Some roofs are just roofs. This one is part of a story.

Tucked into the farmland outside Kingston, NY, this property has been standing for well over a century — original stone walls, a working barn, and the kind of Hudson Valley setting that makes you slow down on the drive in. The main house has grown over the generations: a stone core from the 1800s, later wings and additions, dormers, a sunroom. Every era left its mark on the roofline.

When the owners decided it was time for a new roof, the goal wasn’t just to stop leaks. It was to give a historic home a roofing system that matches its character, ties all of those eras together visually, and outlasts another generation. Here’s how we did it — and what any owner of an older Hudson Valley home can learn from this project.

The Scope: One Roof, Not a Patchwork

This was a full tear-off and replacement covering 68 squares — roughly 6,800 square feet of roofing across the main house, its wings, and the sunroom addition. Every slope, valley, dormer, and ridge came off, down to the wood deck.

That last part matters more than most homeowners realize. A roof that has been added onto for decades usually hides a mix of decking from different eras: original plank boards in one section, plywood from a 1980s addition in another, and soft spots wherever an old leak went unnoticed. Stripping everything to the deck let us inspect every square foot, replace the compromised sections, and build the new system on a sound, uniform base. We also brought the ventilation up to modern standards, so the attic breathes properly under the new roof — the quiet detail that determines whether shingles age gracefully or cook from below.

The result is one continuous, seamless system instead of a patchwork of repairs — every plane of this complex roofline protected by the same underlayment, the same flashing details, and the same warranty.

Why IKO Dynasty in Brownstone

For a home surrounded by stone, timber, and open field, color matters as much as performance. The homeowners chose IKO Dynasty architectural shingles in Brownstone — a blend of warm earth tones, from tan to soft charcoal, that reads almost like natural wood shake from the ground. Against the dark siding and the original stonework, the new roof looks like it has always belonged there. That’s exactly what you want on a historic property: a roof that disappears into the character of the home instead of announcing itself.

Under the surface, Dynasty is a serious performance shingle. It carries a Class 3 impact-resistance rating, and its defining feature is IKO’s ArmourZone — an oversized, reinforced nailing strip woven into every shingle. A wider nailing zone means fewer misplaced fasteners during installation and dramatically better resistance to nail pull-through when the wind starts working on the roof. In a region that sees nor’easters, ice storms, and months of freeze-thaw cycling every winter, that reinforcement is the difference between shingles that stay put for decades and shingles that start lifting at the edges after a few hard seasons.

Seventeen Skylights, One Idea: Let the Light In

The most transformative part of this project isn’t visible from the street at all. Working with the homeowners, we installed 17 VELUX skylights across the roof — rows along the main slopes, and a dramatic six-unit grid over the sunroom that floods the space below with daylight from morning to evening.

Old farmhouses are famously dark. Thick walls, small windows, deep rooflines — beautiful from outside, dim within. Skylights solve that without touching a single historic wall. After this project, nearly every room in the house gets natural light from above, and the sunroom feels like a different building entirely.

How We Install Skylights That Never Leak

Skylights have a reputation problem: ask any homeowner what they fear about them, and the answer is leaks. The truth is that skylights don’t leak — bad installations do. And the only right time to install them is during a roof replacement, when the deck is open and the skylight can be built into the roof system instead of cut into it later.

Every one of the 17 VELUX units on this roof was installed the same way: the opening framed and squared, the curb wrapped in ice and water shield that laps into the surrounding underlayment, and VELUX factory flashing kits woven step-by-step into the shingle courses. No caulk-and-hope shortcuts, no universal flashing bent to fit. Done this way, a skylight is simply part of the roof — it sheds water the same way every ridge and valley does, and it will still be dry when the shingles around it are due for their next replacement. Installed this way, with genuine VELUX flashing, every unit also qualifies for the manufacturer’s 10-year No Leak installation warranty — on top of our own workmanship guarantee.

What It Takes to Re-Roof a Historic Home

A century-old farmhouse doesn’t have the forgiving, uniform geometry of new construction. Rooflines settle over the decades. Additions from different eras meet at odd angles, creating valleys and transitions that were never on any blueprint. Where the new roof meets the home’s original 1800s stone gable, flashing has to be fitted to hand-laid stone rather than straight modern framing.

This is where experience earns its keep. Our crews re-engineered every transition, custom-fit the flashing against the stonework, and treated each section of this roof as its own small project within the larger one. It’s more work upfront. It’s also the only way a roof on a home like this earns its full lifespan — and the reason we never quote a historic home without walking it first.

The Finished Roof

From the air, you can see the whole idea of this project in a single frame: warm Brownstone shingles wrapping every wing of the house, seventeen skylights catching the sky, and the original stone gable standing exactly as it has for more than a century — now protected by a roof built to modern standards. Old bones, modern performance.

Roof Replacement in Kingston and Ulster County

Home Evolution Roofing has been protecting homes across Upstate New York for 20 years — more than 17,500 projects completed, 930+ Google reviews, and a BBB A+ rating. From our Poughkeepsie office we serve Kingston and all of Ulster County, from historic farmhouses like this one to new builds.

If your roof is showing its age — or you’ve been dreaming about skylights — send us your address. We’ll take a look and give you a straight answer about what your home actually needs.