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Find Shed, barn or playhouse repairers in Winnetka

Avatar for EAE Construction

EAE Construction

5.00(
11
)
•Approved Pro

EAE Construction

5.00(
11
)
•Approved Pro
64 local quotes requested
10 years of experience

We invite you to experience a tradition of customer satisfaction that will exceed your greatest expectations. Our professionalism and quality workmanship will accurately reflect your taste and lifestyle. From conception to completion, we work with you until the job is done. We are ethical, honest, and easy to communicate with. Call us today you'll be pleased you did. Thank you

"Anthony did the job promptly. I needed a piece of siding secured before it came off, so I wanted it done properly and quickly. And he did a little extra work. It was a small job but he came thru in a big way. 👍"

Chester L on December 2025

We invite you to experience a tradition of customer satisfaction that will exceed your greatest expectations. Our professionalism and quality workmanship will accurately reflect your taste and lifestyle. From conception to completion, we work with you until the job is done. We are ethical, honest, and easy to communicate with. Call us today you'll be pleased you did. Thank you

"Anthony did the job promptly. I needed a piece of siding secured before it came off, so I wanted it done properly and quickly. And he did a little extra work. It was a small job but he came thru in a big way. 👍"

Chester L on December 2025


Avatar for Handyman Pros

Handyman Pros

4.76(
892
)
•Approved Pro

Handyman Pros

4.76(
892
)
•Approved Pro
Super Service Award
Customers say: Super punctual
Recommended by 91% of Angi customers
Recommended by 91% of HomeAdvisor customers
240 local quotes requested

ONE CALL CAN SOLVE ALL YOUR HOUSE PROBLEMS Professional Handyman Services, Kitchen & Bath Remodeling, Plumbing, Electrical, Carpentry, Tiling, Flooring Insured Bonded Guaranteed LIVE PHONE HELP Mon-Fri 8-5 email chat after hours... Chicago Home Repair License #2209943

"Excellent work and friendly service. Will use again."

Diane D on September 2025

ONE CALL CAN SOLVE ALL YOUR HOUSE PROBLEMS Professional Handyman Services, Kitchen & Bath Remodeling, Plumbing, Electrical, Carpentry, Tiling, Flooring Insured Bonded Guaranteed LIVE PHONE HELP Mon-Fri 8-5 email chat after hours... Chicago Home Repair License #2209943

"Excellent work and friendly service. Will use again."

Diane D on September 2025


"Good. I would hire again đź’Ż"

Matthew S on February 2025

With 15 years experience, IJ Roofing Solutions is dedicated to offering quality services, resulting in happy customers. I offer emergency services and can schedule appointments anytime for your convenience. Call today to schedule your free estimate!

"Good. I would hire again đź’Ż"

Matthew S on February 2025


Avatar for Chrysalis Unbound Custom Decorating and Remodeling

Chrysalis Unbound Custom Decorating and Remodeling

4.72(
25
)
•Approved Pro

Chrysalis Unbound Custom Decorating and Remodeling

4.72(
25
)
•Approved Pro
Customers say: Quick response
24 years of experience
Free onsite estimate

Chrysalis Unbound Custom Decorating and Remodeling prides itself on superior and innovative performance; actively doing our best to bring you the most proficient, detailed work done cleanly & quietly. We will do our best to offer affordable alternatives to high-end products and design.

"Roman is very detailed and knowledgeable. I've never had a contractor who tried that hard to understand the job even before coming for a quote. Very easy to get a hold of as well which is rare for contractors from this site. Would highly recommend."

Robert K on January 2025

Chrysalis Unbound Custom Decorating and Remodeling prides itself on superior and innovative performance; actively doing our best to bring you the most proficient, detailed work done cleanly & quietly. We will do our best to offer affordable alternatives to high-end products and design.

"Roman is very detailed and knowledgeable. I've never had a contractor who tried that hard to understand the job even before coming for a quote. Very easy to get a hold of as well which is rare for contractors from this site. Would highly recommend."

Robert K on January 2025


Avatar for Castino Painting, Stucco, Restoration

Castino Painting, Stucco, Restoration

4.74(
313
)
•Approved Pro

Castino Painting, Stucco, Restoration

4.74(
313
)
•Approved Pro
Customers say: Super punctual
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
231 local quotes requested

Founded in 1974, Castino Restoration is your local neighborhood business that provides water/flood damage clean up & restoration, mold remediation, carpet, rug & upholstery cleaning, interior / exterior painting, stucco, carpentry, handyman, floor installation & refinishing, gutter cleaning & roof snow removal. We pride ourselves in being skilled, ethical, friendly & fast. And we always clean up everyday before we leave. Give us a call, try us out!

"I have been very satisfied with the work performed and finished areas look great. Mike Fuche (co-owner/estimator) is responsive, easy to work with, and quotes fair prices for the work involved. It’s great to have a contractor that I can turn to with trust and rely upon to take care of the job timely and professionally."

Rachel J on September 2020

Founded in 1974, Castino Restoration is your local neighborhood business that provides water/flood damage clean up & restoration, mold remediation, carpet, rug & upholstery cleaning, interior / exterior painting, stucco, carpentry, handyman, floor installation & refinishing, gutter cleaning & roof snow removal. We pride ourselves in being skilled, ethical, friendly & fast. And we always clean up everyday before we leave. Give us a call, try us out!

"I have been very satisfied with the work performed and finished areas look great. Mike Fuche (co-owner/estimator) is responsive, easy to work with, and quotes fair prices for the work involved. It’s great to have a contractor that I can turn to with trust and rely upon to take care of the job timely and professionally."

Rachel J on September 2020


Avatar for Handy Men & Mrs Helper Kitchen & Bath

Handy Men & Mrs Helper Kitchen & Bath

4.70(
1,282
)
•Approved Pro

Handy Men & Mrs Helper Kitchen & Bath

4.70(
1,282
)
•Approved Pro
Customers say: Quality work
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
92 local quotes requested

SUPER SERVICE AWARD WINNER SINCE 2003! Our mission is to offer honest, reliable home remodeling services that set us apart from other service providers. We continually strive to exceed expectations by ensuring that each home repair or remodeling project is done to your satisfaction. Our commitment and assurance to our clients is something we take great pride in. When planning your next home improvement project, rely on a company that offers unparalleled knowledge, experience and expertise. Contact us today to learn more about what sets us apart from the competition.

"THE BEST experience with a contractor EVER! We’ve owned 7 houses and have hired numerous contractors to do a variety of work, this was by far the smoothest, most thorough job we’ve ever had done. The communication, preparation and scheduling made us feel at ease with the project. Everyone of the workers and managers of the job showed up on time and got our job done on the specific schedule we were given. The quality of the work was top notch! The entire team was a pleasure to work with!"

Steve B on October 2021

SUPER SERVICE AWARD WINNER SINCE 2003! Our mission is to offer honest, reliable home remodeling services that set us apart from other service providers. We continually strive to exceed expectations by ensuring that each home repair or remodeling project is done to your satisfaction. Our commitment and assurance to our clients is something we take great pride in. When planning your next home improvement project, rely on a company that offers unparalleled knowledge, experience and expertise. Contact us today to learn more about what sets us apart from the competition.

"THE BEST experience with a contractor EVER! We’ve owned 7 houses and have hired numerous contractors to do a variety of work, this was by far the smoothest, most thorough job we’ve ever had done. The communication, preparation and scheduling made us feel at ease with the project. Everyone of the workers and managers of the job showed up on time and got our job done on the specific schedule we were given. The quality of the work was top notch! The entire team was a pleasure to work with!"

Steve B on October 2021


"Overall Builders and its owner Robert were fantastic. Easy to work with, extremely accommodating, competitive pricing and the quality of work was superb! The tile pattern we chose was extremely challenging and Victor, Robert's tile guy, nailed it! We will, absolutely, use Overall Bulders for all our home remodel/repair needs in the future!"

Dianne R on January 2024

With over 10 years of general contracting and handyman experience, I am here to help address any need or dream you may have.

"Overall Builders and its owner Robert were fantastic. Easy to work with, extremely accommodating, competitive pricing and the quality of work was superb! The tile pattern we chose was extremely challenging and Victor, Robert's tile guy, nailed it! We will, absolutely, use Overall Bulders for all our home remodel/repair needs in the future!"

Dianne R on January 2024


Avatar for The Handy Veteran

The Handy Veteran

4.97(
135
)
•Approved Pro

The Handy Veteran

4.97(
135
)
•Approved Pro
Super Service Award
Customers say: True professional
Recommended by 99% of Angi customers
Recommended by 99% of HomeAdvisor customers
72 local quotes requested

The Handy Veteran is a veteran owned and operated company. We offer free estimates and stand by our motto of professional and dependable services. We want to be the one stop shop handyman for you. We offer active duty and veteran discounts. BOOKED FOR THE REMAINDER OF 2025, NOW BOOKING FOR 2026!

"Brad was awesome! He was so kind and sweet. He took care of the drywall and the painting in the closet. Very professional!"

Anna K on May 2025

The Handy Veteran is a veteran owned and operated company. We offer free estimates and stand by our motto of professional and dependable services. We want to be the one stop shop handyman for you. We offer active duty and veteran discounts. BOOKED FOR THE REMAINDER OF 2025, NOW BOOKING FOR 2026!

"Brad was awesome! He was so kind and sweet. He took care of the drywall and the painting in the closet. Very professional!"

Anna K on May 2025


Avatar for Home Repairs R' Us Inc

Home Repairs R' Us Inc

4.25(
271
)
•Approved Pro

Home Repairs R' Us Inc

4.25(
271
)
•Approved Pro
Customers say: Quality work
910 local quotes requested
24 years of experience

Please NOTE: we DO NOT accept furniture assembly or wall mounting projects. With over 17 years of Plumbing, Interior painting and all facets of general handyman work, Home Repairs R Us continues to be South/Southwest Chicago's "One Stop Home Repair Service Shop". Deal direct with owner Eric Henry and his dedicated, professional crew on any handyman job you need completed. Eric's wide home repair skill set makes it convenient for any home owner to make one call and accomplish just about any service needed at your residence or business. Call us today!

"Everything is beautiful. The two of them tackle it in two days. I'm very happy with the work."

JEROME W on November 2020

Please NOTE: we DO NOT accept furniture assembly or wall mounting projects. With over 17 years of Plumbing, Interior painting and all facets of general handyman work, Home Repairs R Us continues to be South/Southwest Chicago's "One Stop Home Repair Service Shop". Deal direct with owner Eric Henry and his dedicated, professional crew on any handyman job you need completed. Eric's wide home repair skill set makes it convenient for any home owner to make one call and accomplish just about any service needed at your residence or business. Call us today!

"Everything is beautiful. The two of them tackle it in two days. I'm very happy with the work."

JEROME W on November 2020


Avatar for J.B. BRICKWORKS, INC.

J.B. BRICKWORKS, INC.

4.43(
7
)

J.B. BRICKWORKS, INC.

4.43(
7
)
Customers say: Quality work
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers

Award-Winning Hardscape and Masonry Since 1990. We have been installing outdoor environments in the Chicago area for 25 years. Our crews are built with highly qualified individuals, paying special attention to detail. We use only the highest quality products and construction methods for each project. "The difference is in the details".

Award-Winning Hardscape and Masonry Since 1990. We have been installing outdoor environments in the Chicago area for 25 years. Our crews are built with highly qualified individuals, paying special attention to detail. We use only the highest quality products and construction methods for each project. "The difference is in the details".

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FAQs for shed, barn or playhouse repair projects in Winnetka, IL

You’ll know it’s time for a new shed roof if shingles curl or buckle, soft spots sag, or water stains appear inside. Moss or other plant growth on the surface is another red flag that moisture has breached the roofing layers. Replacing the roof quickly stops leaks from spreading, protects stored items, and saves you from costlier structural repairs down the road.

Choosing between a flat and a sloped shed roof comes down to climate, budget, and upkeep. A flat roof is cheaper up front, but still needs a slight pitch for drainage. A sloped roof sheds rain and snow more easily, lasts longer, and often needs less maintenance. Weigh your local weather patterns, the look you want, and how much time you’re willing to spend on upkeep before deciding.

A shed roof’s life span hinges on the material you choose and how well you maintain it. Most standard products last 15 to 30 years, while premium picks like slate or clay tile can protect the structure for 50 to 100 years. Regular inspections, fast fixes, and routine cleaning all help you reach the upper end of those ranges and keep your tools and gear dry year-round.

The Winnetka, IL homeowners’ guide to shed, barn or playhouse repairs

From average costs to expert advice, get all the answers you need to get your job done.