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Top-Rated Gutter repair and replacement pros in Osterville - Updated Nov 2026

T&T Seamless Gutters
4.9(
91
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - InstallSeamless Metal Gutters - Repair

Serving Osterville, MA and surrounding areas

Approved

In business since 2007

Free estimates

Warranties offered

"Couldn't have asked for a better team to replace my gutters. They took the time to educate me on how my gutters were contributing to excessive moisture in my attic (due to water pooling in my gutters which was evaporating into my drip edge vents). I ended up going with commercial gutters (wider). Their cost was HALF of what another gutter company quoted me for residential sized gutters. T&T took the time to do it right. They patched up the holes left by my old gutters. They informed me of wood rotting issues on my trim boards. Again, they were great! Highly recommended!"
Response time7 hrs
4 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for Leafguard
Leafguard
4.2(
311
)
Seamless Metal Gutters - InstallGutter Covers and Accessories - Install or Replace

Serving Osterville, MA and surrounding areas

Approved

In business since 1993

Free estimates

Credit card accepted

LeafGuard is a market-leading, unique, customized gutter protection system for your home. It carries water away from your property faster, protecting it from water damage associated with clogged, or faulty gutters. The system is 20% thicker than regular gutters and provides added strength against the elements. \n \nLeafGuard is the only gutter brand to offer a Lifetime, No-Clog Warranty. What does this mean? Simple--your gutters are guaranteed not to clog for as long as they're installed on your home. If they do, we'll clean them out for free!

Leafguard gutter inside
Leafguard
A new leaf guard system
Leaves going over gutter
Angled view of Leaf Guard

+1

19 neighbors recently requested a quote
Recommended by89%of homeowners
Avatar for Muto, Inc.
Muto, Inc.
4.7(
86
)
Seamless Metal Gutters - Install

Serving Osterville, MA and surrounding areas

Approved

In business since 2007

Free estimates

Warranties offered

"Sebastian was great to work with and the workers were thorough, efficient and they cleaned up nicely at the end. We had solar panels removed and replaced for the job and the extra cost for this was very reasonable. No complaints with this company and we will use them again."
Garage Before
Ugly Deck unsafe stairs
Old deck
New Roof Top Deck
Water side

+83

Response time2 days
148 neighbors recently requested a quote
Recommended by90%of homeowners
Avatar for Espinoza's Home Improvement
Espinoza's Home Improvement
5.0(
5
)
Seamless Metal Gutters - Repair

Serving Osterville, MA and surrounding areas

Approved

In business since 2020

Free estimates

Emergency services offered

Espinoza's Home Improvement is 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.

ROOF REPLACEMENT
ROOF REPLACEMENT
ROOF REPLACEMENT
ROOF REPLACEMENT
ROOF REPLACEMENT

+94

Response time9 hrs
5 neighbors recently requested a quote
Recommended by25%of homeowners
House Calls
3.2(
67
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - Repair

Serving Osterville, MA and surrounding areas

Approved

In business since 1973

Free estimates

Emergency services offered

I know your home is your biggest investment and I want to help you protect,and maintain that investment. With 40 years of experience in handyman, painting, and remodeling services, you can be rest assured your next project will be done right the first time. My success is dependent upon your satisfaction. Give me a call. My company, House Calls, is located in Bourne, Massachusetts. Thank you. Bill W.

1 neighbors recently requested a quote
Recommended by97%of homeowners
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Gutter Repair and Replacement FAQs, answered by experts

There are a handful of things you can look for to determine if you need to pay for gutter repairs, including the following:

  • Water leaking from the underside of your gutters during rainfall

  • Visible gaps between your gutters and your roof

  • Frequent issues with gutters overflowing or holding standing water

  • Gutters that sag or pull away from the house

  • Water damage to soffits, fascia boards, or other building materials

  • Mold growth on your exterior walls

  • Soil erosion underneath your roof overhang

  • Foundation leaks or inward bowing of foundation walls

Yes, many homeowners find that seamless gutters are worth the investment. Although they have a higher upfront cost than standard gutters—an average of $2,700 compared to $2,000—their benefits often outweigh the price difference. Seamless gutters last longer, require less maintenance, and are less prone to clogs and leaks due to having fewer seams. In contrast, standard gutters typically have seams every 10 feet, which can leak and require new sealant every one to five years. Additionally, seamless gutters are considered more aesthetically pleasing, come in a variety of colors to match your home, and can improve your home's curb appeal and potential value.

On average, gutters need to be replaced every 20 years. Unprotected gutters in more extreme weather conditions are more prone to breaking and may need to be replaced sooner. Meanwhile, proper maintenance can extend your gutter’s life span even further. That said, proper installation, gutter hangers to provide additional support, and gutter guards or helmets all play an important role in how long your gutters last.

You may have a clogged gutter. Downspouts can also clog if your gutter collects too much debris. Hire a professional gutter cleaner, and if you still have problems, install a gutter guard (which prevents debris from entering your gutter system) and a downspout extension (which helps drain water further away from your foundation, so it doesn't pool near your house). Follow these tips to keep your gutter downspouts clean.

If your gutters get overwhelmed every time it rains, adding an extra downspout is a solution. First, you'll need to decide where to add the downspout. If your current setup only has a single downspout, one option is to place a new one at the opposite end of the gutter. If you already have a downspout at each end, adding a third one in the middle can help to lighten the load. 

You can hire a professional to add a downspout yourself by cutting into the existing gutter and attaching the necessary parts, such as an outlet and brackets.

The Osterville, 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.