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TWG Insurance | The Winchester Group

Experience you can trust
Personal attention
High-level service

Here at TWG Insurance, we are committed to being your trusted advisor to provide protection, competitive prices, and personalized service. And with a focus on respect, you can trust us to always work with your best interests when serving your insurance needs.

Established in 2002, we have the backing of highly qualified insurance professionals with over 330 years of combined experience. We also work with some of the top insurance companies in the industry. That means no matter what your situation is, we work to meet and exceed all expectations to ensure your satisfaction.

We truly believe that having the right insurance coverage, you can best protect your life and your business. That’s why we are dedicated to providing the highest quality customer service and customized coverage that works best for you. Contact us today to get the help you need from an advisor you can trust.

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Our Core Insurance Services

The Solution To Your Insurance Needs

Providing a variety of business insurance, personal insurance, and employee benefits solutions is what TWG Insurance | The Winchester Group does best.

Business Insurance

Coverage and risk management solutions for companies of all sizes.

Personal Insurance

Trusted insurance solutions to protect what matters most.

Employee Benefits

Coverage that can help attract, retain, and protect your team.

Life Insurance

The biggest investment you can make in your loved ones’ security.

Surety Bonds

Guarantee that a large investment in a project is not lost.

Medicare Insurance

Helping you select the right Medicare insurance for your needs.

Our Clients Trust Us

Check out our reviews and see why you should switch to TWG Insurance | The Winchester Group.

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“We have been clients of The Winchester Group for a long time. They have always been very professional and have taken care of us with our personal and business needs.”

– Kevin Dean
TWG Insurance | The Winchester Group Difference

The Advantage of an Independent Agency Working for You

We represent multiple insurance companies.

We are licensed insurance advisors.

We are by your side every step of the way.

We offer a wide variety of insurance solutions.

We are there for you in your time of need.

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Community Focused

We are proud to contribute to our communities by volunteering, serving, and donating to make positive change.

Clients Come First

We are dedicated to providing the highest level of customer service and personal attention.

Experienced Agents

With 330 years of combined insurance experience, we are here to help you get the right coverage.

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Get a glimpse of the risks you face and how your insurance can protect what matters most.


Providing for Your Family

Risk Factor

Raising a child is a rewarding and important life experience. It is also very expensive. The average cost of raising a child, born in 2013, to age 18 is more than $300,000. If you were to die tomorrow, would your spouse be able to provide food, clothes, daycare, and eventually college tuition for your child? In 2013, the average cost of tuition, fees, room and board for a private college was $41,412 per year.


Having life insurance could secure the future for your children if you have an untimely death. With a life insurance policy, there would be enough income to help pay for everything your child could need while growing up.

Mortgage Payments

Risk Factor

After your death, any outstanding debt and financial obligations do not disappear. Your home is probably the costliest and most significant property you own. A mortgage payment is a large burden for a widow or widower to carry.


A life insurance policy would allow your spouse or children to pay off your outstanding debts and spare them the stress of making monthly payments on the home and car(s).

Auto Payments

Risk Factor

Many families lease or finance their automobiles these days. If the primary earner in the family were to die, the family could be left with outstanding car payments for years to come.


A life insurance policy would allow your spouse or children to pay off your outstanding debts and spare them the stress of making monthly payments on your car(s).

Funeral Costs

Risk Factor

The average funeral costs about $10,000. That high price is for standard things, not unnecessary options or luxurious services. A death in the family is stressful enough; why add the hefty bill of a funeral to that stress?


A life insurance policy can easily cover the cost of a funeral. Your family will be able to think of you and have peace of mind without being burdened by funeral costs.

Protecting Your Retirement Savings

Risk Factor

Once you retire, you will be living off social security, and if you are lucky to have them, a pension or retirement fund, too. But what if the surviving spouse has been relying on you to fund retirement for the couple? Premature death of an earner can affect sources of retirement benefits such as Social Security benefits.


Life insurance can help support a surviving spouse during his or her retirement.

Protecting Your Small Business

Risk Factor

If you passed away, would your business suffer? There are many complications and financial issues that can arise due to the death of a business owner. Many people overlook this predicament.


A life insurance policy can keep a business moving along even during tough times, such as the loss of the business owner/partner. Key person life insurance is payable to the company and provides money for training and hiring of a new employee. A buy-sell agreement, funded by life insurance, allows the other partners in the business to buy the deceased’s share of the business, which will provide money for his or her family.

Spousal Support / Income Replacement

Risk Factor

Many people mistakenly think that they don’t need life insurance if they don’t have children or if their children are grown. However, your financial responsibilities fall to your family when you are gone.


Life insurance can replace the income you would usually bring in and help support your spouse or adult children. Keeping your loved ones living in the way they are accustomed to is an important thing to think about.

Life Insurance 101

Make sure you cover the unique risks you face with life insurance.

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Winchester, VA

24 W Piccadilly Street
Winchester, VA 22601

Located in Winchester, VA, we are proud to serve clients in the Shenandoah Valley, as well throughout Virginia, Maryland, West Virginia, and Washington DC.

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