Updated July 2026 · VirginiaPlanFinder.com — Licensed Health Insurance Producer (NPN #21249133)

Health Insurance for Contractors and Real Estate Professionals in Chesapeake, Virginia

In Chesapeake, self-employed real estate contractors can access plans through Marketplace Virginia (HealthCare.gov), with 6 carriers offering coverage in Rating Area 4 for 2026.
Virginia expanded Medicaid in 2019, making it available to adults, including contractors, with incomes up to 138% of the Federal Poverty Level.
PPO plans ARE available on-exchange in Virginia, alongside HMO and EPO options, offering more network flexibility for Chesapeake residents.
Individual health insurance premiums may be tax-deductible for self-employed individuals not eligible for employer-sponsored plans.

For real estate contractors and self-employed professionals in Chesapeake, Virginia, securing reliable health insurance is a critical business decision. Unlike traditional employees, you're responsible for your own coverage, requiring a clear understanding of the options available through Marketplace Virginia (HealthCare.gov) and potentially Virginia Medicaid. Chesapeake, with a population of 252,583 and an uninsured rate of 5.8% (per U.S. Census Bureau ACS 2024 5-year estimates), offers a robust market for individual health plans. This guide breaks down how to find suitable and affordable health coverage tailored to your unique professional needs in Rating Area 4, which covers Chesapeake and 16 other surrounding counties.

Get Your Free Health Insurance Quote

A licensed agent can compare coverage options for you at no cost.

✓

You're all set!

A licensed agent will reach out shortly.

What Are Your Health Insurance Options as a Contractor in Chesapeake?

As a self-employed real estate professional in Chesapeake, your primary avenues for health insurance include the Affordable Care Act (ACA) marketplace, private off-exchange plans, and state-sponsored programs like Virginia Medicaid.

Marketplace Virginia (HealthCare.gov): This is the official exchange where individuals and families can compare plans and apply for financial assistance (subsidies) to lower monthly premiums and out-of-pocket costs. Eligibility for subsidies depends on your household income relative to the Federal Poverty Level (FPL).
Private Off-Exchange Plans: You can also purchase health insurance directly from carriers outside the marketplace. While these plans are ACA-compliant, they do not qualify for premium tax credits or cost-sharing reductions.
Virginia Medicaid: Virginia expanded Medicaid in 2019. If your income falls below 138% of the FPL, you may qualify for comprehensive, low-cost or no-cost coverage through Virginia Medicaid or FAMIS Plus.
Short-Term Health Insurance: These plans offer temporary coverage and are not ACA-compliant, meaning they don't cover essential health benefits or pre-existing conditions. They are typically much cheaper but offer limited protection.

Understanding Marketplace Plans and Subsidies in Chesapeake

The Marketplace Virginia, which uses the HealthCare.gov platform, is designed to make health insurance accessible and affordable. Plans are categorized into metal tiers: Bronze, Silver, Gold, and Platinum, indicating how costs are split between you and your plan.

Bronze Plans: Lowest monthly premiums, but highest out-of-pocket costs (deductibles, copays, coinsurance). Best for those who expect to use medical services infrequently.
Silver Plans: Moderate premiums and out-of-pocket costs. These plans are particularly valuable if you qualify for Cost-Sharing Reductions (CSRs), which further lower your deductibles, copays, and out-of-pocket maximums. CSRs are only available with Silver plans and are tied to income.
Gold Plans: Higher monthly premiums, but lower out-of-pocket costs. Ideal if you anticipate needing regular medical care or prescription drugs.
Platinum Plans: Highest premiums, lowest out-of-pocket costs. These plans cover a very high percentage of your medical expenses.

As a self-employed individual, your net income (after business deductions) is used to determine your eligibility for subsidies. Premium tax credits can significantly reduce your monthly premium, while cost-sharing reductions can lower your direct medical expenses.

Virginia Medicaid and FAMIS Plus for Lower-Income Contractors

Virginia expanded its Medicaid program in 2019, making health coverage available to many low-income adults who previously did not qualify. If your income is at or below 138% of the Federal Poverty Level, you may be eligible for Virginia Medicaid or FAMIS Plus. This program provides comprehensive benefits, including doctor visits, hospital stays, prescription drugs, and mental health services, often with no premiums or very low out-of-pocket costs. For pregnant women, Virginia Medicaid (FAMIS Moms) covers those with household incomes up to 200% FPL, including prenatal care, delivery, and 12 months of postpartum care. Children in households up to 200% FPL can qualify for FAMIS (Family Access to Medical Insurance Security), with FAMIS Select offering low-cost coverage for children between 200% and 400% FPL. Enrollment for these programs can be done through commonhelp.virginia.gov.

Health Insurance Carriers in Chesapeake

In 2026, 6 carriers offer marketplace plans in Rating Area 4, which covers Chesapeake, Franklin, Franklin, Hampton, Isle of Wight, James City, Newport News, Norfolk, Northampton, Poquoson, Portsmouth, Southampton, Suffolk, Surry, Virginia Beach, Williamsburg, York counties. These carriers provide a range of plan types, including HMO, PPO, and EPO options, to meet the diverse needs of Chesapeake residents. The confirmed carriers for this rating area are:

CareFirst BlueChoice
Cigna
HealthKeepers
Oscar Health
Sentara Health Plans
United Healthcare

It is important to compare plans from these carriers based on network, premium, deductible, and out-of-pocket costs to find the best fit for your specific health needs and budget. Chesapeake General Hospital, the primary acute care facility in Chesapeake, is part of the local healthcare landscape, and it's essential to verify if your chosen plan includes your preferred providers and facilities.

Making the Right Health Insurance Decision for Your Real Estate Business

Choosing the right health insurance plan as a self-employed real estate contractor involves weighing several factors, including your income, health needs, and budget.

Income Level (FPL)	Recommended Action	Key Benefit
Below 138% FPL	Apply for Virginia Medicaid/FAMIS Plus	Comprehensive, low-cost or no-cost coverage
138% - 250% FPL	Consider Enhanced Silver Plans on Marketplace Virginia	Significant premium subsidies and Cost-Sharing Reductions (CSRs)
250% - 400% FPL	Explore Bronze, Silver, or Gold Plans with Premium Tax Credits	Premium subsidies available to lower monthly costs
Above 400% FPL	Compare Marketplace plans (without subsidies) or private off-exchange plans	Full range of ACA-compliant plans; self-employed deduction may apply

Remember that as a self-employed individual, you may be able to deduct your health insurance premiums from your taxes, provided you meet certain IRS criteria and are not eligible for an employer-sponsored plan. Consult a tax professional for specific guidance on the self-employed health insurance deduction. The Chesapeake County area, with a median income of $95,373 and a poverty rate of 9.4% (per U.S. Census Bureau ACS 2024 5-year estimates), reflects a diverse economic landscape where both subsidized and unsubsidized options are relevant.

Frequently Asked Questions

What are the health insurance options for self-employed real estate contractors in Chesapeake?

Self-employed real estate contractors in Chesapeake can choose from plans on the Marketplace Virginia (HealthCare.gov), private off-exchange plans, or Virginia Medicaid if their income qualifies. Key options include HMO, PPO, and EPO plans from carriers like CareFirst BlueChoice, Cigna, and HealthKeepers, among others.

Can I get a PPO plan through the Marketplace Virginia in Chesapeake?

Yes, PPO plans are available on-exchange through the Marketplace Virginia (HealthCare.gov) for residents of Chesapeake. In 2026, you can choose from HMO, PPO, and EPO structures offered by participating carriers in Rating Area 4.

What income level qualifies for Virginia Medicaid for contractors?

Adults in Virginia, including self-employed contractors, may qualify for Virginia Medicaid if their household income is up to 138% of the Federal Poverty Level (FPL). This program provides comprehensive health coverage with no monthly premiums.

Are health insurance premiums tax-deductible for self-employed real estate agents?

Potentially, yes. If you are self-employed and not eligible to participate in an employer-sponsored health plan, you may be able to deduct the premiums you pay for health insurance. This is known as the self-employed health insurance deduction. Consult with a tax professional for personalized advice.