The Best Roofing Contractors in Highland, WI

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

#1

Diamond Roofing & Construction

4.8
(67 reviews)
Verified

Family-owned roofing contractor specializing in both residential and commercial roofing with extensive experience in storm damage restoration and insurance claims. Known for high-quality asphalt shingle and metal roof installations that withstand Wisconsin's harsh winters and severe weather.

312 Oak Street, Highland, WI 53543

Specialties & Features

Storm Damage Restoration
Insurance Claims
Metal Roofing
Emergency Repairs
Roof Inspections

Business Information

Years in Business:15 years
Licensed:Yes
Insured:Yes
#2

Highland Exteriors & Roofing

4.6
(42 reviews)
Verified

Local roofing experts serving Highland and surrounding areas with comprehensive roofing services including installation, repair, and maintenance. Particularly skilled in handling snow load damage and ice dam prevention specific to Wisconsin's climate.

127 Main Street, Highland, WI 53543

Specialties & Features

Residential Roof Replacement
Snow Damage Repair
Ice Dam Prevention
Roof Maintenance Programs
Asphalt Shingles

Business Information

Years in Business:12 years
Licensed:Yes
Insured:Yes
#3

Tri-County Roofing & Siding

4.5
(89 reviews)
Verified

Serving Highland from nearby Dodgeville, this established contractor offers full-service roofing solutions with expertise in various materials including asphalt, metal, and tile. Strong reputation for emergency storm response and commercial flat roof systems.

408 County Road G, Dodgeville, WI 53533

Specialties & Features

Commercial Roofing
Emergency Services
Tile Roofing
Flat Roof Systems
Storm Damage Repair

Business Information

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

Why These Are the Top Roofing Contractors in Highland

Highland's roofing market is characterized by contractors experienced in handling severe weather conditions including heavy snowfall (annual average 45+ inches), ice dams, and occasional severe storms. Roofing providers must be well-versed in Wisconsin building codes and snow load requirements. The market consists primarily of local family-owned businesses with deep community ties and expertise in weather-resistant installations.

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 Highland regulations and climate

Frequently Asked Questions About Roofing in Highland

Get answers to common questions about roofing services in Highland, Wisconsin.

1What is the typical cost range for a full roof replacement on a Highland home?

For a standard asphalt shingle roof on an average-sized Highland home (e.g., 2,000 sq. ft.), you can expect a cost range of $8,500 to $15,000. This range accounts for Wisconsin's material and labor costs, the complexity of your roof (like valleys or dormers common in older Highland homes), and the necessary tear-off of the old roof. Premium materials like metal or architectural shingles will increase this price, but they offer better durability against our local freeze-thaw cycles and heavy snow loads.

2When is the best time of year to schedule a roof replacement in Highland?

The ideal window is typically late spring through early fall (May to October). This avoids the deep cold, ice, and heavy snow of Wisconsin winters, which can make installation unsafe and compromise material adhesion. Highland's summer and early fall provide the most predictable weather for a quality installation. However, reputable local roofers are experienced in working within this compressed schedule, so it's wise to book consultations several months in advance.

3Are there specific roofing materials better suited for Highland's climate?

Absolutely. Given Highland's significant snowfall, freeze-thaw cycles, and potential for severe storms, impact-resistant architectural asphalt shingles (Class 3 or 4) are a top choice for durability and hail resistance. Standing seam metal roofing is also excellent for shedding snow and withstanding high winds. It's crucial to choose materials with high wind ratings (110+ MPH) and proper ice and water shield underlayment at the eaves to prevent ice dam water intrusion, a common issue here.

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

Always verify the contractor is licensed and insured in Wisconsin, and specifically carries workers' compensation and liability insurance. Ask for local references from recent projects in Iowa or Grant counties and view their completed work. A trustworthy Highland roofer will provide a detailed, written estimate, explain the project timeline clearly, and be knowledgeable about local building codes, including required permits for re-roofing in the village.

5What are the most common roof problems you see on homes in Highland, and how can they be prevented?

The most frequent issues are ice dams in winter, wind damage from prairie storms, and general wear from thermal expansion/contraction. Prevention starts with ensuring your attic has adequate ventilation and insulation to keep the roof deck cold and minimize ice dams. Schedule a professional inspection, especially after major hail or wind events common to our region, to catch and repair damaged shingles, flashing, or seals around chimneys and vents before leaks develop.