ENRG SPOTLIGHT: Cheryl Kebalo - Building with Grace, Leading with Heart

From Respiratory Therapy to Real Estate Legacy

Cheryl Kebalo, state broker for ENRG Connecticut.

Some careers begin with a plan. Cheryl Kebalo’s started with a suggestion. After years in the medical field and while raising her family, Cheryl’s husband invited her to join the family business—a development project transforming their Connecticut farmland into a 55+ community. What began as a supportive gesture quickly evolved into a passion. With encouragement from her husband’s aunt, Cheryl earned her real estate license—and never looked back.

That one decision sparked a two-decade career marked by vision, leadership, and an entrepreneurial drive that would see her rise from top-producing agent to owning and operating seven RE/MAX offices across Connecticut. Along the way, she cultivated a culture of family, excellence, and growth—transforming mergers and acquisitions into opportunities for legacy and trust.

Saying Goodbye to Brick & Mortar

In 2016, a startling stat—only 20% of brokerages were profitable—rocked Cheryl’s perspective. Though her own business was thriving, she saw the writing on the wall. By 2018, she sold her RE/MAX offices, recognizing the industry’s shift away from traditional offices toward cloud-based, scalable models. “It took humility and self-reflection,” Cheryl said, “but stepping away gave me the chance to evolve.”

In 2020, she joined eXp Realty alongside her daughter, Alexa. Together, they embraced a progressive model and expanded their downline. But over time, the recruiting-heavy culture felt misaligned with Cheryl’s deeper values. “I just wanted to focus on real estate—on helping clients and building something meaningful,” she shared.

Finding a New Home at ENRG

Cheryl’s journey to ENRG Realty began with a nudge from an industry peer. From the first conversation with founders Erinn and Peter, Cheryl knew she’d found her place. “They’re salt-of-the-earth people,” she said. “Down-to-earth, forward-thinking, and committed to doing things differently.”

What stood out most to Cheryl? ENRG’s boutique model and emphasis on agent productivity over recruitment quotas. “To me, ‘boutique’ means elegant, intentional, gracious. It’s a business that feels like family,” she explained. “Culture matters. Being seen and supported matters.”

That focus on culture mirrors Cheryl’s own leadership legacy. When she still had her brokerages, she hosted holiday parties at home for 60+ agents and their families—building deep community through food, hospitality, and heartfelt connection.

A Heart for Entrepreneurship and Inspiration

Throughout her career, Cheryl has stayed grounded in her core values: entrepreneurial spirit, integrity, and the power of positive energy. “A positive attitude is contagious—it creates extraordinary results,” she shared. Her guiding belief? That success is measured not just in what we achieve, but in how we inspire others.

Cheryl’s accolades—like the Woman of FIRE Award and RE/MAX’s Office Expansion recognition—are testaments to her vision and leadership. But her proudest moment? Walking away from brokerage ownership when she realized the model no longer served her. “If I had been driven by ego, I would’ve stayed. Instead, I evolved.”

Family First, Always

Outside of real estate, Cheryl finds joy in lake life, family dinners, and experimenting in the kitchen. A passionate cook, she blends her Italian heritage with a modern twist—crafting gluten-free, health-conscious meals that nourish both body and soul. Her two granddaughters, whom she lovingly calls her “baby dolls,” keep her heart full and her weekends busy.

A New Chapter Begins

Now, as the state broker for ENRG in Connecticut, Cheryl is ready to bring her full self—experience, values, and vision—to a brand aligned with everything she believes in. “I’m honored to be the chosen broker for Connecticut,” she said. “This is a new beginning, and I couldn’t be more excited.”