From Castle to Cozy: Jerri's Cakery Finds Its Sweet Spot in Eastport

Not every happy ending involves a castle.

For seven years, the iconic, century-old Theophilus Brouwer castle in Westhampton Beach was home to Jerri’s Cakery & Confections — a whimsical setting for a beloved local bakery. But despite its fairy-tale charm, the castle came with some less-than-enchanted quirks. Its curved concrete walls made display space nearly impossible. The plumbing was outdated. And the whole place had a bit of a gloomy vibe.

So when building owners Bejto and Zyli Bracovic sold the property to the Town of Southampton, it marked a kind of Cinderella story in reverse. And for Jerri’s Cakery & Confections owner and baker Jerri Raynor Montillo, that was exactly the fresh start she needed.

“As charming as being in the castle was, we definitely needed something a little new,” Montillo said. “In general, a building that is 120 years old is just always inconvenient ... the castle was a little foreboding. We needed something that was a little bit more updated — and definitely something a little more inviting.”

Earlier this year, Montillo became queen of her own kingdom, relocating just seven minutes away to a cozy storefront on Eastport’s Main Street (495 Montauk Highway). With big, bright display windows, space for parties and workshops, and enough room to showcase her full range of baked goods, the new space is everything the castle couldn’t be.

On February 22, Jerri’s Cakery & Confections officially opened its doors — not just as a cake shop, but as a neighborhood bakery serving fresh pastries, cookies, coffee and community.

“It’s nice to be able to have pastries and cookies on the regular and little cakes ready to go,” Montillo said. “I want people to be able to come in and get a cup of coffee and a pastry or a cookie and sit down.”

Inside, the bakery is designed for comfort — with benches, pillows, books, and games — and plenty of space to admire (and devour) Montillo’s latest creations.

The menu is larger and more dynamic than ever. Think: rugelach, scones, muffins, Venetian rainbow cookies, blondies and blondie bites, brownies, black-and-white cookies, cannolis, cupcakes (including cookie-bottom ones), “big chippers” cookies, and seasonal and holiday-themed goodies. On weekends, there’s a rotating menu of freshly baked breads to explore.

New this Labor Day weekend, Jerri’s introduced “dirty sodas” — fizzy egg-cream-style drinks made with gourmet soda and cream. There’s always something new to try, and regulars are encouraged to check out the weekly bread schedule on social media.

Workshops are also making a comeback this fall — keep an eye on Instagram (@jerricakesdotcom) for announcements.

Of course, custom cakes remain a staple. Whether it’s a birthday, wedding or themed celebration, Montillo’s cakes are one-of-a-kind.

“It’s never the same thing twice,” she said. “It’s always about telling a little story via dessert.”

Many of her cakes are creative mashups — a Harry Potter-Star Wars hybrid for a Sweet 16, for example — or imaginative tributes to clients’ hobbies. One wedding cake idea involved a couple’s dog playing fetch with arrows (they loved archery). Other standout cakes include a sushi platter made of candy and mini-cakes, a piggy bank cake with mini cookie “coins,” and a skull cake filled with red-dyed caramel.

If those sound like something out of Ace of Cakes or The Great British Bake Off, you’re not far off — though Montillo jokes she hasn’t had time for TV since opening her business in 2009.

“I’ve always been baking or managing the shop,” she said.

Though the bakery itself is under a decade old, Montillo has been professionally baking for over 17 years, supplying sweets to restaurants and businesses across the region. Her passion for desserts began much earlier.

“I come from a huge family, so there was always a birthday cake,” she said. “In the beginning, it was more about having something chocolatey or lots of vanilla sweet for our baked goods.”

Now, it’s about providing something meaningful — not just a dessert, but a full experience. And she’s excited to do more of that in Eastport.

“I’m looking forward to Halloween,” Montillo said, noting she plans to go all out decorating the shop’s windows for Eastport’s Trick-or-Treat on Main Street.

“The kids are the best part of this whole thing right now — being amazed and awesome. We love kids here,” she said. “We’re probably going to open up the space for parties. We’re just trying to nail that down a little bit because it is a very fun space.”

Jerri’s Cakery & Confections, now located at 495 Montauk Highway in Eastport, is open daily starting at 8 a.m.