Long Distance Chesapeake House Hunting

The small communities, water views, and rural peace and quiet of the Eastern Shore are legendary—and in today’s market, more people than ever before are looking for their own slice of Chesapeake paradise. That competition has incentivized many buyers from more urban areas far away, and many of those folks are searching for a new home long distance. House hunting in-person can be stressful for many buyers, but searching for a new home remotely can be overwhelming—especially when so many aspects of Eastern Shore life don’t translate to a search engine!  If you’re looking for your Chesapeake home, here’s a few suggestions to make the process as stress-free as possible.

Find An Experienced Relocation Agent

One of the most important things you can do when trying to find a home in the Chesapeake region is to find the right agent. You want to find someone experienced in relocation to this specific region—someone who can help turn your wishlist into reality, understanding the combination of different communities, tributaries and amenities here on the Eastern Shore. Your agent should be willing to look at properties for you, send you pictures, videos, and even do live tours via cellphone, tablet, or drone. They should also be available if/when you get to visit the area.

Since you won’t be there in person, you want to ensure that your chosen agent knows everything you want and need in a property, all the way down to the overall feel and mood of the home. I’ve helped many clients find their perfect forever home here in the Chesapeake region, and I can provide support and expertise in making it as smooth as possible.

Research the Area

When you’re well settled in a community, it’s easy to take for granted the things you love about the place you live. When planning to move to Maryland’s Eastern Shore, it’s important to consider how unique this part of the Chesapeake is, and to think hard about your “must haves” in a new home or community. Be open to the distinctive coastal and rural amenities the Eastern Shore offers.

Your first rule of business is to put on your detective hat and do some online sleuthing. On the Eastern Shore and around the Chesapeake, each county has its own tourism website—a great resource to explore the cultural scene, annual events, and outdoor retreats like marinas, trails, parks, and beaches.

Online resources by county or by state can also help you understand how safe the community you’re considering is, and if you have children, helps you get a sense of the quality of the schools and childcare in the area. Research is vital when relocating to a new area and can ensure you’re comfortable in your new place.

Visit Before Moving

If you are moving to a new part of the country, there’s nothing better than visiting in person. You can do as much internet research as possible, but physically visiting Maryland’s Eastern Shore will give you invaluable insights.Take this time to meet with your agent, visit the different communities or properties you’ve been considering, and to get a feel for the unique sense of place and vibe each offers..

For those seeking an in-town residence, it’s a chance to see how biking or walking friendly your prospective town or village might be. For those looking for waterfront or acreage, walk the property to see if it offers the privacy, landscape or water access you’re seeking. A drive through the county will help you gauge how far it is to areas of interest or critical resources like hospitals or schools. If you have the means, visit more than once to get a true understanding of the area—the Chesapeake transforms markedly from season to season.

Before you move, connect with an experienced agent, spend ample time doing thorough research, and plan a trip to your new destination. All these steps will help make the process a little easier in finding the perfect home in the best location.

Courtney Chipouras, TTR Sothebys Realtor on the Eastern Shore of Maryland

I’m Courtney, and I’m proud to live and work on Maryland’s Eastern Shore.

I’ve spent my whole life in this region, and I genuinely enjoy helping people find a place that feels like home. Whether you’re drawn to quiet waterfront living, small-town charm, or a home that gives you room to grow, I’m here to guide you through the process with honesty, care, and local insight.

If you’re exploring life on the Shore and want something who truly understands the area, I’d be happy to help you get started.

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Courtney Chipouras at her annual Pie Party event

Thinking About Making a Move to Maryland's Eastern Shore?

Whether you’re looking for a change of pace, a stronger sense of community, or just more time near the water, I’d love to help you figure out if the Eastern Shore lifestyle is right for you.

Let’s find the place that fits your next chapter.