Top real estate investing financial advisors in Chicago, IL
The right financial advisor for you depends on how you weigh location, expertise, experience, the clients they typically serve, and how they work with you.
If you're investing in real estate, you likely face complex decisions about property types, financing, and market timing. Without focused expertise, you might overlook key risks like cash flow variability or tax implications specific to your investments.
- Property type insight. Ask how they tailor strategies for residential, commercial, or rental properties, since each has unique challenges.
- Financing strategies. Confirm their approach to leveraging debt and managing mortgage structures to optimize returns without overexposure.
- Market cycle awareness. A strong advisor anticipates local market shifts and advises on timing acquisitions or sales accordingly.
- Tax impact understanding. Even though Illinois has no tax on retirement income, property taxes can be high; check how they factor this into your investment plan.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Thomas H
Series 63, Series 65
Chicago, IL
Charles Schwab
Thomas Halden's 30 years of experience and expertise in real estate investing and multi-state taxation equip him to navigate Chicago's complex property market and tax environment. Affiliated with Charles Schwab, a large firm serving high-net-worth clients with a 0.80% AUM fee, he offers access to alternative investments and multi-asset portfolios, distinguishing him from advisors with smaller firm resources or narrower service scopes.
Experience: 31 years
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Joseph S
CFP®, Series 63, Series 65
Chicago, IL
Lake Street
Joseph Stock's expertise in real estate investing and active portfolio management suits investors navigating Chicago's complex property market. As a CFP® and co-founder of Lake Street, he offers flat-fee consulting and discretionary investment management with up to 2% AUM fees, focusing on high-net-worth clients and institutional cost structures, which differentiates him from advisors with less specialized fee options or firm resources.
Experience: 13 years
Avg account: $1,693,909
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Sharese A
Series 63, Series 65
Chicago, IL
Horizon Family Wealth, Inc.
Sharese Abbadessa brings 13 years of experience in real estate investing and private alternative investments, offering flat-fee financial planning tailored for high-net-worth clients in Chicago. Her firm uses a multi-faceted investment approach with discretionary management and third-party managers, providing comprehensive portfolio management that may suit investors seeking diversified strategies beyond typical real estate advice.
Experience: 13 years
Avg account: $2,997,968
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Charles A
Series 65
Birmingham, AL
Waverly Advisors, LLC
Charles Adair specializes in real estate investing and private alternative investments, offering tailored strategies that consider tax-loss harvesting and ESG factors, which are crucial for Chicago's diverse property market. His firm, Waverly Advisors, LLC, provides flexible fee structures including flat fees and manages portfolios for individuals and corporations, distinguishing him with a blend of customized and centrally designed investment approaches despite his relatively recent advisory experience.
Experience: 2 years
Avg account: $1,639,930
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James B
Series 66
Chicago, IL
Uhlmann Investment Management, L.L.C.
James Baer specializes in real estate investing with 26 years of experience and holds a Series 66 designation, making him well-equipped to navigate Chicago's property market complexities. His firm, Uhlmann Investment Management, offers both discretionary and non-discretionary portfolio management with a focus on fundamental analysis and long-term asset allocation, charging a 1.75% AUM fee and serving high-net-worth clients independently.
Experience: 26 years
Avg account: $572,956
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