The Berkshires have a lot of great towns, and one of the best-known is Lenox. Either watch the video above or read on below–we’ll be going over what makes this town one of the most desirable places to live in the county. Then, we’ll get into the different streets, neighborhoods, and lifestyles that Lenox offers.
Why Choose Lenox? Location, Accessibility, & Vibe
Geographically, Lenox sits just north of Lee and Stockbridge and directly east of Richmond. Our second-home owners come from two directions:
Boston: most come off the Pike at Lee, which makes Lenox closer and more convenient than the towns further south.
New York City: you’ll usually take the Taconic and come over the mountain from Canaan into Richmond and Lenox.
Lenox is the northernmost town of what most of our buying pool considers South County, even though it near the center of the Berkshires. That puts you about 20-25 minutes from Great Barrington, next door to Stockbridge, and a short drive north into Pittsfield for Barrington Stage, the Colonial Theatre, and the bigger box stores you don’t get further south.
The village has a very distinct vibe, and it’s a big part of why people fall for this town. It’s full of locally owned boutiques and has a strong dining scene. In terms of nightlife, this is not a party town, but Ombra does stay open after midnight.
If I had to describe Lenox in three words, it would be boutique, upscale charm.
There’s plenty for the kids here too: ice cream, a candy store, and a beautiful park. Kids and adults alike love Tanglewood.
Culture & History: From the Gilded Age to Tanglewood
Tanglewood is without a doubt one of the biggest draws to Lenox. It’s been the second home of the BSO for almost 90 years, it brings in all sorts of artists, and it’s just an overall different experience. You can get tickets up close and personal, but a lot of people prefer the lawn for picnics. You can keep it low key or go all out with charcuterie and wine, candelabras are common, bring your own lawn chairs, you name it. You’ll see all types of acts on the Tanglewood schedule:
Classical music: from the Boston Symphony Orchestra to Yo-Yo Ma, and plenty in between.
Popular artists: James Taylor, Train, and Brandi Carlisle have all played at Tanglewood multiple times.
Comedians: In recent years, Tanglewood has started to bring in comedy acts like Jon Stewart and John Mulaney.
Historically speaking, city weekenders and second home owners are nothing new here. Back in the Gilded Age, in the late 1800s, there was a building boom in Lenox. The biggest names of the era put up what are known as the Berkshire Cottages, just like the Newport cottages–often, they were constructed by the same families. For example, the Vanderbilts built the Breakers in Newport, and Emily Vanderbilt Sloane built Elm Court right here in Lenox. These families came up to escape the heat of the city for clean air and rolling hills. Building the most impressive house became something of a competition.
Some of the cottages are being preserved for history’s sake:
Ventfort Hall was built for Sarah Morgan, J.P. Morgan’s sister, and is being restored today.
The Mount was Edith Wharton’s place. She wrote The House of Mirth in that house and laid out the gardens herself. The grounds are free, open every day, full of sculptures, and they’re dog friendly.
Others have been repurposed into new lives:
Canyon Ranch is built around the Bellefontaine mansion.
Miraval is built around Wyndhurst, which most of us knew for years as Cranwell.
The Kemble, which I currently have listed, holds an inn license and is being offered just under $4.6 million.
Many of the cottages were lost to fire over the years, so it’s good to see what’s left being kept intact.
Best Neighborhoods & Streets in Lenox
Some of Lenox’s village streets with great walk-to-town-ability are:
Cliffwood Street: a long, consistent street of mostly historic homes in a variety of shapes and sizes. Closer to town, it’s more thickly settled, and as you continue down the street it spreads out, with some remarkable houses set back on long driveways.
Reservoir Road and Under Mountain Road: less walkable, but both consistently have homes with big views and sizable land.
Yokun Avenue: another fairly walkable street, connecting from Cliffwood over to West Street (Route 183). Yokun has everything from cottages to mid-century ranches on a range of lot sizes.
Tucker Street: located on the east side, Tucker is a little more thickly settled than Cliffwood and Yokun, but mostly more walkable, and the homes have a bit less flash from the curb.
Kemble Street: the first house on the right is The Kemble. For some contrast, I recently sold a ranch a few doors down for $689,000. That house is ready for a full remodel, and in a location like that, it is well deserving of the investment.
Continuing down Kemble, the street eventually leads you to Canyon Ranch and Bishop Estates.
If you want privacy and acreage:
Under Mountain Road: probably the most exceptional location. As I mentioned, it connects from Cliffwood over to West Street, essentially letting out at the gates of Tanglewood. For the buyer who wants no compromise, this is it.
Bishop Estates: another strong option on the south end of Lenox, with an HOA that maintains walking trails through the fields. Some of the homes have distant mountain views.
West Mountain Road: located on the north end of Lenox, the homes here often trade a little lower–further from the other South County towns most of this buying pool wants to spend time in.
One area where I’d be careful in your considerations:
Being close to Tanglewood can be a premium when you can walk to the lawn with your chairs and never touch the car. But it’s a different story when your driveway is on the road the traffic sits on.
On a concert night in July, West Street and Hawthorne Street back up for a couple of hours before the show and again after, and summer weekends are exactly when a second home owner wants to be here. So the sweet spot is a short walk from the gate on a side street, not on the route in.
There is also Lenox Dale to consider for its value. Lenox Dale is its own little village down by the Housatonic on the south end of town, closest to Lee and a few minutes from the Pike. It has its own post office, a few streets of older homes, and the lowest-priced single family houses you’ll find with a Lenox address. If you want the town without the village price, this is where to look.
Condo Living in Lenox: Turnkey Communities
Now, what if you want a more hands-off ownership experience? Lenox has a lot of great options for condo buyers.
Canyon Ranch: The most desirable, and the highest trading condos in town. There’s serious cachet to owning one of these, and they’re especially appealing to the buyer who’s drawn to the wellness side of Canyon Ranch. These typically trade between $2 million and $4 million, which is what the penthouse recently sold for.
Winden Hill: Nearby on Old Stockbridge Road, you have a complex with quite a variety of condos. The Vanna units were built around 1930. Many have remarkable views, since the building sits at the top of the hill, and soaring ceilings, with the trade-off of a long climb to the second-floor bedrooms. The Smith units were developed in the 1980s and typically have a more open floor plan. The Chadsey units were built in the late 1990s as a carriage house conversion–some have exposed beams, and most have great views too.
Miraval: Previously known as Cranwell. This is a great spot for golfers, since many units abut the Wyndhurst golf course. The duplex-style Coldbrooke condos were developed in the 1980s, with high ceilings, typically 2,300 to 3,000 sq. ft. of living space, 3-4 bedrooms and 2-4 baths. I currently have a unit here for sale at $1.4 million. There are standalone units around Miraval, too: the Fairwynds HOA is mostly 4,500 to 5,500 sq. ft. homes, some with great views, and many trade just shy of 2 million.
Foxhollow: This complex’s HOA has access to Laurel Lake with a kayak launch, and many units have access to a pool. These condos were mostly developed in the 1980s, with some historic structures mixed in such as Katydid Cottage.
For walk-to-town, there are a few condos right in downtown Lenox, but not enough that I’d count on one coming available even over a 12-month search. They do exist, though.
There are plenty of other condo complexes I’m leaving out here, with prices starting around $200,000 and going as high as you want. If you’re after something specific, I’m happy to help you find the right community.
Lenox Real Estate Market Overview & Short-Term Rental Rules
Before we move onto price, there are things to consider if this won’t be your primary residence. If you’re planning to rent your new condo out when you’re not in the Berkshires, Lenox has short-term rental rules you need to understand before you buy– and they’re different from the towns around it. That’s a whole video on its own, and I plan to put that together for you very soon. Check out my Youtube channel for updates.
I’ve touched on price throughout, but a few points will help you know what to expect. For standalone homes, we very rarely see sales below $400,000 on anything move-in ready. We’ve seen residential sales reach toward $5 million, with the highest prices going to privacy and views without giving up proximity to town and Tanglewood.
If you want that Lenox lifestyle, you can of course shop Lenox exclusively, but it’s often worth looking at the bordering towns. You’ll usually still be within 10 minutes of downtown Lenox, whether you’re in Richmond or West Stockbridge on the other side of Lenox Mountain, or on the water at Stockbridge Bowl.
If you’re considering a property in the Berkshires, I’d love to talk it through with you. I have a strong track record of helping clients find the unique homes they’re dreaming of. I also publish a newsletter that keeps you in the loop on Berkshire happenings, the real estate market, and new videos like this–find the signup at the bottom of this page.
