Either-Or: A Historical Country Home in Chesterfield vs. a Seaport Loft

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

All Photographs by courtesy of Carolyn E. Barnes (Main Road, left); Gibson Sotheby’s (D Street, right)

416 Main Road, Chesterfield$890,000437 D Street, Unit 6C, Boston

5,004 square feet
1,244 square feet

Looking for plenty of space—outdoors and in—for the kids, dogs, and in-laws to stretch their legs? It pays to go west. Built in 1822 by a prominent doctor, this historical Chesterfield home boasts five bedrooms on five picturesque acres—and at just $177 per square foot, it’s a relative bargain. Architecture aficionados will relish period details such as fluted pilasters, a hipped roof, and symmetrical windows, while home chefs will appreciate the updated kitchen with custom cherry cabinetry.

Head eastbound on the Pike, and you’ll trade those five family-friendly bedrooms for a single sleeping alcove accessible by sliding barn doors. But what this Seaport loft lacks in space it more than makes up for in style, with cast-concrete ceilings and floors, and a two-year-old kitchen featuring Caesarstone countertops and a glass backsplash. At $715 per square foot, the condo doesn’t come with any private green space, but those in need of some breathing room can always stroll up to the common roof deck—or over to the nearby Lawn on D.