
Name: Jen Shalley
Location: Nantucket, MA
Job: Real Estate Broker & Director of Research for Windwalker Real Estate
Hometown: Richmond, VA
Motto: Purposefully capturing happy moments expands your soul!
When you close your eyes and picture Nantucket, what do you see?
The South Shore! Oh, I also hear the rolling waves and feel the delicate sea mist. Some of my favorite spots are located on the South Shore of Nantucket.
When were you first introduced to Nantucket? Any standout memories?
I grew up in the South, so never spent much time in New England. After my sophomore year of college a hometown friend who taught sailing at Nantucket Yacht Club suggested that it might be a good place to get a summer job. I left Virginia on a beautiful, spring day and was greeted by a gray, windy May day in Nantucket (after a terrifying Cape Air flight!). Needless to say, I started to question my friendship with said hometown friend … but it didn’t take long before I saw what draws people to this idyllic little island. Waitressing harbor-side at Brant Point Grill was not a bad way to spend my summer. I met fascinating people at each table I served and spent my free time at the beach. What’s better than that? And it paid for my following semester abroad.
One of my standout memories is the first time I traveled to Great Point — having lived in cities most of my life, the experience of driving along a spit of sand, windows down, on a cool summer evening with the Atlantic to my right and Nantucket sunset to my left was simply magical!
What is a typical work day for you? How’s biz?
On a recent and unseasonably warm Spring day, I found myself thinking “I absolutely love my job!” I’m able to spend time at and valuing some of the most spectacular properties in the world. With an average property value of $1.4 million, and many homes valued far above that, the local architerctural and interior designs are second to none. It never gets dull dealing with Nantucket real estate. Plus, the buyers and sellers that I’m lucky enough to work with are some of the most interesting people I’ve ever met. No day is ever the same and I love it!

As a year-round resident, how would you describe life in the ‘off’ season?
I won’t mislead anyone, it’s an adjustment from city life. However, having spent four winters on Nantucket, I’d honestly say that I wouldn’t trade them for anything. Sure, one can get lonely and crave the buzz of a city. I do my best to take frequent trips to Boston. And do a warm get-away each winter. But where else can you have one of the most beautiful islands in the world practically to yourself? It’s quiet, peaceful and absolutely gorgeous. Winters also provide some time for soul-searching. It’s special. Then, just when you are feeling like you’ve had enough alone time, the island comes alive again!
Most delicious meals on the island? We love food so break it down by breakfast, lunch, and dinner!
Well, it depends on whether or not I’m in the mood to be healthy …
BREAKFAST: Usually just a tasty latte from Island Coffee, located behind my office. If I’m feeling like a caloric splurge, I love the delectable baked goods at Petticoat Row Bakery. And if we’re talking Sunday brunch … two words: Boarding House!
LUNCH: Almost always The Green - fresh and healthy. When I splurge I get a lobster roll from Straight Wharf or a tuna burger and truffle fries from Lola 41.
DINNER: Where to begin?!! I love all the restaurants. One of my absolute favorites is Dune, both for food and beverage. And speaking of life in the winter, Dune offers and incredible 3-course pre-fixe during the off season. It’s a steal and always delicious. Another dinner favorite is Pazzo — the creative menu offerings never disappoint. And during the Summer, I love sitting at the bar at The Pearl or Corazon and ordering a sampling of appetizers. This summer I can’t wait to eat dinner at Cru, the new restaurant opening in the former Ropewalk space.
Favorite time on the island?
While I love everything that a Nantucket summer has to offer, some of my favorite times on island are in the fall. The opening day of Scallop Season takes the cake for one of my favorite weekends! It’s so much fun to gather family and friends and get out on the water on a beautiful fall day. After wading (or snorkeling) for those delicate little creatures, it’s great fun to grab beers, shuck the shells and then enjoy an amazingly fresh dinner.
Secret spots or activities you don’t mind sharing?
I love fishing! If you travel far enough you can escape the sight of land, arriving in beautiful waters where the ocean is deep and filled with striped bass swimming through the rips. Hint: head East!