4.5+ Stars · Annapolis
Highly Rated Insurance Agents in Annapolis, MD
Only the best make this list. These insurance agents in Annapolis have earned 4.5+ star ratings from real customers — consistently.
As of May 2026, RatingsNearMe ranks 20 insurance agents in Annapolis, MD by verified customer ratings and review volume. The highest-rated is Mathes Insurance Advisors, Inc. with a 4.9-star rating from 428 verified reviews. Also in the top tier: JSR Insurance and Debbie Hart - State Farm Insurance Agent. The average rating across all listed insurance agents in Annapolis is 4.8 stars from 107 reviews per business on average.
Insurance in Annapolis: agents are typically paid by commission (5–15% of premium) — no cost to you to compare quotes.
Rankings updated May 17, 2026 · Scored by ratings (35%), review volume (30%), sentiment (20%), completeness (10%), availability (5%) · Not paid placement.
Local Market Snapshot
20
Businesses listed
4.8★
Avg rating
107
Avg reviews
May 17, 2026
Last updated
Top Rated Insurance Agents
Mathes Insurance Advisors, Inc.
2525 Riva Rd Suite 105, Annapolis, MD 21401, USA
JSR Insurance
793 Fairview Ave, Annapolis, MD 21403, USA
Debbie Hart - State Farm Insurance Agent
49 Old Solomons Island Rd Ste 203, Annapolis, MD 21401, USA
Insurance Agents Rankings in Annapolis, MD
| # | Business | Rating | Reviews |
|---|---|---|---|
| #1 | Mathes Insurance Advisors, Inc.2525 Riva Rd Suite 105, Annapolis, MD 21401, USA | 4.9★ | 428 |
| #2 | JSR Insurance793 Fairview Ave, Annapolis, MD 21403, USA | 5.0★ | 251 |
| #3 | Debbie Hart - State Farm Insurance Agent49 Old Solomons Island Rd Ste 203, Annapolis, MD 21401, USA | 5.0★ | 251 |
| #4 | Old Bay Insurance Agency133 Defense Hwy #214, Annapolis, MD 21401, USA | 5.0★ | 91 |
| #5 | CNR Insurance Inc166 West St, Annapolis, MD 21401, USA | 5.0★ | 203 |
| #6 | Ramsey's Insurance, Inc2049 West St Suite 202, Annapolis, MD 21401, USA | 4.1★ | 41 |
| #7 | Roslynne Ross: Auto Insurance914 Forest Dr #201, Annapolis, MD 21403, USA | 4.9★ | 89 |
| #8 | Jack Martin Insurance Advisors111 Forbes St, Annapolis, MD 21401, USA | 4.3★ | 31 |
| #9 | Reyes Insurance LLC1831 Forest Dr # A, Annapolis, MD 21401, USA | 4.7★ | 60 |
| #10 | Bay Area Insurance1 Annapolis St STE 100, Annapolis, MD 21401, USA | 4.7★ | 53 |
Ranked by verified ratings & review volume · Data from Google Business listings · Updated May 2026
All Insurance Agents in Annapolis
Old Bay Insurance Agency
133 Defense Hwy #214, Annapolis, MD 21401, USA
CNR Insurance Inc
166 West St, Annapolis, MD 21401, USA
Ramsey's Insurance, Inc
2049 West St Suite 202, Annapolis, MD 21401, USA
Roslynne Ross: Auto Insurance
914 Forest Dr #201, Annapolis, MD 21403, USA
Jack Martin Insurance Advisors
111 Forbes St, Annapolis, MD 21401, USA
Reyes Insurance LLC
1831 Forest Dr # A, Annapolis, MD 21401, USA
Bay Area Insurance
1 Annapolis St STE 100, Annapolis, MD 21401, USA
Goosehead Insurance - Tim Coe
1125 West St Suite 200, Office 244, Annapolis, MD 21401, USA
Sylvia Hopkins - GEICO Insurance Agent
102 Old Solomons Island Rd Suite 301, Annapolis, MD 21401, USA
Goosehead Insurance - Silver Glover
1125 West St Suite 222, Annapolis, MD 21401, USA
Marshelle Ball - State Farm Insurance Agent
175 Admiral Cochrane Dr # 200, Annapolis, MD 21401, USA
Nationwide Insurance: John G Rogers And Associates Inc.
888 Bestgate Rd Suite 104, Annapolis, MD 21401, USA
Dovie Metzger - State Farm Insurance Agent
1410 Forest Dr #23, Annapolis, MD 21403, USA
Goosehead Insurance - Brian Madden
1997 Annapolis Exchange Suite 410, Annapolis, MD 21401, USA
Henry M Murray Insurance Agency
2498 Riva Rd, Annapolis, MD 21401, USA
HUB International
170 Jennifer Rd Suite 205, Annapolis, MD 21401, USA
Simpson and Blom Insurance
108 Old Solomons Island Rd Bldg 2, Annapolis, MD 21401, USA
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Frequently Asked Questions — Insurance Agents in Annapolis
What is the difference between a captive and independent insurance agent in Annapolis?
Captive agents (State Farm, Allstate, Farmers) represent one company and can only quote that carrier's products. Independent agents work with multiple carriers — they shop your policy across companies to find the best rate and coverage for your situation. For most consumers, an independent agent offers more flexibility. Captive agents may have deeper expertise in their specific carrier's products and claims process.
How do I verify an insurance agent's license in MD?
Search the MD Department of Insurance's online license lookup — Google "MD Department of Insurance license lookup" for the direct link. You can verify current license status, license type, and any disciplinary actions. Every agent selling insurance in MD must be licensed with the state.
How much does working with a local insurance agent in Annapolis cost?
In most cases, nothing directly. Insurance agents earn commissions paid by the insurance company — typically 5–15% of your annual premium for property/casualty coverage, 40–100% of first-year premium for life insurance. Fee-based agents charge separately and disclose it upfront. Always ask how your agent is compensated so you understand any potential incentives.
Should I buy insurance online or through a local agent in Annapolis?
Online works for simple auto or renters policies if you understand what you're buying. A local agent in Annapolis adds real value for homeowners insurance, life insurance, commercial policies, or any situation with complexity — rental properties, high-value items, home-based businesses, or coverage gaps. They also advocate for you during a claim, which online portals don't.
How are the insurance agents on this page ranked?
Rankings use a transparent algorithm: star rating (35%), review volume (30%), customer sentiment (20%), profile completeness (10%), and availability (5%). Featured Partner listings have paid for enhanced visibility but must still earn their position through real customer reviews — sponsored listings are clearly labeled.
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How Rankings Work on This Page
Every insurance agents on RatingsNearMe is scored transparently: star rating (35%), review volume (30%), customer sentiment (20%), profile completeness (10%), and availability (5%). Businesses labeled exclusive or premium are Featured Partners — they have paid for enhanced visibility but must still rank through real customer reviews. We cap sponsored boosts so bad businesses can never buy the top spot.
Editorial notice: Ratings are based on publicly available data from Google Business listings. Consumers should independently verify licensing, insurance, and credentials before hiring any service provider. Last updated: May 17, 2026.
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