Top real estate investing financial advisors working with high-net-worth individuals in Massachusetts
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 own or are considering investing in real estate, you need an advisor who understands the unique cash flow, tax, and market risks involved. Without this expertise, you might overlook critical factors like property management costs or local market trends that can impact your returns.
- Property type knowledge. Ask if they have experience with the specific real estate asset you own or want, such as residential, commercial, or rental properties.
- Tax implications. Confirm how they handle depreciation, capital gains, and 1031 exchanges (property swaps to defer taxes) in your investment plan.
- Market cycle insight. A strong advisor will consider local market conditions and timing, not just national real estate trends.
- Financing strategies. Discuss how they approach leveraging debt and refinancing options to optimize your investment's performance.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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William O
Series 63, Series 65
South Natick, MA
Strategic Wealth Management LLC
William O'Neill specializes in real estate investing for high-net-worth clients in Massachusetts, leveraging his four years of industry experience and Series 63 and 65 licenses. His firm, Strategic Wealth Management LLC, offers tailored portfolio management and financial planning with a long-term trading approach that combines cyclical and fundamental analysis, quantitative methods, and modern portfolio theory, differentiating him from advisors with more generic investment strategies.
Experience: 5 years
Avg account: $439,177
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Kimberly S
Series 65, Series 63
Marion, MA
Baldwin Wealth Partners, LLC
Kimberly Swift specializes in real estate investing for high-net-worth clients in Massachusetts, leveraging her firm's expertise in private and alternative investments alongside ESG considerations. Her flat-fee structure offers transparent pricing for account monitoring and consulting, distinguishing her from advisors with traditional AUM fees. With over nine years of experience and a background at Mercer, she serves established professionals and business owners, providing a comprehensive approach that includes both macro analysis and fundamental research.
Experience: 0 years
Avg account: $2,878,883
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Edward V
Series 63, Series 65
Medfield, MA
Silver Pine Capital, LLC
Edward Vahey specializes in real estate investing for high-net-worth clients in Massachusetts, leveraging 10 years of experience and Series 63 and 65 licenses. His firm, Silver Pine Capital, employs a value-oriented investment process combining bottom-up stock selection with top-down macro analysis, offering diversified portfolios and specialized hedged strategies. Unlike some peers, he provides a financial planning subscription fee and performance-based fee arrangements, catering to both individual and institutional clients.
Experience: 10 years
Avg account: $529,114
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Michael O
PFS™, Series 65
Millis, MA
MOK Financial Planning & Tax, Inc.
Michael O'Keeffe specializes in real estate investing for high-net-worth clients in Massachusetts, leveraging 20 years of experience and a Personal Financial Specialist designation to address complex tax and market considerations. His firm offers discretionary portfolio management alongside tax preparation and bookkeeping, with flexible flat-fee consulting and a personalized investment approach, distinguishing him from advisors focused solely on asset management or lacking integrated tax services.
Experience: 20 years
Avg account: $658,951
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Robert R
CFP®, Series 63, Series 65
Wellesley, MA
Peak Financial Management Inc
Robert Roselli's 31 years of experience and CFP® certification equip him to address the complex cash flow and tax considerations involved in real estate investing for high-net-worth clients in Massachusetts. His firm, Peak Financial Management Inc, offers discretionary portfolio management with a model-based investment approach, charging 0.95% annually on assets under management, which may appeal to clients seeking structured investment strategies and comprehensive financial planning.
Experience: 32 years
Avg account: $1,498,005
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