Picture this: After spending the day taking the ferry around Casco Bay and exploring Great Diamond Island, your grandkids scarfed down dinner at your big kitchen table and are happily chattering away. While their parents relax around the fireplace, you take the kids to the backyard and light the bonfire table you'd picked up from the L.L. Bean flagship store last spring. It's time for s'mores and stargazing — and it can all be your treat in one of these homes in Portland, Maine.
"Every season brings a new reason to love New England," we've said about why people choose to retire to the region, despite the possible higher costs of living. Kiplinger has picked Portland as one of the best places to retire in New England, thanks to both its lively downtown and attractions like museum and dining, as well as the natural beauty that abounds and the activities that presents retirees looking to make the most of their new free time.
With that in mind, I sourced three homes from top real estate companies at different price points in Portland, Maine. See where you could live.
From just $107.88 $24.99 for Kiplinger Personal Finance
Be a smarter, better informed investor.
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
This is part of Kiplinger's new series "Listed." Be aware that due to the nature of real estate, property statuses may have changed by the time you read this.
1. Under $500k: Downsize with a spacious backyard
Westbrook is just outside Portland, and this home offers a neighborhood feel along with updated amenities. Ideal for a retiree looking to downsize and simplify your life.
Address: 56 Berkeley Street, Westbrook, Maine (listed by Coldwell Banker Realty)
Price: $399,900 | Specs: 2 beds / 1 bath; 1,176 sq. ft.
Highlights:
- 20-minute drive to East End Beach in Portland
- Fenced-in backyard with deck and fire pit
- 1-car garage
- Heat pumps and new appliances
- Updated mudroom
- Fireplace and smart built-in features
2. Around $1M: Island living on 2 acres
A spacious 2-acre lot on Long Island in Casco Bay offers possibilities in addition to the charming home built in 2000.
Address: 175 Island Avenue, Long Island, Maine (listed by Coldwell Banker Realty)
Price: $1,100,000 | Specs: 3 beds / 1.5 bath; 2,200 sq. ft.
Highlights:
- Just across from the shoreline with views of Casco Bay and a large porch to look from
- Mooring rights in the bay, for boaters
- Fabulous kitchen with gas range on an island
- Elaborate tub set-up in bathroom
- Cathedral ceiling and skylights
- Gas fireplace in the living room
3. Over $1M: A-frame-style chalet with lake views
Standish is about 20 miles outside of Portland and home to some fabulous nature, including the Steep Falls Wildlife Management Area and Sebago Lake. This home sits by Watchic Lake as an accessible retreat.
Address: 31 Dorothy Drive, Standish, Maine (listed by Coldwell Banker Realty)
Price: $1,199,000 | Specs: 4 beds / 4.5 baths; 4,309 sq. ft.
Highlights:
- Double A-frame style home with tons of windows and porch space
- The climate controlled two-car garage has a one-bedroom apartment above it and is connected to the rest of the home by a windowed walkway. This creates privacy for any visiting family or if you want to convert an area into a studio or workspace. It could also be an income-generating opportunity if you were to rent it out
- Double oven and updated amenities in kitchen
- Hand-painted double sinks in primary bathroom along with walk-in closet
- Finished basement with recreation space and access to backyard
- Boat launch access on Watchic Lake, which is private
Related content
- The Best Places to Retire in New England
- Listed: Live Your Snowbird Life Year-Round in These Three Homes
- Will 2025 Be a Good Year to Sell Your House?
-
I’m Over 65 and Itemize: Can I Claim the New $6,000 ‘Senior Bonus’ Tax Deduction?Tax Changes If you’re an older adult, a new bonus deduction could provide a valuable tax benefit.
-
Alphabet Stock Pops After Google Antitrust Ruling: What to KnowGOOGL stock is soaring Wednesday after a judge ruled that Alphabet does not have to divest its Chrome browser.
-
More Than Money: The Hidden Toll of Financial Abuse of Older AdultsFinancial abuse from schemes involving tech support, government impostors, false sweepstakes, grandchild hoaxes and online shopping issues can cause thousands of dollars in losses.
-
Why is My First Medicare Bill So High?Your first Medicare bill may be higher than expected for several reasons. If your premiums aren't taken out of your Social Security benefit, the bill can be huge.
-
11 Unforgettable Road Trips to Take in RetirementMore than a travel trend, the road trip is a quintessential American tradition, with millions of us taking them each year. Here's a guide to helping you choose your next adventure.
-
I'm a Financial Professional: Here Are Four Ways You Can Use Debt to Build WealthUsing debt strategically, such as for homeownership, education and more, can lead to greater financial stability and growth.
-
Five Key Wake-Up Calls for Ambitious Business Owners, From a Biz SpecialistYour personal financial plan needs to include a formal exit strategy for your business, or you could be in trouble.
-
How StoryCorps Works and How You Can Tell Your StoryStoryCorps has recorded conversations between thousands of people, and anyone can participate. National facilitator Alan Jinich explains how to share your story.
-
I'm a Retirement Psychologist: Here's Why Doing What You 'Ought' in Retirement Beats Doing Whatever You WantTrue retirement freedom isn't about simply doing whatever you want, but about finding purpose and direction through commitments that align with your deepest values and allow you to contribute meaningfully.
-
Tactical Roth Conversions: Why 2025-2028 Is a Critical Window for RetireesThe One Big Beautiful Bill (OBBB) extended today's low tax brackets, but they may not last. Here's how smart planning now can prevent costly tax surprises later.
