Best Insurance Agents in Chesapeake, Virginia

    Areas served: Chesapeake, VA and surrounding Hampton Roads region

    30 local businessesRanked by Lantern Score — a measure of reputation and business quality. We don't accept payment for placement.
    Updated April 15, 2026

    Chesapeake, Virginia's second-largest city serves a diverse population of over 250,000 residents with varying insurance needs, from coastal property protection to commercial coverage for the Hampton Roads business community. The city's proximity to military installations, active waterways, and growing suburban neighborhoods creates unique insurance considerations that local agents understand well. This directory provides detailed comparisons of insurance agents serving Chesapeake, evaluated on factors including carrier relationships, specialty coverage options, claims responsiveness, and local market expertise.

    Show businesses best for:
    86
    Lantern
    Score
    Virginia Beach, VA · 17 mi from Chesapeake
    Serves Virginia Beach, Hampton Roads, Tidewater area; serves Virginia, North Carolina, Maryland, and Tennessee
    ★★★★★5.0(1575 Google reviews)

    Lee Hudson State Farm Insurance Agent offers comprehensive auto, home, life, business, and health insurance coverage across Virginia, North Carolina, Maryland, and Tennessee. Led by Lee Hudson since 2014, this agency specializes in personalized insurance plans that maximize discounts and protect your most important assets. The team provides flexible service options—in-office, virtual, or on-site—plus additional services like banking, investments, annuities, and free notary services.

    Best for: Comparing OptionsHomeownersBusiness OwnersSaving MoneyLife Insurance Planning
    Ideal clients: Relocating families, homeowners seeking bundled auto and home coverage, small business owners, individuals wanting comprehensive life and health insurance planning
    What sets them apart
    • Serves all of Virginia, North Carolina, Maryland, and Tennessee with specialized focus on the Hampton Roads and Tidewater region, including Virginia Beach, Chesapeake, Suffolk, Norfolk, and surrounding cities.
    • Beyond insurance, offers banking, investment services, annuities, and free notary services, functioning as a complete financial services center.
    • Available 24/7 via phone, text, email, and virtual meetings, plus in-office consultations. Offers free quotes and helps clients identify all available discounts on their policies.
    Auto InsuranceHome InsuranceLife InsuranceBusiness InsuranceState Farm
    Phone(757) 383-6686
    Lee Hudson - State Farm Insurance Agent
    Updated 4/15/26Learn More →
    86
    Lantern
    Score
    Virginia Beach, VA · 21 mi from Chesapeake
    Serves Virginia Beach, Norfolk, Chesapeake, and surrounding Hampton Roads area
    ★★★★★5.0(613 Google reviews)

    Tidewater Insurance Brokers is an independent insurance agency serving the Virginia Beach area with comprehensive coverage options including auto, home, life, and business insurance. As an independent broker, they work with multiple carriers to find personalized policies that fit each client's needs and budget. Their local expertise and commitment to customer service have earned them strong recognition in the community.

    Best for: HomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Homeowners, auto owners, small business operators, families seeking bundled coverage and personalized insurance guidance
    What sets them apart
    • Works with multiple insurance carriers to compare rates and coverage options, ensuring clients get the best value rather than being locked into a single company's offerings.
    • Based in Virginia Beach with deep knowledge of local insurance needs, including coverage considerations specific to the Hampton Roads region.
    • Takes time to understand individual circumstances and customizes insurance solutions rather than applying one-size-fits-all approaches.
    Independent AgentAuto InsuranceHome InsuranceBusiness InsuranceVirginia Beach
    Phone(757) 302-5639
    Tidewater Insurance Brokers
    Updated 4/15/26Learn More →
    84
    Lantern
    Score
    Hampton, VA · 26 mi from Chesapeake
    Serves Hampton, Norfolk, and surrounding southeastern Virginia; also licensed in North Carolina and Tennessee
    ★★★★★4.9(1227 Google reviews)

    Greg Holestin is an independently owned and operated GEICO insurance agent in Hampton, VA serving the Southeast with over 23 years of insurance experience. He offers a full range of personal insurance products including auto, home, renters, condo, motorcycle, ATV, and boat coverage. Greg is a GEICO Top Performer and holds a Finance degree from Old Dominion University, bringing professional expertise and deep community involvement to his local practice.

    Best for: Comparing OptionsHomeownersSaving Money
    Ideal clients: Hampton and Norfolk residents seeking auto and home insurance, families needing bundled coverage, Spanish-speaking customers
    What sets them apart
    • Greg brings over two decades of insurance industry expertise and holds a Finance degree from Old Dominion University.
    • Recognized as a GEICO Top Performer multiple times (2012, 2014, 2016) for service excellence.
    • Open 9 AM-9 PM weekdays and 9 AM-5 PM Saturday with Spanish-language support available.
    GEICO AgentAuto InsuranceHome InsuranceLocal AgentHampton VA
    Phone(757) 838-5050
    Websitegeico.com
    Greg Holestin - GEICO Insurance Agent
    Updated 4/15/26Learn More →
    84
    Lantern
    Score
    Virginia Beach, VA · 16 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★4.9(357 Google reviews)

    AB Insurance is an independent insurance agency in Virginia Beach specializing in homeowners, auto, life, umbrella, flood, and boat insurance. They shop multiple top-rated carriers to find customized coverage rather than one-size-fits-all solutions, with a dedicated team focused on clear communication and proactive service. Known for their relationship-driven approach, they help customers understand their policies in plain language and stay ahead of life changes.

    Best for: Comparing OptionsHomeownersSaving MoneyLife Insurance Planning
    Ideal clients: First-time homebuyers, families seeking bundled coverage, customers wanting personalized service, those transitioning to new homes
    What sets them apart
    • They represent multiple top-rated insurance carriers, allowing them to compare options and find coverage tailored to your specific needs rather than pushing a single company's products.
    • You work with named agents who understand your situation, are accessible by phone or message, and proactively review your coverage during life changes.
    • They prioritize explaining insurance in plain language so customers know exactly what they're getting and why it matters.
    Independent AgentHomeowners InsuranceAuto InsuranceLife Insurance
    Phone(757) 645-9379
    AB Insurance
    Updated 4/15/26Learn More →
    84
    Lantern
    Score
    Virginia Beach, VA · 14 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★4.9(239 Google reviews)

    A&C Insurance and Multi Service Agency is a full-service insurance brokerage in Virginia Beach serving families and business owners with auto, home, life, health, and commercial insurance solutions. Beyond insurance, they offer a comprehensive suite of services including DMV assistance, notarizations, translations, travel permits, business formation, airline ticket sales, and utility payments. The agency provides personalized education and guidance to help clients make informed decisions about protecting their assets and planning their financial future.

    Best for: Comparing OptionsHomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Bilingual families, small business owners, immigrants seeking comprehensive financial services, clients needing DMV and notary assistance alongside insurance
    What sets them apart
    • Beyond insurance, they handle DMV services, notarizations, translations, travel permits, business formation, airline tickets, and bill payments—eliminating the need to visit multiple locations.
    • Fluent Spanish-language service ensures clients can discuss complex insurance and financial decisions in their preferred language.
    • The agency emphasizes education and long-term planning, helping clients build lasting financial stability and legacy protection rather than just selling policies.
    Insurance AgencyAuto InsuranceHome InsuranceMulti-ServiceBilingual
    Phone(757) 578-2513
    A&C Insurance and Multi Service Agency
    Updated 4/15/26Learn More →
    84
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, VA and surrounding areas
    ★★★★★5.0(50 Google reviews)

    Jessica Hester is a State Farm Insurance Agent in Chesapeake, VA offering comprehensive coverage including auto, homeowners, condo, renters, business, life, health, and pet insurance. As a second-generation State Farm agent with deep family roots in the industry, she emphasizes personalized service and exceeding customer expectations. Her office specializes in bundling multiple policies and providing convenient quotes and claims support during extended office hours.

    Best for: HomeownersBusiness OwnersSaving MoneyLife Insurance Planning
    Ideal clients: Families seeking bundled home and auto insurance, business owners needing comprehensive coverage, homebuyers and renters, customers valuing personalized local service
    What sets them apart
    • Jessica comes from a family of State Farm agents with 49+ years of combined experience, bringing deep industry knowledge and commitment to the business.
    • Offers auto, home, business, life, health, pet, and specialty insurance all in one office, making bundling and policy management seamless.
    • Office motto focuses on delivering better care than expected, with flexible hours including weekends and evenings by appointment for convenience.
    Auto InsuranceHome InsuranceState FarmLife InsuranceBusiness Insurance
    Phone(757) 481-1840
    Jessica Hester - State Farm Insurance Agent
    Updated 4/15/26Learn More →
    83
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, Virginia and surrounding areas
    ★★★★★4.9(154 Google reviews)

    Centerville Insurance Agency is a family-owned, independent insurance agency serving Virginia since 1969, now in its second generation. They specialize in personal insurance (auto, home, life, condo, umbrella), business insurance (commercial auto, property, workers' compensation, business owners policies), and industry-specific coverage for contractors, repair shops, restaurants, and professional services. As an independent agent representing multiple carriers, they focus on finding clients the best rates and personalized guidance through a team of licensed advisors.

    Best for: Comparing OptionsHomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Small business owners, contractors, homeowners seeking competitive rates, high-net-worth individuals, families needing bundled personal and business coverage
    What sets them apart
    • As an independent agency, they represent multiple insurance carriers, allowing them to shop rates and find better coverage options than captive agents tied to a single company.
    • Operating since 1969 with deep community roots and family-oriented values, they prioritize long-term client relationships and professional guidance over transaction volume.
    • They offer specialized coverage for specific industries including contractors, repair shops, restaurants, child care centers, and medical offices—not just standard personal policies.
    Independent AgentMulti-CarrierFamily-OwnedBusiness & Personal InsuranceVirginia Since 1969
    Phone(757) 420-0006
    Centerville Insurance Agency
    Updated 4/15/26Learn More →
    83
    Lantern
    Score
    Portsmouth, VA · 10 mi from Chesapeake
    Serves Portsmouth, VA and surrounding Hampton Roads area
    ★★★★★4.9(126 Google reviews)

    Coppedge Insurance Agency Inc. is a Nationwide Insurance agency in Portsmouth, VA offering comprehensive personal and commercial insurance coverage including homeowners, auto, life, flood, umbrella, renters, landlord, condo, and manufactured home insurance. The agency also serves business clients with commercial auto, business owner policies, and workplace benefits. Run by owner Don Coppedge and a team of experienced agents including Marion Cornish, Brandi Watson, Aisha Coppedge, Doreene Mann, and Cindy Coppedge, the agency is known for responsive, professional service and deep community involvement.

    Best for: HomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Families seeking bundled home and auto coverage, business owners needing commercial insurance, long-term customers prioritizing consistent service, Portsmouth-area residents valuing local relationships
    What sets them apart
    • Offers a full range of personal and commercial insurance products from homeowners and auto to life, flood, umbrella, and business policies, providing one-stop protection for families and business owners.
    • Agency clients report multi-year relationships (15+ years in some cases) built on responsive, helpful service and a friendly, professional approach.
    • Active in local community outreach and maintains a Concierge Directory to connect customers with trusted local services and businesses.
    Nationwide InsuranceAuto InsuranceHomeowners InsuranceLife InsurancePortsmouth VA
    Phone(757) 405-3079
    Nationwide Insurance: Coppedge Insurance Agency Inc.
    Updated 4/15/26Learn More →
    83
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, Virginia and surrounding areas
    ★★★★★4.9(118 Google reviews)

    Ferguson Insurance Center is an independent insurance agency in Chesapeake serving Virginia with personalized coverage solutions across auto, home, life, and business insurance. They work with multiple carriers to find competitive rates and customized policies tailored to each client's needs. Their experienced team focuses on building long-term relationships and providing responsive service.

    Best for: HomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Homeowners, auto insurance shoppers, small business owners, families seeking bundled coverage
    What sets them apart
    • Works with multiple carriers to compare rates and find the best coverage options for each client, rather than being limited to a single company.
    • Offers comprehensive coverage including auto, home, life, and business insurance, making them a one-stop shop for most insurance needs.
    • Based in Chesapeake with local knowledge of Virginia-specific insurance requirements and community needs.
    Insurance AgencyAuto InsuranceHome InsuranceBusiness InsuranceIndependent Agent
    Phone(757) 201-3000
    Ferguson Insurance Center
    Updated 4/15/26Learn More →
    83
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, Newport News, and surrounding areas of Virginia; North Carolina; Maryland
    ★★★★★4.9(107 Google reviews)

    Corey Jones is a State Farm Insurance Agent serving Virginia, North Carolina, and Maryland from offices in Chesapeake and Newport News. A retired 21-year Air Force veteran, Corey offers comprehensive insurance solutions including auto, homeowners, condo, renters, business, life, health, and pet insurance, along with banking products. His team provides personalized quotes and 24/7 availability via phone, text, or in-person appointments, with bilingual service in English and Spanish.

    Best for: Comparing OptionsHomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Families seeking comprehensive insurance coverage, military veterans and their families, bilingual customers, small business owners needing commercial insurance, Virginia residents in the 757 area
    What sets them apart
    • Retired Air Force veteran with 21 years of service who actively volunteers with Habitat for Humanity, sponsors local schools and animal rescue, and mentors students through community programs.
    • Offers a full range of insurance products (auto, home, business, life, health, pet) plus banking services, enabling customers to consolidate their insurance and financial needs with one trusted agent.
    • Available around the clock via phone, text, email, or in-person appointments, with bilingual support in English and Spanish for personalized service.
    State Farm AgentAir Force VeteranMulti-State Coverage24/7 AvailabilityPersonalized Quotes
    Corey Jones - State Farm Insurance Agent
    Updated 4/15/26Learn More →
    83
    Lantern
    Score
    Virginia Beach, VA · 13 mi from Chesapeake
    Serves Virginia Beach, Chesapeake, Norfolk, Suffolk, Portsmouth, VA and Hampton Roads region
    ★★★★★4.9(82 Google reviews)

    Matt Roenker Insurance Agency is a family-owned independent insurance agency serving the Hampton Roads area since 1969. They specialize in auto, home, business, life, health, and recreational vehicle insurance for individuals, families, seniors, and military families. The agency works with multiple carriers to find competitive rates and offers specialized services including non-standard/SR-22 coverage, boat and motorcycle insurance, renters insurance, annuities, and pet insurance through Nationwide.

    Best for: Comparing OptionsHomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Families seeking comprehensive coverage, military families, individuals with non-standard driving histories, business owners, seniors
    What sets them apart
    • Works with multiple insurance carriers to find customers the best rates and coverage options, rather than being locked into one company.
    • Family-owned since 1969 with a hands-on approach; many customers have been with them for 10+ years and receive direct access to agents.
    • Offers non-standard/SR-22 insurance for high-risk drivers, plus boat, motorcycle, RV, pet, and business owner policies—comprehensive beyond standard auto and home.
    Independent AgentFamily-OwnedFull-Service InsuranceMultiple CarriersMilitary-Friendly
    Phone(757) 671-1111
    Matt Roenker Insurance Agency
    Updated 4/15/26Learn More →
    82
    Lantern
    Score
    Virginia Beach, VA · 15 mi from Chesapeake
    Serves Virginia Beach, Norfolk, and surrounding areas in Virginia, North Carolina, and Tennessee
    ★★★★★4.8(1047 Google reviews)

    Greg Holestin is an independently owned and operated GEICO insurance agent serving Virginia Beach and surrounding areas with over 23 years of insurance experience. He offers auto, home, renters, condo, motorcycle, ATV, and boat insurance with extended hours to help customers find the coverage they need. As a GEICO Top Performer, Greg brings local expertise and community involvement to personalized insurance solutions.

    Best for: HomeownersLife Insurance Planning
    Ideal clients: Families seeking auto and home insurance, business owners needing comprehensive coverage, multi-policy customers looking for bundling options
    What sets them apart
    • Greg brings over two decades of relevant insurance experience and holds a degree in Finance from Old Dominion University.
    • Recognized as a GEICO Top Performer in 2012, 2014, and 2016, demonstrating consistent excellence in service.
    • Open weekdays until 7 PM and Saturdays until 6 PM to accommodate busy schedules, with Spanish language services available.
    GEICO AgentAuto InsuranceHome InsuranceLocal Expert
    Phone(757) 583-2200
    Websitegeico.com
    Greg Holestin - GEICO Insurance Agent - Virginia Beach Blvd
    Updated 4/15/26Learn More →
    82
    Lantern
    Score
    Virginia Beach, VA · 13 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★5.0(28 Google reviews)

    Friedman Associates Insurance is an independent insurance agency serving Virginia Beach and the surrounding area. They provide personalized insurance solutions including auto, home, life, and business coverage from multiple carriers. The agency focuses on finding clients the right coverage at competitive rates through their consultative approach.

    Best for: HomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Homeowners needing bundled coverage, Small business owners, Auto insurance shoppers, Life insurance buyers
    What sets them apart
    • Works with multiple insurance carriers to find clients the best coverage options rather than being limited to a single company's products.
    • Takes time to understand each client's unique insurance needs and provides customized recommendations rather than one-size-fits-all solutions.
    Independent Insurance AgencyAuto InsuranceHome InsuranceBusiness InsuranceVirginia Beach
    Phone(757) 420-9600
    Friedman Associates Insurance
    Updated 4/15/26Learn More →
    81
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, VA and surrounding areas in Virginia, North Carolina, Maryland, and South Carolina
    ★★★★★4.8(117 Google reviews)

    Garlow Insurance Agency Inc is an independent insurance agency in Chesapeake, VA serving Virginia, North Carolina, Maryland, and South Carolina. They represent multiple carriers including Safeco and Progressive, offering personal insurance (auto, home, flood, pet, classic car, aviation), business insurance (business auto, business owners, workers' compensation, general liability, commercial umbrella), and industry-specific coverage (aviation, contractors, garage repair, manufacturers, restaurants). As a licensed independent agency with 20+ years of client relationships, they provide personalized guidance and ongoing policy management to help clients protect their assets.

    Best for: Comparing OptionsHomeownersBusiness Owners
    Ideal clients: Small business owners, contractors, real estate professionals, individuals seeking personalized coverage options
    What sets them apart
    • Represents top insurance companies including Safeco and Progressive, offering clients choice and competitive options rather than being locked into a single carrier.
    • Provides industry-specific insurance for contractors, garages, restaurants, manufacturers, and aviation businesses, plus specialty personal policies like classic car and watercraft coverage.
    • Serves clients for 20+ years with responsive, hands-on support and serves real estate professionals and business owners, demonstrating deep local expertise.
    Independent Insurance AgentMultiple CarriersPersonal & Business CoverageLicensed Advisors
    Phone(757) 548-1515
    Garlow Insurance Agency - Nationwide Insurance
    Updated 4/15/26Learn More →
    81
    Lantern
    Score
    Virginia Beach, VA · 16 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★5.0(20 Google reviews)

    Luke Agency is an independent life and health insurance agency in Virginia Beach specializing in Medicare planning and enrollment. Founded and operated by Debbie Luke, the agency helps clients navigate Medicare Advantage, Medicare Supplement (Medigap), and Medicare Part D prescription drug coverage with personalized guidance. Beyond Medicare, Luke Agency also offers life insurance, critical illness insurance, dental insurance, and retirement planning services to help clients make informed financial decisions.

    Best for: Comparing OptionsLife Insurance Planning
    Ideal clients: Medicare-eligible seniors, individuals approaching retirement, life insurance shoppers, people with complex healthcare needs
    What sets them apart
    • Specializes in complex Medicare planning with detailed review of plan networks, medication coverage, and cost comparisons to ensure clients select the best option for their needs.
    • As an independent agent, Luke Agency represents multiple carriers and provides unbiased comparisons rather than pushing a single company's products.
    • Focuses on client education throughout the decision-making process, holding seminars and providing step-by-step guidance to help clients understand their options.
    Medicare PlanningLife InsuranceIndependent AgentHealth InsuranceRetirement Planning
    Phone(757) 761-0812
    Luke Agency
    Updated 4/15/26Learn More →
    80
    Lantern
    Score
    Virginia Beach, VA · 16 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★4.9(1423 Google reviews)

    Evertree Insurance is an independent insurance agency in Virginia Beach serving individuals and businesses with comprehensive coverage solutions including auto, home, life, and commercial insurance. As an independent agent representing multiple carriers, they help clients find the best coverage options tailored to their specific needs rather than being limited to a single insurer.

    Best for: HomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Homeowners seeking bundled insurance, small business owners, individuals comparing multiple carriers, families protecting assets with life insurance
    What sets them apart
    • As an independent agency, Evertree represents multiple insurance carriers, allowing them to compare options and find the best rates and coverage for each client's situation.
    • They offer auto, home, life, and commercial insurance under one roof, making it convenient for clients to bundle policies and potentially qualify for multi-policy discounts.
    • Based in Virginia Beach with direct phone support, they understand local insurance needs and market conditions specific to the Hampton Roads area.
    Independent Insurance AgentAuto InsuranceHome InsuranceBusiness InsuranceLife Insurance
    Evertree Insurance
    Updated 4/15/26Learn More →
    80
    Lantern
    Score
    Virginia Beach, VA · 13 mi from Chesapeake
    Serves Virginia Beach, Hampton Roads, and surrounding areas of Virginia
    ★★★★★4.7(121 Google reviews)

    Choice Insurance Agency is an independent insurance broker serving Virginia Beach and the surrounding Hampton Roads area. They specialize in homeowners, auto, life, and business insurance, offering personalized coverage solutions from multiple carriers. As an independent agency, they help clients find the best rates and policies tailored to their specific needs rather than being limited to a single company's offerings.

    Best for: HomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Homeowners, auto insurance shoppers, small business owners, families seeking bundled coverage
    What sets them apart
    • Represents multiple insurance carriers, allowing them to compare rates and coverage options to find the best fit for each client rather than being tied to one company.
    • Offers homeowners, auto, life, and business insurance in one location, making it convenient to manage all insurance needs with one trusted agent.
    InsuranceIndependent AgentAuto & HomeBusiness Insurance
    Phone(757) 416-5100
    Choice Insurance Agency
    Updated 4/15/26Learn More →
    80
    Lantern
    Score
    Virginia Beach, VA · 13 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★4.7(87 Google reviews)

    Richard C. Barbosa, II is an Allstate Insurance agent serving Virginia Beach and the surrounding area. He provides auto, home, life, and business insurance coverage tailored to individual and family needs. As a local Allstate representative, he offers personalized service and access to Allstate's range of insurance products and discounts.

    Best for: HomeownersBusiness OwnersSaving MoneyLife Insurance Planning
    Ideal clients: Virginia Beach residents seeking auto and home insurance, families looking for life insurance, local small business owners
    What sets them apart
    • Offers auto, home, life, and business insurance products through Allstate's comprehensive portfolio.
    • Provides personalized, face-to-face service at a dedicated Virginia Beach location for policy questions and claims support.
    Auto InsuranceHome InsuranceLife InsuranceBusiness Insurance
    Phone(757) 431-0217
    Richard C. Barbosa, II: Allstate Insurance
    Updated 4/15/26Learn More →
    79
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, VA and surrounding areas
    ★★★★★5.0(15 Google reviews)

    Kursti Woolard is an independent Medicare insurance broker and life & annuity agent serving Chesapeake and surrounding areas. She specializes in helping Medicare-eligible clients navigate complex insurance options, including Medicare Advantage, Medigap, and prescription drug coverage, while also offering life insurance and annuity planning solutions. Her personalized approach focuses on finding coverage that fits individual health needs and budgets.

    Best for: Comparing Options
    Ideal clients: Medicare-eligible seniors, retirees seeking life insurance or annuities, individuals during Medicare open enrollment
    What sets them apart
    • Dedicated expertise in Medicare planning and enrollment, helping seniors understand their options during open enrollment periods and life changes.
    • Works with multiple insurance carriers to provide unbiased recommendations tailored to individual needs rather than promoting a single company.
    • Combines Medicare guidance with life insurance and annuity planning for a complete retirement and wealth transfer strategy.
    Medicare BrokerLife InsuranceAnnuitiesHealth InsuranceIndependent Agent
    Phone(757) 692-8438
    Kursti Woolard Medicare Insurance Broker, Life & Annuity Agent
    Updated 4/15/26Learn More →
    79
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, VA and Hampton Roads area
    ★★★★★5.0(15 Google reviews)

    Fred E. Pettus III is an insurance benefits coordinator serving Chesapeake, VA and the surrounding Hampton Roads area. With expertise in employee benefits planning and insurance coordination, Pettus helps individuals and organizations navigate complex benefits options to find coverage that fits their needs and budget.

    Ideal clients: Individuals seeking benefits guidance, Small business owners managing employee coverage, Those navigating insurance options
    What sets them apart
    • Specializes in employee benefits coordination and planning, helping clients understand and optimize their coverage options.
    • Provides personalized, one-on-one service to Chesapeake residents rather than relying on automated systems.
    InsuranceBenefits PlanningChesapeake VA
    Phone(757) 334-0946
    Fred E. Pettus III, Benefits Coordinator
    Updated 4/15/26Learn More →
    79
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, VA and surrounding areas
    ★★★★★4.8(26 Google reviews)

    Gilmore Insurance Agency is a local Allstate insurance agent serving Chesapeake and surrounding areas. They offer a full range of insurance products including auto, home, life, and business coverage. As an Allstate-affiliated agency, they combine national resources with personalized local service to help customers find the right coverage at competitive rates.

    Best for: HomeownersBusiness OwnersSaving MoneyLife Insurance Planning
    Ideal clients: Chesapeake residents needing auto and home insurance, families seeking life coverage, local business owners
    What sets them apart
    • Access to Allstate's full suite of insurance products and financial stability as a national carrier.
    • Personalized service from a dedicated local agent who understands the Chesapeake community's specific insurance needs.
    • Combine auto, home, life, and business insurance to unlock bundling discounts and simplify your coverage.
    Auto InsuranceHome InsuranceLife InsuranceAllstate Agent
    Phone(757) 574-0040
    Gilmore Insurance Agency: Allstate Insurance
    Updated 4/15/26Learn More →
    78
    Lantern
    Score
    Norfolk, VA · 16 mi from Chesapeake
    Serves Norfolk, VA and Hampton Roads area
    ★★★★★4.6(109 Google reviews)

    Salzberg Insurance Agency is an independent insurance broker serving Norfolk, VA and the surrounding Hampton Roads area. They provide comprehensive coverage across auto, home, life, and business insurance, helping individuals and families find the right policies from multiple carriers. Their experienced team focuses on personalized service and competitive quotes to match each client's specific insurance needs.

    Best for: Comparing OptionsHomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Norfolk families seeking comprehensive insurance coverage, small business owners, individuals comparing auto and home insurance quotes
    What sets them apart
    • Access to multiple insurance carriers allows them to compare quotes and find the best rates and coverage options for each client rather than being limited to one company.
    • Offers auto, home, life, and business insurance in one location, making it convenient to manage all insurance needs with a single trusted agent.
    • Based in Norfolk with deep knowledge of local insurance needs and Virginia-specific coverage requirements.
    InsuranceAuto InsuranceHomeowners InsuranceIndependent AgentNorfolk VA
    Phone(757) 583-1828
    Salzberg Insurance Agency
    Updated 4/15/26Learn More →
    78
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, Virginia and surrounding areas
    ★★★★★4.8(110 Google reviews)

    Direct Auto Insurance is a local insurance agency in Chesapeake offering affordable auto insurance coverage with flexible payment options. As a Direct Auto location, they provide quick quotes and personalized service to help drivers find coverage that fits their budget and driving needs.

    Ideal clients: Budget-conscious drivers, Those seeking flexible payment options, Drivers needing quick coverage
    What sets them apart
    • Direct Auto offers customizable payment options to make insurance more affordable and accessible for drivers.
    • Get insurance quotes quickly without lengthy paperwork or complicated applications.
    Auto InsuranceAffordable CoverageQuick QuotesLocal Agent
    Phone(757) 686-0033
    Direct Auto Insurance
    Updated 4/15/26Learn More →
    77
    Lantern
    Score
    Virginia Beach, VA · 16 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★5.0(10 Google reviews)

    Edge Insurance Agency is an independent insurance agency serving Virginia Beach and the surrounding area. They offer comprehensive insurance solutions including auto, home, life, and business coverage, helping clients find the right protection for their needs. As an independent agent, Edge works with multiple carriers to provide competitive quotes and personalized service.

    Best for: Comparing OptionsHomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Homeowners, auto owners, small business owners, individuals seeking personalized insurance advice
    What sets them apart
    • Works with multiple insurance carriers to compare quotes and find the best coverage options for each client's specific situation.
    • Conveniently located in Virginia Beach with direct phone contact for personalized service and local support.
    Insurance AgencyAuto InsuranceHomeowners InsuranceIndependent Agent
    Phone(757) 260-9866
    Edge Insurance Agency
    Updated 4/15/26Learn More →
    77
    Lantern
    Score
    Virginia Beach, VA · 9 mi from Chesapeake
    Serves Virginia Beach, Norfolk, Hampton Roads, Virginia
    ★★★★★4.9(12 Google reviews)

    Virginia Health Advisors is an independent insurance agency and health consultant serving Virginia Beach and surrounding areas. They specialize in helping individuals and families navigate health insurance options, Medicare planning, and related health services. The team provides personalized guidance to ensure clients select coverage that meets their specific healthcare needs and budget.

    Best for: Comparing Options
    Ideal clients: Medicare-eligible individuals, Families seeking comprehensive health coverage, Self-employed professionals, Healthcare consumers needing personalized guidance
    What sets them apart
    • Works with multiple carriers to find options tailored to individual needs rather than pushing a single insurer's products.
    • Combines insurance knowledge with health consulting to help clients understand coverage options in the context of their healthcare goals.
    Health InsuranceMedicare PlanningInsurance ConsultantIndependent Agent
    Phone(757) 214-8620
    Virginia Health Advisors
    Updated 4/15/26Learn More →
    77
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, Virginia and Coastal Virginia region
    ★★★★★4.8(51 Google reviews)

    COVA Insurance is a full-service insurance agency in Chesapeake, VA offering auto, home, flood, business, and health insurance to individuals and commercial clients. They specialize in industry-specific coverage including church insurance and apartment building policies, with a focus on personalized protection strategies and excess liability coverage.

    Best for: HomeownersBusiness OwnersSaving Money
    Ideal clients: Homeowners, auto owners, small business owners, churches, apartment building investors, families seeking bundled coverage
    What sets them apart
    • COVA offers tailored coverage for specific business types like churches and apartment buildings, not just generic policies.
    • One agency handles auto, home, business, health, and flood insurance, simplifying multi-policy management and bundling.
    • Educational content and detailed consultations help clients understand coverage gaps, including umbrella liability policies and appropriate liability limits.
    Auto InsuranceHome InsuranceBusiness InsuranceHealth InsuranceFlood Insurance
    Phone(757) 410-5800
    COVA Insurance
    Updated 4/15/26Learn More →
    76
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, VA and surrounding areas
    ★★★★★4.6(34 Google reviews)

    W T Jennings Insurance Agency Inc. is a Nationwide Insurance agent serving the Chesapeake area with comprehensive coverage options including auto, home, life, and business insurance. The agency helps families and businesses protect their assets through personalized insurance solutions and competitive rates.

    Best for: HomeownersBusiness OwnersLife Insurance Planning
    Ideal clients: Families needing home and auto insurance, small business owners, individuals seeking life insurance coverage
    What sets them apart
    • Represents Nationwide Insurance, a major national carrier offering stability and comprehensive coverage options.
    • Provides auto, home, life, and business insurance in one convenient location, simplifying policy management.
    • Offers personalized service from a local agency that understands the Chesapeake community's insurance needs.
    Insurance AgencyAuto InsuranceHome InsuranceLife InsuranceBusiness Insurance
    Nationwide Insurance: W T Jennings Insurance Agency Inc.
    Updated 4/15/26Learn More →
    76
    Lantern
    Score
    Chesapeake, VA
    Serves Chesapeake, Virginia and surrounding areas
    ★★★★★5.0(8 Google reviews)

    Excellent Insurance Inc is an independent insurance agency in Chesapeake serving Virginia with a range of personal and commercial coverage options. The agency works with multiple carriers to provide customized insurance solutions including auto, home, life, and business policies. With a 5-star rating, they're known for personalized service and helping clients find the right coverage at competitive rates.

    Best for: Comparing OptionsHomeownersBusiness OwnersSaving MoneyLife Insurance Planning
    Ideal clients: Virginia homeowners, auto insurance shoppers, small business owners, individuals seeking bundled coverage discounts
    What sets them apart
    • Works with multiple insurance carriers to compare rates and find the best coverage options for each client's unique needs.
    • Based in Chesapeake with direct phone support and personalized service for Virginia residents.
    • Offers auto, home, life, and business insurance solutions in one convenient location.
    Insurance AgencyAuto InsuranceHomeowners InsuranceIndependent AgentLocal Service
    Phone(434) 381-4331
    Excellent Insurance Inc
    Updated 4/15/26Learn More →
    76
    Lantern
    Score
    Virginia Beach, VA · 13 mi from Chesapeake
    Serves Virginia Beach, VA and surrounding areas
    ★★★★★5.0(8 Google reviews)

    Cheap Auto Insurance Agency Virginia Beach provides affordable auto insurance solutions to drivers throughout the Virginia Beach area. Specializing in helping customers find competitively priced coverage, they work with multiple carriers to match drivers with policies that fit their needs and budget. Their focus on accessible pricing makes them a practical choice for those seeking to reduce insurance costs without sacrificing coverage.

    Best for: Comparing Options
    Ideal clients: Budget-conscious drivers, First-time insurance buyers, Drivers seeking to lower current premiums
    What sets them apart
    • Works with multiple insurance carriers to provide competitive rate comparisons and help you find the best coverage for your situation.
    • Established local agency familiar with Virginia Beach drivers' specific insurance needs and state requirements.
    Auto InsuranceAffordable CoverageVirginia BeachInsurance AgencyLocal Service
    Cheap Auto Insurance Agency Virginia Beach
    Updated 4/15/26Learn More →
    75
    Lantern
    Score
    Norfolk, VA · 12 mi from Chesapeake
    Serves Norfolk, Virginia and surrounding areas
    ★★★★★5.0(14 Google reviews)

    We Insure Things is an independent insurance agency in Norfolk serving Virginia with comprehensive coverage options including auto, home, life, and business insurance. The agency specializes in personalized service and competitive quotes, helping clients find the right coverage to protect what matters most.

    Best for: Comparing OptionsHomeownersBusiness OwnersSaving MoneyLife Insurance Planning
    Ideal clients: Virginia homeowners, auto insurance shoppers, small business owners, individuals seeking bundled insurance coverage
    What sets them apart
    • Works with multiple insurance carriers to find competitive rates and coverage options tailored to your specific needs.
    • Based in Norfolk with deep knowledge of Virginia insurance requirements and regional risks.
    • Offers auto, home, life, and business insurance through one convenient local agency.
    Insurance AgencyAuto InsuranceHome InsuranceBusiness InsuranceIndependent Agent
    Phone(757) 317-1015
    We Insure Things
    Updated 4/15/26Learn More →

    Frequently Asked Questions

    Who is the top-ranked insurance agent in Chesapeake, VA?

    Lee Hudson - State Farm Insurance Agent is the top-ranked insurance provider in the Chesapeake area with a Lantern Score of 85.82/100 and a 5-star rating from 1,575 reviews. Lee Hudson offers comprehensive auto, home, life, business, and health insurance coverage and is particularly well-suited for relocating families, homeowners seeking bundled coverage, and small business owners.

    Which insurance agents specialize in serving military families in Chesapeake?

    Corey Jones - State Farm Insurance Agent (Lantern Score: 83.06/100) is an excellent choice for military families, as he is a retired 21-year Air Force veteran serving Virginia, North Carolina, and Maryland from offices in Chesapeake and Newport News. Additionally, Matt Roenker Insurance Agency (Lantern Score: 82.74/100) specifically serves military families among other customer groups in the Hampton Roads area.

    What insurance options are available for Medicare-eligible seniors in Chesapeake?

    Chesapeake has two specialists in Medicare planning: Luke Agency (Lantern Score: 80.65/100, 5-star rating) focuses specifically on Medicare planning and enrollment, while Kursti Woolard Medicare Insurance Broker, Life & Annuity Agent (Lantern Score: 79.34/100, 5-star rating) helps Medicare-eligible clients navigate complex insurance options and annuities. Both agencies serve seniors in the Chesapeake and surrounding Hampton Roads area.

    Which insurance agencies are best for first-time homebuyers in Chesapeake?

    AB Insurance (Lantern Score: 83.81/100, 4.9-star rating) is specifically recommended for first-time homebuyers and specializes in homeowners, auto, life, umbrella, flood, and boat insurance. Additionally, Jessica Hester - State Farm Insurance Agent (Lantern Score: 83.51/100, 5-star rating) in Chesapeake offers comprehensive coverage for homebuyers and renters seeking personalized local service.

    Are there any bilingual insurance agents serving Chesapeake residents?

    Yes, A&C Insurance and Multi Service Agency (Lantern Score: 83.65/100, 4.9-star rating) in Virginia Beach specifically serves bilingual families and also provides DMV and notary assistance. Additionally, Greg Holestin - GEICO Insurance Agent (Lantern Score: 84.05/100, 4.9-star rating) offers services to Spanish-speaking customers and serves the Hampton and Norfolk area.

    Which independent insurance agencies offer the most comprehensive coverage options?

    Tidewater Insurance Brokers (Lantern Score: 85.69/100, 5-star rating) is an independent agency serving the Virginia Beach area with comprehensive auto, home, life, and business insurance, and is well-rated for personalized guidance. Evertree Insurance (Lantern Score: 80.46/100, 4.9-star rating with 1,423 reviews) is another highly-reviewed independent agency offering auto, home, life, and commercial insurance to individuals and businesses throughout Virginia Beach.

    This directory of insurance agents local businesses serving Chesapeake, VA is maintained by Lantern. Rankings are determined by the Lantern Score — not advertising or payment for placement. Learn how it works. Last updated April 15, 2026. To claim or update a listing, contact us.