Top real estate investing financial advisors in Bennington, VT

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 in Bennington, VT, you likely face unique challenges like managing property cash flow and navigating local market trends. A common mistake is underestimating ongoing costs and tax implications, which can erode your investment returns.

  • Local market insight. Look for advisors who understand Bennington's rural real estate dynamics and aging demographics affecting property demand.
  • Cash flow management. Confirm how they help you plan for expenses like maintenance, vacancies, and property taxes to keep your investments sustainable.
  • Tax strategy knowledge. Real estate investing involves complex tax rules; ask how they optimize deductions and depreciation benefits.
  • Healthcare access planning. Given local healthcare challenges, see if they incorporate this into your long-term real estate and financial plans.

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

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Shawn L

Series 63, Series 65

Bennington, VT

Commonwealth Financial Network

Shawn Leonard is a financial advisor with Commonwealth Financial Network based in Bennington, VT. He holds Series 63 and Series 65 licenses and has 22 years of industry experience. Prior to his current role, he worked at MountainOne Bank’s investment group for 14 years. Leonard also engages in fixed insurance sales as a minor part of his business activities. Commonwealth Financial Network is a registered investment adviser serving a national network of approximately 2,950 advisors and their clients. The firm provides a range of advisory programs and operational support, including discretionary model portfolios managed by its Investment Management and Research team.

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

Ryley G

Series 66

Bennington, VT

Edward Jones

Ryley Gaudreau is a financial advisor at Edward Jones in Bennington, VT, holding a Series 66 designation with 18 years of industry experience. He has been with Edward Jones since 2008. Edward Jones is a full-service wealth management firm serving over four million individual and institutional clients, including pension plans, corporate clients, and charitable organizations. The firm manages approximately $1.01 trillion in assets and offers a range of advisory services under a fiduciary standard, with a large nationwide network of financial advisors and branch offices.

Retirement income strategy General retirement planning Wealth management Business exit / sale strategy Multi-generational wealth transfer Retired Founder/Business Owner Executive
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Jason J

Series 63, Series 65

Colchester, VT

Equity Services, inc.

Jason Jeffers is a financial advisor at Equity Services, Inc. with 27 years of industry experience. He holds Series 63 and Series 65 credentials and has worked at National Life Group, LPL Financial, People's United Advisors, and People's Securities. Jeffers owns J&S Wealth Advisors, a consulting business focused on non-financial services guidance. Equity Services, Inc. (ESI Financial Advisors) provides financial planning, consulting, and asset management services to individuals, corporations, trusts, estates, charitable organizations, and employer retirement plans. The firm offers multiple advisory platforms, using third-party asset managers and model portfolios, and combines long-term strategies with options for shorter-term trading.

Retirement plans for business owners (SEP, solo 401k) Options & derivatives strategies Income planning Founder/Business Owner Retired Executive
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Daryl S

CFP®, Series 66

North Bennington, VT

Williams Financial, LLC

Daryl Spirka is a CFP® professional with 20 years of industry experience, currently serving at Williams Financial, LLC since 2015. He has prior experience at Lonergan And Thomas Insurance and has operated his own CPA practice since 2002. Outside of financial services, he owns and operates Passion 4 Sports, a sporting goods business in Wilmington, VT. Williams Financial, LLC provides fee-only financial planning, investment management, and pension consulting services to individuals, trusts, estates, and business entities. The firm uses a long-term investment approach combined with tactical asset allocation and multiple analytical methods, offering both integrated wealth management and digital portfolio options.

General retirement planning Tax strategies for small businesses Charitable giving & philanthropy Cash flow / budgeting
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Brian M

CFP®, Series 63, Series 66

Bennington, VT

Bennington Financial Planning Group

Brian McKenna is a CFP® professional with 19 years of industry experience, currently serving as a financial advisor at Bennington Financial Planning Group since 2010. He also maintains a role with D.B. McKenna & Co., Inc., a broker-dealer firm, dedicating half of his time to each business. In addition to his advisory work, McKenna is a member of the Bennington Redevelopment Group LLC, which focuses on revitalizing the downtown Bennington community, and he provides tax preparation services. Bennington Financial Planning Group offers portfolio management and financial planning services to individuals, trusts, estates, charitable organizations, businesses, and government clients. The firm employs a fundamental analysis approach supplemented by technical and cyclical methods, utilizing both long- and short-term trading strategies including covered-call writing, with accounts reviewed regularly and discretionary management available.

College savings (529s, UTMA, etc.)
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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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Richard B

Series 63, Series 66

Austin, TX

Charles Schwab

Richard Brandi is a financial advisor with Charles Schwab based in Austin, TX, holding Series 63 and Series 66 licenses and bringing 32 years of industry experience. He has been with Charles Schwab and Charles Schwab Bank ssb since 2003 and 2005, respectively. Charles Schwab & Co., Inc. serves primarily high- and ultra-high-net-worth individuals through its Schwab Wealth Advisory wrap fee program and affiliated managed-account and financial planning services. The firm offers a mix of non-discretionary and discretionary investment guidance, leveraging multi-asset model portfolios and research from its Schwab Center for Financial Research.

Private / alternative investments Real estate investing Multi-state taxation College savings (529s, UTMA, etc.)
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Matthew M

CFA®, Series 65

Burlington, VT

One Day In July LLC

Matthew Mc Bride is a CFA® charterholder and Series 65 licensee with three years of industry experience. He has worked at One Day In July LLC since 2023 and previously held positions at the University of Vermont and Saint Michael's College. Outside of financial advising, he is involved in a self storage business focusing on facility valuation and market research. One Day In July LLC provides discretionary portfolio management and financial planning to individuals, charitable organizations, corporations, and pension plans. The firm employs an asset-allocation approach centered on passive, low-cost ETFs, supplemented by periodic rebalancing and limited short-term trades, and offers an optional environmental investing strategy.

ESG / Sustainable investing Passive / index investing Real estate investing
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Jace H

CFP®, Series 63, Series 66

Rockwall, TX

Rockwall Wealth Management

Jace Hart is a CFP® with nine years of industry experience and currently serves as a financial advisor at Rockwall Wealth Management. His prior experience includes roles at Leo Wealth, LPL Financial, and Fidelity Brokerage Services. Rockwall Wealth Management provides portfolio management, financial planning, and consulting services to individuals, trusts, plans, charitable organizations, and businesses. The firm emphasizes diversified, low-cost ETF model portfolios with a focus on tax efficiency, liquidity, and systematic macro tilts, offering both traditional and advanced investment strategies tailored to client objectives.

Active portfolio management Options & derivatives strategies Private / alternative investments Retirement plans for business owners (SEP, solo 401k) Retirement income strategy
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Marshall B

Series 66

Cabot, AR

Paladin Investment Advisors

Marshall Butler is a Series 66-registered financial advisor at Paladin Investment Advisors with eight years of industry experience. He has held roles at several firms including Veritas Independent Partners, Pinnacle Wealth Management, and Edward Jones. Butler is a part owner of Pinnacle Consultants, where he is involved in the sale of insurance products. Paladin Investment Advisors provides customized investment advisory and financial planning services to individuals, business owners, nonprofit charities, foundations, and sponsors of ERISA-qualified retirement plans. The firm manages approximately $49.5 million in discretionary assets and employs a holistic wealth management approach using active, passive, or blended strategies.

Real estate investing Annuities Options & derivatives strategies

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