Top tax-loss harvesting financial advisors in Pittsfield, MA

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 have investments with losses that could offset gains, a tax-loss harvesting advisor can help you use those losses to reduce your tax bill. Without careful planning, you might miss opportunities to lower your taxes or accidentally trigger unwanted tax events.

  • Surtax awareness. Ask how they navigate Massachusetts' 'Millionaire's tax' surtax on high incomes to optimize your tax-loss harvesting.
  • Timing strategies. Confirm how they decide when to sell losing investments to maximize tax benefits without disrupting your portfolio.
  • Wash sale rules. Ensure they understand and avoid repurchasing the same or similar securities within 30 days, which can disallow your losses.
  • Portfolio integration. Look for advisors who balance tax-loss harvesting with your overall investment goals, not just tax savings alone.

Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.

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Elizabeth A

Series 63, Series 65

Pittsfield, MA

Eagle Strategies (NY Life)

Elizabeth Ariazi is a financial advisor with Eagle Strategies (New York Life) based in Pittsfield, MA, holding Series 63 and Series 65 licenses and accumulating 18 years of industry experience. She has worked with NYLIFE Securities LLC and New York Life Insurance Company since 2008 and with Eagle Strategies since 2021. Outside of her advisory role, she manages rental of her primary residence through Airbnb. Eagle Strategies serves a diverse clientele including individual investors, defined contribution and benefit plans, and corporate and charitable clients. The firm provides financial planning, investment management, and retirement-plan advisory services, emphasizing tailored recommendations and primarily managing assets on a non-discretionary basis.

Retirement plans for business owners (SEP, solo 401k) Business exit / sale strategy General retirement planning Retirement income strategy Founder/Business Owner Executive
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Michael F

Series 63, Series 65

Pittsfield, MA

LPL Financial

Michael Fazio is a financial advisor with LPL Financial based in Pittsfield, MA, holding Series 63 and Series 65 credentials and possessing 25 years of industry experience. He has worked at LPL Financial (formerly LINSCO Private Ledger) and Greylock Federal Credit Union since 2008. At Greylock Federal Credit Union, he serves as Senior Vice President, dedicating half of his professional time to this role. LPL Financial is a national broker-dealer and SEC-registered investment adviser that provides advisory and brokerage services to individuals, retirement plan participants, banks, trust companies, and other institutions. The firm offers a range of financial planning and investment management solutions through a large network of advisors and utilizes various portfolio strategies, technology tools, and institutional platforms.

Wealth management Retirement income strategy College savings (529s, UTMA, etc.) Tax-loss harvesting Annuities Retired Founder/Business Owner Executive
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William K

CFP®, Series 63, Series 65

Pittsfield, MA

Raymond James Financial

William Kirby is a CFP® with 50 years of experience in the financial industry, currently serving at Raymond James Financial Services Advisors Inc. He previously worked for Wells Fargo Advisors for 12 years. Kirby is chair of the investment committee for the Berkshire Community College Foundation. Raymond James Financial Services Advisors, Inc. provides financial planning, investment consulting, and advisory services to a diverse client base, including individual and high-net-worth clients, institutions, and charitable organizations. The firm offers tailored, non-discretionary planning and consulting using analytical tools and supports its clients through various advisory programs.

Wealth management Tax strategies for small businesses Business succession planning General estate planning guidance Founder/Business Owner Executive
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Darrell C

Series 66

Pittsfield, MA

Raymond James & Associates

Darrell Colvin is a financial advisor at Raymond James & Associates with three years of industry experience. He holds a Series 66 designation and has prior experience with Prudential Insurance Company of America, Guardian Life, and Wayfair L.L.C. Colvin volunteers with the Berkshire Theatre Group in Pittsfield, MA. Raymond James & Associates is a large, dually registered broker-dealer and SEC-registered investment adviser managing approximately $501 billion in assets. The firm serves a diverse client base including individuals, institutions, and municipal entities, offering financial planning and investment consulting through a range of portfolio management styles and affiliated research.

General retirement planning Retirement income strategy Business succession planning Founder/Business Owner Executive
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Kevin O

CFP®, Series 63, Series 65

Pittsfield, MA

Commonwealth Financial Network

Kevin O'Donnell Jr. is a CFP®-designated financial advisor with 28 years of industry experience, currently affiliated with Commonwealth Financial Network and Beacon Investment Services. His prior work includes tenures at UBS Financial Services, Merrill, Quick & Reilly, Banc of America Investment Services, and Berkshirebanc Investment Services. He is also involved in fixed insurance sales at his branch location. Commonwealth Financial Network is a dual-registered broker/dealer and SEC-registered investment adviser serving a nationwide network of approximately 2,900 advisors and managing about $212.7 billion in client assets. The firm provides a comprehensive adviser-support platform with a variety of managed-account programs, access to third-party asset managers, and custody and clearing services.

Passive / index investing Active portfolio management Tax-loss harvesting Wealth management Retirement income strategy Founder/Business Owner Executive Retired
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Edwina M

Series 65

Cincinnati, OH

Waverly Advisors, LLC

Edwina Martin is a Series 65 licensed financial advisor with two years of industry experience, currently with Waverly Advisors, LLC. She previously worked at 9258 Wealth Management for five years and was employed at Teradata Corp for eleven years. Martin also serves as assistant director of tax planning at 9258 Tax and Planning, a non-investment related business. Waverly Advisors is a multi-team registered investment adviser managing portfolios for individuals, retirement plans, and pooled investment vehicles. The firm combines traditional equity and fixed-income strategies with alternative and private-market allocations, offering a range of investment management and financial planning services.

Private / alternative investments Real estate investing Options & derivatives strategies Tax-loss harvesting Multi-generational wealth transfer Founder/Business Owner Executive
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Jeffrey P

Series 66

Dacula, GA

Merrill

Jeffrey Park is a financial advisor at Merrill with eight years of industry experience. He holds a Series 66 designation and has worked at Merrill and affiliated firms since 2011, including roles at JPMorgan Chase Bank and J.P. Morgan Securities. Outside of his advisory work, he is a sole owner and co-owner of family rental properties in Lawrenceville, Georgia. Merrill, together with its affiliate Managed Account Advisors LLC, provides managed account services to Bank of America fiduciary clients through the Select Portfolio Solutions Program, offering model-based and discretionary strategies for individuals, high-net-worth clients, and institutional investors.

Tax-loss harvesting Active portfolio management Wealth management
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Hassan A

Series 63, Series 65

Rockville, MD

LPL Financial

Hassan Al Kadhimi is a financial advisor with LPL Financial, holding Series 63 and Series 65 licenses and two years of industry experience. His prior roles include positions at J.P. Morgan Securities LLC and JP Morgan Chase Bank, N.A. He is also involved with NIHFCU Wealth Advisors, a related business entity. LPL Financial is a national broker-dealer and SEC-registered investment adviser serving individuals, retirement plan participants, banks, trust companies, and institutions. The firm offers a range of advisory and brokerage services, including financial planning, model portfolio programs, and institutional platforms, supported by a large network of investment adviser representatives.

Wealth management Retirement income strategy College savings (529s, UTMA, etc.) Tax-loss harvesting Annuities Retired Founder/Business Owner Executive
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Sarah C

CFP®, Series 63, Series 65

Boston, MA

Santander Securities LLC

Sarah Currier Barrella is a CFP® professional with 26 years of experience in financial advisory services. She currently works at Santander Securities LLC and Santander Bank, NA, having previously held positions at TD Bank and Citizens Securities, Inc. Barrella is based in Boston, MA. Santander Securities LLC serves a broad retail client base with approximately $3.14 billion in regulatory assets under management across 10,800 client relationships. The firm offers investment advisory services, portfolio management through wrap-fee programs, and financial planning, operating both as a registered investment adviser and a FINRA-registered broker-dealer.

ESG / Sustainable investing Tax-loss harvesting General retirement planning Income planning Founder/Business Owner
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Deborah E

Series 63, Series 66

Cape Girardeau, MO

Edward Jones

Deborah Etherton is a financial advisor at Edward Jones in Cape Girardeau, MO, holding Series 63 and Series 66 licenses with 20 years of industry experience. She has been with Edward Jones since 2005. Edward Jones is a full-service wealth management firm serving over four million individual and institutional clients. The firm manages approximately $1.01 trillion in assets and offers a range of advisory strategies, including discretionary and non-discretionary wrap fee programs, separately managed accounts, and affiliated mutual funds, operating under a fiduciary standard.

Wealth management Tax-loss harvesting Multi-generational wealth transfer Retired Founder/Business Owner Executive

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