28+ Years Experience
Licensed MHIC #51349
Locally Owned & Operated
Free Estimates
Pikesville is known for its larger homes, wide rooflines, and established neighborhoods with mature landscaping. These features add character—but they also place higher demands on gutter systems than those found in tighter suburban developments.
Long roof runs, multiple valleys, and expansive surface area can move thousands of gallons of water during a single storm. When gutters are undersized, poorly pitched, or clogged with debris, that water ends up where it doesn’t belong: along foundations, near basements, and against exterior walls.
For more than 28 years, Shepherd & Sons Inc. has provided professional gutter services throughout Pikesville. We design systems that handle volume, distance, and debris—not just average rainfall—and we install them with the precision required for higher-end homes.
If your gutters struggle during heavy rain, the system isn’t designed for your home.
Call (410) 737-2131 or fill out our online form for your free estimate today!
Services
What we install:
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Seamless aluminum gutters (no leaky seams)
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Custom-fabricated on-site to fit your exact measurements
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5-inch or 6-inch capacity options
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16 color choices to match your home
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Professional downspout placement and extensions
Why seamless matters: Sectional gutters leak at every joint. Our seamless gutters only have seams at corners, dramatically reducing leak potential.
How long it takes: Most homes completed in one day
Guard types we install:
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Aluminum micro-mesh blocks leaves and debris
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Flat profile works under most roof types
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Balance of performance and cost
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Very durable material
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Best for homes with heavy tree coverage
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Sheds oak leaves and acorns effectively
Hydro Flo
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Premium stainless steel micro-mesh
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Best option for homes with large amounts of pine needles
Do guards work? Yes, if you get quality professionally-installed systems. Cheap hardware store guards don't work. Our guards reduce maintenance by 80-90%.
What's included:
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Complete removal of leaves, debris, and buildup
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Downspout flushing to clear blockages
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Visual inspection for damage
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Debris hauled away from your property
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Water flow test to verify proper drainage
Recommended schedule:
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Spring cleaning: April-May (remove winter debris)
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Fall cleaning: October-November (before leaves pile up)
Why it matters: Clogged gutters overflow, damaging siding, foundations, and landscaping. Two cleanings per year prevent thousands in water damage.
Why Pikesville Residents Choose Shepherd & Sons Inc.
✅ Over 28 Years Serving Pikesville & Northwest Baltimore County
Since 1997, we’ve protected homes throughout Pikesville, Owings Mills, Reisterstown, and the Greenspring area. We understand the demands of larger homes, wide rooflines, mature trees, and the heavy water volume common in this part of Baltimore County. Our experience allows us to design gutter systems that perform reliably during intense Maryland storms—not just look good on install day.
✅ Locally Owned & Operated — Not a National Chain
We’re a locally owned Maryland company, not a franchise or out-of-state operation. Our reputation in Pikesville is built on long-term relationships, repeat customers, and referrals from homeowners who expect quality, professionalism, and accountability. When you call Shepherd & Sons Inc., you’re working directly with a company that’s invested in this community.
✅ No Subcontractors — Ever Every gutter installation, repair, cleaning, and gutter guard project is completed by our in-house, trained team. We never subcontract our work. This ensures consistent workmanship, clear communication, and full accountability—especially important for larger or higher-value Pikesville homes.
✅ Licensed & Fully Insured
MHIC #51349. We carry full liability insurance and workers’ compensation, protecting you and your property during every service.
✅ Quality Materials & Workmanship
We use premium aluminum gutters and proven installation techniques. Every project includes a satisfaction guarantee and warranty coverage.
✅ Free, No-Pressure Estimates
We provide detailed written estimates with transparent pricing. No hidden fees, no high-pressure sales tactics—just honest recommendations for your home's needs.
Proudly Serving Pikesville MD and Surrounding Areas
Shepherd & Sons Inc. proudly serves the entire Pikesville area, including:
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Pikesville proper (ZIP 21208) – Single-family homes and established neighborhoods
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Greenspring & Greenspring Valley – Estate-style homes with mature trees
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Old Court Road Area – Older residential communities with drainage concerns
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Reisterstown Road Corridor – Residential and mixed-use properties near major roads
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Owings Mills Border Areas – Homes near shopping centers and commuter routes
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Randallstown Border Areas – Mid-century and newer residential neighborhoods
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Northwest Baltimore County Communities – Surrounding areas served by our local team
We also service nearby communities including Owings Mills, Reisterstown, Randallstown, Woodlawn, Greenspring Valley, and West Baltimore. Our centrally located Baltimore office at 4210 Leeds Avenue allows for quick response times throughout Northwest Baltimore County and Central Maryland.
Whether your home is near Greenspring Valley Road, along Reisterstown Road, or tucked into a quiet residential neighborhood surrounded by mature trees, we provide dependable gutter services with free estimates and flexible scheduling designed around your needs.
See What Our Customers Have to Say
What to Expect: Our Process
We deliver a smooth, top-notch installation experience. Here’s our concise process:
Free Estimate
1.
Call or fill out our online form. We'll schedule a time to visit your home, measure your gutters, assess any problems, and provide a written quote on the spot or over email.
No pressure. No obligation.
Scheduling
2.
Once you approve the estimate, we schedule installation based on your availability. We call the day before to confirm arrival time.
Expert Installation
3.
Our crew arrives on time with all materials. Remove existing gutters (if applicable), craft seamless gutters on-site, and install with accuracy.
Clean Up
4.
We clean up all materials and leave your home as clean as when we arrived.
Final Inspection
5.
Before we leave, we walk you through the completed work, answer questions, and ensure you're completely satisfied.
Payment: Due upon completion
Common Pikesville Gutter Problems
Problem: Water Pooling Around Foundation
Why it happens: Gutters aren't directing water far enough from house
Solution: Add downspout extensions (6-10 feet from foundation) or underground drains
Problem: Gutters Overflow During Heavy Rain
Why it happens: Gutters too small for your roof, clogged downspouts, or improper pitch
Solution: Upgrade to 6-inch gutters, clear blockages, adjust pitch for proper flow
Problem: Gutters Constantly Clog with Leaves
Why it happens: Trees dropping debris into open gutters
Solution: Professional gutter guards block debris while allowing water flow
Problem: Basement Water After Storms
Why it happens: Usually related to gutters overflowing or not extending far enough
Solution: Fix gutter capacity issues, ensure proper drainage away from foundation
Frequently Asked Questions
Common questions from Pikesville homeowners
Do Pikesville homes usually need larger gutters?
Many do. Homes with wide rooflines, multiple valleys, or attached garages often move more water than standard systems can handle. During your estimate, we evaluate roof size and pitch to determine whether 5" or 6" gutters are the right fit.
How often should gutters be cleaned in Pikesville?
At least twice per year for most homes—typically spring and fall. Properties with heavy tree coverage often need a third cleaning unless gutter guards are installed.
How long does a typical gutter installation take?
Most Pikesville homes are completed in one day. Larger or more complex properties may take longer, which we review with you upfront before scheduling.
Can poor gutter drainage cause basement issues?
Absolutely. When water isn’t carried far enough away from the home, it can saturate soil near the foundation and increase the risk of basement moisture or leaks over time.
Are gutter guards worth it in Pikesville?
Yes, for most homes. Mature trees drop leaves, seed pods, and debris throughout the year. Quality gutter guards significantly reduce clogging and lower long-term maintenance costs.
Get Reliable Gutter Protection for Your Pikesville Home
Get your free, no-obligation estimate today