Cait Berry

Berkshire Hathaway True Realty

13 Years of Experience

(41)

$24M

Total Sales Last Year

Years of Experience

Recent TransactionsTransactions from the last 3 years

$531.1K

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

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About Cait Berry

Cait Berry is a lifelong Madisonian, sixth-generation local, and founder of Insiders Realty--a boutique team helping people buy, sell, and relocate across Dane County with expert guidance and a personal touch. Her family helped shape neighborhoods like Shorewood Hills, Westmorland, and Sunset Village, and today Cait brings that legacy full circle with honest advice, deep local insight, and a straightforward approach that puts her clients at ease. In 2024, Cait and her team helped more than 50 families move, closing over 25 million dollars in sales. Clients--whether relocating for work, upsizing for their next chapter, or searching for the right school district--appreciate her responsive communication, strategic pricing, and ability to make complex decisions feel clear and manageable. Her Inside Madison Relocation Guide is a free resource filled with neighborhood insights and lifestyle tips--from school zones and walkability to the best coffee shops, local parks, and hidden gems--designed to help buyers feel like locals from day one. Sellers benefit from Cait's thoughtful listing prep, lifestyle-focused marketing, and smart negotiation that consistently delivers strong results. A mom of three and lifelong resident of Madison, Cait sponsors Fetch Wisconsin Rescue and Westmorland Summer Nights, and never misses a Saturday at the Farmers' 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.

Specialties

Sellers
Buyers
Residential Property

Cait’s sweet spot is working with clients in transition—families relocating, homeowners ready for a change, or anyone who needs a steady hand and a smart plan to make a move feel less overwhelming.

Awards

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Cait Berry's Reviews & Ratings

41 Reviews

(5/5)

Note: Reviews may include other agents on their team

What clients say about this agent....

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

Kevindalexander

Review for Member: Cait Berry

August 13, 2025

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Ashlee was fantastic. She helped us quickly list our house - provided guidance about staging, timing, got our house cleaned, and professionally photographed. She has a strong marketing strategy including outreach to many other agents and effective social media push. Personally, she seemed to care deeply about our sale and was willing to do whatever it took to help (including packing/moving clutter out of our house). I also really appreciated her responsiveness which was often within minutes of texting her. This all led to a great outcome - a strong accepted offer after only a few days on the market. She was a great partner through inspection, appraisal, and closing as well.

Nicholas S.

Review for Member: Cait Berry

July 2, 2025

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

My wife and I absolutely loved working with Ashlee! She found us a great home despite an extremely competitive market (and having to work with us remotely while we still lived out of state), and then helped us to sell when we were ready to leave Wisconsin a few years later. Ashlee is extremely knowledgable, professional, and easy to communicate with. I highly recommend working with her if you're looking to buy or sell in the Madison, WI area!

Patrickkeav

Review for Member: Cait Berry

May 30, 2025

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Stephanie is great to work with! She is nice, knowledgeable, and responsive. Absolutely recommend. She was willing to answer my questions throughout the entire process no matter how silly they were.

Jay W.

Review for Member: Cait Berry

May 9, 2025

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Ashlee continues to stand out with her expertise, empathy, insight and experience making our home look as amazing as possible and ensuring a smooth closing process, even with complications brought on by third parties during the process. I will always (continue) to recommend her and her agency for their attention to detail and experience. I'd recommend Ashlee and plan to leverage her abilities when we make our next home purchase without hesitation.

Taylor R.

Review for Member: Cait Berry

May 8, 2025

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

We would highly recommend Stephanie to anyone who is looking to purchase a home! We just closed on our first house and she made the whole process less daunting and incredibly smooth. From sitting us down and explaining the whole process, guiding us through showings and offers, and answering any questions we had, we could not have asked for anyone better. We wouldnt be where we are today without her!