Either-Or: Rockport, Maine vs. Jamaica Plain

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 courtesy of Camden Real Estate Company and RE/MAX Destiny

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 between a single-family home and a condominium, where the decision comes down to square footage.

The first home is a Federal-style manse in Rockport, Maine, built in 1855. The time-honored house near the coast is made for relaxing—in fact, it was once a vacation rental property. The second is a top-floor condo in a three-decker in Jamaica Plain. You might not know it from the street, but the place is spick and span on the inside. Both share a price tag of $459,000.

29 Main Street, Rockport, Maine
Price: $459,000
Size: 2,200 square feet
Bedrooms: 3
Baths: 3.5

51 Creighton Street #3, Jamaica Plain
Price: $459,000
Size: 943 square feet
Bedrooms: 3
Baths: 1



Situated on Rockport Village’s Main Street, the antique yellow abode offers a working fireplace, wide pine floors, and plenty of period details. More modern updates to the 2,200-square-foot house include a spacious master suite and a sunny deck with views of the harbor. There’s even enough room for a gallery space on the lower level.

But in Jamaica Plain, there’s a bit less room to spread out. The 943-square-foot condo is more than two times smaller than the house in Rockport. It does have a reasonably sized backyard for the city (with apple and peach trees, to boot) and it’s comparable to the small yard in Maine. The condo also boasts an oversized kitchen with a breakfast bar, as well as a recently remodeled bathroom, off-street parking, and in-building laundry.

The biggest difference between the two properties is in the price breakdown. The house in Vacationland asks $209 per square foot, a relative bargain compared to Boston’s condo, which is double the price at $487 per square foot. It seems the right choice comes down to preference: would you rather go for coastal charm or city convenience?