Cait Berry

Real Broker LLC

14 Years of Experience

(31)

$24M

Total Sales Last Year

Years of Experience

147

Recent TransactionsTransactions from the last 3 years

$524.6K

Average Price Point

Service Areas

Belleville, WI Black Earth, WI Blue Mounds, WI Brooklyn, WI Cambridge, WI Cottage Grove, WI Cross Plains, WI Dane, WI Deerfield, WI Deforest, WI Edgerton, WI Evansville, WI Lake Mills, WI Lodi, WI Madison, WI Marshall, WI Mazomanie, WI Mcfarland, WI Middleton, WI Mount Horeb, WI New Glarus, WI Oregon, WI Stoughton, WI Sun Prairie, WI Verona, WI Waterloo, WI Waunakee, WI Windsor, WI

View All Service Areas

About Cait Berry

Cait Berry is a Madison, WI Realtor and founder of Insiders Realty, brokered by Real Broker. A lifelong Madisonian and sixth-generation local Realtor, Cait helps buyers, sellers, and relocation clients throughout Madison and Dane County make smart, confident real estate decisions.

Cait works with first-time buyers, move-up buyers, sellers, relocation clients, luxury buyers and sellers, downsizers, new construction buyers, and families navigating school districts, commute patterns, and neighborhood fit. In 2025, Cait and the Insiders Realty team helped more than 60 families move, closing over $35 million in sales.

Her approach combines deep local insight, strategic pricing, thoughtful listing preparation, strong negotiation, and clear communication from the first conversation through closing. Through Insiders Realty, clients get the benefit of Cait's local roots and leadership, along with a team-based experience built around preparation, honest advice, and confident decision-making in the Madison real estate market.

OTHER LANGUAGES

English

Community Involvement

A passionate advocate for all things Madison, Cait sponsors local events, supports animal rescue efforts, and uses her growing social media platform to spotlight the neighborhoods, small businesses, and lifestyle that make Madison feel like home.

HOBBIES/INTEREST

Outside of real estate, Cait is a mom of three who loves spending weekends at the Farmers' Market, supporting local events like Westmorland Summer Nights, and giving back through her work with Fetch Wisconsin Rescue. She's passionate about community, design, and helping people feel grounded during big life transitions. Whether she's cheering from the sidelines at her kids' activities or exploring new Madison neighborhoods, Cait brings heart, hustle, and a deep love for where she lives.

FAMILY

Cait lives in Madison with her husband Ryan and their three kids, who keep life busy, meaningful, and full of purpose. Her family is the reason she shows up every day with heart, hustle, and perspective.

Credentials

LICENSE

Real Estate - Wisconsin - # 76382-94

Specialties

Buyer's Agent
Investment Properties
Listing Agent
Relocation
Staging & Home Preparation

Awards

2026
TOP AGENT
Sun Prairie, WI
2026
TOP AGENT
Waunakee, WI
2026
TOP AGENT
Lodi, WI

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Cait Berry's Reviews & Ratings

31 Reviews

(5/5)

Note: Reviews may include other agents on their team

What clients say about this agent....

Responsive
Knowledgeable
Communicative
Professional
Outstanding
Available Remotely
Great for new buyers
Trustworthy
Attentive
Excellent negotiator

Abbielev123

Review for Member: Cait Berry

April 21, 2026

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

My husband and I cannot recommend Cait enough. This was our second time working with her. We struck gold as first time home buyers when we first chose Cait as a realtor. Then, fast forward five years, when it came time to sell that home and move to our (hopefully) now forever home, going with Cait again was a no brainer. As a buyers agent, Cait is outstanding, but let me tell you, as a selling agent, she truly shines. She goes WAY above and beyond with marketing, staging, helping to clean and prep the home so it's ready for sale. Constantly available, easy communication, a well oiled team to work with and expert professional recommendations. Cait does it all. We put YEARS of work into our first home that we recently sold, and Cait made sure all our effort was showcased beautifully. Within hours of our home going live, we had an offer- over asking price! The entire selling-buying process was easy with her on our team and we were able to move forward confidently. If you're looking for a realtor who is willing to kindly answer all your dumb questions, guide you through the process with grace, experience and ease, show up for you AT EVERYTHING, as well as go out of their way to ensure your home is represented in its best state, then Cait is your gal. 10/10 could not recommend more!

Daniellecrider

Review for Member: Cait Berry

October 14, 2022

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait is wonderful! I highly recommend her particularly if you are new to the area, she knows all the inside scoop! Her team was easy to work with and so patient with us during a very difficult market!

Hannahlacy44

Review for Member: Cait Berry

August 11, 2022

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was so helpful, responsive, and took the best care of us. We were first-time homebuyers from out of town and she made us feel incredibly comfortable with the process and was so detailed whenever we did a virtual walkthrough. I couldn't recommend Cait more--we'll definitely continue working with her in future.

Anthony B.

Review for Member: Cait Berry

July 16, 2022

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait helped me with both the purchase of my first home and the sale of it after a few years. She is fantastic to work with and has many contacts in her area to do whatever work needs to be done. I was able to leave most decisions to her in order to get as many people interested in my property as possible and it paid off.

Jordynnpeter

Review for Member: Cait Berry

May 4, 2022

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was amazing to work with! We were first time home buyers in the most insane market, but Cait was super helpful and told us we should at least try. Fast forward about 60 days, and we have closed on our dream home! Home-buying is super stressful and things were very fast-paced, but Cait was always in close contact with us. Her and Ryan provided us with great tools to be able to view homes ASAP and they were willing to do everything within their power to help us. Then towards the end, we had Alexa provide us with organized aEURoenext stepaEUR? emails in preparation for closing and really good checklists to make sure we were on track. We likely wont move again for several years, but I will certainly recommend Cait and her team to everyone I know!

Zuser20200616190324467

Review for Member: Cait Berry

January 15, 2022

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait is the best! We recently worked with her as our agent for both buying and selling. It was a very spur of the moment purchase - we saw what looked like our dream house pop up on Zillow and reached out to her, since we'd had such a great experience years ago when we bought our first home.A Within a day, she not only was showing us the property, but had us well educated about the entire gameplan for how we could buy a house when we hadn't been planning on selling our current one. Within a weekend, she whipped up a very competitive offer for us that the sellers accepted. We got our dream house! Throughout the process, she was a great advocate for us - making the homebuying process very pain free, even through some road bumpsA like post-inspection negotiation. Next up - selling. Cait went above and beyond here as well. In a very late decision, we decided we wanted to try and sell our house quickly for various financial reasons. Within a week of making that decision - and while my family and I were out of town on vacation - Cait got our house cleaned, photographed, and listed. She hustled hard, and we had EIGHT offers within two days of that. While still on vacation, she hopped on a Zoom with us very late at night, walked us through each offer inside and out, and we ultimately accepted quite a bit over asking price with various contingencyA protections. Oh, I almost certainly buried the lede - this was just a month or two after she'd had a baby and right in the thick of the holiday season. Cait really went above and beyond to make us feel cared for, like we were her top priority. We couldn't be happier that we stumbled across Cait at an open house seven years ago. She's gone above and beyond in working withA us, teaching us, and ultimately, changed the course of our lives multiple times now! Thank you so much!

Jgarvens1

Review for Member: Cait Berry

December 6, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait provided excellent service as our realtor both on the buying and selling side. During buying her guidance on putting in offers was very effective and led us to getting ultimately getting an accepted offer several thousand dollars under asking price after our home inspection all within the hot housing market of 2021. On the selling side Cait did a great job of advertising and putting together a amazing selling photos and drone footage of the property to share to prospective buyers. She provided cleaners to prep the home prior to being listed which was above expectations. Cait has certainly earned her commissions through this process. I fully recommend user her services for buying or selling.

Tmacy1656

Review for Member: Cait Berry

August 23, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was wonderful to work with and I would recommend her to anyone. She was not only super helpful in finding us the land we were looking for but was very thorough as she led us through the process. And it's not just Cait - her Transaction Manager, Alexa, was extraordinarily helpful and kept the process on track. Truly a great team!

Fb1854107221

Review for Member: Cait Berry

August 5, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

My wife and I moved from out of state. We only had a week to look at homes and Cait was immensely helpful in showing us around the area and getting us in to see all the houses we were interested in. The Madison area was ultra competitive, with most houses selling the week of listing, but Cait helped us find a house during our trip and her advice helped us submit a competitive offer that secured us the sale. Afterwards, she and her team were great help coordinating inspections and all the other things that need done between the offer and closing before we moved up to the area. Her knowledge of all the local vendors and procedures were an immense help.

Reid H.

Review for Member: Cait Berry

May 28, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

My wife and I moved to Madison to be closer to family, while leaving a major metro area. When we first started to look at homes with Cait what truly impressed us first was just how deep her knowledge of where we would like to live went. She knows the city was well and was able to offer detailed guidance about neighborhoods, pricing in areas, historical information, and access offered from different areas. Cait was never late to a single showing and always had very prompt response times to any emails with questions we had or desire to go look at homes. This was my wife and I's first time buying a house, and when touring homes Cait was able to teach us a ton about local home build qualities and variations in those home build qualities that were worth noting when looking to purchase a home. From basement design; looking for leaks and ability to convert into a bedroom, to being able to just look at any piece appliance and know the age/durability of it. It was impressive to listen to her wealth of knowledge, and I would personally recommend her in your search for a home in the Madison area.

Jacalyn D.

Review for Member: Cait Berry

May 11, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was recommended to us by a friend, and after meeting with her via Zoom, we were immediately eager to work with her. We came to Cait as first-time home buyers and had a lot of anxiety about the home-buying process in general and also about entering the market when it's as crazy as it is right now. Cait has a wealth of knowledge with tips and tricks about how to navigate any market. We felt confident in her knowledge and expertise. She helped us find a home that was "Coming Soon", helped us reach out to the seller, and write an offer competitive enough to convince the seller to not even list the house. We ultimately got lucky with the FIRST house we looked at. We would have never thought that was possible, but Cait made the entire process seamless. She took the time to explain the process, answer ALL our questions (we had a lot!), and get us in a home we love. After the accepted offer, Cait's team has the home buying process outlined perfectly: everything we needed to do, in what order, and important deadlines were clearly communicated. They worked hand in hand with our local lender to ensure that everything happened smoothly and that we could close on time. We cannot rave about Cait and Alexa and team enough.

Renee S.

Review for Member: Cait Berry

April 20, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Beyond the Gold Standard- Cait is platinum! My senior mom utilized Cait's services as a stellar realtor when selling her home to move into senior living. I live out of state and we needed someone with compassion and expertise- in steps Cait. She was completely hands-on and made the process seamless. She literally helped my mom pack items for staging and coordinated large items to be removed/donated. She explained each step of the process and has the patience of a saint. The house looked amazing and my mom had over 20 offers. Sold. Ty Cait!!!

Gilheru

Review for Member: Cait Berry

March 28, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

The most important thing I can tell you about Cait is that at no point did I ever think she wasn't doing everything in her power to get us into our ideal home at the best price possible. She was there for us nights, weekends, and holidays, even when she was halfway across the country. Beyond that, her insight and expertise were invaluable in navigating a strange, volatile market. And she was honest and transparent about every step in the process. I'm sure there are many great realtors in the Madison area, but you will not regret putting your trust in Cait.

Mrandmrsdkicks

Review for Member: Cait Berry

January 7, 2021

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

What a great experience! Cait and Alexa are really on top of it and know their stuff! Communication was great. Knowledge was great. Suggestions, advice, staging, were all great. Truly top notch service, and top notch knowledge of the market. There were a couple moments where we said 'Wow, they do that for us???' They helped us both sell and buy at the same time. There were some bumps in the road from the other parties and circumstances, and Cait guided us through it all step by step.

Aseleen

Review for Member: Cait Berry

November 10, 2020

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

We've worked with Cait twice, and both times she was responsive, generous, and extraordinarily concerned with our needs and situation. A+ experience, and would recommend to anyone.

Mollyshelt

Review for Member: Cait Berry

June 26, 2020

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Exceptional work, spent plenty of time walking us through the process of selling, helping us understand what options we could consider to raise the value of the property. Cait was flexible to the current market and our needs, and got us numerous offers above listing price. We accepted a great offer 2 days after listing, in the middle of a pandemic! Cait is super friendly and helpful, and went above and beyond the call of duty on numerous fronts. I would highly recommend her to anyone looking to sell their house!

Michelle L.

Review for Member: Cait Berry

May 16, 2020

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

We loved working with Cait. She was friendly and professional. She got to know us and really got a feel for what we were looking for in a house. As COVID started shutting things down, she was very flexible and helped us through it! We would absolutely work with Cait again!

Welch J.

Review for Member: Cait Berry

May 10, 2020

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was phenomenal to work with! We have worked with her on three different properties since moving to the Madison area. She has a bright and uplifting personality and she truly cares about her clients. She joins the client in the experience through providing a high level of communication during the entire process. Her knowledge and expertise show up at every turn. She was able to sell our home for us during COVID-19 without a foot stepping into the home before an accepted offer was made for over asking price! On top of that, she helped us find our dream home :) We love working with Cait and will gladly refer her and work with her again in the future!

Dr. F.

Review for Member: Cait Berry

March 20, 2020

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

My wife and I really made her work. She did 6 to 10 showings on a large share of Saturdays or Sundays throughout the entire fall and into the new year. She was well informed and came to really understand us as time went with continued improvement in her showings. She had a great report with her colleagues on both the seller and buyer side. Cait was masterful at helping on negotiations and getting people in to check the house and gauge the number of repairs required which led to a great price reduction. Beyond that, she is just the most friendly and personable agent we have ever dealt with.

Zuser20171203181206150

Review for Member: Cait Berry

December 10, 2017

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait is a pro! Cait made this complicated and overwhelming process possible for me, a first time home buyer. She walked me through all the steps and explained the process and answered each of my questions with extensive expertise in a way that was very accessible. She's kind, quick to respond, and very knowledgeable. She's making my dream of owning a home a reality!

Bizsalesguru

Review for Member: Cait Berry

August 24, 2016

Local Knowledge

Process Expertise

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Negotiation skills

ZillowVERIFIED

Cait has the qualities of professionalism and experience that every real estate agent should have when serving their clients. She displayed a high level of competence in her ability to guide my wife and I through the whole purchasing process.

Aseleen

Review for Member: Cait Berry

August 23, 2016

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was fantastic for us as first-time buyers. She was always willing to walk us through basics when we didn't understand something and answer tons of questions. Despite shopping in a tough, competitive part of the market, she was able to help us find a great first home. Working with her made a stressful, intimidating process much more manageable and understandable, and I'd recommend her to anyone I know.

S A.

Review for Member: Cait Berry

August 23, 2016

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was fantastic right from our very first meeting, when she talked us (a pair of nervous first-time homebuyers) through what to expect from househunting, helped us clarify what we were looking for, and answered all our many questions clearly and in detail. As she showed us places and helped us write offers, her wealth of knowledge, responsiveness, and incredible attention to detail were an invaluable asset and made a stressful time much easier to navigate. Up to and well past the time when she congratulated us and put the keys in our hand, she's been an absolute pleasure to work with. I love our new home and would enthusiastically recommend Cait to anyone.

Ktspeed6

Review for Member: Cait Berry

November 13, 2014

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait is a great realtor to work with because she is very knowledgeable about the local area. Being a first time home owner, I found Cait to be extremely helpful and patient throughout the whole home buying process. She was very professional in answering my questions and was positive and optimistic through the home search process. I believe she truly loves helping people find their ideal home and felt she went above and beyond in making sure I became a satisfied home owner! She is extremely personable and would recommend her to anybody looking to find their dream home!

User27651340

Review for Member: Cait Berry

November 3, 2014

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was a great help in helping me find the perfect home, I was able to tell her what I was looking for, from a safe neigborhood to a garage, she very knowledgable about the areas and helped me find the perfect place for me to live. I woudn't have picked a different realitor if I had to do it over again!

User5758139

Review for Member: Cait Berry

June 3, 2014

Local Knowledge

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Negotiation skills

ZillowVERIFIED

It was just wonderful to work with Cait. She was always there to helps us with our dogs and other appointments related to our house whenever we needed her. She made our moving process to DC very easy. Thank you Cait!

User4456241

Review for Member: Cait Berry

May 22, 2014

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait took the time to know my priorities and then sought out homes that matched those priorities. I'm in the home of my dreams because of her knowledge and expertise. I would consider her my most valuable asset in this journey.

User57362886

Review for Member: Cait Berry

March 26, 2014

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was wonderful! She was responsive to our requests, easily accessible and truly motivated to help us purchase our first home. I would recommend her to anyone, hands down!

Mike H.

Review for Member: Cait Berry

March 25, 2014

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Cait is wonderful! She returned calls quickly, and was very flexible concerning the listings we wanted to see, and offered insights at every step of the way. I wouldn't have wanted my first home buying experience to have been with a different agent.

User7018346

Review for Member: Cait Berry

November 20, 2013

Local Knowledge

Process Expertise

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Negotiation skills

ZillowVERIFIED

Cait was a pleasure to work with and had a lot of good insight for me as a first time home buyer. Always responsive and punctual to my questions and ideas, she proved herself to be a very savvy representative. She was incredibly helpful and I couldn't be more pleased with where I ended up.

PaulOrco

Review for Member: Cait Berry

November 18, 2013

Local Knowledge

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Responsiveness

Negotiation skills

ZillowVERIFIED

Cait was truly an amazing agent. Her patience was endless, and she always made me feel like I was her only client. It was a pleasure working with her.