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Avatar for Bradford Home Services

Bradford Home Services

145 S. Main St
No reviews yet

Bradford Home Services

145 S. Main St
No reviews yet
1 years of experience

Bradford Home Services is your personal maintenance company for your home, condo, rental property, or seasonal property! Born from our sister company Bradford Construction Management, you can trust your home is being reviewed by seasoned home builders! We have over 70 years of experience in the residential construction market, building high end homes, from design to finish. Take advantage of our bi-annual assessments for only $25/Month! We will review your whole home Exterior, Interior, plumbing, electrical, heating etc! we will then send you a detailed report with pictures, videos, and recommendation on fixes! But it doesn't stop there, we can price and repair any aspect of your home!

Bradford Home Services is your personal maintenance company for your home, condo, rental property, or seasonal property! Born from our sister company Bradford Construction Management, you can trust your home is being reviewed by seasoned home builders! We have over 70 years of experience in the residential construction market, building high end homes, from design to finish. Take advantage of our bi-annual assessments for only $25/Month! We will review your whole home Exterior, Interior, plumbing, electrical, heating etc! we will then send you a detailed report with pictures, videos, and recommendation on fixes! But it doesn't stop there, we can price and repair any aspect of your home!


Johnnatan Santos

23 HARBACK RD
No reviews yet

Johnnatan Santos

23 HARBACK RD
No reviews yet
4 years of experience

Golden Gutters, Roofing & Siding is your reliable expert for gutters and siding in Sutton, MA, and the surrounding areas. As top-rated installers and contractors, we deliver premium materials and skilled craftsmanship. Improve your home's exterior with our dependable, customized services designed to suit your specific needs.

Golden Gutters, Roofing & Siding is your reliable expert for gutters and siding in Sutton, MA, and the surrounding areas. As top-rated installers and contractors, we deliver premium materials and skilled craftsmanship. Improve your home's exterior with our dependable, customized services designed to suit your specific needs.




Latham Roofing & Siding

640 Loudon Rd.
No reviews yet

Latham Roofing & Siding

640 Loudon Rd.
No reviews yet
Free onsite estimate

A dependable company that handles roofing and siding. We offer competitive pricing, fantastic service and an overall great experience for homeowners and businesses. Please feel free to reach out for a free quote today!

A dependable company that handles roofing and siding. We offer competitive pricing, fantastic service and an overall great experience for homeowners and businesses. Please feel free to reach out for a free quote today!


Avatar for SageWood Home Exteriors

SageWood Home Exteriors

PO Box 25
4.50(
8
)

SageWood Home Exteriors

PO Box 25
4.50(
8
)
Customers say: Quality work
12 years of experience

"Choose the One That Loves What They Do" SageWood Home Exteriors is a family owned business nestled in the Hilltowns, serving all of Western MA and CT. We pride on beautifying your curb appeal by offering different options and design consultation. We believe all homeowners deserve to have a home they can be proud of if it is affordable. Our goal is to build relationships with our clients so they continue to reach when there is a new project or need. We don't cut corners and we get the job done right, so you don't have to worry. SageWood Home Exteriors was founded on the principle of offering designer quality exterior installations using durable products and skilled craftsmen at an affordable price. You will not find us in TV commercials because ultimately, it reflects on those higher quotes for comparable quality work. We keep our costs of doing business low so you can save on your next home project. That means more money is left in your pocket! Last of all, we believe in maintaining great communication, in having integrity and being fair. After a scheduled visit from one of our project managers, you will feel empowered to make the right decision for you, your family and your home. ​Thank you for visiting our website! https://sagewoodhome.com/index.html

"I couldn’t be happier with SageWood. They were responsive, efficient, reasonably priced, clean and professional. My neighbors called to tell me they were watching and how great they were. 5 stars."

Dan R on August 2023

"Choose the One That Loves What They Do" SageWood Home Exteriors is a family owned business nestled in the Hilltowns, serving all of Western MA and CT. We pride on beautifying your curb appeal by offering different options and design consultation. We believe all homeowners deserve to have a home they can be proud of if it is affordable. Our goal is to build relationships with our clients so they continue to reach when there is a new project or need. We don't cut corners and we get the job done right, so you don't have to worry. SageWood Home Exteriors was founded on the principle of offering designer quality exterior installations using durable products and skilled craftsmen at an affordable price. You will not find us in TV commercials because ultimately, it reflects on those higher quotes for comparable quality work. We keep our costs of doing business low so you can save on your next home project. That means more money is left in your pocket! Last of all, we believe in maintaining great communication, in having integrity and being fair. After a scheduled visit from one of our project managers, you will feel empowered to make the right decision for you, your family and your home. ​Thank you for visiting our website! https://sagewoodhome.com/index.html

"I couldn’t be happier with SageWood. They were responsive, efficient, reasonably priced, clean and professional. My neighbors called to tell me they were watching and how great they were. 5 stars."

Dan R on August 2023


Avatar for The Empire Company

The Empire Company

459 E River St
4.95(
93
)

The Empire Company

459 E River St
4.95(
93
)
Customers say: Quality work
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers

We know how important it is to choose a company that will meet and exceed your expectations. We work with honesty and partner with our customers, as we're both always seeking 100% satisfaction.We're a family owned business. My wife and I run this to have a better life for our families. We offer interior & exterior painting, all types of handyman work, pressure washing, and housecleaning services.

"Excellent job! Took care of a fair amount of carpentry to get things looking good. Bruno was very responsive to how I wanted things to look and adjusted as necessary. Everyone loves how things came out. Highly recommend!"

Michael T on September 2025

We know how important it is to choose a company that will meet and exceed your expectations. We work with honesty and partner with our customers, as we're both always seeking 100% satisfaction.We're a family owned business. My wife and I run this to have a better life for our families. We offer interior & exterior painting, all types of handyman work, pressure washing, and housecleaning services.

"Excellent job! Took care of a fair amount of carpentry to get things looking good. Bruno was very responsive to how I wanted things to look and adjusted as necessary. Everyone loves how things came out. Highly recommend!"

Michael T on September 2025


Avatar for Gunner Roofing

Gunner Roofing

78 Halloween Blvd
4.86(
57
)

Gunner Roofing

78 Halloween Blvd
4.86(
57
)
Customers say: True professional
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers

Gunner Roofing knows your home is everything. That’s why Gunner was founded with one clear mission: to bring your home improvement project to life with exceptional quality, a personalized experience, and innovative tech to make your project easier than ever. We’re the first roofing company to service nationally as well as the first to offer accurate online quotes in under an hour meaning no more hours on the phone or juggling appointments to meet a dodgy contractor. Gunner is here to make it easy for you - we even help you navigate financing your project through Wells Fargo and assist with permitting. We’re proud to be your go-to roofing, siding, windows, and gutter installer, working with only the industry’s most trusted suppliers like Andersen Windows, Brava Roof Tile, GAF, and James Hardie. Whether you want to upgrade your home’s exterior or ensure your house will protect your family through the next storm, Gunner is excited to work with you as your trusted partner. Skeptical? We get it, this is no small decision. Check out our hundreds of 5-star reviews on google and find us on Inc. 5000 Fastest Growing Companies List, Fast Company’s Most Innovative Companies List, Good Housekeeping Home Reno Award Winners Page, Architectural Digest and more! If you’re curious about how much your project would cost, get your free roofing quote at https://www.gunnerroofing.com/ today - no commitment necessary.

"I am sure that all positive reviews for this company are fake. Nothing that was promised to me was delivered. My siding project is still ongoing for over 1 month. Was told that it would be done in week. Had one rain day. They have system like this: 1) sales person who never installed anything he will promise you things that obviously are not true, 2) crew that is subcontracted but not Gunner, mine was driving for over 2 hours away, 3) person who oversees the project but has little control over anything, no supply, doesn't know the crew, crew does not listen to him, main office does not listen to him, 4) main office does not reply to you. They just tell me to talk to project manager who has no control. So you understand that if there are any issue you are on your own. Quality or work is not good. Many times I had to point to the crew what's wrong, planks are broken yet they were still installing it, caulking is done they way that I can do it better, they cut wires to awning etc"

Eduard S on September 2025

Gunner Roofing knows your home is everything. That’s why Gunner was founded with one clear mission: to bring your home improvement project to life with exceptional quality, a personalized experience, and innovative tech to make your project easier than ever. We’re the first roofing company to service nationally as well as the first to offer accurate online quotes in under an hour meaning no more hours on the phone or juggling appointments to meet a dodgy contractor. Gunner is here to make it easy for you - we even help you navigate financing your project through Wells Fargo and assist with permitting. We’re proud to be your go-to roofing, siding, windows, and gutter installer, working with only the industry’s most trusted suppliers like Andersen Windows, Brava Roof Tile, GAF, and James Hardie. Whether you want to upgrade your home’s exterior or ensure your house will protect your family through the next storm, Gunner is excited to work with you as your trusted partner. Skeptical? We get it, this is no small decision. Check out our hundreds of 5-star reviews on google and find us on Inc. 5000 Fastest Growing Companies List, Fast Company’s Most Innovative Companies List, Good Housekeeping Home Reno Award Winners Page, Architectural Digest and more! If you’re curious about how much your project would cost, get your free roofing quote at https://www.gunnerroofing.com/ today - no commitment necessary.

"I am sure that all positive reviews for this company are fake. Nothing that was promised to me was delivered. My siding project is still ongoing for over 1 month. Was told that it would be done in week. Had one rain day. They have system like this: 1) sales person who never installed anything he will promise you things that obviously are not true, 2) crew that is subcontracted but not Gunner, mine was driving for over 2 hours away, 3) person who oversees the project but has little control over anything, no supply, doesn't know the crew, crew does not listen to him, main office does not listen to him, 4) main office does not reply to you. They just tell me to talk to project manager who has no control. So you understand that if there are any issue you are on your own. Quality or work is not good. Many times I had to point to the crew what's wrong, planks are broken yet they were still installing it, caulking is done they way that I can do it better, they cut wires to awning etc"

Eduard S on September 2025


Avatar for J&D Windows and Doors General Contracting, LLC.

J&D Windows and Doors General Contracting, LLC.

Draper Avenue
4.97(
32
)

J&D Windows and Doors General Contracting, LLC.

Draper Avenue
4.97(
32
)
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers

Fully insured General Contracting company with free home estimates specializing in Windows and Doors. Our products have a life time warranty with them as well as a variety of different options to accommodate your wants, needs, and budgets! Check out our Facebook, google page, and website listed below for yourself to see that you’re in good hands with J&D! To help with your long and late work hours, we are now offering E-Quotes on all windows, sliding glass doors, and ProVia door products! Go to our website, click on E-Quotes to learn more.

"Ok so I am writing a review everywhere I can for David and crew. Basically havr been using David and J&D for every aspect of the house! Windows, Doors, Facade wall, Kitchen, Siding etc. Have yet to have any bad experience with these guys!! Wonderful, efficient, courteous, professional, and I cannot say this enough… what a crack up! Thank you so much guys for taking care of me and my winderful “new” home. It is an honor and a pleasure working with you!"

Danielle M on September 2024

Fully insured General Contracting company with free home estimates specializing in Windows and Doors. Our products have a life time warranty with them as well as a variety of different options to accommodate your wants, needs, and budgets! Check out our Facebook, google page, and website listed below for yourself to see that you’re in good hands with J&D! To help with your long and late work hours, we are now offering E-Quotes on all windows, sliding glass doors, and ProVia door products! Go to our website, click on E-Quotes to learn more.

"Ok so I am writing a review everywhere I can for David and crew. Basically havr been using David and J&D for every aspect of the house! Windows, Doors, Facade wall, Kitchen, Siding etc. Have yet to have any bad experience with these guys!! Wonderful, efficient, courteous, professional, and I cannot say this enough… what a crack up! Thank you so much guys for taking care of me and my winderful “new” home. It is an honor and a pleasure working with you!"

Danielle M on September 2024


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Gutter Repair and Replacement questions, answered by experts

Yes, it is okay to knock down icicles yourself. Just make sure to take the proper safety precautions. If you’re not comfortable doing it yourself, contact a roofing professional.

Whether it’s better to repaint or replace gutters will depend on their overall state. One or two small damages can easily be fixed and covered up with a fresh coat of paint for minimal additional costs. On the other hand, you’ll likely pay less to install a new set-up rather than fixing one that’s heavily damaged.

Any small amount of standing water can be damaging to your gutters. It’s recommended that a ¼ inch puddle or more should be addressed. Failure to keep water from pooling in your gutters can result in clogs, algae growth, and pests that damage your gutters over time. 

When it comes to which gutter material is better, the choice really boils down to what you're looking for in a gutter system. If saving money is the most important factor, then your best option is to go for aluminum gutters. If longevity and durability are more important to you, then copper gutters could be the best fit. If you want to customize the color of your gutters, aluminum takes the cake, but if you're looking for a more natural appearance, copper might be a better choice.

Whether you need to remove your home's gutters before installing a drip edge depends entirely on their installation. In most cases, you can work around the gutters and not have to remove them. This process is straightforward because the drip edge should extend past the back edge of the gutter. However, if your gutter placements are high on the fascia, you may have to take them down to install the drip edge properly. 

The Cheshire, MA homeowners’ guide to gutter repairs and replacements

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