Siding Contractors in Southold, NY

Siding Southold's Oldest Houses the Right Way

Southold hamlet is one of the earliest English settlements in New York, and the housing stock along Main Road, Oaklawn Avenue and the streets near the Presbyterian church reflects that. There are 1700s and 1800s houses under hand-split cedar, Greek Revivals with clapboard, and Victorians with every kind of trim. Away from the center, Bayview and the Sound-side lanes have postwar capes, ranches and contemporaries. AP Siding & Windows installs real cedar shake and board and batten where owners want to honor the house, and fiber cement, vinyl shake or insulated vinyl where they want the look with less upkeep. Windows and roofing ride along.

Southold hamlet is squeezed between Long Island Sound and Southold Bay, so nearly every house gets water on one side or the other. The Sound bluff lots off Soundview Avenue take winter northwesters that sandblast a north wall. Bayview and Founders Landing face south over the bay and get salt on a mild breeze all summer. Cedar has survived here for centuries because it was installed with air behind it, and we build the same way now, with a drainage gap, breathable wrap and stainless fasteners. On vinyl and fiber cement jobs we tighten the nailing and double the flashing on whichever elevation faces the water.

Siding styles we install

Horizontal Vinyl Lap Siding

The classic look for capes, ranches, and colonials. Low maintenance, dozens of colors, and never needs painting.

Cedar & Cedar-Look Shake Siding

The signature look out east. Choose real cedar, or cedar-look vinyl and fiber cement shingles that skip the staining and splitting.

Board & Batten Siding

Vertical siding for farmhouse, modern, and coastal exteriors, often mixed with lap siding for contrast.

Fiber Cement Siding

The premium option: heavy, fire-resistant, and very durable, with a real painted-wood look.

Signs it's time to replace your siding

• Cracked, warped, or loose panels, especially after a storm
• Faded or chalky color that no longer cleans up
• Soft spots, rot, or mildew along seams and trim
• Water stains or peeling paint on interior walls
• Drafty rooms and rising heating and cooling bills

Siding and windows in one project

Replacing windows at the same time as siding is the smartest way to do both. With the old siding off, new windows can be flashed and sealed properly on every side, and all the exterior trim comes out clean and consistent. You get one crew and one schedule for the whole exterior.

How We Replace Siding in Southold

1. Free on-site estimate We measure, look for hidden damage, and go over materials and colors with you. You get a clear written quote.
2. Tear-off We remove the old siding down to the sheathing and protect your landscaping and walkways.
3. Repairs underneath Any rotted or damaged sheathing is replaced before anything new goes on.
4. Weather barrier and flashing We install house wrap, then flash windows, doors, and corners.
5. New siding and trim We install siding, soffit, fascia, and trim to manufacturer specifications so your warranty stays valid.
6. Cleanup and walkthrough We haul away all debris, sweep for nails with a magnet, and do a final walkthrough with you.

Southold at a Glance

ZIP

11971

Township

Town of Southold

Permits

Town of Southold Building Department

County

Suffolk County

Estimates

Free, in person, written price after measuring

Crew

In-house, based in East Northport

Where We Work in Southold Hamlet

The historic core along Main Road, Youngs Avenue and Oaklawn Avenue near the Custer Institute and the Southold Historical Society has the hamlet's oldest cedar-clad houses. Founders Landing and the streets off Terry Lane sit right on Southold Bay, with a mix of summer-turned-year-round cottages and newer waterfront homes. Bayview, across Jockey Creek, is a peninsula of ranches, capes and contemporaries on bay and creek lots. North of Route 48, Soundview Avenue and Kenney's Beach are the bluff and beach-cottage area. The lanes between Route 25 and Route 48, like Boisseau Avenue and Horton Lane, hold mid-century houses on former farm ground.

Southold Hamlet, Bayview and the Sound Shore

We serve all of Southold hamlet, from the Sound bluffs and Kenney's Beach down through the historic center to Founders Landing and the Bayview peninsula. Southold is the hub of our eastern North Fork block, so Peconic, Cutchogue and Greenport jobs are usually scheduled around a Southold install and the same crew covers them all.

• Peconic, NY
• Cutchogue, NY
• Greenport, NY
• Mattituck, NY
• Orient, NY
• Jamesport, NY

Frequently asked questions

What does it cost to re-side a historic house in Southold?

Historic houses carry more trim, taller walls, and often a cedar or board and batten choice that costs more than vinyl. Beyond that the price follows the same factors as any job: measured square footage, material, how much old siding comes off, and trim and window wrap. Vinyl is cheapest, fiber cement and cedar sit higher. We measure on site; the quote goes in writing.

Do I need a permit to re-side a house in Southold hamlet?

Southold hamlet is unincorporated, so the Town of Southold Building Department on Main Road is the permit authority. Replacing siding in kind usually does not need a permit. Structural repair, new window sizes, or work on a designated landmark does, and landmark facades also go to the Historic Preservation Commission. We check your property's status before quoting and handle the filings.

Is cedar shake still a good choice in Southold with the salt air?

It is, if installed the way the old houses were. Cedar lasts on the North Fork when it can dry from behind, so we use a rainscreen gap, breathable wrap and stainless nails, and we tell you the water-facing wall weathers faster. If you want the look without the sealing schedule, vinyl shake or fiber cement shingle panels hold the profile with little upkeep.

How long does siding take on a Southold home?

Plan on three to five working days for vinyl on an average Southold cape or ranch. The old Main Road houses take longer because of trim and the repairs we find under original shingles, and cedar or fiber cement hangs slower. We block out eastern North Fork work so your crew stays through to the end. Sound or bay weather can add a day.

Can you replace windows along with the siding on my Southold house?

Yes, and on the older houses it is the only clean way to do it. With the siding off we can pull weighted wood sash, set new vinyl or fiberglass double-hungs, casements, bay and bow, sliders, awning or custom-shaped units, and flash them properly to the sheathing. We also offer period grille patterns for the Main Road houses so the look holds from the street.

My Southold house is a designated landmark. What does that mean for siding?

Southold Town's landmark chapter requires a certificate of appropriateness from the Historic Preservation Commission before the street-facing facade of a designated landmark is altered, and the Building Department will not issue a permit without it. That generally means matching material and profile, so cedar stays cedar. We have prepared these applications before, bring samples to the meeting, and sequence the job around the approval.

Why Southold Homeowners Choose AP

• In-house crews. Our own installers do the Southold work, including the cedar and board and batten jobs that need a steady hand. We do not farm historic houses out to a sub.
• Written price after we measure. We measure every elevation, note the trim and any landmark constraints, and give you a written price before you commit to anything.
• Based nearby in East Northport. Southold is a little over an hour from our shop along the LIE and Route 48, so we do not run out for a single afternoon. We schedule North Fork jobs in blocks and the crew stays on site until your house is finished.