Wood Siding Repair in Deerwood & Glen Kernan

By Thomas Drake, Founder & Owner, A New Leaf Painting Contractors  ·  Painting since 1988  ·  Updated April 2026

Deerwood and Glen Kernan estates were largely built between the late 1970s and the late 1990s, and many feature extensive cedar, redwood, or pine siding — much of it now 30+ years old. Wood that age in a Florida climate behaves predictably: certain elevations rot, others split, others go gray and chalky from UV. The work to bring a wood-sided estate back is part carpentry, part restoration, and part premium-finish painting — and it can’t be rushed or shortcut. Here’s what 30-year-old wood actually looks like up close, what’s repairable, what needs replacement, and what 15 years of painting Jacksonville’s highest-end gated communities has taught us.

Deerwood was developed starting in 1972 as Jacksonville’s first true gated community, with major buildouts continuing through the 1990s. Glen Kernan came online in the late 1990s as the modern equivalent — large-lot estate homes designed for high-end buyers who wanted architectural sophistication. Both communities were built during eras when premium wood siding (cedar lap, redwood shake, tongue-and-groove pine, board-and-batten) was the standard exterior material for estate-class homes.

That wood is now 25 to 50 years old. The original homeowners are aging, properties are turning over, and new owners are discovering that the gorgeous wood exterior they fell in love with needs serious work before any repaint can be considered.

Wood at this age in this climate falls into four predictable conditions, often on different elevations of the same house. Sun-exposed south and west elevations: deeply weathered, gray, often with raised grain and surface checking — usually salvageable with aggressive sanding, restoration treatment, and a thicker paint film. Shaded north and east elevations: held up structurally but often showing mildew staining, soft spots near horizontal trim, and paint adhesion failure where moisture got behind the finish.

Lower courses near grade: highest rot exposure from sprinklers, splash-back, and ground moisture — frequently requires partial replacement. Hidden behind landscaping: often the worst because nobody has inspected it in years, and irrigation has been hitting it daily for decades. Walking the home with a probe and a moisture meter is the only way to know what you actually have.

Three categories drive the decision. Surface weathering with no rot — the wood is sound, just visually aged from UV. This gets aggressive sanding, brightener treatment if cedar or redwood, primer, and a high-build topcoat that fills the texture. Salvageable. Localized rot in otherwise sound boards — a single soft pocket on a generally good board. Smaller pockets get cut out, treated with rot-arresting epoxy, and patched with PVC or matching wood.

Larger pockets mean full board replacement. Full-board failure or structural compromise — the board has lost integrity along its length, or the rot has reached the substrate behind it. This always gets full replacement. We don’t fill failing boards; we replace them, prime both faces and all four edges before installation, and then paint as part of the full system.

A wood-sided Deerwood or Glen Kernan repaint isn’t a 5-day job. It’s typically 2 to 4 weeks of carpentry, prep, priming, and finish work — staffed by crews that can swap between trades as the project demands. The carpentry alone on a 4,500 square foot wood-sided estate can run 5 to 10 days depending on rot exposure. Sanding and surface prep is another 3 to 5 days. Priming with the manufacturer-specified system (typically an oil-based stain-blocker on bare wood, then a bonding primer over weathered painted surfaces) takes 1 to 2 days.

Two coats of premium topcoat (Sherwin-Williams Emerald or Benjamin Moore Aura) takes another 4 to 6 days on a home this size. Total project costs range from $35,000 on the low end (lighter restoration, smaller footprint) to $80,000+ on the high end (heavy carpentry, large footprint, complex architecture).

A homeowner in original Deerwood inherited a 1981 cedar-lap-sided estate that hadn’t been painted in over a decade. Three other contractors had quoted a straight repaint, two had told her the home ‘needed to be re-sided,’ and one had walked away from the project entirely. We spent two days on initial inspection — probing every elevation, mapping rot zones, and identifying which boards could be restored versus replaced. The final scope: 38 boards fully replaced (matched to original cedar profile from a specialty supplier), 12 board sections partial-cut with PVC patches, full sand-and-restore on the remaining 80 percent of siding, oil-based stain-blocking primer on every bare wood surface, and two coats of Sherwin-Williams Emerald in a custom-matched color. Six weeks of work, total project cost in the mid $60,000s. Five years in, the topcoat is intact across all elevations and the homeowner has had zero callbacks. The ‘cheaper’ bids would have failed within 18 months.

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A New Leaf Painting is Jacksonville’s most reviewed painting contractor — founded in 2010 by Thomas Drake and trusted by more than 5,000 homeowners and business owners across Greater Jacksonville, Ponte Vedra Beach, Nocatee, Fleming Island, Amelia Island, and all of Northeast Florida. Our 700+ reviews across Google, Facebook, Angi, Yelp, BBB, Houzz, and Nextdoor reflect one thing above everything else: a painting experience that actually feels easy. From the first phone call to the final walkthrough, every project is backed by proper preparation, premium exterior house painters near me and reliable interior painting contractors near me painting products from Sherwin-Williams® and Benjamin Moore®, and our Iron-Clad Guarantee — professional results or your paint is 100% free.

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