Cheryl Robb Real Estate

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Bolton, ON
Cheryl Robb Real Estate

Helping people with their Real Estate needs for over 3 decades in the Caledon and surrounding area'

MEET CHERYL ROBB - Cheryl was born and raised in the Caledon area and has been helping people with their Real Estate Goals for over 35 years! Knowing the Caledon area she can be a helpful asset in either Buying or Selling Real Estate. With a reputation as a caring professional who produces results and whose clients not only return to her but recommend her to their family and friends. Cheryl cares

about her clients and their objectives, knows the real estate market and is an expert negotiator with meticulous attention to every detail! With the team of experts at her fingertips Cheryl can navigate the steps to getting your home show ready. Whether it includes packing, moving, staging, cleaning and organizing the team has all the tools to make the move a smooth as possible. Trust, hard work, perseverance, and dedication has earned her the prestigious Red Diamond Award which places her in the top 2% of Real Estate Professionals in Canada. While always an award winner for Cheryl it is never about the awards it is about being placing clients needs first. Involved in her community Cheryl believes in giving back and has been involved in many local charities and as always supports the Royal Lepage Shelter Foundation. Feel free to reach out with your real estate questions.

🏡 Helping people buy and sell real estate in Caledon and beyond for over 35 years.
📍 Born and raised in Caledon – I live here, work here, and give back here.
💼 Ranked in the top 1% of Royal LePage Realtors across Canada.
🥇 #1 Individual Realtor in Ontario (2024) | #2 Nationally – Royal LePage
🎓 Background in Urban Planning from Western University
🤝 Known for my experience, honesty, insight, and a sense of humour when it counts. Whether you're buying your first home or selling your family property, I'm here to guide you every step of the way. Cheryl Robb
Royal Lepage RCR Realty
www.cherylrobb.com
B 905-857-0651
C 416-805-1316

09/03/2026

Every once in a while, I like to look back through some of my Google reviews, and this one really jumped out at me. ❤️

The words “work entirely 100% for the client” mean a lot because, really, that’s been my goal for the past three decades.

Buying or selling a home can be exciting, stressful, emotional — and sometimes all three in the same day! My job has always been to be there from beginning to end, give my clients my full attention, and help get them where they want to go.

Thirty+ years later, that hasn’t changed.

I’m so grateful for every client who has trusted me to be part of their journey over the years. 🏡❤️

Cheryl Robb Team
Queen of Caledon
📞 416-805-1316

09/01/2026

A great traditional country fair close to Caledon.

🚜 Orangeville Fall Fair
📆 Friday, Sept. 4 – Sunday, Sept. 6
📍 Orangeville Fairgrounds, Mono

This year's theme is “Cows and Corn Stalks.”

There'll be agricultural shows, midway rides, entertainment, a truck and tractor pull Friday night, plus demolition derbies Saturday and Sunday.

08/31/2026

One week of summer break before school is back in, what’s on your Caledon summer bucket list?

🌿 Spending an afternoon in Belfountain
🥾 Hiking at Albion Hills
🏞️ Exploring the trails at Terra Cotta Conservation Area
🚗 Taking a scenic drive along Forks of the Credit Road

I'm not ready to rush into fall just yet! There’s still plenty of summer left to enjoy. ☀️

Which one are you choosing? Or do you have a favourite Caledon summer spot I missed? 👇

Cheryl Robb Team

08/28/2026

🏡 NEW LISTING | 46 Cross Country Boulevard, Bolton
Looking for more room for your family without adding a renovation list? This one is ready for you.

Welcome to 46 Cross Country Boulevard, a beautifully maintained 3-bedroom home in a family-friendly Bolton neighbourhood with plenty of space to grow.

A few highlights you'll love:

✨ 9-ft ceilings on the main floor
✨ Engineered hardwood flooring
✨ Walk-in closets in ALL 3 bedrooms
✨ Convenient second-floor laundry
✨ Updated main bath + primary ensuite
✨ Finished basement with cozy gas fireplace
✨ Composite deck + 10' x 12' gazebo
✨ Premium metal roof
✨ Smart-home features
✨ Composite shed (Durashed) with metal roof
✨ Updated windows, insulation, flooring & more

The finished basement gives you that extra family space for movie nights, a playroom, gym or home office, while the backyard is ready for BBQs, entertaining and relaxing under the gazebo.

And location matters! You're close to parks, schools, walking trails, shopping and restaurants, with convenient access for commuters.

This is one of those homes where so much has already been done — you can simply move in and start enjoying it.

Want to take a look? Send us a message to book your private showing.

Cheryl Robb Team
Queen of Caledon
📞 416-805-1316

08/27/2026

Recognize this spot? 👀

Here’s a hint… you’ll find it in one of Caledon’s most charming little villages.

This beautiful cedar canoe is more than something that caught my eye. It’s part of an Indigenous art installation honouring the history and culture of the Mississaugas of the Credit First Nation.

The canoe is planted with traditional Indigenous plants and features the words “As Long as the River Flows,” a reference to the Ajetance Treaty No. 19 of 1818 and an expression representing an enduring relationship.

One of the things I love about exploring Caledon is discovering the stories behind places I’ve driven past countless times.

So… do you know where I am?
Drop your guess below BEFORE reading the comments! 👇😉

08/25/2026

🌽 Is there anything better than Caledon corn in August?

This is one of my favourite times of year in Caledon East. The farm stands are full, the tomatoes actually taste like tomatoes 😂 and local sweet corn is at its BEST.

If you haven't stopped by Rock Garden Farms , late summer is the perfect time to grab some fresh corn, tomatoes, garlic, peaches and whatever else catches your eye.

It's one of those simple things I love about living in Caledon — fresh, local food right down the road. ❤️

Now the important question… butter & salt or straight off the BBQ? 🌽👇

Cheryl Robb Team

08/24/2026

🚩 ASK CHERYL: IS THIS A RED FLAG?

There’s a long gravel driveway. Red flag?

Not necessarily! In Caledon and the surrounding countryside, a long driveway can come with some pretty great perks — more privacy, less road noise and that beautiful tucked-away country feel. 🌳🏡

But after 30+ years in real estate, I can tell you there are a few questions I’d be asking BEFORE falling in love with the view:

🚜 Who’s plowing it in February? A long driveway feels a whole lot longer after 20 cm of snow.

🪨 How well is it maintained? Gravel needs grading and topping up from time to time, especially after a rough winter or heavy rain.

💧 How’s the drainage? Look for washouts, pooling water and low spots.

🚗 Can two vehicles pass? And where are your guests, delivery drivers or contractors going to turn around?

🔥 What about emergency access? You’ll want to know that fire trucks and other emergency vehicles can safely access the property.

So, red flag? 🚩 No.

But it's definitely something you want to understand before you buy.

And personally... there’s something pretty special about turning down a long country driveway and leaving the rest of the world behind. ❤️

Would a long driveway be a PLUS or a PASS for you? 👇

— Cheryl Robb Team

08/20/2026

If I were upsizing with a young family today, here’s what I’d be looking for:

1️⃣ A backyard they can actually USE.
One of the great things about Caledon is that you can still find homes with bigger yards and country properties with room to roam. I’d want space for a swing set, soccer net, trampoline, dog…and whatever giant plastic toy somehow follows you home. 😂

2️⃣ A house we can grow INTO—not out of.
An extra bedroom. A finished basement. A mudroom for the backpacks, hockey bags and muddy boots. Maybe even a home office. When you're upsizing, I always tell families to think about what life might look like five or ten years from now—not just what works today.

3️⃣ A Caledon lifestyle for the kids.
I’d want trails nearby, parks to explore, local sports and activities, great community events and space to spend more time outside. Whether that's Bolton, Caledon East, Valleywood, Southfields or a country road somewhere in between, each part of Caledon offers something a little different.

After 30+ years of helping families move around Caledon, I've watched a LOT of little kids grow into teenagers…and I've seen how quickly a house that once felt huge can suddenly feel very small. 😉

Thinking it's time your family had a little more room?

Tell me what's driving the upsize: more bedrooms, bigger backyard, finished basement or ALL OF THE ABOVE? 👇

Cheryl Robb Team

08/18/2026

🎶 Summer nights + live music in Caledon? Yes, please!

If you're looking for something local to do this Thursday night, Music in the Park is a great excuse to grab your lawn chair, round up the family and enjoy a summer evening outside.

🎤 Cody Luciano | 6–7 PM
🎤 Mikee Vibe | 7–8 PM
📅 Thursday, August 20
⏰ 6–8 PM
🎟️ FREE

Bring a blanket or lawn chair, settle in and enjoy some live music right here in our community.

These are the simple summer nights I love — good music, fresh air and nowhere you need to rush off to. ❤️

Who are you bringing with you?

— Cheryl Robb Team

08/17/2026

I remember when buyers rarely asked me about internet speed when we were looking at country properties. 😂

Back then, the questions were more like:

“Where’s the well?”
“How old is the septic?”
“Who plows this road?”
“And just HOW long is this driveway?” 🚜

Today?

“How’s the Wi-Fi?” 📶

With so many people working from home, streaming everything, running home businesses and trying to keep multiple devices connected at once, reliable internet has become a pretty important part of country living.

After 30+ years of selling real estate in Caledon and the surrounding area, I can tell you—buyer priorities change, but doing your homework never goes out of style.

And yes… before falling in love with that gorgeous country property, you might want to check whether your Zoom call will actually work from it. 😉

What would be YOUR first question: internet, well, septic or driveway? Tell me below! 👇

Cheryl Robb Team
Queen of Caledon
📞 416-805-1316

Address

12612 Highway 50
Bolton, ON
L7E1T9

Telephone

+14168051316

Website

http://www.cherylrobb.com/

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