Siding, Roofing & Windows
in Cherry Valley, IL
Serving Cherry Valley homeowners from our Loves Park shop just north on Route 20 — same local crew, honest estimates, since 1986.
Three generations of exterior expertise, rooted right here
Littlefield Siding is a family business. Tom Littlefield learned the trade from his father, and the company's combined experience spans more than 60 years of siding, roofing, window, and exterior work. We incorporated in 1986 and have operated from our Loves Park shop ever since.
When a Cherry Valley homeowner calls us, they get an actual local crew — not a 1-800 number that routes to a sales rep in another state. Our shop is on Riverside Blvd in Loves Park, a quick drive north on Route 20. We've worked on homes throughout Cherry Valley and southeastern Winnebago County for years.
Our Story
Why Cherry Valley homeowners choose Littlefield
We know Cherry Valley housing stock
Cherry Valley has a mix of long-established residential neighborhoods near the village center and newer subdivision development around Cherry Valley Commons. Many older homes are hitting the age where original siding and roofing need replacing — and newer builds are approaching their first major exterior maintenance cycle.
Cherry Valley is in Winnebago County. We pull permits through the Village of Cherry Valley and Winnebago County for unincorporated properties.
We understand Cherry Valley weather
8 confirmed ground hail reports in the Cherry Valley area in the past 12 months. 35 inches of annual snowfall. Positioned southeast of Rockford along the I-90 corridor, Cherry Valley sees storm cells that can arrive fast and hit hard.
We handle the insurance paperwork
Filing a storm damage claim is usually more stressful than the damage itself. We walk Cherry Valley homeowners through the full process — from inspection through adjuster documentation through supplementing short estimates.
Our services for Cherry Valley homes
One contractor. Five services. Everything your home's exterior needs.
Siding
Vinyl, steel, and insulated siding — built for Cherry Valley winters. We'll show you options that look better and outlast what's on the house now.
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Roofing
Asphalt shingle, metal, and steel roofing from GAF and Owens Corning. Storm damage replacement, full replacement, and emergency repair.
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Windows
Double-hung, casement, picture, bay & bow — energy-efficient vinyl windows that make a real difference in heating and cooling bills.
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Soffit & Fascia
Aluminum soffit and fascia — the parts most vulnerable to ice dams, moisture, and animal entry. Repair and full replacement.
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Storm Damage Repair
Hail and wind damage to roofs, siding, and windows. We work directly with your insurance carrier on documentation and claim filing.
Get Help NowWhy Cherry Valley homes need the right contractor
8 confirmed ground hail reports in the Cherry Valley area in the past 12 months. 35 inches of annual snowfall. Positioned southeast of Rockford along the I-90 corridor, Cherry Valley sees storm cells that can arrive fast and hit hard.
Add freeze-thaw cycles, heavy snowfall, and northern Illinois rainfall — and you have a climate that accelerates exterior wear far faster than the national average. We install to the conditions, not the catalog.
Storm Damage ServicesCherry Valley homeowners trust Littlefield
"Littlefield Siding did a fantastic job on our home! Tom took great care of everything and made sure the work was done right. The crew was on time, professional, and the new siding looks amazing. Highly recommend them for any siding project!"
Frequently asked by Cherry Valley homeowners
Yes, most exterior replacement work in Cherry Valley requires a permit through the Village of Cherry Valley. We pull all required permits on your behalf as part of the job. If your property falls within the unincorporated areas of Winnebago County nearby, the permit process may differ slightly — we handle both.
Most full roof replacements take 1–2 days. Full siding replacements generally take 3–5 days depending on home size and siding type. We plan the schedule around your availability and the weather forecast — we don't start a job we can't finish cleanly.
We install year-round, but the best window for most projects is April through October. Winter installations are possible but weather-dependent. Storm damage repairs happen whenever they're needed, regardless of season.
Yes. We provide the inspection documentation, photographs, and scope of work that adjusters need, and we'll meet with the adjuster on-site when it helps. If an initial claim comes back short, we'll help you supplement. We never pressure a homeowner to file a claim that isn't warranted.
For roofing we work with GAF and Owens Corning systems. For siding and windows we'll walk you through current options during your free estimate. We only install products we stand behind and will tell you honestly what's right for your home and budget.
Call (815) 636-6446 or use the contact form. We'll schedule a visit — usually within a few days — do a full exterior walkthrough, and give you a written estimate. No pressure, no high-pressure sales tactics.
Our process — simple and transparent
Free Estimate
Full exterior walkthrough, written estimate, all questions answered. About 45–60 minutes.
Material Selection
You choose colors, styles, and specs. We bring samples. No rushing.
Scheduling
A start date that works for your calendar and the weather.
Installation
Our crew works, cleans up daily, and walks the completed job with you before we leave.
Ready to Transform Your Cherry Valley Home?
Get a free estimate from your local exterior contractor. Honest pricing, local crew, no pressure.