Cait Berry

Madison WI

Berkshire Hathaway HomeServices True Realty

200 Closed Sales

$92.8M Total Value

$232K - $2M Price Range

$464.1K Average Price

Prior five years

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.

Home Types: Condo, MultiFamily, Townhouse, House, Lot/Land

Years of Experience: 13

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$18,449,600

Average Sale Price

$559,079

Price Range

$305K - $2M

Buyer Deals

Total Deals

Total Value

$18,028,930

Average Sale Price

$546,331

Price Range

$240K - $1.3M

1 Year View by Quarter

Seller Deals

Total Deals

Total Value

$22,293,005

Average Sale Price

$543,732

Price Range

$232K - $2M

Buyer Deals

Total Deals

Total Value

$30,823,830

Average Sale Price

$505,309

Price Range

$156K - $1.3M

2 Year View by Quarter

Seller Deals

Total Deals

Total Value

$36,154,805

Average Sale Price

$469,543

Price Range

$150K - $2M

Buyer Deals

Total Deals

123

Total Value

$56,660,747

Average Sale Price

$460,656

Price Range

$100K - $1.8M

5 Year View

Neighborhoods Cait Has the Most Experience In

Cait's Active Listings

$285,000
- 1 Bed
- 1 Bath
- 626 Sq Ft
111 N Hamilton St

Unit 202

Madison, WI
Live in the heart of downtown—just half a block from the Capitol Square with unbeatable access to the Farmers Market, live music, and downtown festivals. This second-floor condo offers a smart layout that makes the most of its space, with generous closets, in-unit laundry, and a spacious bathroom. Recent upgrades include sleek quartz countertops, new sink and cabinet hardware, a curved breakfast

Cait Berry Berkshire Hathaway HomeServices True Realty

$1,350,000
- 5 Beds
- 5.5 Baths
- 5,898 Sq Ft
5870 Persimmon Dr

Fitchburg, WI
A rare architectural masterpiece on a quiet street in Fitchburg’s Lacy Heights. Rooted in Prairie-style tradition, this home blends timeless design w/ thoughtful functionality. The layout offers multiple living areas, a main-level office & seamless indoor-outdoor flow. A screened porch, veranda off the dining room & private backyard patio connect the home to its natural surroundings. Rich

Cait Berry Berkshire Hathaway HomeServices True Realty

$1,550,000
- 5 Beds
- 4.5 Baths
- 4,540 Sq Ft
6835 Angelica Trail

Windsor, WI
Step inside this modern European Tudor on a private lot in a choice neighborhood. Less than 15 minutes from east side hospitals, shopping and restaurants. Here, every detail has been curated for elegance, from the steep roof pitches, custom beams, white oak flooring with an incredible layout. The main level is perfect for daily life and entertaining, featuring an open great room, home office,

Cait Berry Berkshire Hathaway HomeServices True Realty

$1,000,000
- 4 Beds
- 4 Baths
- 4,958 Sq Ft
39 Hawk Feather Cir

Madison, WI
Elegant all-brick ranch tucked on a wooded cul-de-sac in sought-after Blackhawk (Middleton schools). Light-filled great room with vaulted ceilings and gas fireplace flows into dining and sunroom. Gourmet kitchen by Dream Kitchens features cherry cabinetry, granite, SubZero/Wolf appliances, island with breakfast bar, and a built-in dinette with butler’s pantry and laundry. Step out to a screened

Cait Berry Berkshire Hathaway HomeServices True Realty

$525,000
- 3 Beds
- 2 Baths
- 2,342 Sq Ft
2 Red Cedar Trail

Madison, WI
Stylish and move-in ready, this extensively updated freestanding ranch in Tamarack Trails offers bright, open living with hardwood floors, vaulted ceilings, and a cozy gas fireplace. The kitchen impresses with quartz countertops, custom cabinetry, tile backsplash, stainless appliances, and a spacious island. Glass doors open to a private deck and beautifully landscaped yard. A main-level den adds

Cait Berry Berkshire Hathaway HomeServices True Realty

Other Experience

First Time Home Buyers, Investments, Luxury Homes, Military Families, New Construction, Property Management, Senior Communities, Short Sales, Veteran Programs

Cait Berry

(608) 292-2137

Cait Berry

About Cait

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Cait Has the Most Experience In

Cait's Listings and Deals

Cait's Active Listings

Other Experience