for comfort and lower utility costs

  • Proper sealing and flashing to help prevent leaks and drafts

Gutter Services in Middlebury, CT

  • Gutter cleaning and routine maintenance

  • Gutter repairs (leaks, loose gutters, pitch issues)

  • New gutter installation and downspout upgrades

  • Drainage improvements to help protect foundations and landscaping

Get a Free Estimate in Middlebury, CT

If you need roofing, siding, windows, or gutters in Middlebury, call 203-693-2225 to schedule your free consultation and estimate.

Call now: 203-693-2225

10 Fun Facts About Middlebury, Connecticut

  1. Middlebury was incorporated in 1807 and is located in New Haven County.

  2. Middlebury is part of the Naugatuck Valley Planning Region.

  3. Middlebury’s population estimate (July 1, 2024) is 8,025.

  4. Hop Brook Lake & Dam sits in Middlebury/Naugatuck/Waterbury and is operated by the U.S. Army Corps of Engineers.

  5. Hop Brook Lake Recreation Area spans 536 acres and offers activities like picnicking, hiking, paddling, swimming, and fishing.

  6. Whittemore Glen State Park is a 242-acre undeveloped area with hiking and horseback riding access via the Larkin State Park Trail, near Hop Brook Lake.

  7. Middlebury is home to Lake Quassapaug, a popular local lake and recreation spot.

  8. Quassy Amusement Park & Waterpark is located on Lake Quassapaug in Middlebury.

  9. Middlebury’s early economy was rooted in agriculture with small supporting industries, according to Connecticut history sources.

  10. With wooded neighborhoods and four seasons, many Middlebury homeowners prioritize roof durability and properly pitched gutters/downspouts to manage snow loads, runoff, and leaf debris—especially in fall and spring. (Local relevance supported by the town’s landscape + lake/park environment.)