Valley Champions - Kline May Realty

Valley Champions

Isai Bradshaw & Nakaila Gray — REALTORS® with Kline May Realty

Two Shenandoah Valley natives. One championship mindset. Isai and Nakaila bring athlete-level dedication, deep community roots, and a team-first approach to every real estate transaction. Whether you’re buying, selling, or investing in the Harrisonburg and Rockingham County market, the Valley Champions are in your corner.


Isai Bradshaw

REALTOR®
isai.bradshaw@klinemay.com
540-228-0277

As a Harrisonburg and Rockingham County real estate professional, I combine local expertise, community connections, and a long-standing reputation for trust and integrity to help clients achieve their real estate goals. With over two decades in the Shenandoah Valley area, I bring both deep regional insight and a people-first approach to every transaction, whether you’re buying, selling, or investing in Virginia real estate.

Originally from Cambridge, Massachusetts, I moved to Harrisonburg in 2002 to attend James Madison University (JMU), where I played football, earned All-Conference honors, and contributed to the team’s 2004 NCAA Division I-AA Football Championship and a Hall of Fame honoree. My years as a student-athlete instilled discipline, teamwork, and leadership: qualities I now apply to real estate every day.

After graduation, I continued building strong community relationships as a JMU football coach for seven years. My professional background includes a management career with Enterprise Rent-A-Car, where I led three branch locations and developed high-performing teams focused on top-tier customer service. I later transitioned into the insurance industry, helping families across the Valley protect their homes and financial futures. These experiences reinforced my belief that clear communication, strong relationships, and consistent follow-through are the foundation of success, both in business and in life.

Today, as a Realtor serving Harrisonburg, Rockingham County, and the greater Shenandoah Valley, I’m dedicated to guiding clients through every step of the real estate process. From first-time homebuyers to seasoned investors, I provide personalized service, local market insight, and professional negotiation skills that deliver results.

Beyond real estate, I’m a proud husband, father of four, and grandfather of two. I have stayed active in the local sports community by coaching at Spotswood High School and Harrisonburg High School, as well as Rockingham County Recreation flag football.

If you’re ready to make your next move in the Harrisonburg or Rockingham County real estate market, I’m here to be your trusted guide every step of the way.

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Nakaila Gray

REALTOR®
nakaila.gray@klinemay.com
540-214-7553

The Shenandoah Valley has always been home to me, and it’s where my passion for helping others began. Growing up in Rockingham County gave me a deep appreciation for this community. My goal in real estate is to guide, support, and advocate for my clients every step of the way.

I attended both Broadway High School and Spotswood High School, where I had the unique opportunity to win the Virginia 3A State Championship in basketball at both schools. Being a student-athlete shaped who I am today, teaching me discipline, accountability, teamwork, and perseverance. These are qualities that directly influence how I approach my work with clients.

I continued my basketball career at Concord University in Athens, West Virginia, where I further developed a strong work ethic and a commitment to achieving results. While I valued my time there, I always knew that the Shenandoah Valley was where I wanted to return, build my future, and serve my community.

After graduating, I worked in student housing, where I discovered a passion for helping people navigate important housing decisions. That experience confirmed what drives me most: being a trusted resource for others during meaningful life transitions.

As a real estate professional, I bring the same dedication, focus, and team-oriented mindset that I developed as an athlete. I am committed to working hard, communicating clearly, and always putting my clients’ best interests first.

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