A City on the Water

More people than ever are calling Portland home, an ideal location for those seeking both big city amenities and a small-town vibe
Words By Jennifer Wolcott
Photos By Liz Daly

Ezra Winters and Tess Carley moved to Portland last spring primarily to live closer to Tess’s family. But the young professionals, Ezra a writer-producer and Tess a physician, also chose to settle in Maine’s largest city because of its cultural vibrancy, which reminded Ezra of his hometown of New Orleans.

Marketing guru Kelly Fleming is proud to be part of the team at Town & Shore Real Estate.

“At this stage of our lives, before kids, we wanted to be in the thick of things in a bustling urban setting,” he says, “to just walk out our door to fantastic restaurants and a live-music scene that feels like home.”

Ezra and Tess bought a condo in a historic building located “kind of on the cusp of neighborhoods,” between the lively Old Port and the quiet, residential West End. They might have purchased a single-family home, but inventory was low and competition fierce.

“We needed a lot of hand-holding,” Ezra says, adding that they feel fortunate to have connected with Town & Shore Real Estate, who “helped us every step of the way and treated us like we were family.”

Town & Shore, a 65-year-old boutique firm, where its 17 brokers share ownership and represent Greater Portland—from Biddeford to Brunswick, Long Island to Long Lake—has long been reputed for putting client relationships first.

These days that approach matters even more than ever. In today’s hot housing market, with its much-publicized multiple cash offers and bidding wars, the best brokers are doing more hand-holding than usual as they guide anxious clients in navigating a market that is intensely competitive and complex—especially in a county (Cumberland) where the median home price has soared 68% in the past five years.

History and charm abound in Greater Portland, especially in the city’s Old Port, where picturesque cobblestones, brick, and ivy-covered facades, including that of gorgeous Italian-inspired restaurant Via Vecchia, impress tourists and locals alike. But just as precious as its past is the area’s cool, contemporary, and brilliantly creative vibe, for which accolades keep pouring in.  

Low interest rates have fueled the frenzy somewhat, but even more influential is the more enduring, pandemic-prompted rise in remote and hybrid work, which gave people the freedom to move to places they’d previously only dreamed about.

“In the past 10 years, Portland and its surroundings became much more desirable,” says Lynn Hallett of Town & Shore, “so the real estate market was already changing, but remote work is really the crux of the recent surge.”

Her fellow broker, Sue Lessard, who grew up in Cape Elizabeth and now lives in nearby South Portland, would concur. “The opportunity to work remotely drew people in at breakneck speed,” she says. “It’s really been a matter of quality of life and the chance to pursue one’s dream.”

Recent newcomers to Greater Portland include not only retirees and second-home buyers but also young professionals like Ezra and Tess and families looking for the whole package—good schools, top-quality restaurants, plentiful opportunities for outdoor adventures in every direction, and the term that is perhaps most bandied about: “walkability.” The surrounding Portland suburbs are highly desirable as well, with easy access to downtown not barred by traffic. Yet, that degree of removal offers a “best of both worlds” scenario with access to golfing, deeded moorings for boats, quiet trails for hiking, and more of a neighborhood feel.

From Main Street in Biddeford to Washington Avenue in Portland, where a seat at The Shop is hard to score, revitalization efforts have been transformative. Meanwhile, recent renovations at Scratch Baking Co. in South Portland’s Willard Square have only made a good thing even better.  

“Buyers have educated us during the past couple of years by telling us what brings them here,” says Sue. “We hear over and over about walkability. They also mention the slower pace of life, the fact that you can get in your car and go anywhere in a reasonable amount of time, access to nature—hiking trails, dog parks, lakes, mountains, beaches. Bottom line, there is a rhythm and a cycle here that allows people to refresh.”

Those moving to the area often have cherished memories—maybe from college, camp, or family vacations—and they can finally return to their “happy place” for good. They might subscribe to the oft-heard saying: “I wasn’t born here, but I moved here as fast as I could.”

For two decades, Space, a Portland-based nonprofit, has supported contemporary art projects and championed artists.
Less famous than Portland Head Light, Spring Point Ledge Lighthouse is also a must-see. Built in 1897, it features a 950-foot-long breakwater.

Mark Hankowski, for example, had fond memories of childhood summers on Sebago Lake, so he and his wife, Corina, decided during the summer of 2020, after a change in his work that freed them up to live anywhere, to move full-time from Amherst, Massachusetts, to Portland. They purchased an architectural gem that needed updates in the West End, close to Waynflete School, which their two daughters attend.

With renovations now behind them, they are happily hunkered down and love living in a quiet, historic, tree-lined neighborhood within a thriving urban setting, where the girls can walk to school, and they can enjoy date nights at so many outstanding restaurants—and sometimes even have a well-known chef stop by their table. “At Chaval last Saturday,” says Corina, “Ilma Lopez was helping to serve. How cool is that to come face-to-face with an award-winning chef? That wouldn’t happen in other cities.”

“It’s that sense that you’re living in a small town, but at the same time you have all of the perks and amenities of a big city, which adds so much to the appeal,” says Sandy Johnson, Portland’s go-to broker for luxury condos, also on Team Town & Shore. In recent years, such condos have popped up all over Portland and especially in the booming East End, close to the majestic Eastern Promenade, which runs along the waterfront, overlooks Casco Bay and its islands, and is the city’s most treasured destination—though some might argue for Standard Baking Co., where each day the intoxicating aroma of fresh-baked bread wafts outdoors to the line of eager customers.

Maine College of Art & Design resides in the Porteous Building, a 1904 beaux arts masterpiece.

Portland newcomer Chris Davin was far from the waterfront in Sudbury, Massachusetts, where he and his wife raised their children, and since moving into a condo at Hobson’s Landing last year, he now savors daily walks along the eastern waterfront with his black lab. “With Bee, I zigzag around the Eastern Prom and beyond for sometimes 6 or 7 miles. It’s simply breathtaking.”

Some residents who moved here long ago can only shake their heads at how others are finally catching on.

Lynn Hallett recalls when she first moved to Maine 36 years ago after living in New York and Boston and “people thought I was out of my mind to leave those cities,” she says. “Now those same people are saying, “Wait a minute. I want to be there, too!”