Accomplished Living in Middlebury, Connecticut


Welcome to Benson Woods, an active adult community located in the picturesque rural community of Middlebury, where the beauty of nature meets a carefree, active lifestyle.

Nestled in a quiet wooded glen with Eight Mile Brook on its western border, Benson Woods has been thoughtfully designed with a classic New England neighborhood feel. 96 acres of beautiful landscaping and inviting porches greet you, reminiscent of the historical charm of classic homes of Middlebury.

Benson Woods offers a variety of home designs that complement classic New England architecture and traditional neighborhood style as exemplified in our popular Winthrop and Hopkins models. Single-level living, lush landscapes, two-car garages and maintenance services make Benson Woods an ideal choice for active adults 55 and better.

At Benson Woods you will enjoy the quiet surroundings of Middlebury and the convenience of the maintenance-free living without sacrificing the comforts of your lifestyle.


Deer in woods

Award winning, thoughtfully designed homes with a classic New England neighborhood feel.

Prices start at $299,000

Century 21 Home Services: New Homes Division

Sales Model

Our sales office is open Friday through Sunday. For hours and appointments:

Corporate Office

Century 21 Home Services
New Homes Division

Benson Woods neighborhood