Cait Berry

Cait Berry

REALTOR® / Team Leader / Real Estate Agent at Insiders Realty
WI: 76382-94
  •   5   (12 reviews)

Cait's sales performance at a glance

See how Cait has performed in the last 12 months on RateMyAgent*

0
Reviews
0
Properties for sale
2
Sold properties
$948k
Average sale price
$1.9m
Total sales value

*Includes all properties sold (last 12 months) as lead and supporting agent and published on ratemyagent.com. It may not be complete and can exclude off-market, private sales and undisclosed pricing and sold dates. Contact agent for full sales history.

About Cait

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.

Cait's reviews

  5  
Cait has 12 reviewsacross 9 different locations, showing 6.
Review Cait
Seller review
 It was a great experience, and we would highly recommend Cait and her team!!
6 months ago
It was a great experience, and we would highly recommend Cait and her team!!

We recently sold our home with Cait Berry and her team, and our experience was excellent. Very thorough analysis and we felt fully informed in our approach to the sale. Moving through the process, Cait consistently had a team of resources available for us as needed, which made navigating moments that could have been a challenge truly seamless. Great communication throughout, and we never felt out of the loop. It was a great experience, and we would highly recommend Cait and her team!! Appreciate everything to all who participated in this monumental moment for us.

Buyer review
Cait was so helpful, responsive, and took the best care of us
almost 4 years ago
Cait was so helpful, responsive, and took the best care of us

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.

Seller review
Cait helped me with both the purchase of my first home and the sale of it after a few years
almost 4 years ago
Cait helped me with both the purchase of my first home and the sale of it after a few years

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.

Buyer review
Cait was amazing to work with! We were first time home buyers in the most insane market, but Cait wa
about 4 years ago
Cait was amazing to work with! We were first time home buyers in the most insane market, but Cait wa

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 “next step” emails in preparation for closing and really good checklists to make sure we were on track. We likely won’t move again for several years, but I will certainly recommend Cait and her team to everyone I know!

Seller review
Cait is the best! We recently worked with her as our agent for both buying and selling
over 4 years ago
Cait is the best! We recently worked with her as our agent for both buying and selling

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. 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 bumps 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 contingency 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 with us, teaching us, and ultimately, changed the course of our lives multiple times now! Thank you so much!

Show all 12 reviews
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Cait's properties

Cait has sold 3 properties in the last 12 months, showing 3, sorted by most recent activity

SoldNov 3, 2025
$570,000
509 East Verleen Avenue
Waunakee WI 53597
5
4
2
Single-Family
SoldSep 5, 2025
$1,325,000
5870 Persimmon Drive
Fitchburg WI 53711
5
6
3
Single-Family
SoldAug 29, 2025
$540,000
2330 Mica Road
Madison WI 53719
3
3
2
Single-Family
Show all 3 properties

Cait's sold properties

Cait has sold 3 properties in the past 12 months, showing 3.

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Property imageAddressBedroomsBathroomsCarparksProperty TypeClosing PriceDate Sold
509 East Verleen Avenue, Waunakee, WI, 53597
509 East Verleen Avenue
Waunakee WI 53597
5
4
2
Single-Family$570,000Nov 3, 2025
5870 Persimmon Drive, Fitchburg, WI, 53711
5870 Persimmon Drive
Fitchburg WI 53711
5
6
3
Single-Family$1,325,000Sep 5, 2025
2330 Mica Road, Madison, WI, 53719
2330 Mica Road
Madison WI 53719
3
3
2
Single-Family$540,000Aug 29, 2025

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