Lessons from Local Leaders:

Kristen Winters

From Corporate “Widgets” to Keys in Hand: How Realtor Kristen Winters Built a Purpose-Driven Life in Real Estate

When Kristen Winters left Kansas for Northern Virginia after the 2008 downturn, she didn’t expect the road to wind through a decade in corporate tech, single motherhood, and a pandemic before landing in her true lane: helping people build home.

Today, Kristen is a Long & Foster real estate agent serving all of Northern Virginia and into West Virginia—especially Jefferson and Berkeley counties. Licensed in both states, she brings a rare mix of creativity, tech chops, and deep empathy to every transaction.

The detour that taught her grit

With a background in studio art and psychology, Kristen originally worked in web design, then spent nearly ten years in a tech role at Gannett/USA TODAY. The job was “good on paper,” but stifled the soft skills she loved most—listening, problem-solving, and human connection. As a newly single mom of two in NOVA, she shouldered stability over passion…until 2020 forced a reset.

When the market shifted, so did she

The pandemic brought remote work, a frenzied housing market—and clarity. After being repeatedly outbid as a one-income buyer, Kristen decided to change sides of the table. Real estate offered what corporate never could: one-to-one purpose. Every hour invested directly helped a family find safety, stability, and joy.

She took the leap, lived on her saved down payment for a season, earned her license, and—eventually—bought a home in Harpers Ferry, WV. “Real estate gave me back time with my kids and a mission I believe in,” she says.

Empathy you can feel

Kristen’s teens live with POTS and Ehlers-Danlos, conditions that require daily management. That lived experience fuels her patience and advocacy for clients juggling complex realities—tight timelines, accessibility needs, or financial constraints. She listens longer, explains more clearly, and fights for fair outcomes.

What she loves most (besides a great velvet blazer)

Call it “adventure real estate.” Kristen lights up touring historic homes, spectacular new builds, and raw land parcels (even the kind where you hike through brambles to find the lot line). She’s as comfortable workshopping a site plan as she is styling a listing—her art/design eye shows up in every prep and photo day.

Her north star: trust yourself

If there’s a theme to Kristen’s journey, it’s this: self-trust fuels self-worth. She encourages clients—especially women and single-income buyers—to trust their intuition, make informed moves, and keep going through the inevitable ups and downs.

“You can’t let a job title—or a market—define your value. Determine it for yourself. Then build the life that matches.”

Work with Kristen

• Areas served: All of Northern Virginia + Jefferson & Berkeley Counties, WV
• Specialties: First-time buyers, single-income strategies, move-ups/downsizing, land & lifestyle properties, historic charmers, cross-border VA↔WV transactions
• What you can expect: Calm communication, creative problem-solving, and a champion who treats your transaction like her own

Ready to find your footing—and your front door? Kristen’s here for the journey.

Reach Kristen Winters Below