We believe in being consistent. Attentive. Data-driven. Caring. We promise to distinguish ourselves with expertise catered to your personal situation, with services extending well beyond the closing table.

Since the beginning, we have taken a creative approach to the real estate world, offering full-service solutions and commitments to make your goals a reality. Our vision is to be trail-blazing leaders in an industry where going “above and beyond” should be the guiding light, rather than the rare exception.

What gets us up in the morning (besides great coffee)? A desire to give our best and leave each client with a 5-star experience. Otherwise, we have not done our job. That’s just who we are.

Your home purchase or sale is likely the most significant transaction of your life, and we don’t take that lightly.

Our Manifesto


Ashlee Aplin

meet ashlee


Ryan Berry

meet ryan

Team lead, realtor

Cait Berry

meet cait

Cait started in the Real Estate business in 2012 and operated as a one-woman show for most of her career. In 2020 the Insiders Realty team was formed as a 3-person full-service boutique real estate team with a modern customer-centered approach and an immense love for the local community.

Our Team




contact ryan

family adventures

6. Fav. weekend activity

strictly discs

5. favorite local biz


4. favorite city to visit


3. favorite sport


2. Vacation of choice


1. Favorite food

Mountains, hockey and adventures... Time to reveal a few of my favorites. See anything we have in common?

The Quiz

When I’m not working you’ll most likely find me loading up the RV for a weekend adventure in one of the local  State Parks. I love applying my passion for the outdoors to real estate by introducing people to Madison's parks, bike paths, summer festivals and events around town. Helping people find the perfect niche neighborhood for their lifestyle is what gets me rockin' and rollin' in the morning. If you love adventure, then I'm your guy. 

I'm a madison native and my greatest passion is getting outdoors and exploring our city!

i'm ryan

People mostly know me for my cool as a cucumber personality and my uncanny ability relate to anyone and make them feel truly comfortable.

I have been unofficially involved in Real Estate since 2012, when Cait got her license and have been a support system and a bit of a gopher helping her with the day-to-day operations and behind-the-scenes tasks. In 2020 I pursued getting my license and joined her full-time, because it was way past time to do so!

I work with both buyers and sellers and can bring a wealth of knowledge and deep life-long connections, resources and hyper-local Insiders knowledge to any transaction. 

contact ashlee

trying new restaurants 

6. fun fact

the greenbay packers

3. Fave weekend activity

bloom bake shop

4. fave local business

can fit a skittle in dimples

5. fave sports team

tropical beaches

2. vacation of choice

cheese curds

1. Favorite Food

Cheese Curds, Tropical Beaches, Coffee Shops... Time to reveal a few fun facts. See anything we have in common?

The Quiz

I'm best known for going above and beyond for each and every one of my clients. I seek to make the home buying and selling process as stress-free as possible, often times bending over backwards to make the magic happen. My down to earth personality, care for others, and relentless work ethic makes me an exceptional resource for buyers and sellers. My favorite part of being a REALTOR is the relationships that transpire. I often walk away from closings with new lifelong friendships!

On my days off, I enjoy attending sporting events, Madison’s local food scene, traveling the world, hiking with my family, and getting lost in a good book!

I'm an experienced agent with a modern approach to the client experience.  

i'm ashlee

I've been keeping it real in Madison, Wisconsin since 1986. I'm a REALTOR, the CEO of my little family and the future host of an HGTV show (just manifesting that into reality). I am obsessed with social media marketing, impacting my client's lives in the best ways possible and telling the tales of the wild world of Real Estate! 

I specialize in helping awesome people move to, from and around the Madison Area and forging friendships along the way. I LOVE all things home and design - you should see my Pinterest board. A wealth of local neighborhood and community knowledge - I want everyone to love where they live. A total nerd when it comes to numbers - I love myself a good investment.  I am equally a 2 and 3 on the Enneagram Personality Test - a helper who cares a great deal about relationships mixed with a high achiever with a contagious zest for life.


i'm cait

hey there

Check out small biz madison

small biz madison

I also am a huge supporter of local businesses and am the founder and operator of a social media community called, Small BIZ Madison over on Instagram. I create content to support local small businesses and bring awareness to around the importance of keeping our small business community thriving. It is also a great place for you to visit if you are interested to learn more about the great restaurants, shops, services and events that Madison has to offer.

my little family

My story

This isn't a story about how I discovered that Real Estate was my path in life. I think I always knew it would be. It is a story about how I grew up in this business, but had to rebuild it after tragedy and loss.

Real Estate isn't just a hobby or a job, it's in my blood. My roots are deep. Madison has always been and will always be my home. I was born and raised here and am following in the footsteps of five generations of Madison REALTORS ahead of me, including my Dad. Many of Madison’s most desirable neighborhoods were developed by my family including: Shorewood Hills, Sunset Village, Westmorland, Orchard Ridge and more that I discover all the time! My Grandmother lived in 37 homes on the Near-West Side growing up! Her Father was an early Madison developer who would develop neighborhoods, build homes on spec and move his wife and 5 kids multiple times a year. When the spec they were living in sold, it was time to build a new one! 

As a kid, I went to the office with my Dad most days and flipped through MLS listings when they were in a binder BEFORE the Internet! I went to open houses, showings and helped him measure his new listings. I could walk you through the process of selling your home at 7 years old. When I was 10 years old, my life was changed forever. My Dad was diagnosed with cancer and rapidly declined in about 9 months time. When he died, so did the family Real Estate business. When he died, so did a part of me.

In rebuilding the family Real Estate business, I was finally able to heal from the loss that shaped my childhood. I have never felt closer to my Dad. 

It wasn't until 2012 when I was miserable in my career, that a spark went off and I was like "what am I doing?" I went to college and changed my majors all the time - nothing ever felt right. I got a job that I dreaded going to everyday. I remember the exact moment when I was sitting at my desk and just got off the phone crying to my husband, that I pulled out my wallet and signed up for the Real Estate Exam. I delivered my two weeks notice THAT DAY and with absolutely no plan, no income and a ton of support from my family - I got my license, joined a Brokerage, got a waitressing job so I could afford the start up costs of my new business... and then I HUSTLED. 

Fast forward to almost a decade later and here I am. In rebuilding the family Real Estate business, I was finally able to heal from the loss that shaped my childhood. In this journey of building my business, I have never felt closer to my Dad. I now have a business that keeps me busy, allows me to impact and add value to my client's lives and has allowed me to revive the family biz - Ryan works for the team now too. 

contact cait


6. Fav. weekend activity

sundara spa

5. Guilty pleasure


4. favorite city to visit


3. Cocktail order


2. Vacation of choice


1. Favorite food

Sushi, Margaritas, Disney... Time to reveal a few of my obsessions. See anything we have in common?

The Quiz

small but mighty 

organic referral  based business model

resources dedicated to client experience


total Sales Since 2012




Business that comes from past clients or referrals


Year I Got MY Real Estate License


number of homes i've sold

By The Numbers

Schedule Coffee or a Zoom Chat

Let us use our expertise in the industry, paired with our local insiders knowledge to take all the stress of real estate off your hands, so that you can truly enjoy the process.


We'll take it from here

aka- a no pressure consultation for whatever stage you are at