Listed: 3 Homes for Retiring in Portland, Maine

A home for sale in Portland, Maine. — (Image credit: Rhonda Farnham Photography)

(Image credit: Rhonda Farnham Photography)

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.

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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.

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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.

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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.

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A home for sale near Portland, Maine. — (Image credit: Rhonda Farnham Photography)

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

TOPICS

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.