Classic homes on wooded lots near St. Matthews — detailed inspections from a former custom home builder.
Windy Hills is an established small city just northeast of St. Matthews, known for its rolling, wooded streets, classic brick homes, and quiet residential feel — all just minutes from Brownsboro Road, Westport Road, and the shops of St. Matthews. Many homes here were built in the mid-20th century and have been updated and expanded over the years. ProChek Home Inspections serves Windy Hills buyers and sellers from our Louisville office.
Mature trees, sloping lots, older systems, and additions or renovations of varying quality are common considerations in Windy Hills. Darryl evaluates roofs and gutters under heavy tree cover, drainage around the foundation, and the condition of the home’s mechanical systems. Owner Darryl Willoughby spent more than 12 years as a custom home builder before becoming a Kentucky licensed home inspector (#HI-2038) and ASHI member, and he has 20 years of inspection experience.
Whether you need a buyer’s inspection, a pre-listing inspection, a luxury home inspection, or radon testing, ProChek delivers a thorough inspection, a plain-language walk-through, and a detailed digital report with photos you can access anytime. Darryl’s wife Dee-Dee runs the office and scheduling, and we’re open 7 days a week — call 502-802-6336 to schedule your Windy Hills inspection.
Here are the inspections Windy Hills buyers, sellers, and homeowners call ProChek for most — all performed personally by Darryl.
A complete top-to-bottom inspection before you buy, with a detailed report and photos.
Find and fix issues before you list — fewer surprises and smoother negotiations.
Detailed inspections for larger, high-end homes with complex systems.
A yearly check-up that catches small problems before they become expensive ones.
Add a radon test to any inspection — the only way to know your level.
Confirm negotiated repairs were completed — and done right — before closing.
Clients consistently describe Darryl the same way — thorough, knowledgeable, and honest. Here’s what a few of them have to say.
"Darryl did a very thorough inspection on my new construction. It was peace of mind for me. I would highly recommend ProCheck for new or existing properties!"
"I could not be more pleased with the service provided by ProChek Home Inspections. Darryl was very punctual, extremely thorough, and highly professional. Following the comprehensive inspection, Darryl took the time to review his findings with me and provide his honest assessment of every aspect of the home I was purchasing. Overall, the report I received was detailed, well-organized, and gave me confidence in making informed decisions. As a result of the quality service that he provided, I asked them to perform a follow-up inspection to verify that the recommended repairs had been completed correctly prior to closing on my home. Their service exceeded my expectations, and I highly recommend anyone looking for a trustworthy home inspection company to reach out to ProChek."
"Dee Dee and Darryl were very easy to work with, and the inspection report that was provided was very comprehensive! Darryl included pictures of everything from the foundation to the roof with arrows pointing to every problem area on each pic. Having all that data helped me dodge a bullet on a house that would have needed extensive repairs had I proceeded with the purchase. I am still looking for another house at the moment, and when I find one I want to put an offer in on, I will use ProChek again!"
From our Louisville office on McKenna Way, ProChek serves Windy Hills and nearby communities including St. Matthews, Graymoor-Devondale, Indian Hills, and Rolling Fields.
Answers to the questions Windy Hills-area buyers, sellers, and homeowners ask us most.
Yes. Darryl inspects the home’s major systems and components, including added and renovated areas, and notes visible concerns with workmanship.
They can. Darryl looks closely at roofs, gutters, and drainage, which are often affected by mature trees.
Yes — see our Luxury & Estate Home Inspection page.
Call 502-802-6336 or request an inspection on our contact page. We’re open 7 days a week, and Dee-Dee will get you on the calendar quickly.
ProChek serves 50 communities across Louisville and the surrounding counties. Click any community to learn more about home inspections there.
20 Years Experience • KY Licensed #HI-2038 • ASHI Member • Open 7 Days • Serving Louisville & Surrounding Areas