Verified · Chesapeake
Trusted Insurance Agents in Chesapeake, VA
Trust matters when you're inviting a pro into your home or business. These insurance agents in Chesapeake have earned it through hundreds of verified reviews.
As of May 2026, RatingsNearMe ranks 20 insurance agents in Chesapeake, VA by verified customer ratings and review volume. The highest-rated is Joe Sictor - State Farm Insurance Agent with a 4.9-star rating from 470 verified reviews. Also in the top tier: Michelle Benson-Dumas - State Farm Insurance Agent and Jenel Proctor - State Farm Insurance Agent. The average rating across all listed insurance agents in Chesapeake is 4.7 stars from 112 reviews per business on average.
Insurance in Chesapeake: 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
4.7★
Avg rating
112
Avg reviews
May 17, 2026
Last updated
Top Rated Insurance Agents
Joe Sictor - State Farm Insurance Agent
1365 S Military Hwy Ste 100, Chesapeake, VA 23320, USA
Michelle Benson-Dumas - State Farm Insurance Agent
1428 Kempsville Rd ste b, Chesapeake, VA 23320, USA
Jenel Proctor - State Farm Insurance Agent
1428 Kempsville Rd ste b, Chesapeake, VA 23320, USA
Insurance Agents Rankings in Chesapeake, VA
| # | Business | Rating | Reviews |
|---|---|---|---|
| #1 | Joe Sictor - State Farm Insurance Agent1365 S Military Hwy Ste 100, Chesapeake, VA 23320, USA | 4.9★ | 470 |
| #2 | Michelle Benson-Dumas - State Farm Insurance Agent1428 Kempsville Rd ste b, Chesapeake, VA 23320, USA | 5.0★ | 270 |
| #3 | Jenel Proctor - State Farm Insurance Agent1428 Kempsville Rd ste b, Chesapeake, VA 23320, USA | 5.0★ | 256 |
| #4 | Albearlie Affordable Insurance Agency - Chesapeake VA524 Albemarle Dr Suite 207, Chesapeake, VA 23322, USA | 4.6★ | 10 |
| #5 | Garlow Insurance Agency - Nationwide Insurance312 Cedar Lakes Dr suite 201, Chesapeake, VA 23322, USA | 4.8★ | 117 |
| #6 | Stephanie Grayson - State Farm Insurance Agent1111 Eden Way N, Chesapeake, VA 23320, USA | 4.9★ | 66 |
| #7 | COVA Insurance638 Independence Pkwy Ste 220, Chesapeake, VA 23320, USA | 4.8★ | 51 |
| #8 | Direct Auto Insurance1437 Sam's Dr #121, Chesapeake, VA 23320, USA | 4.8★ | 114 |
| #9 | Nationwide Insurance: W T Jennings Insurance Agency Inc.676 Battlefield Blvd N Ste A, Chesapeake, VA 23320, USA | 4.6★ | 35 |
| #10 | Chesapeake Insurance Services1105 Madison Plaza #100, Chesapeake, VA 23320, USA | 2.6★ | 22 |
Ranked by verified ratings & review volume · Data from Google Business listings · Updated May 2026
All Insurance Agents in Chesapeake
Albearlie Affordable Insurance Agency - Chesapeake VA
524 Albemarle Dr Suite 207, Chesapeake, VA 23322, USA
Garlow Insurance Agency - Nationwide Insurance
312 Cedar Lakes Dr suite 201, Chesapeake, VA 23322, USA
Stephanie Grayson - State Farm Insurance Agent
1111 Eden Way N, Chesapeake, VA 23320, USA
COVA Insurance
638 Independence Pkwy Ste 220, Chesapeake, VA 23320, USA
Direct Auto Insurance
1437 Sam's Dr #121, Chesapeake, VA 23320, USA
Nationwide Insurance: W T Jennings Insurance Agency Inc.
676 Battlefield Blvd N Ste A, Chesapeake, VA 23320, USA
Chesapeake Insurance Services
1105 Madison Plaza #100, Chesapeake, VA 23320, USA
Shawn Fischer - State Farm Insurance Agent
825 S Battlefield Blvd Ste B, Chesapeake, VA 23322, USA
Corey Jones - State Farm Insurance Agent
237 Carmichael Way #225, Chesapeake, VA 23322, USA
Kathy Kretz - State Farm Insurance Agent
838 Old George Washington Hwy N H, Chesapeake, VA 23323, USA
Janney Agency, LLC: Allstate Insurance
1369 S Military Hwy, Chesapeake, VA 23320, USA
Allison Plante - State Farm Insurance Agent
300 Battlefield Blvd N # B, Chesapeake, VA 23320, USA
AAA Chesapeake Insurance and Member Services
111 Kempsville Rd, Chesapeake, VA 23320, USA
Kursti Woolard Medicare Insurance Broker, Life & Annuity Agent
103 Watson Rd, Chesapeake, VA 23320, USA
Cedar Road Insurance Agency Inc.: Goosehead Ins Broker
801 Kent Pl, Chesapeake, VA 23320, USA
Centerville Insurance Agency
516 Innovation Dr Ste 301, Chesapeake, VA 23320, USA
Ferguson Insurance Center
1407 Stephanie Way Ste A, Chesapeake, VA 23320, USA
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Frequently Asked Questions — Insurance Agents in Chesapeake
What is the difference between a captive and independent insurance agent in Chesapeake?
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 VA?
Search the VA Department of Insurance's online license lookup — Google "VA 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 VA must be licensed with the state.
How much does working with a local insurance agent in Chesapeake 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 Chesapeake?
Online works for simple auto or renters policies if you understand what you're buying. A local agent in Chesapeake 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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