Either-Or: A Maine Island Retreat vs. a South End Condo

Two listings. The same price. What's worth it?

Welcome to Either-Or, where we compare two listings with the same price—one in Boston and one outside. Build your own conclusions.

maine vs south end

Portland | Boston / Photos via Megan Booth and Luxury Residential Group

Exorbitant housing costs in Boston are nothing new. It’s really, really expensive to live here. With tiny condos going for millions without a second thought, it’s entirely possible that Bostonians are becoming conditioned to accept outrageously high prices.

To prevent this from becoming the new normal, we present these two homes listed at the same price. The first is technically in Portland, Maine, located on Great Diamond Island. Built in 1890, it’s a sprawling seasonal estate. The second is a pretty small condo in Boston’s South End, with one bedroom and one bathroom.

The Snapshot Comparison

111 Sunset Ave., Great Diamond Island, Portland, Maine
Price: $529,000
Size: 3,134 square feet
Bedrooms: 5
Baths: 2

483 Massachusetts Ave. #2, Boston
Price: $529,000
Size: 819 square feet
Bedrooms: 1
Baths: 1


Portland | Boston / Photos via Legacy Properties Sotheby's International Realty and Luxury Residential Group

Portland | Boston / Photos via Megan Booth and Luxury Residential Group

Portland’s residence offers a living room with a stone fireplace, a sunroom, a wrap-around teak porch, a European outdoor shower, and multiple decks. The house was built by famed Maine architect John Calvin Stevens. Its listing describes the home as a “cottage,” but with more than 3,000 square feet of living space, it’s anything but.

The condo in the South End, on the other hand, boasts pocket doors, wide-plank hardwood floors, and intricate crown moldings. Circa 1899, it’s a classic brownstone unit, sizing up at only 819 square feet. The condo is listed at a cool $646 per square foot, whereas the Portland manor is going for $169 per square foot.

“A lot of people from Massachusetts are buying up here,” says Carrie Martin, a listing agent for the seasonal home on Great Diamond Island.

Perhaps that’s a sign to pick up and head north while you can still afford it. Or maybe it’s a really good reason to stay away.