Living in Pleasant Prairie, WI
Kenosha County, Wisconsin
By Kaeley Simek, REALTOR® · Updated November 2026
Pleasant Prairie is a village on Kenosha's south side, right on the Illinois border, with newer neighborhoods, a large community recreation complex, and fast I-94 access to both Milwaukee and Chicago.
Real estate & homes in Pleasant Prairie
Pleasant Prairie offers newer subdivisions, ranches and two-story homes, condos and townhomes, plus established neighborhoods near Lake Michigan.
Local favorites & things to do
- LakeView RecPlex
- Lake Andrea and Prairie Springs Park
- Pleasant Prairie Premium Outlets
- Chiwaukee Prairie State Natural Area
- Kenosha County Bike Trail
Schools & education
Pleasant Prairie is served by the Kenosha Unified School District.
School assignments can vary by address, so always verify with the district before you buy. You can compare districts and schools on the Wisconsin DPI School and District Report Cards.
Map of Pleasant Prairie
Buying or selling in Pleasant Prairie with Kaeley
I’m Kaeley Simek, a REALTOR® with Keller Williams Milwaukee Southwest, and I help buyers and sellers throughout Kenosha County and southeastern Wisconsin. If Pleasant Prairie is on your list, I can walk you through how its neighborhoods compare, what homes are selling for right now, and which nearby communities might be a good fit, too.
New to buying? Start with my first-time buyer roadmap, see how I help buyers, or learn how I help sellers. Need to buy and sell at the same time? I can help with that, too.
What my clients say
“Kaeley is the only person I ever want to work with - buying, selling, whatever! She LISTENED to my preferences and found me the most amazing house, under budget! Kaeley was on top of EVERYTHING and had great resources for lenders & inspections. She never once made me feel stupid for not knowing something, or like I was a burden. She is THE agent!”
Read more reviews from my clients →
Nearby communities
Not sure which town is the right fit? Take my neighborhood quiz →
Thinking about buying or selling in Pleasant Prairie?
I’d love to help you understand the local market, explore available homes, or put together a plan for your next move.
About the author: Kaeley Simek, REALTOR®
I’m a REALTOR® with Keller Williams Realty Milwaukee Southwest, helping buyers and sellers across Milwaukee, Waukesha, Washington, Kenosha and Walworth Counties. I grew up in a real estate family and studied marketing and psychology at Carroll University.
I take great pride in doing everything I can to give you the ultimate buying or selling experience. My top values are communication, honesty, kindness and having the heart of a teacher: guiding you and explaining your options so you can make great decisions. I’m extremely experienced with unique and tough challenges, and I love to negotiate.
- RealTrends Verified: top 1.5% of agents nationally
- Top 20% of agents in my Keller Williams office
- 104% average sale-to-list ratio and 99% contract-to-close ratio
- 67 five-star Google reviews
Kaeley Simek, REALTOR® · WI License #86708-94 · Keller Williams Realty Milwaukee Southwest
Photos via Wikimedia Commons: Garrison Point (CC BY-SA 4.0), AlphaBeta135 (CC BY 4.0). Map © Google.
