Either-Or: Portland vs. the South End

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.

Photos by Lynn Dube - Wave5 photography and courtesy of Keller Williams Realty

Portland photos by Lynn Dube – Wave5 photography, South End photos courtesy of Keller Williams Realty

To remind you that price tags in Boston are a special breed, we’ve been presenting two homes listed at the same price from time to time. This round, it’s a battle of two stately New England houses, where the decision comes down to a preference in exclusive neighborhoods.

The first is an outstanding property in Portland, Maine’s tony West End. The 1900s manse mixes antique charm with modern luxury. The second is a regal rowhouse in the South End. It, too, has its fair share of contemporary flair. Both homes share a price tag of $1,195,000.

37 Carroll St., Portland
Price: $1,195,000
Size: 4,103 square feet
Bedrooms: 5
Baths: 4

159 W Brookline St. #1, South End
Price: $1,195,000
Size: 1,020 square feet
Bedrooms: 2
Baths: 2



The Portland residence incorporates a bit of Colonial Revival architecture, and is surrounded by clusters of equally stunning palaces. It boasts a wealth of original details, including stained glass, a built-in china cabinet, and a staircase with intricate woodwork. The manor also has a fireplace, a master suite with a custom bath, and an impressive remodeled kitchen.

In the South End, the unit off of Tremont Street offers the ultimate combo in a living room: soaring ceilings and oversized windows. Aside from a spacious master suite with a marble bathroom, the lower level offers views of the garden. The property’s quaint patio space has often been a stop on the South End garden tour. But at 1,020 square feet, the South End rowhouse is four times smaller than the house up north.

Indeed, the sprawling property in Portland offers more space to stretch out, plus three more bedrooms and two additional bathrooms. However, neither of the homes have large yards—just charming laid-brick patio areas.

The biggest difference between the two properties can be found in the price breakdown. The house in Vacationland asks $291 per square foot, a relative bargain compared to Boston’s condo. It’s four times more expensive and asks $1,172 per square foot. The right choice, it seems, depends on how far you want to stretch your dollar—and how far away from downtown you’re willing to venture.