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Hillary Ottaway Virginia Beach, VA Real Estate Agent Headshot

Hillary Ottaway

Real Estate Agent

Get To Know Me

I am a lifelong resident of the Hampton Roads area, with deep roots in the community. My father proudly served in the U.S. Navy for 32 years, allowing me to experience life in both Norfolk and Virginia Beach while growing up. I graduated from Kempsville High School in 1987 and have since built a life centered around family, real estate, and the incredible lifestyle this region offers.

I am happily married and the proud mother of two amazing children. Lilly, 17, has a deep passion for horses and is a natural across multiple riding disciplines. Ryan, 15, is an incredibly driven and self-taught athlete whose latest passion is golf—he currently plays for the Windsor High School Golf Team. Our family also includes Willow, our sweet five-year-old English Chocolate Lab, and Coco, our beloved eight-year-old Thoroughbred.

Throughout my life, I have had the privilege of living in Virginia Beach, Chesapeake, Suffolk, and now Windsor, where my husband and I built our dream home on 4.4 acres in 2022. While I have always loved the beach, I also appreciate the peacefulness of country living. Hampton Roads provides the perfect balance of both, offering diverse lifestyle options within just a short drive. Our family enjoys taking full advantage of the area's many recreational opportunities, including boating, farm life, and the numerous parks and outdoor activities available.

My journey in real estate began in 2020, and since then, I have helped clients buy and sell 95 properties, totaling $28 million in sales over just 48 months. My firsthand experience in real estate extends beyond my career—I have personally bought five homes and sold six, including four new construction properties. This experience gives me a unique perspective on the buying and selling process, allowing me to guide my clients with confidence and insight.

Negotiation and communication are two of my strongest skills, which have allowed me to secure winning offers in competitive, multiple-offer situations. I approach real estate with a strategic mindset, always prioritizing my clients’ best interests. Beyond the transactions, I value the relationships I build and take pride in helping my clients find not just a house, but a home that fits their needs, lifestyle, and long-term goals.

I believe that buying a home is a step toward stability, opportunity, and long-term wealth. I have a deep passion for helping people find security and independence through homeownership. Owning a home isn’t just about having a place to live … It's about having a space where you feel in control, where you make the rules, and where you can build a future on your own terms. Whether it’s a first-time buyer looking for a fresh start, a growing family needing more space, or someone overcoming challenges to achieve homeownership, I love being part of that journey. Helping people step into that next chapter with confidence is one of the most rewarding parts of what I do.

I would love the opportunity to sit down with you and discuss your plans for buying or selling a home. With my personal experience and professional expertise, I am confident I can provide valuable guidance throughout the process. Feel free to reach out—I am happy to answer any questions you may have!

Theodore W.
Buyer
Buyer
WHAT MY CLIENTS SAY

End to End (viewing properties to closing day) Hillary was amazing, she understood our wants, and needs and helped us find the perfect house in the price rang and area we wanted. She was very professional, friendly, engaging, a great listener and very knowledgeable, if she didn't know something or needed to get an answer she had it within the hr. When looking at properties it's easy to get excited and ov...

— Theodore W.

WHAT MY CLIENTS SAY

We worked with Hillary a little over a year ago when it was still a seller's market, and between interest rates steadily climbing and bidding wars occurring on the homes were wanted, we had to put a hold on our purchase. During this time, Hillary remained in contact with us while also providing information on the areas we were previously seeking to purchase a home. She sent us information on a condo and ...

— Buyer

WHAT MY CLIENTS SAY

Hillary is amazing and I would recommend her to anyone purchasing or selling a home. She is kind, honest, and very responsive. I would definitely contact her again for buying or selling in the area.

— Buyer

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I love helping my clients find the house that fits them, their family and their budget best. The relationships that I get to form are more important then just making transactions.