Discover the Best Neighborhoods in Pittsfield, MA: Your Ultimate Guide to What Neighborhood is Best for You

What are the best neighborhoods in Pittsfield, MA?  It depends on what you’re after, but there’s something to offer all walks of life in Berkshire County’s biggest city. As a Pittsfield resident, every corner of the county is within an easy driving distance–you’re never too far from your new favorite hiking trail, the hottest new stage production, an idyllic lakeside picnic, or a fresh powder day on the ski slopes. If you want to find out more about what your lifestyle can look like in Pittsfield, check out my previous blog post

Downtown Pittsfield

Gated communities, scenic views, historic homes and new builds can all be found within Pittsfield. A wide range of budgets can find a happy home within the town’s limits. Whether you’re a retiree, a young professional, or looking for a home to raise a family in, you’re bound to find a place you love in Pittsfield. Now, let’s dive into the heart of our guide—exploring some of the best neighborhoods that this town has to offer.

Woodmonte Estates: Pittsfield’s Luxurious Private Community

Situated in west Pittsfield near Berkshire Community College is Woodmonte Estates,  a picturesque gated community that gives the feeling of remote living while still being a short drive from all of your essential amenities. Woodmonte Estates features a range of impressive and luxurious homes, along with land opportunities for you to build your own dream house within the privacy that comes from gated living. 

Woodmonte Estates

The well-manicured lawns of these estates sit in front of lush greenery courtesy of the Pittsfield State Forest, which holds more than 30 miles of trails for you to explore. From Woodmonte Estates, you can easily go for a tranquil hike or bike ride as well as enjoy the community tennis courts. 

Woodmonte Estates is where luxury meets the great outdoors, and is the perfect place to start looking if new builds are at the top of your priority list. And while you’ll feel as though you’re in your own sanctuary, you only need to drive about 10 minutes to shop, dine or enjoy some live entertainment downtown. 


Mountain Drive: Breathtaking Views from Your Bedroom Window

Looking for your dream house on the hill? Nestled in the southeast corner of Pittsfield is a neighborhood with some of the most stunning views in Pittsfield. Residents of Mountain Drive are, predictably, treated to year-round breathtaking views of the Berkshire hills. Whether it’s the vibrant colors of fall foliage, the pristine winter landscapes, or the lush greenery of spring and summer, the scenery never fails to impress.


Thes homes on Mountain Drive are mostly single-family, and often feature spacious yards, perfect for gardening or other outdoor activities. The neighborhood’s older homes exude character and charm, often featuring details such as hardwood floors, fireplaces, and architectural elements that reflect the historic character of traditional New England living.


Just around the corner from Mountain Drive is Kirvin Park. The park holds a disc golf course, a dog park, and play structures to keep the kids entertained. You can also pick up trails within the park that locals enjoy year-round on hiking and snowshoeing adventures. 


When you enjoy the slow-paced life on Mountain Drive, you can pick up fresh eggs and other goodies from nearby farm stands. Do you have a soft spot for hand-made goods?  Within your neighborhood, you can find a new scent to warm up your home at Shire Fire Candles. What’s more, you’ll find a new favorite weekend tradition at the nearby Shire Donuts. This hidden gem of the Berkshires offers fresh, made-to-order artisan donuts each Saturday and Sunday. Life on Mountain Drive can really be sweet! 


Onota Lake: Your Dream Life On The Water 

If waterfront living is your dream, you’ll find it in the neighborhoods around Onota Lake. Wake up to the soothing sounds of water and the sight of sunrises glistening off the lake’s surface. 


Blythewood Drive: Onota Lake’s Exclusive Retreat

Similarly to Woodmonte Estates, living on Blythewood Drive offers the convenience of living just off of one of Pittsfield’s most traversed roads. While Blythewood isn’t a gated community, this private road’s woodsy streets still offer a serene and remote-feeling getaway. On Blythewood, you’ll find a mix of well-established homes and newer constructions. Best yet, the neighborhood is situated on the southwest side of Onota Lake, offering a stunning view of the water from your backyard.

Blythewood Dr. Onota Lake

With nearby parks like Osceola, and the vast expanses of the Pittsfield State Forest, the abundance of nearby green spaces make Blythewood a fantastic place to enjoy a peaceful retirement or raise a family. Camp Winadu, located just a short drive away, attracts young campers from far and wide for their sporty summer youth programs. 

Whether you seek an isolated haven in neighborhoods like Blythewood, or wish to join in on community-building events, you can build your dream life around Onota Lake. To learn more about the many pros of lakeside living, check out my blog post about why Onota is one of the best places to live in Pittsfield MA


If life on Blythewood Drive sounds too quiet for your taste, there’s plenty of other neighborhoods to suit your fancy around the lake’s 7.4-mile shoreline. Homes vary from charming cottages to upscale lakefront properties, offering something for everyone. Boating, fishing, and lakeside picnics are just a few activities you can enjoy when you live near Onota. The area around Pecks Road can serve a variety of budgets, from cozy 1-2 bedroom homes to scenic waterfront estates. 

Onota Lake Real Estate

Even without a waterfront home, you can enjoy life on the lake when you live close by to Burbank Park. Utilize the public boat launch, swimmable beaches or take an easy stroll along the park’s paved walking path. In the summer, Pittsfield’s “Live On The Lake” concert series transforms the public pavilion into a rocking community gathering point complete with food and ice cream trucks. 


You can shop homes for sale on Onota Lake here!


Ridge Avenue: Lake Homes and Condominium Living


Ridge Avenue is a charming residential neighborhood located along Pontoosuc, Pittsfield’s other, slightly smaller lake. The single-family homes on Ridge Ave offer waterfront access at a convenient distance from North Street, the city’s main drag. 

Pontoosuc Lake: The Berkshires

If stepping from your back door and into the water isn’t your number one priority, there’s homes that fit a range of budgets just off of Ridge Avenue. This includes Lakecrest Condos, a condominium complex that features a gym, pool, and clubhouse for the members of this community to enjoy. Besides the condominiums, you’ll find single-family homes of different sizes, from cozy cottages to more spacious residences. This diversity allows individuals, couples, and families to find a home that meets their needs.


Dalton Avenue: Convenience and Suburban Charm


Dalton Avenue’s surrounding neighborhoods are another wonderful location in Pittsfield that combine the convenience of city living with the charm of a suburban setting. Situated along one of Pittsfield’s main thoroughfares, Dalton Avenue offers a mix of housing styles, including cozy single-family homes and well-kept apartments.


In the communities of Dalton Avenue, you’ll discover a mix of families, retirees, and young professionals. Living so close to one of Pittsfield’s main roads makes for an easy commute to some of the city’s largest employers, including the nearby General Dynamics facility and Berkshire Medical Center. If a short and easy drive to work is at the top of your priority list, don’t miss out on the serene neighborhoods surrounding Dalton Avenue. 


Pittsfield, boasts a diverse array of neighborhoods to suit various lifestyles and preferences. Whether you’re drawn to the elegance of Woodmont Estates, the hidden charm of Blythewood Drive, the scenery of Mountain Drive, or the lakeside allure of Onota Lake, you’re sure to find a neighborhood that feels like home. I look forward to helping you on your journey to find a home in your ideal neighborhood!

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