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Jake Barr - Milwaukee Investing Expert

Agent
5.0 stars
89 Reviews

Markets served


Bayside, WI
Shorewood, WI
Greenfield, WI
Fond du Lac, WI
Brookfield, WI
West Allis, WI
Waukesha, WI
Mequon, WI
Whitefish Bay, WI
Wauwatosa, WI

Licenses, Designations or Certificates


Real Estate Salesperson License
Certificate of Real Estate - University of Wisconsin Milwaukee

More ways to connect


About us


Jake Barr | Top 1% Milwaukee Real Estate Agent | BiggerPockets Preferred Agent | Investment Property Specialist

Jake Barr is a Top 1% Milwaukee real estate agent and BiggerPockets Preferred Agent Partner specializing in Milwaukee investment properties, cash-flow real estate, and portfolio growth strategies. Recognized as a Rising Star in Real Producers Magazine and a market leader in Milwaukee investment real estate, Jake delivers a high-level, results-driven experience tailored to serious investors.

In 2026, Jake helped 44 clients close over $10.5M in Milwaukee real estate transactions, consistently identifying undervalued properties, high ROI investment opportunities, and emerging neighborhoods in Milwaukee, WI. His approach combines data-driven real estate analysis, local market expertise, and strategic negotiation, helping clients secure strong cash flow, appreciation, and long-term wealth through real estate investing.

Jake works with real estate investors, out-of-state buyers, and high-performing professionals seeking a trusted Milwaukee investment real estate expert. If you're looking to buy investment property in Milwaukee, scale a real estate portfolio, or invest in high-return rental properties, Jake provides the strategy, access, and execution to help you win.

Specialties


Residential

Single-Family Rental
Primary Residence
Multi-Family (2-4 units)
Short-term rental
Mid-term rental
Long-term rental

Reviews (89)


5.0 stars
89 Reviews
5.0 stars
89 Reviews
0.0 star
0 Reviews

reviewer image
5.0 stars
|
2 months ago
Reviewed by Zachary O
As a seller, Jake was an excellent agent to work with throughout both the listing and closing process. As someone who would be overwhelmed trying to DIY the sale of my property thousands of miles away (I live in Alaska) Jake made sure to take care of all the details and advocate for getting a fair deal, even through unforeseen issues with the condition of my property. He was transparent, honest, reasonable and responsive. I would highly recommend him on either side of any real estate transaction.
reviewer image
5.0 stars
|
3 months ago
Reviewed by Daniel Szwed
Working with Jake Barr was an outstanding experience. He was incredibly knowledgeable, responsive, and helpful throughout the entire process of purchasing our condo in Milwaukee. His knowledge of the local market exceeded our expectations and gave us confidence every step of the way. Jake made the experience smooth and stress-free. We highly recommend him to anyone looking to buy or sell a home!
reviewer image
5.0 stars
|
3 months ago
Reviewed by Peter Konkel
Jake was an outstanding listing agent to work with. He made the entire process smooth and comfortable for both me and my buyers. His communication was excellent—he was always quick to respond to questions and kept everyone informed throughout the transaction. Jake made it easy for my clients to access the property for showings and walkthroughs, and he was always receptive, professional, and willing to answer any questions that came up along the way. His teamwork and attention to detail made for a great experience from start to finish. I look forward to working with Jake again in the future and would highly recommend him to anyone looking for a knowledgeable, responsive, and professional real estate agent. Peter Konkel MAP Realty Group
reviewer image
5.0 stars
|
Edited 3 months ago
Reviewed by Nicole Aitchison
Jake was fantastic to work with.! He was knowledgeable, responsive, and always had our best interests in mind. He made everything feel easy and stress-free, and fun. He kept us informed every step of the way, and was always available to answer our questions. We highly recommend Jake to anyone looking for a trustworthy and dedicated real estate agent! Can’t wait to work with him again!
reviewer image
5.0 stars
|
3 months ago
Reviewed by mk
I can’t recommend Jake highly enough. Selling this property was one of the more challenging real estate transactions I’ve experienced. It was a distressed property located in a very difficult area, and as an out-of-state seller, I needed someone I could fully trust to take ownership and handle everything on the ground. From the beginning to the closing, Jake stepped up and managed every challenge that came up. We ran into almost every possible issue, including last-minute buyer concerns, inspection problems, repair issues, and unexpected complications that needed immediate attention. Jake stayed calm, patient, and professional through it all. He communicated clearly, kept me updated, and worked tirelessly to get each problem resolved. What impressed me most was that Jake took charge and became someone I could rely on. He was responsive, knowledgeable, friendly, and always focused on finding solutions. Despite all the issues with this distressed property, he helped get the property sold quickly and successfully. If you’re looking for a real estate agent who is dependable, proactive, and especially someone you can trust when you’re not physically there, I would highly recommend Jake. He made a very stressful situation much easier, and I’m extremely grateful for his help.
reviewer image
5.0 stars
|
2 months ago
Reviewed by Zachary O
As a seller, Jake was an excellent agent to work with throughout both the listing and closing process. As someone who would be overwhelmed trying to DIY the sale of my property thousands of miles away (I live in Alaska) Jake made sure to take care of all the details and advocate for getting a fair deal, even through unforeseen issues with the condition of my property. He was transparent, honest, reasonable and responsive. I would highly recommend him on either side of any real estate transaction.
reviewer image
5.0 stars
|
3 months ago
Reviewed by Daniel Szwed
Working with Jake Barr was an outstanding experience. He was incredibly knowledgeable, responsive, and helpful throughout the entire process of purchasing our condo in Milwaukee. His knowledge of the local market exceeded our expectations and gave us confidence every step of the way. Jake made the experience smooth and stress-free. We highly recommend him to anyone looking to buy or sell a home!
reviewer image
5.0 stars
|
3 months ago
Reviewed by Peter Konkel
Jake was an outstanding listing agent to work with. He made the entire process smooth and comfortable for both me and my buyers. His communication was excellent—he was always quick to respond to questions and kept everyone informed throughout the transaction. Jake made it easy for my clients to access the property for showings and walkthroughs, and he was always receptive, professional, and willing to answer any questions that came up along the way. His teamwork and attention to detail made for a great experience from start to finish. I look forward to working with Jake again in the future and would highly recommend him to anyone looking for a knowledgeable, responsive, and professional real estate agent. Peter Konkel MAP Realty Group
reviewer image
5.0 stars
|
Edited 3 months ago
Reviewed by Nicole Aitchison
Jake was fantastic to work with.! He was knowledgeable, responsive, and always had our best interests in mind. He made everything feel easy and stress-free, and fun. He kept us informed every step of the way, and was always available to answer our questions. We highly recommend Jake to anyone looking for a trustworthy and dedicated real estate agent! Can’t wait to work with him again!
reviewer image
5.0 stars
|
3 months ago
Reviewed by mk
I can’t recommend Jake highly enough. Selling this property was one of the more challenging real estate transactions I’ve experienced. It was a distressed property located in a very difficult area, and as an out-of-state seller, I needed someone I could fully trust to take ownership and handle everything on the ground. From the beginning to the closing, Jake stepped up and managed every challenge that came up. We ran into almost every possible issue, including last-minute buyer concerns, inspection problems, repair issues, and unexpected complications that needed immediate attention. Jake stayed calm, patient, and professional through it all. He communicated clearly, kept me updated, and worked tirelessly to get each problem resolved. What impressed me most was that Jake took charge and became someone I could rely on. He was responsive, knowledgeable, friendly, and always focused on finding solutions. Despite all the issues with this distressed property, he helped get the property sold quickly and successfully. If you’re looking for a real estate agent who is dependable, proactive, and especially someone you can trust when you’re not physically there, I would highly recommend Jake. He made a very stressful situation much easier, and I’m extremely grateful for his help.

Our Team


Jake Barr