Listed: Three Homes for Retiring in Portland, Maine
Enjoy a lively downtown, museums and dining — and, of course, nature in its splendor.
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
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
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?
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Alexandra Svokos is the digital managing editor of Kiplinger. She holds an MBA from NYU Stern in finance and management and a BA in economics and creative writing from Columbia University. Alexandra has over a decade of experience in journalism and previously served as the senior editor of digital for ABC News, where she directed daily news coverage across topics through major events of the early 2020s for the network's website, including stock market trends, the remote and return-to-work revolutions, and the national economy. Before that, she pioneered politics and election coverage for Elite Daily and went on to serve as the senior news editor for that group.
Alexandra was recognized with an "Up & Comer" award at the 2018 Folio: Top Women in Media awards, and she was asked twice by the Nieman Journalism Lab to contribute to their annual journalism predictions feature. She has also been asked to speak on panels and give presentations on the future of media and on business and media, including by the Center for Communication and Twipe.
-
How to Plan a Microvacation That Actually Feels RestfulHow a simple long weekend can boost your mood, reduce stress and make winter feel shorter.
-
We're retired and fight more than ever. Should we take a break?Can taking a break save a marriage? We asked professional relationship therapists for advice.
-
Turning 59½: 5 Planning Moves Most Pre-Retirees OverlookAge 59½ isn't just when you can access your retirement savings tax-free. It also signals the start of retirement planning opportunities you shouldn't miss.
-
We Are Retired and Fight More Than Ever. I Want to Take a Break to Save Our Marriage.Can taking a break save a marriage? We asked professional relationship therapists for advice.
-
Turning 59½: 5 Planning Moves Most Pre-Retirees OverlookAge 59½ isn't just when you can access your retirement savings tax-free. It also signals the start of retirement planning opportunities you shouldn't miss.
-
Are Your Retirement Numbers Not Looking Good? A Financial Adviser Runs Through Your OptionsIf you're worried about a shortfall between your income and expenses in retirement, you're not alone. But there are ways you can make up the difference.
-
How to Make the Most of These 2 Tax Breaks ASAP (They Have Expiration Dates)Taxpayers can strategically use these temporary tax opportunities in particular to lock in long-term tax savings. Here's how.
-
What to Watch for When Refinancing Your Home MortgageA smart refinance can save you thousands, but only if you know how to avoid costly pitfalls, calculate true savings and choose the right loan for your goals.
-
The 10 Best Splurge Destinations for Retirees in 2026Come for the luxury vacation. Retire for the lifestyle (if the vacay goes well). What better way to test a location for retiring abroad?
-
Builders Are Offering Big Mortgage Incentives — What Homebuyers Should Watch ForBuilder credits and below-market mortgage rates can ease affordability pressures, but the savings often come with trade-offs buyers should understand before signing.
-
What Changed on January 1: Check Out These Opportunities Created by the New Tax LawA deep dive into the One Big Beautiful Bill Act (OBBBA) reveals key opportunities in 2026 and beyond.