Lenox, MA

Berkshire County · Massachusetts

Lenox, MA Homes for Sale & Real Estate

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Lenox is a cultural hub of the Berkshires, known for Tanglewood, the summer home of the Boston Symphony Orchestra, and for the grand Gilded Age estates that once earned the area the nickname of inland Newport. Its village center is lined with historic homes, shops and restaurants, and the village of Lenox Dale sits along the Housatonic River on the eastern side of town.

Homes in Lenox include historic colonials and Victorians in the village, mill-era houses in Lenox Dale, capes and ranches in residential neighborhoods, condominiums, and estates on larger lots in the hills. Dolan O’Rourke helps buyers explore Lenox and nearby Berkshire towns and works with sellers to present their homes to the right buyers.

Living in Lenox

Tanglewood music festival

Tanglewood hosts the Boston Symphony Orchestra each summer, with concerts in its music shed and on its lawns overlooking the Stockbridge Bowl.

The Mount

The Mount, the estate Edith Wharton designed and built, offers tours of the house and formal gardens, plus lectures and seasonal events.

Shakespeare and Company

Shakespeare and Company stages plays each season on its Lenox campus, a cornerstone of the town’s busy summer arts calendar.

Kennedy Park

Kennedy Park offers wooded trails close to the village center, popular for walking, mountain biking and cross-country skiing in winter.

Berkshire County · Massachusetts

Homes for sale in Lenox, MA

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Getting around and the outdoors

Getting around

Route 7 and Route 20 run through Lenox, connecting north to Pittsfield and south to Stockbridge and Great Barrington. The Mass Pike is reachable in nearby Lee, Berkshire Regional Transit Authority buses serve the area, and Pittsfield offers Amtrak service.

Parks and recreation

Kennedy Park, Mass Audubon’s Pleasant Valley Wildlife Sanctuary and October Mountain State Forest offer hiking and wildlife viewing. Laurel Lake and the Housatonic River provide boating and fishing, and Tanglewood’s lawns are a summer favorite for picnics before evening concerts.

Villages and neighborhoods in Lenox

Lenox DaleNew Lenox

Nearby communities

Buying or selling in Lenox?

Whether you are buying your first home, moving up, downsizing or investing, our agents will guide you from the first conversation to the closing table.

Client reviews

What our clients say

5.0★★★★★9 reviews on Google and Yelp
★★★★★

I had the absolute pleasure of working with John Dolan and Dolan O’Rourke Real Estate Services while selling my mother’s home. We were going through an extremely difficult transition. We were both unfamiliar with the process of selling a home. From day one, John made himself readily available and kindly explained every part of the process to my mother, always making sure she understood each detail. His knowledge and expertise goes far and above what we expected. His constant communication never left us guessing – we felt very involved in every part of the process. I was caring for my mother on my own and he did everything in his power to ease the burden of selling her property. John knew I had great anxiety over our difficult situation and would always tell me not to worry. He always found a resolution to every bump in the road- and now I am finally worry free! John made us feel cared for and safe. We cannot thank him enough for his hard work. He helped us find a deal that we never could’ve imagined and changed our life for the better!  

Molly O.August 2024 · Yelpwith JohnRead full review
★★★★★

John was amazing with helping us in our home buying journey! His knowledge and patience made things very easy for us as first time home buyers. I highly recommend John to anyone who wants professionalism and someone who’s gonna get the job done! Thanks John!  

DaVaughn G.June 2023 · Googlewith JohnRead full review
★★★★★

We worked with John of Dolan O’Rourke Real Estate Services to purchase our first home in the Greater Boston area. As first time home buyers, John invested a lot of time early on to educate us about what to expect and strategies to consider. Throughout the process John had great communication, listening and advice as we navigated a challenging market. John was approachable, knowledgeable and always fun to be around as we looked at numerous houses, and helped us shape our conversations to really dial in to what we were looking for. We would love to recommend John for future real estate services and are so appreciative of his hard work.

Stephanie C.June 2022 · Googlewith JohnRead full review

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