Caitlin O’Brien

Sales Representative

p: 705.300.6833

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It’s Great To Meet You

Meet Caitlin O’Brien, a Sales Representative with the Peggy Hill Team who is known for her genuine, no-pressure approach and passion for helping clients make confident real estate decisions.

It’s Great To Meet You

Meet Caitlin O’Brien, a Sales Representative with the Peggy Hill Team who is known for her genuine, no-pressure approach and passion for helping clients make confident real estate decisions.

About Caitlin

Before entering real estate, Caitlin worked in healthcare as a medical radiation technologist, where she developed strong skills in communication, empathy, and problem-solving; qualities that continue to shape how she supports her clients today. She now proudly helps multiple families each year navigate buying and selling with clarity, strategy, and support.

Caitlin is a first-time home buyer specialist, with a strong focus on education and guidance throughout the entire process.She understands that buying your first home can feel overwhelming, and her goal is to make it feel informed, manageable, and even exciting, without pressure or unnecessary stress.

Drawn to the Peggy Hill Team for its authenticity and collaborative culture, Caitlin knew she had found a professional home aligned with her values.

Whether working with first-time buyers or sellers planning their next move, Caitlin is committed to providing honest advice, strong market insight, and a positive experience from start to finish.

Outside of Real Estate

Caitlin enjoys tackling DIY home renovation projects on a budget, exploring her love of photography, discovering new coffee shops, and spending quality time outdoors on local trails with her dogs, as well as with family and friends.

Testimonials

Don’t just take our word for it, learn what our valued clients have to say about Caitlin’s exceptional service and commitment. See how you can benefit by choosing Caitlin to guide you along the way.

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"We are so thankful for Caitlin and the rest of the Peggy Hill Team. What seemed like an incredibly overwhelming first time buying process was nothing short of amazing with Caitlin's help. She brings industry knowledge, compassion and care for her clients while being super funny, making her so easy to work with."
— Jessie P.
"Awesome experience working with Caitlin! She was friendly, professional and incredibly helpful, always making us feel comfortable and informed during the sale of our home. Not only is she great at what she does, she is also a genuinely kind and wonderful person to work with!"
— Lori S.
"Our experience with Caitlin and the Peggy Hill team was amazing. This is a team dedicated to finding you your perfect fit in a home. We are so grateful to Caitlin for all of the hard work and long hours she put into selling our house and finding our forever family home."
— Alexis L.
"We had a truly great experience working with Caitlin O’Brien and would highly recommend her, especially to first-time home buyers. From the very beginning, Caitlin was patient, understanding, and supportive, even as we took our time deciding what we really wanted. We never once felt rushed or pressured, which made a huge difference for us. Our work schedules were challenging and often meant late hours, but Caitlin was always flexible and willing to accommodate showings that worked around our availability. What really set Caitlin apart was that she went far beyond simply showing us houses. She took the time to educate us throughout the process, pointing out what to look for in a home, things to be cautious of, and potential issues to avoid. As first-time buyers, this guidance was incredibly valuable and gave us a lot of confidence in our decisions. Caitlin was consistently professional, friendly, and extremely knowledgeable. She was always available when we needed her, quickly answering calls and questions, which made the entire process feel far less stressful and much more manageable."
— Simon G.
"Caitlin O'Brien was absolutely incredible to work with here at The Peggy Hill Team! As first-time home buyers, we were pretty nervous about the whole process, but she made everything feel so much easier and less overwhelming. She truly went above and beyond our expectations in every way. Caitlin was always available whenever we needed her, answered all our questions with patience, and guided us through each step with so much knowledge and care. Not only is she extremely professional, but she's also so friendly and genuinely invested in helping her clients find the perfect home. It really felt like she was just as excited as we were when we found the one! We're so grateful for all her hard work and support in helping us find our first home. We couldn't have asked for a better experience and would highly recommend Caitlin to anyone looking for a realtor, especially first time home buyers!"
— Brittany D.
"We had such a positive experience working with our agent Caitlin O'Brien from the Peggy Hill Team. Professional, knowledgeable and personable, the perfect combination in a realtor!"
— Sabrina A.
"Our real estate agent Caitlin was absolutely amazing and made everything throughout this process so smooth." She explained things very clearly and made buying our first home an exciting experience! Nothing but amazing things to say and would work with her again for our next home journey!
— Kiana B.

Simcoe County and Barrie Listings

See All Listings
Coming Soon |$679,900

6 Oren Boulevard, Barrie, ON

Sunnidale 

3 2

For Sale |$1,895,000

46 Yonge Street South, Elmvale, ON

Elmvale 

Commercial Retail

Coming Soon |$349,000

111 Worsley Street #309, Barrie

City Centre 

1 1

Coming Soon |$650,000

35 Victorway Drive, Barrie, ON

Holly 

3 3

Coming Soon |$649,000

11 Harriet Street, Coldwater, ON

 

4 2

For Sale |$748,800

5 Allan Court, Elmvale, ON

Elmvale 

3 3 2,638 Sq Ft

For Sale |$449,000

857 Birchwood Drive, Midland, ON

Midland 

4 2 1,655 Sq Ft

For Sale |$570,000

52 Harbour Crescent, Wasaga Beach, ON

Wasaga Beach 

3 2 1,889 Sq Ft

For Sale |$947,900

96 Redmond Crescent, Springwater, ON

Springwater 

3 2 1,911 Sq Ft

For Sale |$629,000

34 Arch Brown Court, Barrie, ON

East Bayfield 

3 3 1,409 Sq Ft

For Sale |$899,900

3664 Hogback Road, Clearview, ON

Clearview 

3 3 1,408 Sq Ft

For Lease |$2,500 Monthly

111 Garden Drive, Barrie, ON

Barrie 

3 2 1,648 Sq Ft

For Sale |$699,000

164 Wagner Crescent, Angus, ON

Angus 

3 3 1,285 Sq Ft

For Sale |$1,049,000

8064 9th Line, Thornton, ON

Rural Essa 

3 2 2,178 Sq Ft

For Lease |$2,600 monthly

1081 Innisfil Beach Road Main B, Innisfil, ON

Innisfil 

Commercial

For Sale |$950,000

1002 Cowbell Lane, Gravenhurst, ON

Morrison 

7 7 5,076 Sq Ft

For Sale |$895,000

5 Magna Carta Road, Barrie, ON

Barrie 

5 4 2,740 Sq Ft

For Sale |$799,000

7 Bentley Crescent, Barrie, ON

400 West 

4 3 2,477 Sq Ft

What Our
Clients Say

We’ve built a repeat and referral business by doing real estate differently.

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Real Results From Our Clients

“One of the best decisions we've made. Peggy and her team were extremely professional with the sale of my mother’s home. We were always kept up-to-date and in the loop. 70+ viewings and 17 offers in 7 days speaks for itself.”

— John K. | See All Reviews

"The professionalism and kindness was exemplary. We sold our home after 35 years. This team are marketing geniuses. From photos and varying listing sites to open houses and requests for showings and staging, every step of this journey was handled efficiently and timely."

— Harley & Cindy L. | See All Reviews