Kaitlyn Shepherd License ID: 95344-94
Agent5552 S 108th St Suite 103, Hales Corners WI 53130
Kaitlyn Shepherd's Profile
Hi, I’m Kaitlyn, a dedicated real estate professional serving the Greater Milwaukee and Waukesha County areas. With a passion for helping people achieve their homeownership goals, I specialize in guiding buyers, sellers, and investors through a thoughtful, seamless real estate experience.
Over the years, I’ve built my business around three core areas of expertise:
✔ First-Time Home Buyers
I love working with first-time buyers and making the process approachable, educational, and enjoyable. I pride myself on creating a comfortable, judgment-free space where no question is too small and every step is clearly explained. My goal is to empower new buyers with confidence as they make one of the biggest decisions of their lives.
✔ Senior Transitions & Families Selling a Loved One’s Home
Supporting seniors as they transition out of homeownership—and families navigating the sale of a loved one’s home—is some of the most meaningful work I do. I’ve developed a streamlined process with trusted local vendors to reduce stress and provide full-service support, including movers, cleaners, stagers, junk removal, senior living partners, and more. My focus is ensuring seniors and families feel cared for, respected, and supported every step of the way.
With local market expertise, strong negotiation skills, and a relationship-centered approach, I’m committed to making every transaction smooth, rewarding, and deeply personal. Whether you’re buying your first home, helping a parent transition, selling a family property, or exploring investment opportunities—I’m here to support you every step of the way.
Outside of real estate, I enjoy golfing, live music, and spending time outdoors with friends and family. I also stay actively involved in the community through GMAR YPN and charitable initiatives like the Milwaukee Homeless Veterans Initiative.
Looking to buy or sell? I’d love to connect and help you achieve your real estate goals!
3 Beds2 Baths880 SqFt1/29 29Pending
2 Beds1.5 Baths1,278 SqFt1/29 29Active
$918,000
$925,000
0.8%W253N5552 Crescent Hill Dr, Sussex, WI 53089
Listed by Braden Team* First Weber Inc - Menomonee Falls
$761,000
$724,990
5.0%Lisbon, 53089
Listed by Scott J Pinzer Kaerek Homes, Inc.
$715,000
$665,000
7.5%6065 S Preston Ln, New Berlin, WI 53151
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$570,000
$569,000
0.2%Greenfield, 53228
Listed by Gaby Boutillier Coldwell Banker Realty
$551,300
$499,900
10.3%Muskego, 53150
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$542,000
$524,900
3.3%Oconomowoc, 53066
Listed by Alesia M Fugleberg RE/MAX Service First Lake Country
$528,000
$449,900
17.4%Vernon, 53189
Listed by Mary P Skanavis Homeowners Concept
$526,000
$525,000
0.2%Oak Creek, 53154
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$513,000
$499,900
2.6%Hartford, 53027
Listed by Joseph C Jewell Lake Country Flat Fee
$491,500
$499,000
1.5%5845 S Oxford Ln, New Berlin, WI 53146
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$475,000
$475,000
Ixonia, 53066
Listed by Erin E Waldron Property Dynamics/Appraisal Specialists
$460,000
$399,900
15.0%21715 Hillcrest Dr, Brookfield, WI 53186
Listed by The Krickeberg Group* Keller Williams Realty-Milwaukee Southwest
$460,000
$450,000
2.2%1009 Canterbury Ln, Waukesha, WI 53188
Listed by Brian J Johnsen First Weber Inc- Greenfield
$449,000
$449,000
8336 Stonegate Rd, Norway, WI 53185
Listed by Kaitlyn R Shepherd EXP Realty, LLC~MKE
$430,000
$399,900
7.5%206 Sunset Ct, Mayville, WI 53050
Listed by Joseph C Jewell Lake Country Flat Fee
$421,000
$414,900
1.5%1661 Falcon Dr, Hartford, WI 53027
Listed by Doug Hughes RE/MAX Advantage Realty
$417,500
$424,900
1.7%N8973 E Miramar Dr, East Troy, WI 53120
Listed by Gina Dingman Realty Executives Integrity-Ea
$406,000
$370,000
9.7%Greenfield, 53220
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$389,000
$389,900
0.2%Milwaukee, 53213
Listed by Leigh J Jackson First Weber Inc - Brookfield
$365,000
$360,000
1.4%Menomonee Falls, 53051
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$361,000
$349,900
3.2%Waukesha, 53189
Listed by Sarah D Pelikan Valor Realty LLC
$360,000
$250,000
44.0%New Berlin, 53151
Listed by Kaitlyn R Shepherd EXP Realty, LLC~MKE
$350,000
$329,900
6.1%2253 W Vista Bella Dr, Oak Creek, WI 53154
Listed by Kaitlyn Shepherd Real Broker Milwaukee
$345,000
$324,900
6.2%West Allis, 53227
Listed by Randy Rosen HomeBuyers Advantage, LLC
$337,000
$319,000
5.6%3136 N 79th St, Milwaukee, WI 53222
Listed by Kaitlyn Shepherd Real Broker Milwaukee
$325,000
$275,000
18.2%Milwaukee, 53220
Listed by Lifetime Realty Group* Keller Williams Realty-Milwaukee Southwest
$322,000
$314,900
2.3%3319 S 86th St, Milwaukee, WI 53227
Listed by Pamela Coleman PRC Realty LLC
$320,000
$289,900
10.4%Greendale, 53129
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$320,000
$295,000
8.5%Milwaukee, 53221
Listed by Tyler P Vandermolen Real Broker Milwaukee
$305,000
$309,900
1.6%2202 S 67th Pl, West Allis, WI 53219
Listed by The Blend Group* Coldwell Banker Realty
$302,500
$309,900
2.4%3320 S 92nd St, Milwaukee, WI 53227
Listed by Kaitlyn Shepherd Real Broker Milwaukee
$300,000
$289,900
3.5%Milwaukee, 53221
Listed by Matthew J. Stong Becker Stong Real Estate Group, Inc.
$295,000
$299,900
1.6%Brookfield, 53045
Listed by Turner W. Jacques Keller Williams Realty-Lake Country
$292,000
$276,000
5.8%Franklin, 53132
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$287,000
$279,000
2.9%West Allis, 53219
Listed by Jacklyn M. Rynish-Knapp Keller Williams-MNS Wauwatosa
$275,000
$253,000
8.7%Milwaukee, 53219
Listed by Kaitlyn R Shepherd EXP Realty, LLC~MKE
$270,000
$236,900
14.0%West Allis, 53219
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$245,000
$244,000
0.4%Milwaukee, 53207
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$235,000
$229,900
2.2%3731 N 77th St, Milwaukee, WI 53222
Listed by Sandy Weller The Real Estate Studio
$226,000
$220,000
2.7%West Allis, 53219
Listed by Lynn A Friedman Century 21 Benefit Realty
$219,900
$219,900
Waukesha, 53186
Listed by Alison M Miller Tanking Epique Realty Germantown
$213,500
$189,000
13.0%West Allis, 53214
Listed by Julie A Deomampo Shorewest Realtors, Inc.
$140,000
$139,900
0.1%Greenfield, 53221
Listed by Kaitlyn R Shepherd Real Broker Milwaukee
$100,000
$100,000
700 W Shields Rd, Saint Germain, WI 54558
Listed by Kaitlyn Shepherd Real Broker Milwaukee