Upstate Down boutique real estate company merges home sales and design

Walking into the Upstate Down storefront on Rhinebeck’s East Market Street feels more like entering the home of your most stylish friend, not a real estate brokerage firm.

A front window papered in home listings is replaced by an airy entrance, white open shelving boasting buys that range from vintage wooden bowls and plush pillows to kitchen accessories. Further back, the business of buying and selling makes itself known, but only slightly so — single shots of homes that are available for sale or rent line adorn gallery walls in gold frames, an arrangement that reads more like decor than a sales pitch.

It’s a fitting juxtaposition for two entrepreneurs who are set on transforming the way real estate is done in the area.

“The reality is, we want to be a brand and a company that — whether someone wants a pillow because it helps bring joy to their living room, to buy a new house, to sell their current house, [or needs] a consultant on a rental or to maximize the existing value of their home — we want to be there to service all those people,” said co-owner Delyse Berry.

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In designing a multi-pillar brand that serves local buyers and sellers throughout their entire life cycle, she and her partner and husband Jon Berry have struck upon a unique formula. But it wasn’t always this easy.

Married at 21 (Delyse) and 24 (Jon), and thrust into the trenches of parenthood shortly thereafter, the pair began their life together in Brooklyn. Jon put in long, unforgiving hours at a finance firm that asked much but paid little, while Delyse took to raising their brood of three young children. They were on government assistance at the time, their zeroed-out bank account a constant reminder of what was at stake as they built their family and chased their dreams.

“We were totally broke, madly in love, and just sort of like — let’s figure life out,” laughed Delyse. The duo ditched Brooklyn, heading north to the Hudson Valley in search of opportunity, a cheaper cost of living, and a slower pace of life.

For her part, Delyse, who originally hails from New Jersey, always had her sights set on the real estate market. The daughter of an interior designer, she began to feel the pull of the workforce as their children got older. While working towards her real estate license, she began asking her mother’s local clients if they’d allow her to manage their home rentals on Airbnb, which was new at the time, creating an unconventional entry into a burgeoning real estate market that ended up paying off in more ways than one.

“The owners were gaining a lot of trust in me as I managed their homes, and the guests staying there also became familiar with me,” explained Delyse. “It became so much easier for me to break into the area’s multimillion-dollar market because I was establishing these relationships.”

A decade-long successful career as an agent followed, but Delyse found the industry lacking a focus on the importance of interpersonal relationships and multiple touchpoints throughout the lifecycle of a client.

“I was unimpressed by the way real estate traditionally functions up here,” she said. “The traditional model is, you know, an agent puts a home in a multiple listing service and it gets fed to large brokerage sites. I just felt like the models haven’t changed, yet real estate has changed so much. What is the future of real estate that can’t be replaced by an algorithm? It’s thinking outside the box and inventing yourself in a new way that actually produces value for clients.”

Delyse imagined a multi-dimensional real estate business that focused not only on getting clients into the right homes but helping them rent out their properties, stage them for selling, navigate the renovation process, and design them for approachable living.

“The Hudson Valley has been an emerging market long before COVID hit — the more people catch on to the authenticity of the lifestyle and how incredible it is, the more it builds, and I’m so excited by that,” she explained. “I really wanted to develop a brand of services that bundled both real estate and design elements, from the perspective of people who really believe in the area.”

Jon had spent the past 10 years establishing himself in the financial world, working his way up to a senior position at Morgan Stanley but all the while questioning if that’s where his true passion lay. Growing up in Delaware, Jon lost his mother to cancer at the age of 14, giving him a unique perspective on the brevity of life. “As I neared my mom’s age, I thought to myself — if these were the last 10 years of my life, do I really want to spend this time behind a desk doing a lot of things that just don’t make me feel well?”

The answer was a resounding “no” and, after a soul-searching anniversary trip in early 2018, he left his established career to join Deylse in growing the brand that the two soon dubbed Upstate Down.

“When he decided to leave [his job], it gave me the confidence to say, let’s let some of these dreams come true,” Delyse said of the pivotal role Jon’s presence made in the business. “His endless support gave me the freedom to try and create something incredible.”

The pair grew their team, taking on their first full-time hire in 2019 and building a roster of properties all around the area, from homes for sale in Amenia and La Grange to rental properties in Clinton Corners and their hometown of Rhinebeck. Learning to translate their passion for each other — and their family — into a business relationship was a challenge too, but one the pair took head-on like everything else.

“Figuring out how to keep everything in its lane and let this be a great opportunity to create a stronger foundation in our relationship, instead of a negative, was something that we had to really learn,” explained Delyse. “I think we both felt really strongly about our commitment to figuring it out.”

That positive attitude proved pivotal this past year. Suddenly, the successful business the two built was at risk due to stay-at-home orders — and then, just as quickly, real estate was in excessive demand thanks to buyers looking for long-term rentals and snatching up inventory faster than you could say “sold.” Delyse and Jon found the pandemic the perfect time to level up their business yet again — this time, with a storefront in Rhinebeck’s buzzing village, which opened its doors at the beginning of June.

Delyse and Jon Berry have translated their passion for each other and their family into their working relationship, too. "I hope we're teaching our kids that the goal is to do what you love in conjunction with who you love," said Jon. 

Delyse and Jon Berry have translated their passion for each other and their family into their working relationship, too. “I hope we’re teaching our kids that the goal is to do what you love in conjunction with who you love,” said Jon. 

Sharon Schuster courtesy Upstate Down

“To be completely honest, we thought we were going to function predominantly from home and do design projects and brokerage, but within a couple of weeks, we saw the property for rent and I was like, we have to go see it,” said Deylse.

The pair were hyper-conscious of using the storefront to fulfill multiple needs for their community, meeting locals “where they were at” and connecting with residents whether they had a home to sell or not.

“I love that it’s a store when you first go in because it lets us really emphasize the lifestyle part of the brand by creating a little perspective on real estate and interiors that everyone can access through purchasing,” said Delyse.

Often thought of as one of those movie-perfect quintessential Hudson Valley towns, Rhinebeck has proven to be the perfect location for the first iteration of the Upstate Down brand — though it certainly won’t be the last. The duo say they’re “100 percent positive” there will be another Upstate Down storefront within the year, though they’re still deciding on where.

“Coming out of Brooklyn as an interracial marriage, raising three kids, we were really sensitive to being in a community where you know you are welcome,” said Delyse. “It’s been just like, an extra gift of being here, to know that we’ve felt nothing but total love and inclusion from our community.”

The pair are already indoctrinating their children into the family biz. When the family chose to rent out their primary residence during the peak of the pandemic while they stayed in a 700-square-foot cottage on the property, they gave each child $5 a day from the rental income the couple was earning. Jon described the opportunity as a good chance for the kids to learn mobility, while Delyse instituted the kids’ rental income to help the trio foster ownership over their space.

Ultimately though, it’s not so important to Delyse and Jon that their children follow in their real estate footsteps as it is that they have the same passion for what kicked off the couple’s whole journey to begin with: love.

“I hope we’re teaching our kids that the goal is to do what you love in conjunction with who you love,” said Jon. “Like taking care of family first and building our life around our family, but simultaneously never being too afraid to go after it.”

“We followed our hearts,” added Delyse, summing up their journey towards marital and entrepreneurial success thus far. “I hope they’re able to do the same.

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