CFP®-certified, general retirement planning financial advisors in Winchester, VA

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.

Planning for retirement in Winchester, VA often means navigating the area's unique housing market influenced by high incomes and a large federal workforce. Without a clear plan, you might misjudge how your housing costs and income sources will affect your retirement budget. CFP® certification means these advisors have met rigorous education and ethical standards, helping you with comprehensive retirement planning.

  • Housing market insight. Ask how they factor local housing costs and trends into your retirement income needs.
  • Income source coordination. Confirm they integrate Social Security, pensions, and other income streams into a cohesive plan.
  • Withdrawal strategy. Look for advisors who explain how to sequence withdrawals to manage taxes and sustain your savings.
  • Longevity planning. Ensure they consider your life expectancy and healthcare costs to avoid running out of money.

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

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Karis H

Series 66

Winchester, VA

Edward Jones

Karis Holnagel Frey is a financial advisor at Edward Jones in Winchester, VA, holding a Series 66 designation with 1 year of industry experience. She has been with Edward Jones since 2010. Edward Jones is a full-service wealth management firm serving more than four million individual and institutional clients, offering a range of advisory programs and investment solutions supported by a nationwide network of over 23,700 financial advisors.

Retirement income strategy College savings (529s, UTMA, etc.) General estate planning guidance Retirement withdrawal strategies Retired Founder/Business Owner Executive LGBTQIA
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Ricky L

Series 63, Series 65

Winchester, VA

Planmember Securities Corporation

Ricky Leonard is a financial advisor with PlanMember Securities Corporation in Winchester, VA, holding Series 63 and Series 65 licenses and bringing 11 years of industry experience. His background includes roles at PlanMember Securities Corporation, Old Dominion Insurance & Investments Inc., and Staunton City Schools. Leonard is also involved with Old Dominion Insurance & Investments Inc. as a non-producing licensed sales assistant. PlanMember Securities Corporation provides retirement-plan advisory services to employers and plan participants, acting as an ERISA Section 3(38) fiduciary for many plans and offering participant-level investment options through its PlanMember Asset Allocation Portfolios. The firm employs a top-down strategic asset allocation framework and manages unitized, risk-based mutual fund portfolios, delivering education and support services such as seminars and personalized retirement planning.

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

Series 63, Series 66

Winchester, VA

LPL Financial

Amy Flores Velasquez is a financial advisor with LPL Financial in Winchester, VA, holding Series 63 and Series 66 registrations and 17 years of industry experience. Her prior work includes roles at Waddell & Reed Inc and various insurance carriers. Outside of her advisory work, she is involved with Associates of Clifton Park in a non-variable insurance capacity. 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 wide range of advisory and brokerage services, including financial planning, third-party asset management, and institutional platforms, supported by proprietary research and technology tools.

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

Series 66

Winchester, VA

Thrivent Investment Management

Paul Haecker is a financial advisor at Thrivent Investment Management with two years of industry experience. He previously operated his own firm, Paul Haecker LLC, for 31 years before joining Thrivent in 2023. Thrivent Investment Management provides Dedicated Planning Services to individuals, families, businesses, and nonprofit clients through its network of Financial Advisors. The firm offers goal-based financial planning on a variety of topics without discretionary portfolio management, allowing clients to combine planning with managed-account services under a consolidated billing option called “WealthPlan.”

Business ownership considerations
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Gayle C

Series 63, Series 65

Winchester, VA

OSAIC

Gayle Canini is a financial advisor at OSAIC with 32 years of industry experience. She holds Series 63 and Series 65 designations and has previously worked with Securities America Advisors and SECURITIES AMERICA, Inc. Outside of her advisory role, she serves as president, secretary, and treasurer of Employee Benefits Administration, Inc., and volunteers with the Shenandoah Apple Blossom Festival. OSAIC serves a diverse client base, including individuals, high-net-worth investors, pension plans, corporations, and charitable organizations, through a large network of affiliated advisors. The firm employs various tools and platforms to deliver integrated brokerage and advisory services, offering portfolios constructed with stocks, bonds, options, mutual funds, ETFs, and alternative investments managed on both discretionary and non-discretionary bases.

Annuities Wealth management Tax-loss harvesting Private / alternative investments Retirement plans for business owners (SEP, solo 401k) 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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Amanda S

Series 66

Ft. Wayne, IN

Raymond James & Associates

Amanda Scheele is a financial advisor with Raymond James & Associates in Ft. Wayne, Indiana, holding a Series 66 designation and 16 years of industry experience. Prior to joining Raymond James in 2024, she worked at Wells Fargo Clearing from 2016 to 2024 and is involved with Lucky Duck since 2025. Raymond James & Associates is a large, dually registered broker-dealer and SEC-registered investment adviser serving a diverse client base that includes individuals, institutions, and municipal entities. The firm offers financial planning and non-discretionary consulting services, drawing on various portfolio management styles and affiliated research.

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

Lori F

Series 66

East Lansing, MI

Edward Jones

Lori Fell is a Series 66 credentialed financial advisor with Edward Jones in East Lansing, MI, where she has worked since 2009, accumulating 17 years of industry experience. Outside of her advisory role, she is the owner of LAF Properties LLC, a business she maintains in East Lansing. Edward Jones is a full-service wealth management firm serving over four million individual and institutional clients. The firm offers a range of discretionary and non-discretionary investment solutions, including managed account strategies and affiliated mutual funds, and operates under a fiduciary standard.

Charitable giving & philanthropy Multi-generational wealth transfer General retirement planning Wealth management Retired Founder/Business Owner Executive
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Kenneth B

Series 63, Series 65

Portland, ME

Headinvest

Kenneth Blaschke is a financial advisor at HeadInvest in Portland, ME, holding Series 63 and Series 65 licenses with 16 years of industry experience. He has been with HeadInvest since 2009. HeadInvest serves a diverse range of clients, including individuals, trusts, endowments, and government entities, providing discretionary portfolio management and financial planning. The firm employs a holistic, asset-allocation driven approach, combining fixed-income selection with low-cost ETFs and emphasizing tax efficiency.

Wealth management General retirement planning Tax strategies for small businesses Founder/Business Owner Retired
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Michael I

Series 63, Series 65

Livingston, NJ

Raymond James Financial

Michael Ipp is a financial advisor with Raymond James Financial, holding Series 63 and Series 65 designations and bringing 42 years of industry experience. He has been with Raymond James Financial Services Advisors since 2010 and serves as an independent contractor for 1792 Wealth Advisors. Raymond James Financial Services Advisors provides financial planning, investment consulting, and advisory services to a diverse client base, including individuals, high-net-worth clients, corporations, and institutional clients. The firm offers tailored, non-discretionary planning and uses analytical tools to support client decision-making, while also maintaining specialized programs such as municipal advisory services and SIMPLE IRA Employer Advisory & Consulting Services.

Wealth management Tax strategies for small businesses Business succession planning General estate planning guidance 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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Elanna G

CFP®, Series 66

Cleveland, OH

Cambridge Investment Research Advisors

Elanna Gould is a CFP® professional with six years of experience, currently advising at Cambridge Investment Research Advisors in Cleveland, OH. Her background includes roles at PepsiCo and The Cleveland Clinic Lerner Research Center, as well as academic experience at The Ohio State University. She is also an independent insurance agent for various companies. Cambridge Investment Research Advisors serves a broad client base, including individuals, retirement plans, and charitable organizations, offering financial planning, investment management, and retirement advisory services through a network of independent professionals. The firm provides a range of portfolio management options, proprietary and third-party strategies, and various custody platforms tailored to client objectives.

Wealth management Retirement plans for business owners (SEP, solo 401k) Retirement income strategy Annuities Self-Employed
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Ethan S

CFP®, Series 65

Auburn Hills, MI

Plante Moran financial advisors

Ethan Siekkinen is a CFP® and holds a Series 65 license, currently serving as a financial advisor with Plante Moran Financial Advisors. He has one year of industry experience and has previously worked at J Wilson Wealth Management and operated Rizzo Lawn Care. Plante Moran Financial Advisors, LLC provides investment advisory, financial planning, and estate planning services to a diverse client base including individual households, institutional clients, and sovereign wealth funds. The firm employs a multi-disciplinary investment process and offers both discretionary and non-discretionary portfolio management, manager search, and tax-lot accounting services.

Active portfolio management Options & derivatives strategies Private / alternative investments Concentrated stock management Retirement plans for business owners (SEP, solo 401k) Founder/Business Owner Executive
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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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Jeffrey M

CFP®, ChFC®, Series 66

Greenville, DE

Investment Management & Planning LLC

Jeffrey Macdonald is a CFP® and ChFC® with 18 years of industry experience. He has worked at Investment Management & Planning LLC and LPL Financial since 2010, following two years at Wells Fargo Clearing. Investment Management & Planning LLC provides investment advisory and financial planning services primarily to individual and high-net-worth clients. The firm constructs tailored portfolios using mutual funds, ETFs, equities, and fixed-income securities, employing fundamental analysis and continuous supervision, and operates as both a wrap program sponsor and affiliated registered representatives of LPL Financial.

General retirement planning Business succession planning Tax strategies for small businesses Retirement plans for business owners (SEP, solo 401k) Founder/Business Owner Executive Mid-Career Professionals Approaching retirement
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