6 Charming Maine Communities To Retire Around Portland
Maine is a mixture of rich history, exciting culture, and strangers waiting to become friends. The state has a plethora of towns waiting to be discovered. It’s never been easier to find a home within two hours of Portland, either. The market makes room for buyers and renters alike. Retiring in rural Maine means staying away from the larger communities with endless avenues of chain stores. Find a town where everyone knows everyone. When everyone knows everyone, everyone smiles. Smell the sea air. Taste the land’s fruits. Welcome to easy living in the Pine Tree State, also known as Vacationland.
York
Anyone doubting that life can be a 24/7 golf vacation has never been to York, less than 45 minutes from Portland. The seaside town is home to Ledges Golf Club. Tee off on a course that won Golf Digest’s “Best Course You Can Play” distinction. If golf is not the game of choice, there is always the famous beach. Long Sands is beautiful all year round. There is no shortage of greenspace in York, either. For starters, there are the trails surrounding Mount Agamenticus. Agamenticus translates to ‘the other side of the river.’ It is an apt moniker as the trails lead to astonishing views featuring 30,000 acres of preserved wild area.
York’s Parks and Recreation Department are all-stars in the field. In addition to facilitating trails, trees, and special events, they also host a Center for Active Living, open to all above 50 years of age. The first Exercise and Wellness class is always free to try. Indulge in a meal prepared by the Center's in-house chef Tuesdays to Thursdays. Despite its natural assets, York has not been targeted by real estate speculators.
According to Realtor.com, homes in York “sold for 5.6% below asking price on average in December 2024." Life can be both happy and easy. Welcome to the other side of the river.
Bath
A tranquil life on the water is only 40 minutes from the big city. No one should have to give up their boat when they retire. Bath's Linwood E. Temple Waterfront Park has public docks open from May to November. The town is ideally placed for medical peace of mind. Maine Health’s laboratory services are located directly in Bath. Convenient medical access does not mean paying too much for housing in Bath. Homebuyers rejoice: Bath has an abode for every budget. The median home sold price was $369,500 in December 2024 and is trending down -18.9% year over year.
The town has a practical way of weaving its elegant past into the present. The historic Chocolate Church was built in 1847. Today, it is the Chocolate Church Arts Center, showcasing music, plays, workshops, and many more surprises. Mystery fans will fawn over their production of Agatha Christie’s The Mousetrap, debuting in March 2025.
Bangor
Bangor, Maine, is a hub like no other. It is less than two hours away from the big city amenities of Portland. Convenience and adventure are both within arm's reach. There has never been a better time to buy a house in Bangor, either. Prices are climbing but still low. The median home sales price currently sits below $330k. If that is not enough, it is worth mentioning that the town's amenities are unbeatable.
Northern Light Maine Coast Hospital is a 24/7 operation. Residents feel safe with the facility’s policy of transparency, and patients can read every specialist's profile on the hospital's website. There is more than enough adventure to go around in Bangor. Seniors with a taste for the spooky will love the spider-clad, wrought iron gates of Stephen and Tabitha King’s Victorian mansion. Today, the house in the Whitney Park Historic District is home to a foundation that donates millions to community initiatives.
Art lovers, beware: you may never want to leave. Bangor’s University of Maine campus hosts the Zillman Art Museum. The Zillman’s permanent collection includes works by Picasso, Hockney, and Rauschenberg. If history is more compelling than canvas, stroll into the past at the Cole Land Transportation Museum, featuring bygone models of trains, cars, and carriages.
Brunswick
A half-hour North on I-295 brings forth the paradise of Brunswick. Watch the Androscoggin River flow by from a famous bridge on the border of Brunswick and Topsham. The Androscoggin Swinging Bridge was built over a century ago and now enjoys a spot on the National Registry of Historic Places. Living inside a history does not mean breaking the bank. Brunswick was classified as a buyer's market by Realtor.com in December 2024, with median home sold prices under $500,000. In addition to comfortable housing, safety and good health are assured in Brunswick.
Maine Health’s Mid Coast Hospital complex services every need and, thankfully, never closes. If you love history, explore the Cold War-era practice of hunting submarines at the Brunswick Naval Aviation Museum. Are you expecting guests for Thanksgiving? Grandkids can tire themselves out at The Rumpus Room, a comprehensive play spot filled with puzzles, toys, and an impressively sizeable wooden pirate ship.
Waldoboro
Welcome to Waldoboro, a haven of fresh air on the beautiful Medomak River that is less than a 1 hour and 15 minutes from Portland. You may want to purchase a home quickly in this up-and-coming neighborhood, as median home listing prices are trending up 30% year-over-year. There is plenty to do to get the blood moving. Play pickleball in the summer and join the ski club in the winter. Have you been bitten by the travel bug? Town recreation programs include group trips. The world awaits from Waldoboro. Never spend an insecure minute, thanks to the stellar healthcare in this town.
MaineHealth’s Primary Care Clinic includes a free annual wellness visit. Waldoboro has the solution in the unlikely case that your health challenges make living at home difficult. The town approaches assisted living with a personal touch. The Village Care Homes are a network of senior living options such as the Waldoboro Green, which overlooks a series of parks. Everything has been considered to ensure retirees can enjoy sites like the 1936-built Waldo Theater, Sammi's famous Family Entertainment Center, and the incomparable Heywood Art Gallery. Small-town America never disappeared.
Kittery
History buffs have found their heaven. Kittery is about a 45-minute drive from Portland. It is the oldest incorporated town in the state of Maine. The first ships to serve in the Revolutionary War were built on Badger’s Island, which is a part of the town. The Whaleback Lighthouse at the mouth of the Piscataqua River was built in 1872 and still stands today. Warning: shopping in Kittery can be addictive. The town has the greatest collection of outlet stores in New England. It is impossible not to find a bargain. The savings do not stop with clothes and furnishings.
As per Realtor.com, it is currently a buyer's market, and "homes in Kittery, ME sold for 1.61% below asking price on average in December 2024." The Kittery Community Center programs a year-around schedule of fitness, entertainment, and meals. After the Community Center closes, friends congregate at the Tributary Brewing Company. Indulge in a glass of East Coast Extra XPA, made with tropical fruit and hops from the other side of the world.
There is a world of retirement bliss just down the road from Portland. Deciding where to retire ought not be an urgent decision. Remember that before embarking on any move, take time to do your research. Everywhere in Maine oozes charm. Finding the charm that fits the retiree is a process. Finally, it is important to be mindful that the territory the state sits on was occupied long before the arrival of Europeans. The Wabanaki Confederacy consisted of several nations, including the Mi'kmaq, Wolastoqiyik, and Peskotomahkati. Please support Native American businesses in Maine whenever possible.
