Kaitlyn Shepherd - Milwaukee Realtor

Kaitlyn Shepherd - Milwaukee Realtor Greater Milwaukee Area Realtor

09/18/2026

🚚 It’s almost time to Pack the Truck again! 🇺🇸

For the past three years, I’ve been proud to take part in GMAR YPN’s annual Pack the Truck drive supporting the Wisconsin Homeless Veterans Initiative — and this September will be my fourth year helping make it happen.

The video is a look back at previous years— seeing everything come together, from collecting donations to delivering much-needed food and supplies, is exactly why this event means so much to us.
WHVI’s food pantry serves 50–100 veterans every week, and right now their shelves need our help. At the end of September, the GMAR YPN Board will take the monetary donations raised and head to Costco to purchase as many of WHVI’s most-needed items as possible.
There are two ways you can help:

📦 Shop the Amazon Wish List: link in the bio
💙 Donate to Pack the Truck: link in the bio

Every item and every donation helps us fill those shelves a little more. If you’re able to contribute, we would truly appreciate it — and even sharing this post can help us reach more people.
Let’s see how full we can get that truck this year. 🚚🇺🇸

The September Market Newsletter is here! 🍎📚🏡Back to school, back to routines, and a new month of real estate updates! As...
09/02/2026

The September Market Newsletter is here! 🍎📚🏡

Back to school, back to routines, and a new month of real estate updates! As we head into fall, we’re sharing what’s happening across Milwaukee & Waukesha County and what you should know about the local market.

📚 Back-to-school season
📊 Local market updates
🏡 Recent listings & real estate activity
💙 Community highlights & more

Want to stay in the know? Subscribe to our newsletter through the link in our bio for all the details each month! ✏️🍂

NEW LISTING IN MILWAUKEE! 🏡✨A great opportunity on Milwaukee’s South Side is officially on the market!📍 3367 S 14th St, ...
08/24/2026

NEW LISTING IN MILWAUKEE! 🏡✨

A great opportunity on Milwaukee’s South Side is officially on the market!

📍 3367 S 14th St, Milwaukee, WI
🏡 2 Units | 4 Bedrooms | 3 Bathrooms
🚗 2.5-Car Detached Garage
✨ Finished Basement

Whether you're looking to owner-occupy, generate rental income, or add to your investment portfolio, this one is worth a closer look!

Check my story for more details 👀

Every home-buying journey is different, so advice based on someone else’s experience doesn’t necessarily apply to you.Wh...
08/14/2026

Every home-buying journey is different, so advice based on someone else’s experience doesn’t necessarily apply to you.

What matters more: what they went through, or what *you’re* about to go through?

That’s why having someone who understands the process, the market, and your specific goals in your corner can make all the difference.

I’m just one DM away. Let’s set up a quick mini consult where you can ask your questions, talk through your options, and walk away with a clearer plan.

DM me “CONSULT” for your free mini consult!

Confession: handing my clients the keys to their new home will never get old.You’d think after enough closings, it might...
08/11/2026

Confession: handing my clients the keys to their new home will never get old.

You’d think after enough closings, it might start to feel like routine, but every one is different. There’s always a story behind the keys—and usually a few twists and turns along the way.

From preapproval and negotiations to inspections, repairs, unexpected delays, and everything in between, my job is to help navigate the details, solve the problems, and keep my clients moving forward with confidence.

Because at the end of the day, it’s not just about a transaction. It’s about helping people get to the next chapter.

If you or someone you love is thinking about making a move, let’s start with a conversation. DM me “CONSULT” and we’ll get you on the calendar.

The August Market Newsletter is here! ☀️🏡From local market updates and recent listings to community highlights and summe...
08/06/2026

The August Market Newsletter is here! ☀️🏡

From local market updates and recent listings to community highlights and summer events, this month’s newsletter is packed with what’s happening across Milwaukee & Waukesha County!

🎡 Wisconsin State Fair Guide
📊 July Market Highlights
🏡 Recent Listings & Homes Under Contract
💙 Updates from our Seniors and Veterans Programs

Want all the details? Subscribe to our newsletter through the link in our bio so you never miss an update! 💌

For the record... there are **no dumb questions.** 🤍I've helped clients buy multiple homes, and they *still* have questi...
07/07/2026

For the record... there are **no dumb questions.** 🤍

I've helped clients buy multiple homes, and they *still* have questions when it's time to buy again. It's not your job to memorize the process—that's mine.

And yes, I get texts like this all the time. I'm always happy to answer your questions.

But if you're thinking, *"I have so many questions, I don't even know where to start,"* that's exactly what **Summer Strategy Sessions** are for. ☀️🏡

The July Newsletter is here! 🇺🇸🏡As we celebrate Independence Day, there's no better time to appreciate the place we call...
07/02/2026

The July Newsletter is here! 🇺🇸🏡

As we celebrate Independence Day, there's no better time to appreciate the place we call home. Whether you're dreaming of buying your first home, making a move, or simply staying informed, I'm here to help you navigate the market every step of the way.

Wishing you a safe, fun, and happy Fourth of July! ❤️🤍💙

06/30/2026

Looking for Fourth of July fun this weekend? Here's a few local celebrations to add to your plans!

📍 July 3 – Muskego
🎿 Water Bugs Show at Idle Isle Park – 6:00 PM
🎆 Fireworks over Little Muskego Lake – Dusk

📍 July 4 – Hales Corners
🚗 Holtz Motors Car Show – 8:00 AM–12:00 PM
🎉 Hales Corners Independence Day Parade – 11:00 AM

📍 July 4 – New Berlin
🎶 Malone Fest – 6:00 PM
🎆 Fireworks – 10:00 PM

Wishing everyone a safe, fun, and memorable Fourth of July weekend!

Did I miss one of your favorite local events? Drop it in the comments so everyone can check it out! 🎇

As we head into Independence Day week, I'm reminded that the American Dream looks different for everyone. For some it's ...
06/29/2026

As we head into Independence Day week, I'm reminded that the American Dream looks different for everyone. For some it's buying their first home, for others it's a place to raise a family, retire, or create memories with the people they love. What does 'home' mean to you? Tell me in the comments!

Address

5552 S 108th Street
Hales Corners, WI
53130

Telephone

+14148016054

Website

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