Four Leaf Contracting
Four Leaf Contracting

Four Leaf Contracting

Top Pro

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Introduction: Four Leaf is the Top Roofing, Siding, Windows and Gutter Pro in Wisconsin. They are featured in Milwaukee Magazine for March 2021. 5 Star Rating on Google. Highest Reviewed on Thumbtack 2019-2020. $20,000 Workmanship Guarantee from Roofing Insights. Super Service Award Winner 2019-2020 They are Veteran Owned and carry out all projects with detailed precision. They are known for their craftsmanship, attention to detail, planning and communication. You have a team of Industry Professionals working behind the scenes to ensure your project is done correctly and a timely manner. Four Leaf’s customers send referrals and leave great reviews for folks like you to read. Their crews and staff act and are dressed professionally. There is no loud music to annoy you and your neighbors. You won't find installers smoking on the job or goofing off. You and your neighbors will appreciate their professionalism and efficiency. Four Leaf keeps their job site tidy. They take extra steps to ensure your house is protected before the crew starts the demo or install. You will have 3 points of contact. The Install Foreman, Project Coordinator and Production Manager. All speak English but we do have staff that can speak Spanish, French, Mandarin and Arabic if requested. They have 25 years of construction science and a knowledge at your fingertips. There is not a one size fits all approach to your home. The Project Coordinator will listen to you and walk through the solution together with you. Together you will come up with a budget and a plan to complete your project. The staff will actually measure your roof by going on your roof. If YOUR roofer doesn’t go on your roof during the inspection don’t hire them. Four Leaf ALWAYS go on the roof if it’s safe. Management teaches that it's quality, not quantity that matters. They are a licensed, insured and veteran owned company. They focus on doing the job at hand rather than the job they have next week. Their customers are their livelihood and they are grateful for them. They are grateful that you are reading this now. Yes we are talking about YOU!! They are certified by their manufacturers and take classes throughout the year to stay up on new procedures and products to better serve their clients. They are the most experienced roofing crew in the metroplex. Veteran, Teacher and First Responder Discounts 5 Star Rating on Google Super Service Award 2020 Top Pro on Thumbtack $20,000 Workmanship Guarantee from Roofing Insights. 50 Year Asphalt Shingle Guarantee They have been operating since 1994 so whether it is a new roof, siding, gutters or brand new windows you are in good hands. Thanks for stopping by and we look forward to working with you. Regards, Joseph O’Brien Four Leaf Roofing and Windows President

Current Top Pro

Hired 73 times

3 similar jobs done near you

Background checked

License verified

14 employees

27 years in business

Payment methods

Apple Pay, Cash, Check, Credit card, Google Pay, PayPal, Square cash app, Venmo, Zelle

Social media

Facebook, Instagram

Currently a top pro

Top Pros are among the highest-rated, most popular professionals on Thumbtack.

All year

Current Top Pro

This pro indicated that they reviewed CDC safety guidelines for COVID-19 and pledged to do the following:

Maintain 6 feet of distance from customers

Wear masks during the job

Wear gloves during the job

Disinfect surfaces touched during the job

Featured Projects

126 photos

  • New Roof- Racine 2020

    Roof Repair or Maintenance

  • Roof Repair or Maintenance - Milwaukee 2019

    Roof Repair or Maintenance

  • Atlas Pinnacle Pristine

    Roof Installation or Replacement


Customers rated this pro highly for responsiveness, professionalism, and work quality.

Great 4.8

45 reviews


Read reviews that mention:

Molly S.

Gutter Installation or Replacement

After having a difficult time finding someone to replace my gutter, I tried Thumbtack for the first time and found Four Leaf. They were super responsive, did a great job and the rate was very reasonable. We would definitely hire them again.
Four Leaf Contracting's reply
Molly you made me smile. Thanks for those kind words and glad we could knock it out of the park for you!
Jan 30, 2021
Mark K.

Response time was incredible- had my new roof and gutters done in 10 days. Fantastic product, warranty and workmanship! Highly recommend Joe and Four Leaf ⭐️ ⭐️⭐️⭐️⭐️
Four Leaf Contracting's reply
Thanks Mark. Glad you trusted us to handle your roof. You being an ex roofer says that much more about us!
Jan 30, 2021
Mary O.

5 Star. They did everything they said they’d do. We needed a new roof and they had it installed within 3 weeks. Salesman and crew were very professional
Four Leaf Contracting's reply
Mary we appreciate it. If we can help you out with anything else we hope we are your first call.
Jan 30, 2021
Dre S.

Joe and his crew did a great job replacing our windows. No more cold drafts and our heating bill is noticeably different! We are very satisfied with their cleanliness and the finish product looks amazing!
Four Leaf Contracting's reply
Dre thanks for the kind words. New Windows make a huge difference in energy costs. Glad you trusted us and hired us instead of one of the double the price companies you told us about. If you refer us to a friend we are happy to send you a referral reward!
Jan 30, 2021
Nic B.

Roof Installation or Replacement

Joe and his crew did a great job replacing my roof. The crew arrived on time and were very friendly. The finished product looks great, and I have no doubts about the quality of the work. I was also impressed with how much emphasis was put on cleaning-up during and after installation. Joe is quick to respond to any texts/messages and very open to asking him questions. I had a question on the warranty and Joe offered to put me in touch with his contact at the manufacturer, and we did a conference call together. The price was also reasonable. Overall, a very good experience.
Four Leaf Contracting's reply
Thanks Nic. I’m glad you asked the questions you did. It keeps me on my toes. I enjoyed our conversations.
Apr 2, 2020

License Type: Dwelling Contractor Qualifier (WI)

License verified on 1/15/2021

Background Check

Joseph O'brien


  • What should the customer know about your pricing (e.g., discounts, fees)?

    We offer discounts to Veterans, Teachers, First Responders and Senior Citizens. 0% Financing for 18 months on approved Credit. We also offer a special of $102/Month for your next project for qualifying buyers. The average roof cost is $8,000. Siding average cost is $12,000. The average gutter job is $2,450. These prices all vary depending on the size and details of your project. If you have a specific budget you need to stick to we will come up with a plan to accommodate your budget.

  • What is your typical process for working with a new customer?

    We listen. Before we even come to your house we will ask you details about your project. What are you looking to accomplish, how old is your house, when do you want to do it, do you have a budget in mind. When we arrive to your house we will talk with the home owner, explain our process and complete the home inspection. After the inspection we will show you pictures and walk you through what we saw. Together we will come up with a solution that best firs your needs and budget. We will ask if you would like to finance your project. We offer many creative financing solutions. We will go over any discounts that you may be eligible for and discuss our solution and estimated price to complete the job. Once we have agreed to a plan we will go over the process once again and find a date that best fits your timeline for the install. Once we agree to an install date we will collect the down payment and order the materials.

  • What education and/or training do you have that relates to your work?

    We are licensed by the State of Wisconsin and Illinois. We are required to complete training and education classes to have a license. Throughout the year our crews and staff meet with manufacturers for further training. Once a month we go over installation procedures with our installers and highlight any specialty product training as well. All of our employees sign and are educated on OSHA safety rules as well as CPR and injury prevention training.

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