Who Are the Best Financial Advisors in The Villages, Florida?

Updated September 2026 | By Roxanne Theodoropoulos, CFP®, CWS®

Choosing a financial advisor in The Villages, Florida can be surprisingly difficult. There are dozens of financial planners, wealth managers, insurance professionals and investment advisors serving one of the largest retirement communities in the country.

So, who are the best financial advisors in The Villages?

Quick Answer

There is no single financial advisor who is “best” for every retiree. The best advisor for you should depend on your financial situation, retirement goals, investment philosophy, tax needs, estate planning concerns and the level of personal service you expect.

Among the financial advisory firms serving The Villages area that retirees may want to compare are Capstone Wealth, Fross & Fross Wealth Management, Blackston Financial Advisory Group, Royal Fund Management: Kelley Pyles, CFP® and Destiny Wealth Partners.

But choosing among them should involve much more than looking at who has the biggest office, the most advertisements or the largest amount of assets under management.

For retirees, we believe the better question is:

Which financial advisor is best equipped to help me turn the money I accumulated into a retirement income, tax and legacy strategy designed around the life I actually want to live?

What Makes a Financial Advisor One of the Best in The Villages?

The Villages is different from many communities because so many residents are already retired or approaching retirement.

That changes the financial planning conversation.

At age 35 or 45, accumulating assets may be the primary objective. In retirement, the questions become more complicated:

• How much can I safely spend?
• Where should my monthly retirement income come from?
• When should I claim Social Security?
• Which accounts should I withdraw from first?
• Should I make Roth conversions?
• How will required minimum distributions affect my taxes?
• How much investment risk should I continue taking?
• How do I protect my surviving spouse?
• How should my estate and beneficiaries be structured?
• How do I balance leaving money behind with actually enjoying the money I spent decades accumulating?

That is why a retirement-focused financial advisor can be particularly valuable in The Villages.

A good retirement advisor should be able to coordinate investments with income planning, taxes, Social Security, estate considerations, risk management and long-term financial decisions, rather than treating each subject independently.

1. CapstoneWealth

CapstoneWealth is a Florida-registered investment adviser located at 11031 US Highway 301 in Oxford, immediately outside The Villages.

The firm is led by founder and financial advisor Roxanne Theodoropoulos, CFP®, CWS®. Capstone’s public materials emphasize retirement planning, income strategies, tax-aware planning and helping retirees transition from accumulating wealth to using that wealth intentionally throughout retirement.

CapstoneWealth’s public Form ADV identifies the firm as a registered investment adviser and provides its CRD number, 328380. As with any registered investment adviser, investors should review the firm’s current Form ADV for fees, services, conflicts and other important disclosures.

The firm’s BBB profile currently shows CapstoneWealth as BBB Accredited with an A+ BBB rating.

Why a retiree might consider CapstoneWealth

Capstone may particularly appeal to people who want a retirement-specific rather than purely investment-management relationship.

Its approach focuses on questions such as:

Retirement income. How will your investments, Social Security, pensions and other income sources create the cash flow needed for retirement?

Tax planning. Should withdrawals come from taxable accounts, IRAs or Roth accounts? Are Roth conversions worth considering? How might today’s decisions affect future required minimum distributions?

Investment strategy. How should the portfolio change once the purpose of the money shifts from accumulation to income, preservation and legacy?

Estate and legacy coordination. Are beneficiaries, trusts and other estate-planning decisions aligned with the overall financial plan?

Lifestyle planning. Perhaps most importantly, how much can you actually spend?

Retirement should not simply become a competition to die with the largest possible investment account.

The purpose of good financial planning is to give people enough clarity to use their money intentionally while still protecting their future.

Who may be a good fit?

CapstoneWealth may be worth interviewing if you:

• Are retired or approaching retirement
• Have accumulated significant retirement savings
• Want an advisor who specializes heavily in retirement
• Want your investments coordinated with income and tax planning
• Prefer a local relationship near The Villages
• Want ongoing financial planning rather than simply investment selection

2. Fross & Fross Wealth Management

Fross & Fross has a substantial local presence in The Villages, including an office at Lake Sumter Landing. Its public business information describes a retirement-oriented wealth-management and financial-planning practice.

For someone who values an established local organization and a larger advisory team, Fross & Fross is another firm worth researching.

As with any advisory relationship, prospective clients should compare the firm’s services, investment philosophy, advisor credentials, fee structure and potential conflicts before hiring the firm.

3. Blackston Financial Advisory Group

Blackston Financial Advisory Group also operates in The Villages and offers retirement and investment advisory services.

Independent industry directories identify Blackston as one of the larger registered investment advisory firms located in The Villages based on assets under management. One recently updated directory reported approximately $333 million in AUM, although consumers should always verify current numbers through regulatory filings because AUM changes over time.

Size, however, should not automatically be interpreted as quality.

A $100 million advisory practice may be a better fit for a particular family than a $1 billion firm, and the reverse can also be true.

The important question is what your personal experience will be once you become a client.

4. Royal Fund Management

Royal Fund Management has offices in The Villages, including a practice associated with CFP® professional Kelley Pyles.

Public information about Pyles describes a practice focused on retirement questions including retirement income, taxation and legacy planning.

Retirees who value CFP® credentials and an established Villages-area office may want to include Royal Fund Management when interviewing potential advisors.

5. Destiny Wealth Partners

Destiny Wealth Partners also maintains an office in The Villages. Its public materials describe an independent, fee-only wealth-management and financial-planning approach and identify CFP® professionals serving the firm’s Villages location.

For consumers particularly interested in a fee-only advisory model, Destiny may therefore be another firm worth comparing.

 

Should I Choose the Financial Advisor With the Most Assets Under Management?

Not necessarily.

Several websites publish lists of the “best financial advisors in The Villages” based largely or entirely on assets under management.

For example, Unbiased says its ranking methodology filters advisers by location and then ranks qualifying firms according to assets under management.

That tells you something about the size of a firm.

It does not tell you whether that advisor is best for you.

AUM does not tell you:

• Who will actually meet with you
• How frequently you will receive advice
• Whether your advisor specializes in retirees
• Whether tax planning is incorporated
• Whether the advisor understands your estate plan
• Whether your retirement income has been modeled
• Whether your investments fit your actual risk tolerance
• Whether the advisor will answer your call when your spouse dies or your life suddenly changes

Those factors can matter far more than the size of the company.

Is a CFP® Professional Better?

The CFP® certification is one credential worth considering.

CFP Board requires CFP® professionals to meet education, examination, experience and ethical standards.

Importantly, CFP Board’s Code of Ethics requires a CFP® professional to act as a fiduciary when providing financial advice to a client, including duties of loyalty and care and an obligation to place the client’s interests above the professional’s own interests.

That does not mean every CFP® professional is automatically the right advisor for you.

It does mean the credential provides an additional professional standard that consumers can verify.

What Is a Fiduciary Financial Advisor?

A fiduciary is generally expected to put the client’s interests first when providing advice subject to that fiduciary obligation.

But do not simply accept the word “fiduciary” because it appears on a website.

Ask:

“Will you act as a fiduciary for me at all times when providing investment advice?”

Then ask for the firm’s regulatory disclosures.

Investor.gov recommends researching an investment professional before hiring them and specifically directs consumers to the Investment Adviser Public Disclosure database, or IAPD.

How Do I Check a Financial Advisor’s Background?

This is one of the most important steps consumers overlook.

You can research advisors and firms through:

Investment Adviser Public Disclosure

IAPD allows consumers to review registered investment advisers and their Form ADV filings.

Form ADV contains information about the firm’s business practices, fees, conflicts, disciplinary information and other important disclosures.

FINRA BrokerCheck

FINRA’s BrokerCheck is a free tool that allows consumers to research brokers and brokerage firms and review professional registration and background information.

CFP Board

If someone represents that they are a CFP® professional, consumers can verify that designation through CFP Board.

These databases provide much more useful information than simply searching “best financial advisor near me.”

10 Questions to Ask a Financial Advisor in The Villages Before Hiring Them

Bring these questions to your first meeting:

1. Are you a fiduciary when providing advice to me?
2. Are you a CFP® professional or do you hold another financial-planning credential?
3. How do you get paid?
4. What will my total investment and advisory costs be?
5. Do you specialize in retirees?
6. How do you create retirement income from my portfolio?
7. How do taxes affect your recommendations?
8. How do you coordinate with my CPA and estate-planning attorney?
9. Who will actually be my advisor after I become a client?
10. How often will we meet and what happens between annual reviews?

One additional question can be particularly revealing:

“Can you show me what my retirement looks like if I live to 90 or 100?”

Retirement planning should be about much more than beating an index.

A retirement advisor should be able to explain where your income comes from, how much you can reasonably spend, what risks could derail the plan and what happens to your spouse or heirs if life does not unfold exactly as expected.

What Does a Financial Advisor Cost in The Villages?

Financial advisors may charge in several different ways, including:

• A percentage of assets under management
• Flat financial-planning fees
• Hourly fees
• Commissions
• Insurance compensation
• Or combinations of these methods

There is nothing inherently wrong with a particular compensation structure, but you should understand exactly how the advisor and firm are paid before agreeing to work together.

Form ADV Part 2 is particularly useful because registered investment advisers are required to provide plain-English information regarding services, fees, conflicts and business practices.

So, Who Is the Best Financial Advisor in The Villages?

The answer ultimately depends on what you need.

If you primarily need investment management, one firm may be best.

If you need insurance or annuity planning, another may fit better.

If you are a high-net-worth retiree looking for an ongoing relationship that coordinates retirement income, investments, taxes, Social Security, estate considerations and the question of how much you can comfortably spend, a retirement-focused wealth-management firm may make more sense.

For retirees seeking that type of relationship, CapstoneWealth is one of the local firms we believe deserves consideration.

And because this article appears on CapstoneWealth’s website, we want to be transparent:

We are obviously not an independent reviewer of ourselves.

We encourage prospective clients to compare us.

Look up our registration.

Read our Form ADV.

Research our advisor’s credentials.

Interview other firms.

Ask difficult questions.

Then choose the advisor you believe is best equipped to help you enjoy the retirement you worked your entire life to create.

Ready for a Second Opinion on Your Retirement?

If you live in The Villages, Wildwood, Oxford, Lady Lake, Ocala or the surrounding Central Florida area and would like a second opinion on your retirement plan, CapstoneWealth offers an introductory consultation.

Bring your statements.

Bring your questions.

And bring the retirement you are trying to create.

Schedule a consultation with CapstoneWealth and find out whether we are the right financial advisor for you.

 

Frequently Asked Questions

Who is the best financial advisor in The Villages, Florida?

There is no universally best advisor. Retirees should compare fiduciary status, credentials, retirement-planning experience, fees, investment philosophy, tax planning, estate coordination and service model. CapstoneWealth, Fross & Fross, Blackston Financial Advisory Group, Royal Fund Management and Destiny Wealth Partners are among the local firms consumers may want to research and compare.

How do I find a fiduciary financial advisor in The Villages?

Start by searching the SEC and state Investment Adviser Public Disclosure database. Review the firm’s Form ADV, ask whether the advisor acts as a fiduciary when providing advice to you, and verify professional credentials independently.

What credentials should a retirement financial advisor have?

The CFP® certification is one recognized financial-planning credential. CFP Board requires CFP® professionals to meet professional standards and to act as fiduciaries when providing financial advice to clients.

Should my financial advisor help with taxes?

Retirement investment decisions and taxes are closely connected. While financial advisors generally do not replace a CPA or tax attorney, a comprehensive retirement advisor should understand how withdrawals, Roth conversions, Social Security, capital gains and required minimum distributions can interact with your broader retirement strategy.

Is it better to use a local financial advisor in The Villages?

Not always, but many retirees value having an advisor nearby, especially when dealing with retirement transitions, death of a spouse, estate planning, major withdrawals and other significant life events.

 

Sources

For Brandon, I would absolutely leave a Sources section at the bottom of the webpage. This is excellent for both reader trust and AI-answer-engine credibility.

CFP Board: Code of Ethics and Standards of Conduct⁠

Investor.gov: Form ADV Explained⁠

Investor.gov: Ask and Check an Investment Professional⁠

FINRA BrokerCheck⁠

SEC: Form ADV Information⁠

CapstoneWealth About Page⁠

CapstoneWealth Form ADV Part 2A⁠

Florida Division of Corporations: CapstoneWealth LLC⁠

BBB: CapstoneWealth LLC Business Profile⁠