Top real estate investing 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.

If you're investing in real estate in Winchester, VA, you likely face unique challenges like navigating local market trends influenced by Northern Virginia's high incomes and federal workforce. Without focused expertise, you might overlook how these factors affect property values and rental demand.

  • Local market insight. Confirm how the advisor tracks Winchester's housing trends and economic drivers that impact real estate returns.
  • Investment strategy alignment. Ask how they tailor real estate investments to fit your overall financial goals and risk tolerance.
  • Tax implications. Real estate investing has complex tax rules; check how the advisor integrates tax planning with your property investments.
  • Portfolio diversification. Inquire how they balance real estate with other assets to manage risk and growth potential.

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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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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