A Family Brokerage Built on Trust, Results, and Community

We're a boutique brokerage rooted in Winter Garden, proudly recognised as one of Orlando's Top 3 Best Brokerages in 2024. Our team delivers hands-on real estate and property management services built around long-term relationships — not one-off transactions.

Real Estate
our mission

We are a family-owned boutique brokerage rooted in the heart of the Winter Garden community, proudly recognised as one of Orlando's Top 3 Best Brokerages in 2024.

For us, this business is personal. This is our home, and we care deeply about the people, properties, and relationships we build here.

What sets us apart is our hands-on, relationship-driven approach combined with expert-level property management and real estate strategy. Whether you're a homeowner, buyer, investor, or landlord, we provide tailored solutions designed to protect your asset, maximise your return, and simplify the entire process.

From helping you buy or sell with confidence to managing your rental property with precision and care, our team is here to guide you every step of the way.

At Winter Garden Real Estate & Property Management, we don't just complete transactions — we create long-term partnerships built on trust, communication, and results while contributing to the growth and vitality of the community we love.

AREAS WE SERVE

Local Expertise Across Central Florida

Rooted in Winter Garden, serving the communities we know and love.

Meet the team

THE PEOPLE BEHIND THE RESULTS

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Anthony O'Reilly-Brookes—Broker/Owner

With over a decade of experience in sales and marketing and a Master's degree from Oxford Business School, Anthony brings a wealth of knowledge and expertise to the real estate industry. After moving his family to the U.S. from the U.K. in 2011, he quickly became a trusted resource for buyers and sellers in the local market.

Anthony earned his real estate licence in 2013, followed by his Broker licence in 2020. With a passion for helping homeowners and investors maximise their real estate potential, he founded Winter Garden Real Estate & Property Management — a company dedicated to providing exceptional service and peace of mind to property owners.

Whether you're looking to buy, sell, rent out your home, manage an investment property, or need a reliable team to oversee your portfolio, Anthony is committed to ensuring you feel supported every step of the way.

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Maria O'Reilly-Brookes—Property Manager

Maria brings a warm, family-oriented approach to her work, creating meaningful connections with clients while delivering top-tier real estate and property management services.

With 14 years of experience as a Property Manager, Maria has a deep understanding of what it takes to successfully manage and maintain rental properties. From tenant relations and lease agreements to property maintenance and financial oversight, she ensures that every home under her care is well-managed and thriving. She is also hands-on in the leasing process, personally showcasing properties to prospective tenants and matching them with homes that meet their needs.

Maria's passion for real estate is rooted in her commitment to providing exceptional service and peace of mind to homeowners and investors alike. Whether you're looking to rent out your property, find the perfect home, or need expert guidance on property management, Maria is here to help every step of the way.

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Olivia Swales—Licensed Real Estate Agent

With a background in real estate both in the U.K. and the U.S., Olivia brings a global perspective and a keen understanding of the housing market. Before joining the family business in Florida, she spent four years in the real estate industry in the U.K., honing her skills in sales, leasing, and client relations. She holds a bachelor's degree in Mass Communications from the University of South Florida, which fuels her expertise in marketing and digital engagement.

As a licensed real estate agent, Olivia plays a key role in helping buyers, sellers, and renters while also spearheading the company's social media presence. Her innovative marketing strategies ensure properties receive maximum exposure across online platforms, helping clients attract the right buyers and tenants. Beyond marketing, Olivia is actively involved in the leasing process, personally showcasing homes and ensuring they find the perfect match.

Whether you're looking to buy, sell, or lease, Olivia is dedicated to making the process seamless and stress-free. Connect with her today to learn how she can help with your real estate needs.

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Elizabeth Hofstetter—Property Manager

Elizabeth is a dedicated Property Manager and the primary point of contact for both property owners and tenants. With a keen eye for detail and exceptional organisational skills, she ensures a seamless and stress-free experience for all parties involved.

From preparing and managing leases to coordinating maintenance requests and overseeing work orders, Elizabeth takes care of every aspect of property management with efficiency and professionalism. She also plays a crucial role in rent collection and financial oversight, ensuring that payments are received on time and that properties remain in top condition.

Elizabeth's proactive approach and commitment to excellence make her an invaluable asset to both property owners and tenants alike. She prides herself on her ability to anticipate challenges, resolve issues swiftly, and create a smooth rental experience for everyone involved.

Whether you're a homeowner looking for reliable property management or a tenant in need of assistance, Elizabeth is here to help — bringing expertise, dedication, and a personal touch to every interaction.

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Testimonial

Trusted by Clients Across Winter Garden & Beyond

Hear from homeowners, buyers, and investors who trust Winter Garden Real Estate & Property Management to deliver results.

"Anthony's knowledge of Central Florida gave us confidence in narrowing down where we wanted to buy. He was always available — phone, text, or email. Highly recommend Winter Garden Real Estate to anyone looking in the area."

Jaz, P.
Homebuyer

"Anthony listens to all your needs and spends countless hours helping you find the right house — not just any house. He's a great negotiator and makes sure his clients come first. The best realtor I've ever worked with."

Beth, W.
Homebuyer, Relocated to Florida

“They helped us find the right property direction with clarity and confidence. Professional, responsive, and highly knowledgeable throughout the process.”

Daniel Morgan
Property Investor

“Working with them simplified complex property choices and saved us valuable time. A trusted partner with strong market understanding.”

Michael Turner
Commercial Developer

"From the very first day, they were patient, kind, and incredibly knowledgeable. Not once did I feel pressured or rushed. They made what could've been an overwhelming experience feel totally manageable. Anthony and Olivia are the real deal."

Caroline, A.
Homebuyer, Relocated to Florida

"Anthony and his team were incredible. We were moving from out of town, navigating both selling our previous home and buying a new one at the same time. He handled both sides of the process seamlessly."

Nicole, F.
Homebuyer, Relocated to Florida

“The team guided us through every decision with practical advice. Reliable support that made the entire experience smooth.”

Sophia Reynolds
Real Estate Manager

“Their approach was thoughtful, transparent, and focused on real outcomes. We felt confident at every step of the property journey.”

Emily Carter
Homeowner & Client
FAQS

Frequently Asked Questions Answered about Winter Garden Real Estate

What areas do you serve?
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What makes you different from a large brokerage?
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Do you handle both real estate sales and property management?
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I'm not sure whether to sell or rent out my property. Can you help me decide?
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How do I get started?
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Do you work with first-time homebuyers?
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