The Best Roofing Contractors in Middletown, NY

Compare the highest-rated roofing professionals in Middletown, New York. All contractors are licensed, insured, and verified through our rigorous screening process.

#1

Orange County Roofing & Restoration

4.8
(142 reviews)
Verified

A premier full-service roofing contractor serving Middletown and Orange County since 1998. Specializes in high-quality residential and commercial roof replacements, storm damage restoration, and emergency repairs. Known for expert handling of insurance claims and superior craftsmanship with both asphalt shingle and metal roofing systems.

789 North Street, Middletown, NY 10940

Specialties & Features

Storm Damage Restoration
Insurance Claims
Emergency Repairs
Asphalt Shingles
Metal Roofing

Business Information

Years in Business:26 years
Licensed:Yes
Insured:Yes
#2

Hudson Valley Roof Pros

4.7
(118 reviews)
Verified

A locally owned and operated roofing company with deep roots in the Middletown community. Excels in roof inspections, maintenance programs, and complex repairs designed to withstand the harsh Hudson Valley winters and summer storms. Offers a wide range of materials including premium architectural shingles and standing seam metal roofs.

421 Highland Avenue, Middletown, NY 10940

Specialties & Features

Roof Inspections
Preventative Maintenance
Snow & Ice Damage Repair
Tile Roofing
Skylight Installation

Business Information

Years in Business:18 years
Licensed:Yes
Insured:Yes
#3

Middletown Metal Masters

4.6
(96 reviews)
Verified

Specialists in durable and energy-efficient metal roofing solutions for both homes and businesses. Highly regarded for their expertise in commercial flat roof systems, slate repairs, and restoring historic properties. Their focus on superior installation techniques makes them a top choice for long-term roofing investments in the region.

202 Wickham Avenue, Middletown, NY 10940

Specialties & Features

Metal Roofing
Commercial Flat Roofs
Slate & Tile Repair
Historic Restoration
Energy-Efficient Roofing

Business Information

Years in Business:15 years
Licensed:Yes
Insured:Yes

Why These Are the Top Roofing Contractors in Middletown

The roofing market in Middletown, NY, is driven by the region's variable climate, which includes heavy snowfall in winter, strong thunderstorms in summer, and the potential for hail. This creates consistent demand for durable roof installations, storm damage repairs, and preventative maintenance. Local contractors must be well-versed in New York State building codes and the specific challenges of protecting homes from ice damming and water infiltration. The market is competitive with a mix of long-established local companies and newer entrants, emphasizing quality materials and insurance claim assistance.

High Ratings

4.7+ star average from verified customer reviews

Fully Licensed

All contractors are properly licensed and insured

Proven Experience

10+ years average experience in the industry

Local Experts

Familiar with Middletown regulations and climate

Frequently Asked Questions About Roofing in Middletown

Get answers to common questions about roofing services in Middletown, New York.

1What is the typical cost range for a full roof replacement on a single-family home in Middletown, NY?

In Middletown, a full asphalt shingle roof replacement for an average 2,000-2,500 sq. ft. home typically ranges from $12,000 to $25,000. The final cost depends on roof complexity, material choice (e.g., architectural shingles cost more than 3-tab), and the extent of underlying decking repair needed. Regional material and labor costs in the Hudson Valley, along with the need for durable materials to handle local snow loads, influence this pricing.

2When is the best time of year to schedule a roof replacement in Middletown, considering the local climate?

The ideal windows are late spring (May-June) and early fall (September-October). These periods typically offer mild, dry weather which is optimal for installation and allows materials like shingles to seal properly. Avoiding deep winter is crucial due to snow, ice, and safety concerns, while peak summer heat can make shingles too pliable and midday thunderstorms common in the Hudson Valley can disrupt the work schedule.

3Are there specific local building codes or permits required for roofing work in Middletown?

Yes, a building permit from the City of Middletown Building Department is almost always required for a full roof replacement. The permit ensures the work complies with the New York State Uniform Fire Prevention and Building Code, which includes critical requirements for wind uplift resistance and snow load capacity (Middletown is in a region requiring roofs to support significant snow weight). Your licensed contractor should typically pull this permit.

4How do I choose a reliable roofing contractor in the Middletown area?

Always verify that the contractor is licensed and insured in New York State, and ask for proof of both liability and workers' compensation insurance. Seek out local companies with a long-standing physical address in Orange County, check reviews on local community pages, and ask for references from recent jobs in Middletown or nearby towns like Wallkill or Goshen. A trustworthy roofer will provide a detailed, written estimate and warranty information.

5What are the most common roof problems you see on Middletown homes due to the local weather?

The most frequent issues are ice dam damage in late winter/early spring, wind-driven rain infiltration during nor'easters, and damage from falling tree limbs during heavy snow or thunderstorms. The freeze-thaw cycles we experience can also accelerate wear on shingles and flashing. Regular inspections, especially after severe weather, and ensuring proper attic ventilation to prevent ice dams are key preventative measures for local homeowners.