Premium Insurance that Protects What Matters Most
When you insure with Penny Insurance Agency, you join a very select group of responsible, financially successful clients with unique home and lifestyle needs. You’ve built a life, and that life needs top-of-the-line protection. With over 86 years of industry longevity and luxury insurance knowledge, Penny Insurance Agency understands the unique nature of your home, lifestyle and collections, and will work with you to safeguard your high-value assets. Our agency, backed by internationally-acclaimed insurance providers like Chubb, Pure and Travelers, will tailor a suite of insurance products to offer you quality protection and outstanding service. No matter your stage of life, Penny Insurance Agency is your partner in peace of mind.
“After working in the entertainment industry in Los Angeles and having lived in California for decades, switching our business over to Penny Insurance was a welcome change when we moved to Hendersonville, NC. Protecting our family’s assets and future is not a responsibility we take lightly, and Will Penny goes above and beyond the norm to help us safeguard the lives we have worked hard to build.”
Doug and Dale Llewlyn


A Message from Will Penny, President, Penny Insurance Agency
As the third-generation president of Penny Insurance Agency, I am honored to carry on our legacy of providing outstanding insurance services to many families and businesses in Western North Carolina and Upstate South Carolina. Since 1931, my family has built this business on the importance of personalized service and relationships. It’s so much more than just the price of your insurance coverage. We act as advisers, advocates, and resources. When you purchase insurance from us, you get a true partner. We work hard to earn your confidence, understanding that you are entrusting us with your hard-earned assets.
When choosing to insure with Penny Insurance Agency, you join a very select group of responsible, financially successful clients with unique home and lifestyle needs. Penny Insurance Agency understands the specialized nature of your home, lifestyle and collections, and will work with you to safeguard your high-value assets. We pride ourselves on providing individualized attention to customize a comprehensive premium insurance platform for you and your family.
I encourage you to contact us today so we can work together to develop a smart solution that protects what matters most.
Arrange a Complimentary Lifestyle Portfolio Review
How confident are you that your insurance policies adequately meet your unique home, lifestyle and collections needs? With nearly a century of industry longevity and luxury insurance knowledge, Penny Insurance Agency is ready to be your partner in peace of mind. We will review your specific needs and lifestyle to offer insight into the type of comprehensive premium insurance coverage recommended for you and your family to safeguard your hard-earned assets. Please complete the brief form below and a member of our team will reach out to arrange a complimentary lifestyle portfolio review.
Penny Insurance Agency is proud to provide a variety of insurance plans to our valued clientele, such as:
High Value Homeowners: Customizable protection for exceptional residences
A home is not only one of your most valuable assets; it’s a special space to make memories with friends and family. Homes valued in excess of $750,000 are often considered high value and have unique needs that may not be covered under standard homeowners’ insurance. Contact us today to experience Penny Insurance’s concierge approach to developing a custom, comprehensive coverage plan.
Private Fleet Automobile: With our specialized plans, you’re in the driver’s seat
Penny Insurance offers a customizable comprehensive coverage plan for your fleet of vehicles, including vintage automobiles, motor homes, and motorcycles. Our ultimate goal is to protect both you and your assets in the event of an accident and protect the longevity of your automobiles.
Collectibles: One-of-kind insurance for your unique, high-value assets
Unique collectibles of high-value require specialized protection plans developed by the experts. With over 86 years of industry experience, Penny Insurance’s concierge approach to insurance will provide the proper coverage for your priceless assets. Our insurance experts can customize a plan that covers a wide range of items including:
Fine China and Crystal
Firearms
Furs
Sporting Equipment (golf clubs, skis, etc.)
Jewelry and Watches
Musical Instruments
Silverware
Wine Collections
Works of Art (paintings, rugs, rare books, sculptures)
There are many unlisted items that are important to you and that can qualify for proper coverage.
Private Aviation: Look to the skies, with peace of mind
While private aviation provides you with maximum travel freedoms, it can also bring about numerous liability concerns. Let us develop a comprehensive coverage plan for your unique travel accommodations.
Personal Excess Liability: Reliable coverage when life can be anything but
You’ve worked hard for your assets and that’s why you deserve to enjoy the fruits of your labors without fear of losing them. Experience the ultimate peace of mind with Penny Insurance’s personal excess liability plans, unique to you and your needs. Personal Excess Liability Insurance, or Umbrella insurance, is a layer of Liability insurance that covers above and beyond your High Value Home and Private Fleet Automobile insurance plans, providing an extra layer of needed protection. After all, liability issues are everywhere and you never know what could result in a lawsuit. Connect with Penny Insurance today to establish your first line of defense.
Watercraft: Premier service for smooth sailing
From jet skis to private yachts, Penny Insurance offers a comprehensive coverage plan for your unique watercrafts. Contact us today to begin your personalized policy experience.
