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Gutters & downspouts cleaners in Winchester

Avatar for HILLSIDE GUTTER AND DRAINAGE LLC

HILLSIDE GUTTER AND DRAINAGE LLC

1299 Old State Rd
5.00(
4
)
•
Approved Pro

HILLSIDE GUTTER AND DRAINAGE LLC

1299 Old State Rd
5.00(
4
)
•
Approved Pro
Free onsite estimate
Warranties offered

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!

"Good communication and excellent work. "

Matthew P on September 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!

"Good communication and excellent work. "

Matthew P on September 2025

Avatar for LeafFilter Gutter Protection

LeafFilter Gutter Protection

1595 Georgetown Road
4.30(
1,521
)
•
Approved Pro

LeafFilter Gutter Protection

1595 Georgetown Road
4.30(
1,521
)
•
Approved Pro
Customers say: Quality work
12141 local quotes requested
20 years of experience

As the most reliable gutter protection brand in North America, LeafFilter Gutter Protection has improved the strength and longevity of gutter systems from coast to coast. The LeafFilter team provides gutter replacement, cleaning, and repairs in addition to installing gutter guards. From its innovative design and award-winning technology to its professional installation, LeafFilter protects the value of your home and is the perfect complement to your roof. Its patented three-piece system features a stainless steel micromesh screen, structural hangers, and uPVC framing to optimize debris repellence and weather resistance.

"Good job!! "

Morgan P on August 2025

As the most reliable gutter protection brand in North America, LeafFilter Gutter Protection has improved the strength and longevity of gutter systems from coast to coast. The LeafFilter team provides gutter replacement, cleaning, and repairs in addition to installing gutter guards. From its innovative design and award-winning technology to its professional installation, LeafFilter protects the value of your home and is the perfect complement to your roof. Its patented three-piece system features a stainless steel micromesh screen, structural hangers, and uPVC framing to optimize debris repellence and weather resistance.

"Good job!! "

Morgan P on August 2025

Avatar for Window Genie of Lexington

Window Genie of Lexington

2529 Regency Road, Suite 103
4.85(
153
)
•
Approved Pro

Window Genie of Lexington

2529 Regency Road, Suite 103
4.85(
153
)
•
Approved Pro
Customers say: Quick response
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
25 local quotes requested

Window Genie of Lexington, is Lexington's leader in home services. We specialize in window cleaning, window tinting, pressure washing, gutter cleaning, and more. Our commitment to customer satisfaction and professionalism is what sets us apart from the competition. With over 20 years of experience, Window Genie of Lexington, has earned the trust of homeowners throughout Lexington and the surrounding areas. You can feel safe knowing our team of field technicians are fully trained, insured, bonded, and drive custom wrapped GENIEMOBILES for easy identification. Estimates are always fast and free! We look forward to earning your business.

"Very satisfied"

Roger C on October 2024

Window Genie of Lexington, is Lexington's leader in home services. We specialize in window cleaning, window tinting, pressure washing, gutter cleaning, and more. Our commitment to customer satisfaction and professionalism is what sets us apart from the competition. With over 20 years of experience, Window Genie of Lexington, has earned the trust of homeowners throughout Lexington and the surrounding areas. You can feel safe knowing our team of field technicians are fully trained, insured, bonded, and drive custom wrapped GENIEMOBILES for easy identification. Estimates are always fast and free! We look forward to earning your business.

"Very satisfied"

Roger C on October 2024

LeafFilter Gutter Protection

1595 Georgetown Road
4.29(
1,488
)
•
Approved Pro

LeafFilter Gutter Protection

1595 Georgetown Road
4.29(
1,488
)
•
Approved Pro
Customers say: Quality work
20 years of experience
Free onsite estimate

As the most reliable gutter protection brand in North America, LeafFilter Gutter Protection has improved the strength and longevity of gutter systems from coast to coast. The LeafFilter team provides gutter replacement, cleaning, and repairs in addition to installing gutter guards. From its innovative design and award-winning technology to its professional installation, LeafFilter protects the value of your home and is the perfect complement to your roof. Its patented three-piece system features a stainless steel micromesh screen, structural hangers, and uPVC framing to optimize debris repellence and weather resistance.

"Professional and fair pricing"

Patrick K on February 2025

As the most reliable gutter protection brand in North America, LeafFilter Gutter Protection has improved the strength and longevity of gutter systems from coast to coast. The LeafFilter team provides gutter replacement, cleaning, and repairs in addition to installing gutter guards. From its innovative design and award-winning technology to its professional installation, LeafFilter protects the value of your home and is the perfect complement to your roof. Its patented three-piece system features a stainless steel micromesh screen, structural hangers, and uPVC framing to optimize debris repellence and weather resistance.

"Professional and fair pricing"

Patrick K on February 2025

Avatar for Ison's Maintenance and Repair

Ison's Maintenance and Repair

65 Outlook Drive
5.00(
6
)
•
Approved Pro

Ison's Maintenance and Repair

65 Outlook Drive
5.00(
6
)
•
Approved Pro
Customers say: Quick response
12 local quotes requested
1 years of experience

Ison's Maintenance and Repair is dedicated to providing our customers with the best quality and craftsmanship. We are here to build relationships with our customers and communities and to provide our employees with a great place to work. We look forward to working with you!

"Efficient and fair pricing. Works untill the job is done "

JENNIFER W on August 2025

Ison's Maintenance and Repair is dedicated to providing our customers with the best quality and craftsmanship. We are here to build relationships with our customers and communities and to provide our employees with a great place to work. We look forward to working with you!

"Efficient and fair pricing. Works untill the job is done "

JENNIFER W on August 2025

Avatar for Wildcat Gutters, Etc

Wildcat Gutters, Etc

3735 Palomar Centre Dr. Ste. 150-52
4.74(
94
)
•
Approved Pro

Wildcat Gutters, Etc

3735 Palomar Centre Dr. Ste. 150-52
4.74(
94
)
•
Approved Pro
Super Service Award
Customers say: Quality work
10 local quotes requested
25 years of experience

Wildcat Gutters is your solution for all your siding related installation needs. We take great pride in our professionalism, timeliness, and superior customer service on every job. We specialize in a variety of gutter work. Contact us today for a free estimate.

"Just finished the install and we’re very pleased with the nice look it gives our house. Job was finished within three days after we signed contract. Company had good communication from sales rep to installers. Now we’re waiting for rain. "

Jim M on August 2025

Wildcat Gutters is your solution for all your siding related installation needs. We take great pride in our professionalism, timeliness, and superior customer service on every job. We specialize in a variety of gutter work. Contact us today for a free estimate.

"Just finished the install and we’re very pleased with the nice look it gives our house. Job was finished within three days after we signed contract. Company had good communication from sales rep to installers. Now we’re waiting for rain. "

Jim M on August 2025

J&T Pressure Washing

4113 Mcclure Road
4.94(
63
)
•
Approved Pro

J&T Pressure Washing

4113 Mcclure Road
4.94(
63
)
•
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
33 local quotes requested

I pride myself on my professionalism, as well as my ability to complete every job to the homeowner's total satisfaction. I never leave a job unfinished, or a homeowner not 100% satisfied with my level of service - Call today!

"J&T pressure washing called me with in an hour of my request. Came out to survey the deck, gave me an estimate and started the work the following week. Owners were hands on the entire project. Staff was extremely competent….polite, professional and did a great job pressure washing, sanding and staining deck. I have already given their business cards to friends. BEST company. ⭐️⭐️⭐️⭐️⭐️"

Sharon H on July 2025

I pride myself on my professionalism, as well as my ability to complete every job to the homeowner's total satisfaction. I never leave a job unfinished, or a homeowner not 100% satisfied with my level of service - Call today!

"J&T pressure washing called me with in an hour of my request. Came out to survey the deck, gave me an estimate and started the work the following week. Owners were hands on the entire project. Staff was extremely competent….polite, professional and did a great job pressure washing, sanding and staining deck. I have already given their business cards to friends. BEST company. ⭐️⭐️⭐️⭐️⭐️"

Sharon H on July 2025

Avatar for Stone Age Masonry

Stone Age Masonry

2705 Stetson Lane
4.72(
98
)
•
Approved Pro

Stone Age Masonry

2705 Stetson Lane
4.72(
98
)
•
Approved Pro
Customers say: Quality work
Recommended by 93% of Angi customers
Recommended by 93% of HomeAdvisor customers
27 years of experience

Stone Age Masonry, serving homeowners in Lexington, is your go-to for all your masonry needs. With our expertise and attention to detail, we ensure top-notch installations and repairs. Contact us today and let Tina Copley and our team transform your garage into a functional and stylish space.

"I made my request to Angi. They said that the contractors will come out and they said they will come out the next day and give me an estimates. But he send me a message that he couldn't come because he had a family emergency and I understand that and I told him that he can few days later and he said that was fine, but he never showed up, never calls nor send an email. Nothing. I am very disappointed with this. His name is Eddie."

Colleen H on July 2025

Stone Age Masonry, serving homeowners in Lexington, is your go-to for all your masonry needs. With our expertise and attention to detail, we ensure top-notch installations and repairs. Contact us today and let Tina Copley and our team transform your garage into a functional and stylish space.

"I made my request to Angi. They said that the contractors will come out and they said they will come out the next day and give me an estimates. But he send me a message that he couldn't come because he had a family emergency and I understand that and I told him that he can few days later and he said that was fine, but he never showed up, never calls nor send an email. Nothing. I am very disappointed with this. His name is Eddie."

Colleen H on July 2025

Avatar for Barnhill Chimney Co

Barnhill Chimney Co

824 Winchester Rd
4.53(
78
)
•
Approved Pro

Barnhill Chimney Co

824 Winchester Rd
4.53(
78
)
•
Approved Pro
Customers say: Quality work
32 local quotes requested
25 years of experience

Servicing the Greater Lexington area in Central Kentucky. Local and family owned; serving you since 2000. Additional DBA - Barnhill Chimney Supply, making custom chimney caps and chase covers for shipment nationwide. We offer 10% off exterior estimates up to $500. We offer $25 off gas servicing, usually $295.

"Great job!"

Katy R on October 2023

Servicing the Greater Lexington area in Central Kentucky. Local and family owned; serving you since 2000. Additional DBA - Barnhill Chimney Supply, making custom chimney caps and chase covers for shipment nationwide. We offer 10% off exterior estimates up to $500. We offer $25 off gas servicing, usually $295.

"Great job!"

Katy R on October 2023

J&T Pressure Washing LLC

4113 McClure Rd
5.00(
7
)
•
Approved Pro

J&T Pressure Washing LLC

4113 McClure Rd
5.00(
7
)
•
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
190 local quotes requested

Residential pressure washing Can do concrete,siding,decks,roofs,exterior dwellings,campers,large equipment

"On time. Efficient. Took pictures. Good price. I recommend."

Clinton M on May 2025

Residential pressure washing Can do concrete,siding,decks,roofs,exterior dwellings,campers,large equipment

"On time. Efficient. Took pictures. Good price. I recommend."

Clinton M on May 2025

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FAQs for gutters & downspouts cleaning service projects in Winchester, KY

You’ll want to clean gutters once or twice a year—in early spring and again in fall—to keep water flowing and avoid pricey leaks. Homes tucked beneath tall trees or hit with heavy debris may need two to four visits instead. Staying on schedule protects your roof, siding, and foundation from costly water damage.

Even with gutter guards, plan on an occasional cleaning—just not as often as homes without guards. Installing gutter guards blocks leaves, but grit and shingle granules still slip through and pile up over time. A quick sweep keeps water moving and stops overflow that can damage your roof or foundation.

Watch for overflowing water, slow or silent downspouts, sagging sections, or debris peeking over the gutter edge. You might also spot water stains, weeds, or an increasing number of ants in certain areas. Any of these red flags means it’s time to call a gutter cleaning pro for service before minor clogs turn into major leaks.

Skip cleanings for too long and gutters overflow, sending water under shingles, down siding, and toward the foundation. The result can be mold, rotted fascia, basement leaks, and repair bills that dwarf the price of a quick cleaning. It can also mean that future cleanings will be more expensive as it will take pros longer to deep clean gutters that are full of heavy debris. Staying on schedule saves money and headaches.

Plan on gutter cleaning service to take an average of one hour for an average single-story home and two to three hours for taller houses. Add extra time if gutter guards need to come off or clogs are packed in. Pros work methodically, clearing every linear foot so water can flow freely again.

The Winchester, KY homeowners’ guide to gutters & downspouts cleaning services

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

See all articles