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Gutters & downspouts cleaners in Chestertown

Avatar for LeafFilter Gutter Protection
LeafFilter Gutter Protection
1595 Georgetown Road
4.29(
1,507
)
Approved Pro
LeafFilter Gutter Protection
1595 Georgetown Road
4.29(
1,507
)
Approved Pro
Customers say: Quality work
12266 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.

"Completed quick while still maintaining quality"

Darneesha L on June 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.

"Completed quick while still maintaining quality"

Darneesha L on June 2025


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 Ned Stevens Gutter Cleaning
Ned Stevens Gutter Cleaning
150 Cross Street
4.33(
2,905
)
Approved Pro
Ned Stevens Gutter Cleaning
150 Cross Street
4.33(
2,905
)
Approved Pro
Customers say: True professional
3947 local quotes requested
60 years of experience

When you choose Ned Stevens for your gutter cleaning, gutter repair, gutter installation, window cleaning and other services, you can count on exceptional quality of work and outstanding customer service. Our labor staff are all our own employees, and we train them in our state-of-the-art training facility focusing on quality work. Our work is 100% Guaranteed. Your satisfaction is our goal. We want to make your gutter cleaning experience effortless. You never need to be home! We are fully insured and guarantee all of our work. Our family owned company has been cleaning and installing gutters for over 50 years.

"They did a great job."

Edward M on July 2025

When you choose Ned Stevens for your gutter cleaning, gutter repair, gutter installation, window cleaning and other services, you can count on exceptional quality of work and outstanding customer service. Our labor staff are all our own employees, and we train them in our state-of-the-art training facility focusing on quality work. Our work is 100% Guaranteed. Your satisfaction is our goal. We want to make your gutter cleaning experience effortless. You never need to be home! We are fully insured and guarantee all of our work. Our family owned company has been cleaning and installing gutters for over 50 years.

"They did a great job."

Edward M on July 2025


Avatar for Sunny Day Landscaping and More
Sunny Day Landscaping and More
1418 Harford Square Dr
4.59(
37
)
Approved Pro
Sunny Day Landscaping and More
1418 Harford Square Dr
4.59(
37
)
Approved Pro
Customers say: Quality work
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
10 years of experience

Sunny Day Landscaping and More are committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests and make their concerns the basis of our business.

"They were wonderful! Wr were so impressed we recommended them to our neighbors. They did 3 houses on our street. 100% would recommend."

Courtney W on November 2022

Sunny Day Landscaping and More are committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests and make their concerns the basis of our business.

"They were wonderful! Wr were so impressed we recommended them to our neighbors. They did 3 houses on our street. 100% would recommend."

Courtney W on November 2022


Avatar for GLR Home Improvement
GLR Home Improvement
3153 Chancellor Point
4.93(
15
)
Approved Pro
GLR Home Improvement
3153 Chancellor Point
4.93(
15
)
Approved Pro
Customers say: True professional
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
2018 local quotes requested

We have over 30 years experience! Our company is based on the belief that our customers' needs are of the utmost importance. Our entire team is committed to meeting those needs. As a result, a high percentage of our business is from repeat customers and referrals. We would welcome the opportunity to earn your trust and deliver you the best service in the industry.

"I love the new pvc decking, drink rail and railing. Could not be happier. Great work."

Mary A on April 2025

We have over 30 years experience! Our company is based on the belief that our customers' needs are of the utmost importance. Our entire team is committed to meeting those needs. As a result, a high percentage of our business is from repeat customers and referrals. We would welcome the opportunity to earn your trust and deliver you the best service in the industry.

"I love the new pvc decking, drink rail and railing. Could not be happier. Great work."

Mary A on April 2025


Avatar for Lawson Home Services, LLC
Lawson Home Services, LLC
115 Atlantic Avenue
4.63(
35
)
Approved Pro
Lawson Home Services, LLC
115 Atlantic Avenue
4.63(
35
)
Approved Pro
Customers say: True professional
Recommended by 91% of Angi customers
Recommended by 91% of HomeAdvisor customers
269 local quotes requested

Full service Radon testing and mitigation, air duct and dryer vent cleaning, and blown-in attic insulation company. We service the entire state of Delaware and eastern Maryland.

"Very professional, knowledgeable, courteous and very customer focused. Would definitely use their services again!"

Chris A on November 2023

Full service Radon testing and mitigation, air duct and dryer vent cleaning, and blown-in attic insulation company. We service the entire state of Delaware and eastern Maryland.

"Very professional, knowledgeable, courteous and very customer focused. Would definitely use their services again!"

Chris A on November 2023


Avatar for Chimney Experts
Chimney Experts
681 John Fitch Blvd Unit 16P,
4.87(
39
)
Approved Pro
Chimney Experts
681 John Fitch Blvd Unit 16P,
4.87(
39
)
Approved Pro
Customers say: Quick response
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
1743 local quotes requested

Chimney Experts is a trusted provider of comprehensive chimney services for homeowners. Our team of experienced professionals takes pride in ensuring the safety and functionality of your chimney. Whether you need chimney cleaning, inspections, repairs, maintenance, or installations, we have you covered. Safety is our utmost priority. We fully understand the potential hazards associated with chimneys and strictly adhere to safety regulations. Our team is well-trained to implement necessary precautions, guaranteeing a safe and secure chimney operation for your home. What sets us apart is our commitment to personalized service. We know that each chimney has unique requirements, and we take the time to understand your specific needs. Whether it's routine maintenance or complex repairs, our experts offer tailored solutions that meet your chimney's demands, ensuring optimal performance. At Chimney Experts, we prioritize quality workmanship. We use top-of-the-line tools and materials to deliver lasting repairs and installations. Our team of skilled technicians stays up-to-date with industry practices, ensuring that every project is completed to the highest standards. Customer satisfaction is our ultimate goal. We value your time, and our reliable and punctual service reflects our commitment to meeting your needs. When you choose Chimney Experts, you can expect thorough and efficient service that leaves your chimney in excellent condition. If you're in need of superior chimney services, trust Chimney Experts. With our expertise, attention to detail, and dedication to customer satisfaction, we provide the best solutions for all your chimney maintenance and repair needs. Contact us today to schedule an appointment and experience the Chimney Experts difference for yourself.

"Repair went well. Technician arrived on time and was working all day to re point the chimney and re line it. He even repainted where paint had flaked off accessing the chimney to re-line."

Gregory S on June 2025

Chimney Experts is a trusted provider of comprehensive chimney services for homeowners. Our team of experienced professionals takes pride in ensuring the safety and functionality of your chimney. Whether you need chimney cleaning, inspections, repairs, maintenance, or installations, we have you covered. Safety is our utmost priority. We fully understand the potential hazards associated with chimneys and strictly adhere to safety regulations. Our team is well-trained to implement necessary precautions, guaranteeing a safe and secure chimney operation for your home. What sets us apart is our commitment to personalized service. We know that each chimney has unique requirements, and we take the time to understand your specific needs. Whether it's routine maintenance or complex repairs, our experts offer tailored solutions that meet your chimney's demands, ensuring optimal performance. At Chimney Experts, we prioritize quality workmanship. We use top-of-the-line tools and materials to deliver lasting repairs and installations. Our team of skilled technicians stays up-to-date with industry practices, ensuring that every project is completed to the highest standards. Customer satisfaction is our ultimate goal. We value your time, and our reliable and punctual service reflects our commitment to meeting your needs. When you choose Chimney Experts, you can expect thorough and efficient service that leaves your chimney in excellent condition. If you're in need of superior chimney services, trust Chimney Experts. With our expertise, attention to detail, and dedication to customer satisfaction, we provide the best solutions for all your chimney maintenance and repair needs. Contact us today to schedule an appointment and experience the Chimney Experts difference for yourself.

"Repair went well. Technician arrived on time and was working all day to re point the chimney and re line it. He even repainted where paint had flaked off accessing the chimney to re-line."

Gregory S on June 2025


Avatar for Santa and Claus Chimney Sweep LLC
Santa and Claus Chimney Sweep LLC
7 North Pole
5.00(
12
)
Approved Pro
Santa and Claus Chimney Sweep LLC
7 North Pole
5.00(
12
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
84 local quotes requested

Hi this is Dave with Santa and Claus Chimney Sweep LLC .We are a small local business offering quality work at an affordable price. Specializing in sweeping(furnace and fireplace wood stoves pellet stoves) repointing -flu liners- caps-crowns-firebox and smoke chamber repairs and pressure washing.

"Dave quickly solved out leaking chimney problem at a reasonable cost."

Ken B on April 2025

Hi this is Dave with Santa and Claus Chimney Sweep LLC .We are a small local business offering quality work at an affordable price. Specializing in sweeping(furnace and fireplace wood stoves pellet stoves) repointing -flu liners- caps-crowns-firebox and smoke chamber repairs and pressure washing.

"Dave quickly solved out leaking chimney problem at a reasonable cost."

Ken B on April 2025


Aire Serv Heating & Air Conditioning - Air Duct Cleaning
Servicing Bel Air, Newark, Middletown, Wilmington,
5.00(
1
)
Approved Pro
Aire Serv Heating & Air Conditioning - Air Duct Cleaning
Servicing Bel Air, Newark, Middletown, Wilmington,
5.00(
1
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
161 local quotes requested

Air duct and dryer vent cleaning division servicing Bel Air, Newark, Middletown, Wilmington, Elkton, and Landenberg areas. If you are looking for a full-service HVAC business, air conditioning repair company, heating repair service, or furnace repair provider, look no further than Aire Serv. At Aire Serv, you will receive licensed and knowledgeable heating and air conditioning repair technicians who provide you with upfront pricing and some of the best-written guarantees in the business, like our 100% satisfaction guarantee on all heating and air conditioning services. Call Aire Serv today or request an appointment online!

"Everything went great! The tech that came to clean the air ducts was very helpful and showed up before and after pictures. I would definitely use them again!"

Rebecca B on March 2024

Air duct and dryer vent cleaning division servicing Bel Air, Newark, Middletown, Wilmington, Elkton, and Landenberg areas. If you are looking for a full-service HVAC business, air conditioning repair company, heating repair service, or furnace repair provider, look no further than Aire Serv. At Aire Serv, you will receive licensed and knowledgeable heating and air conditioning repair technicians who provide you with upfront pricing and some of the best-written guarantees in the business, like our 100% satisfaction guarantee on all heating and air conditioning services. Call Aire Serv today or request an appointment online!

"Everything went great! The tech that came to clean the air ducts was very helpful and showed up before and after pictures. I would definitely use them again!"

Rebecca B on March 2024


Avatar for Chesapeake Cleaning Services Inc
Chesapeake Cleaning Services Inc
Surrounding Areas
4.63(
32
)
Approved Pro
Chesapeake Cleaning Services Inc
Surrounding Areas
4.63(
32
)
Approved Pro
Customers say: Quality work
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
437 local quotes requested

Chesapeake Cleaning Services Inc., a family-owned and operated business led by Laura Grahm and her son John, has been proudly serving the Annapolis, MD area and its surroundings since 1996. Dedicated to delivering outstanding cleaning services, Laura and John have built a reputation based on trust, quality, and customer care. Their team of over 12 skilled professionals handles each job with precision, using eco-friendly, chemical-free products to ensure both safety and a spotless finish. Whether you need routine maintenance, deep cleaning, or specialized services, Chesapeake Cleaning Services is committed to meeting your unique needs with top-tier quality and reliability. For personalized service that truly cares about your space, contact us at 410-693-5263—we’re ready to make your home or office shine.

"Laura and her team have done a wonderful job cleaning our house for close to 20 years. Laura is always available if I need to contact her and she is flexible re schedule changes. Top quality work and reliable. Highly recommended!"

Ruth R on November 2024

Chesapeake Cleaning Services Inc., a family-owned and operated business led by Laura Grahm and her son John, has been proudly serving the Annapolis, MD area and its surroundings since 1996. Dedicated to delivering outstanding cleaning services, Laura and John have built a reputation based on trust, quality, and customer care. Their team of over 12 skilled professionals handles each job with precision, using eco-friendly, chemical-free products to ensure both safety and a spotless finish. Whether you need routine maintenance, deep cleaning, or specialized services, Chesapeake Cleaning Services is committed to meeting your unique needs with top-tier quality and reliability. For personalized service that truly cares about your space, contact us at 410-693-5263—we’re ready to make your home or office shine.

"Laura and her team have done a wonderful job cleaning our house for close to 20 years. Laura is always available if I need to contact her and she is flexible re schedule changes. Top quality work and reliable. Highly recommended!"

Ruth R on November 2024

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FAQs for gutters & downspouts cleaning service projects in Chestertown, MD

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 Chestertown, MD homeowners’ guide to gutters & downspouts cleaning services
From average costs to expert advice, get all the answers you need to get your job done.
professional cleaning up a construction site
Jun 25, 2025
Jun 25, 2025
Budget for post-construction cleaning costs based on factors such as home size, accessibility, type of cleaning, waste disposal, and more.
vacuum hose cleaning vent in wooden floor of home
Jun 24, 2025
Jun 24, 2025
Budget for air duct cleaning costs based on factors such as number of vents, mold remediation, accessibility, ductwork type, repairs, labor, and more.
homeowner cleaning the leaves out of home gutters
Jun 21, 2025
Jun 21, 2025
Budget for gutter cleaning costs based on factors such as number of stories, gutter length, gutter conditions, additional related services, and more.
woman doing laundry
Jun 17, 2025
Jun 17, 2025
Budget for dryer vent cleaning costs based on factors such as vent location, type, length, obstructions, potential repairs, accessibility, labor, and more.
professional powerwashing the roof of a house
Apr 24, 2025
Apr 24, 2025
Budget for roof cleaning costs based on factors such as your home’s size, the roof’s condition, accessibility, professional labor, repairs, and more.
A metal pipe chimney with cap
Apr 26, 2025
Apr 26, 2025
Budget for chimney cap replacement costs based on factors such as cap size, material, shape, type, customization, labor, and more.
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