Financial Advisors & Retirement Planning in Dennis

Financial Advisors & Retirement Planning serving Dennis from elsewhere on the Mid Cape. None are based in Dennis itself, which is normal for a town this size. If you're not sure where to start, the Dennis Council on Aging (508-385-5067) will point you in the right direction for free.

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9 listings · each dated when a person last checked it · ordered by review count and rating; nobody can pay to move up

Pier 42 Advisors

Financial Advisors & Retirement Planning

Based in Dennis

5.0 on Google · 21 reviews

(508) 258-9300

More details

Office: South Dennis
Cost: Free 15-min consultation
Address: 434 Route 134, Unit G6, South Dennis (second office: 28 Route 6A, Sandwich)
How to start: Call or book a 15-minute introductory call online
For older adults: Fee-only fiduciary firm; helps with retirement income, Social Security timing, and Medicare filing choices

Visit website Email them

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

May also cover Dennis: ask when you call (8)

Cape Cod Wealth Strategies & Insurance

Financial Advisors & Retirement Planning

Based in Yarmouth · says it covers the whole Cape; ask about Dennis

4.9 on Google · 45 reviews

(508) 776-1168

More details

Top-rated by volume

Office: South Yarmouth
Cost: Intro consult often free; ask if fee-only fiduciary
Address: 16 Forsythe Ave, South Yarmouth
How to start: Call or use the website request form
For older adults: Covers retirement-income topics such as 401(k) rollovers, pension choices, Medicare supplement and long-term-care insurance

Visit website

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

Cutter Financial Group

Financial Advisors & Retirement Planning

Based in Falmouth · says it covers the whole Cape; ask about Dennis

4.9 on Google · 35 reviews

(508) 388-7175

More details

Office: Falmouth
Cost: Intro consult often free; ask if fee-only fiduciary
Address: 84 Davis Straits, Falmouth
How to start: Call the Falmouth office or use the website contact form to set up a meeting
For older adults: Focuses on retirement income, tax, and legacy planning for people nearing or in retirement

Visit website Email them

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

Fairway Financial

Financial Advisors & Retirement Planning

Based in Barnstable · says it covers the whole Cape; ask about Dennis

5.0 on Google · 18 reviews

(508) 398-3337

More details

Office: Hyannis
Cost: Free retirement review
Address: 540 Main St, Unit 9, Hyannis
How to start: Call or book a free retirement review online
For older adults: Works on retirement income, Social Security timing, and long-term-care and life insurance

Visit website Email them

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

Wealth Enhancement Group

Financial Advisors & Retirement Planning

Based in Barnstable · says it covers the whole Cape; ask about Dennis

5.0 on Google · 8 reviews

(508) 771-8900

More details

Office: Hyannis
Cost: Intro consult often free; ask if fee-only fiduciary
Address: 1575 Iyannough Rd, Suite 1A, Hyannis
How to start: Call the Hyannis office to set up a meeting
Hours: May close early on summer Fridays; call to confirm
For older adults: Offers retirement income planning, estate planning, and in-house tax preparation

Visit website

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

Chris Chapin, CFP - UBS

Financial Advisors & Retirement Planning

Based in Barnstable · says it covers the whole Cape; ask about Dennis

5.0 on Google · 4 reviewsVery few reviews

(508) 362-1811

More details

Office: Hyannis
Credentials: CFP
Cost: Intro consult often free; ask if fee-only fiduciary
Address: 1471 Iyannough Rd (Route 132), Hyannis
How to start: Call the office or use the contact form on his UBS page
For older adults: Works with retirees and families on retirement and estate planning alongside his father as The Chapin Group

Visit website

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

Montgomery Financial Group

Financial Advisors & Retirement Planning

Based in Orleans · says it covers the whole Cape; ask about Dennis

4.0 on Google · 4 reviewsVery few reviews

(508) 240-1151

More details

Lower Cape option

Office: Orleans
Cost: Hourly fees; free first meeting
Address: 195 Route 6A, Suite 8, Orleans
How to start: Call to book a no-charge get-acquainted meeting
For older adults: Fee-only, pay-by-the-hour advice with no income or asset minimums; also offers bill-pay help, tax preparation, and Social Security claiming advice

Visit website

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

Robinson Financial Services (Sarah Robinson, CFP)

Financial Advisors & Retirement Planning

Based in Brewster · says it covers the whole Cape; ask about Dennis

5.0 on Google · 2 reviewsVery few reviews

(508) 240-1056

More details

Lower Cape option

Office: Brewster
Credentials: CFP
Cost: Intro consult often free; ask if fee-only fiduciary
Address: 230 Holly Ave, Brewster
How to start: Use the website contact form or book a time online; meets in person or by video
For older adults: Focuses on women and female-led households, including Social Security planning and life changes like losing a spouse

Visit website Email them

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 23 Oct 2026 Nobody pays to be listed Is this number wrong? Tell us

Bessette Financial Services

Financial Advisors & Retirement Planning

Based in Barnstable · says it covers the Mid Cape; ask about Dennis

(508) 775-5510

More details

A local advisor for retirement income, IRA rollovers, investments, and life and long-term-care insurance.

William R. Bessette. The firm's own website is currently offline; the link goes to his public FINRA record. Fee- and commission-based.

Office: Hyannis
Credentials: Registered rep & investment adviser rep (CRD# 2078999), no disclosures on BrokerCheck
Official record: FINRA BrokerCheck: actively registered since 1990, no disclosures (Sept 2026)
Address: 100 Independence Drive, Suite 7, Hyannis

Visit website

What to ask when you call

Are you a fiduciary, in writing, all of the time?
How are you paid — fee, commission, or both?
Do you sell insurance or annuities, and do you earn a commission on them?

Print these as a call sheet

Checked 26 Sept 2026 Nobody pays to be listed Is this number wrong? Tell us

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