Our Community

Rolling Hills is a community of 108 units in nine buildings, with on-site full-time management.

  • 50 acres of protected woodlands and walking trails

  • Two tennis courts

  • Pickle-ball court
  • Community gardens

  • Clubhouse with swimming pool, hot tub, wireless Internet, and social center

  • Fenced dog run

  • Social and educational activities - or just peace and tranquility

Despite the tranquil setting, Rolling Hills is close to shopping, golf, outdoor activities, and the arts centers of the Berkshires. 

Download this file (About Rolling Hills.pdf)About Rolling Hills.pdf[Printable Fact Sheet]54 kB

Location, Location, Location...

tanglewood-lawn-apillowLenox is at the epicenter of the Berkshires arts scene, anchored by Tanglewood, the summer home of the Boston Symphony - 10 minutes from your front door at Rolling Hills. Shakespeare & Co. is even closer, and just a short distance away is Jacobs Pillow, the nation's premier dance venue. And in Stockbridge, Williamstown and Pittsfield you can see Broadway-quality theatre all summer.

xcersWhen summer is gone some of our residents head south, but those who stay are rewarded with outdoor activities in the pristine woodlands of the Berkshires.


The Rolling Hills Web site provides general information about our community to visitors and prospective buyers and renters; and provides owners with restricted access to documents, extended contact information, and other resources. The site was created in 2005 and redesigned in 2012 by a former owner Charlie Brenner, .

Access to owners' information is controlled by a user id and password. If you have forgotten your password, please contact the office.

Please contact the Webmaster via email at This email address is being protected from spambots. You need JavaScript enabled to view it. with comments and suggestions.

Contact / Directions


Rolling Hills Condominium Trust
10-1 Rolling Hills
Lenox, MA 01240

(413) 637-2781 phone
(413) 637-8035 fax


From the Mass Pike Exit 2:

Follow Route 20 West for 7 1/2 miles. Route 20 takes several turns, so follow the signs.

Turn right onto New Lenox Road. Then immediately turn right into our driveway.

Interactive Google Map

Overview Map from the Mass Pike to Rolling Hills:


Photos - Public

Click on any "thumbnail" to see the full-size picture. Then, to move quickly through the pictures, use the left or right arrows on your keyboard, or hover your most over the top-right or top-left edges of the picture to see "Next" and "Previous" buttons.

Rolling Hills from the Air

Around the Grounds

Clubhouse and Pool Area

Tennis Courts

Community Garden


Aerial Photo

Rolling Hills from the Air - Google Earth View