Top Picks · Annapolis
Best Insurance Agents in Annapolis, MD
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As of June 2026, RatingsNearMe ranks 20 insurance agents in Annapolis, MD by the RNM Score — a 0–100 rating built from Google ratings, review volume, sentiment, and profile completeness. The top-ranked is Mathes Insurance Advisors, Inc. with a 4.9-star rating from 428 Google reviews and an RNM Score of 87/100. 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 June 9, 2026 · RNM Score = ratings (35%), review volume (30%), sentiment (20%), completeness (10%), availability (5%) · Not paid placement.
Annapolis, MD is home to a variety of insurance agents offering coverage for home, auto, life, and business needs. Consumers should research local agents' specialties, customer reviews, and pricing to find the best fit for their insurance requirements.
- ✓Diverse selection of insurance agents in Annapolis, MD
- ✓Agents offer coverage for home, auto, life, and business
- ✓Research agent specialties, reviews, and pricing to find the right fit
How to Choose a Insurance Agent in Annapolis
What to look for
- • Local presence and knowledge of the Annapolis, MD market
- • Experience working with clients in your industry or with similar needs
- • Strong communication skills and ability to explain insurance options clearly
- • Positive reviews and references from other Annapolis, MD clients
Questions to ask
- • How long have you been an insurance agent serving the Annapolis, MD area?
- • What types of insurance policies and coverage do you typically recommend for clients like me?
- • Can you provide references from other Annapolis, MD customers you've worked with?
Red flags
- ⚠ Agent is not licensed or registered to sell insurance in Maryland
- ⚠ Unwillingness to provide details about their experience and qualifications
- ⚠ Aggressive sales tactics or inability to clearly explain policy details
In Maryland, insurance agents must be licensed by the Maryland Insurance Administration. Be sure to verify the agent's license and standing before engaging their services.
Local Market Snapshot
20
Businesses listed
4.8★
Avg rating
107
Avg reviews
Jun 9, 2026
Last updated
Top Rated Insurance Agents
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 | Ramsey's Insurance, Inc2049 West St Suite 202, Annapolis, MD 21401, USA | 4.1★ | 41 |
| #6 | Roslynne Ross: Auto Insurance914 Forest Dr #201, Annapolis, MD 21403, USA | 4.9★ | 89 |
| #7 | Jack Martin Insurance Advisors111 Forbes St, Annapolis, MD 21401, USA | 4.3★ | 31 |
| #8 | Reyes Insurance LLC1831 Forest Dr # A, Annapolis, MD 21401, USA | 4.7★ | 60 |
| #9 | Bay Area Insurance1 Annapolis St STE 100, Annapolis, MD 21401, USA | 4.7★ | 53 |
| #10 | Goosehead Insurance - Silver Glover1125 West St Suite 222, Annapolis, MD 21401, USA | 4.9★ | 17 |
Ranked by verified ratings & review volume · Data from Google Business listings · Updated June 2026
All Insurance Agents in Annapolis
2049 West St Suite 202, Annapolis, MD 21401, USA
914 Forest Dr #201, Annapolis, MD 21403, USA
1125 West St Suite 222, Annapolis, MD 21401, USA
Top-rated Annapolis insurance agent with a perfect 5.0★ score from over 200 reviews.
166 West St, Annapolis, MD 21401, USA
Trusted Annapolis insurance agent with a solid 4.4★ rating from nearly 200 reviews.
102 Old Solomons Island Rd Suite 301, Annapolis, MD 21401, USA
Trusted by hundreds of customers with a flawless 5.0-star rating in Annapolis.
1125 West St Suite 200, Office 244, Annapolis, MD 21401, USA
175 Admiral Cochrane Dr # 200, Annapolis, MD 21401, USA
888 Bestgate Rd Suite 104, Annapolis, MD 21401, USA
1410 Forest Dr #23, Annapolis, MD 21403, USA
1997 Annapolis Exchange Suite 410, Annapolis, MD 21401, USA
108 Old Solomons Island Rd Bldg 2, Annapolis, MD 21401, USA
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Insurance Agents in Annapolis, MD — Compared
| # | Business | RNM Score | Rating | Reviews |
|---|---|---|---|---|
| 1 | Mathes Insurance Advisors, Inc. | 87/100 | 4.9 ★ | 428 |
| 2 | JSR Insurance | 88/100 | 5.0 ★ | 251 |
| 3 | Debbie Hart - State Farm Insurance Agent | 88/100 | 5.0 ★ | 251 |
| 4 | Old Bay Insurance Agency | 83/100 | 5.0 ★ | 91 |
| 5 | Ramsey's Insurance, Inc | 63/100 | 4.1 ★ | 41 |
| 6 | Roslynne Ross: Auto Insurance | 81/100 | 4.9 ★ | 89 |
| 7 | Jack Martin Insurance Advisors | 65/100 | 4.3 ★ | 31 |
| 8 | Reyes Insurance LLC | 76/100 | 4.7 ★ | 60 |
| 9 | Bay Area Insurance | 75/100 | 4.7 ★ | 53 |
| 10 | Goosehead Insurance - Silver Glover | 72/100 | 4.9 ★ | 17 |
Ranked by RatingsNearMe Score · ratings (35%), review volume (30%), sentiment (20%), completeness (10%), availability (5%) · June 2026
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: June 9, 2026.
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