luxury houses for sale Pittsfield, United States

A stunning three-story residence with breathtaking views for an easy-care lifestyle in the Berkshires. Majestic and magical perfectly describe this exquisite three-story mountaintop home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community, or work from home with glorious views of the Berkshire Hills. Prime location for nature and culture. Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors. Quality Craftsmanship, Thoughtful Design, and Energy Star Rated: This quality-built and immaculately maintained two-owner home features an expansive floor plan that enhances three distinct levels of living space. The layout is ideal for those seeking abundant room, making it perfect for multi-generational living options. On the first floor, the spacious living room is thoughtfully planned mid-level, complimenting the dining room, office space, a first floor primary suite option, and a first floor laundry room, all providing one-level convenience. Gourmet Kitchen with Scenic Views: The oversized gourmet kitchen invites you to prepare homestyle recipes while enjoying panoramic mountain views. Granite counters top timeless-style maple cabinetry with an island that expands over 10', built-in breakfast bar, and computer station for two cooks to comfortably create, laugh, and live. Luxurious Private Suites and Modern Conveniences: Upstairs, you'll find two additional primary suites plus two guest bedrooms, offering privacy and comfort, making them perfect retreats for guests, including a laundry area for added functionality on each level. Versatile Lower Level for Entertainment and Relaxation: The lower walkout level expands your living possibilities, featuring a second fireplaced living room, a second kitchen, a movie theatre media room, an exercise room, a sixth bedroom, and a fourth full bath. This versatile space is ideal for entertaining, wellness, and accomodating guests. Ample Garage Space for Adventure and Everyday Living: A four-car garage provides ample shelter for both everyday vehicles and sports or all-terrain vehicles, supporting a lifestyle full adventure as you explore everything mountaintop living has to offer. Easy Care Homesite: Creating lasting experiences with this unique, tiered homesite. Live an easy-care lifestyle and and creating lasting experiences on this low-maintenance property. Enjoy a hike through Wahconah Falls National Park, join the CSA of Holiday Farm, mountain bike at The Boulders, and discover the history that abounds in Dalton, while residing in this sought-after neighborhood. Move in to a solidly-built home, relax, enjoy, and feel soothed while gazing at mystical skies and mountains from each room. Embrace the beauty of the central Berkshires inside or out.

Set along the shoreline of Pontoosuc Lake, this lakefront home offers beautiful water views from most rooms and an easy connection to one of the Berkshires' most loved recreational lakes. With an eastern exposure, mornings begin with peaceful sunrises over the water, while the large rear deck and private dock create the perfect setting for boating, kayaking, swimming, or simply enjoying life at the lake. Inside, the home blends classic Cape-style charm with a spacious and functional layout. The main level features an open kitchen, dining, and sitting area overlooking the lake, creating a bright and inviting gathering space. A separate living room with fireplace adds warmth and character, while a first-floor bedroom and full bath provide flexibility for guests or single-level living. The second floor includes three additional bedrooms, another full bath, and a generous landing area ideal for a reading nook, office space, or additional lounge area. The heated lower level provides bonus space for recreation, storage, or overflow guests. Additional features include a fenced yard, oversized one-car garage, generator, six wall-mounted A/C units, and convenient access to the nearby town beach at the end of the street. Whether you're searching for a year-round residence or a Berkshire waterfront escape, 15 Sunrise Street offers the rare opportunity to enjoy relaxed lakefront living on Pontoosuc Lake.

2 bed, 2 full bath Berkshire retreat. The bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch and 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand new back deck, an ideal setting for summer evenings. 2 bedrooms on the second floor, with a full bath and dreamy tub. Meticulously-maintained home with a new 200-amp electrical service, this turnkey retreat ensures total peace of mind. Expansive back yard with basketball court and shed. Whether you're enjoying the classic rocking-chair porch or exploring nearby trails and boutiques, this sweet sanctuary is a rare find in the heart of Berkshires.

Berkshires luxury and new lakeside living. Enjoy distant lake and mountain views from each first floor room. This elevated ranch style home creates one level living with grand open sun-filled spaces. This floorplan features open floor plan capturing lake views from each room on the main living level. This beauty is what you have been waiting for - a brand new never lived in newly constructed home is ready for you to live and enjoy the Berkshires at it's best now. Expansive gourmet kitchen topped with quartz quality counters, stainless appliances, breakfast bar and oversized walk-in pantry. Dining room flows to living room with sliders leading to a glorious continuous wrap-around upper level deck. Custom wire railings enhance views and is oversized for outside dining and chaise lounging. Primary first floor suite gives you vacation views from your king size bedroom, enjoy luxury double sink vanity, Kohler fixtures, and luxury tiles walk in shower. A dream walk in closet is outfitted with shelving, drawers, hanging options you will love for each season of clothing. Walk down to the lower level walkout level giving guests and family the privacy they desire on their own level. Spacious family room with sliders to covered patio invite the outdoors indoors. An office nook can function for work or as a separate TV gaming area. Two additional bedrooms and a tub-shower guest bath for full convenience on this level. Two car garage is finished with gleaming epoxy floor and access to storage-utility room. The homesite embodies so many possibilities for you to design and enjoy with flat rolling lawns and natural scape boulders inviting Berkshire native perennials. Walk to the end of Aqua St and meander into the lake. Seek water entrance with your boat, kayaks and more at the multitude of common rights of way on Pontoosuc Lake for 4 seasons of fun and excitement. Enjoy the beautiful Berkshires in this central location, close to hiking at Pittsfield State Forest, skiing at Jiminy Peak 15 minutes north, Downtown Pittsfield arts, culture, shopping, and dining just 10 minutes away. So much to enjoy and the luxury of move-in ready new.

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The second floor functions as its own private level, featuring three bedrooms and two full baths. The guest house feels like a second home entirely. With two bedrooms, two full baths, a dramatic stone fireplace, and a kitchen finished with Caesarstone quartz, it offers independence without compromise. Mini-split systems provide year-round comfort, while a private laundry and generous scale make it equally suited for extended stays or full-time living. Both residences feature claw-foot tubs and roofs replaced within the past three years. A two-car garage at both houses, potting shed, fire pit ring, and expansive grounds complete the offering. This is a property defined by flexibility and scale--where multiple generations can live together while maintaining independence, and where land, light, and structure align to create lasting possibility.

Escape to an exceptional post and beam Berkshire retreat nestled on the east side of Jiminy Peak Mountain Resort. Set on 25+ acres for seclusion and privacy-- eat, play, and live in this 4 bedroom, 2.5 bath chalet style home with countless modern updates. Spectrum was recently added for everyday internet and TV streaming, as well as 5 new high-efficiency mini split air conditioning units for those steamy summer nights. New granite countertops and GE Café and Bosch stainless appliances in the recently refurbished kitchen are a true cook's delight. An open living concept, under a soaring 25 foot ceiling, creates great gathering spaces, from the huge sectional to the plentiful island seating, floor to ceiling window dining frames the outdoors inside, while at the same time cheering on the fun and games at the foosball table. Stoke up the new custom ordered woodstove finished with floor to ceiling stone wall and topped with transom windows to heat the entire upper two floors. Bask in the sunlight streaming through the surrounding glass doors and skylights, letting you gaze at the clouds by day and the stars by night, or walk out to the massive wrap around deck and catch the sounds of nature all around. The floorplan flows to a screened-in porch for outdoor dining, or sit in the midst of all the fun on the deck facing to the east for morning sun or the south for afternoon lounging. An open balcony and loft invite you upstairs to catch a movie or game separate from the great room action and crowd, yet lets you stay connected at the same time. The primary suite is sizable and spacious with a full length window seat for a cozy vantage point watching all that nature has to share. Vaulted ceilings, exposed beams, walls of windows, and tongue-and-groove walls envelope you in the warm glow and rich smell of natural pine walls and floors. The lower level living space offers guest or children's quarters on its own, private level with an additional family room, 3 bedrooms, and a full bath. Comfortably sleeping 12 guests in all, there is plenty of room to host a winter gathering for friends and memories of a lifetime. The new electric 80 gallon hot water heater accommodates a full house of hot showers and baths with ease. The cool, wooden frame built-in double bunk beds add to the allure and enchantment of summer camp or a winter ski lodge. Have it all here as you hike nearby at Mount Greylock or get your game on hunting and target shooting at the Pittsfield Sportmens's Club. Nearby Pontoosuc Lake in Lanesborough is a joy for boating and fishing fun, and ski to your heart's content just over the hill at Jiminy Peak, and partake using your Icon ski pass as the newest mountain on their list. The Clark Art Institute, featuring a new wing beginning in 2026, showcases a a renowned collection and it's just minutes up the road. You pass incredible rolling meadows and farmland with some of the most spectacular views in Berkshire County on your way, but first stop at Jake's Java and Lanesborough Local for coffee and the best breakfast wraps around. Welcome to the sweet country life at home in the Berkshires, with a truly wonderful blend of privacy, nature, sport, country, and culture.

Set on approximately 3 picturesque acres in Dalton, this beautifully restored New England farmhouse seamlessly blends rich Berkshire history with thoughtful modern updates. Once operated as both an inn and stagecoach stop, the property is filled with timeless character. The home features 5 bedrooms and 3 full baths, including a spacious first-floor primary bedroom along with an additional first-floor bedroom and two full baths, ideal for guests or convenient single-level living. Warm and inviting gathering spaces include a library, living room, family room and formal dining room all filled with natural light and historic architectural details. Cozy gas stoves in both the kitchen and family room add modern touches to the home's classic New England feel. Upstairs, you'll find three additional bedrooms, an office space, full bath, and dedicated laundry room. Throughout the home, original details tell the story of its remarkable past, including a pre-Revolutionary War fireplace complete with crane arm and bread oven, wide plank floors, and unique artifacts uncovered during renovation, including a cannonball hidden within the walls and a historic U.S. Mail horse bridle medallion. The second floor of the original inn once served as a gathering space for town meetings, with original floorboards still spanning the full width of the home. Outside, a welcoming front porch and expansive deck overlook the grounds, creating the perfect setting to relax, entertain or garden. A detached 3-car garage with a storage loft offers ample space for vehicles, hobbies, or workshop potential. The property has also operated successfully as an Airbnb, offering excellent income potential or flexibility for multigenerational living. A new roof provides added peace of mind. A rare opportunity to own a truly special Berkshire property where historic charm, modern comfort, and timeless New England character come together in an unforgettable setting.

Tucked away on 4 acres of wooded and partially cleared land, this lovingly maintained 1960 cape-style home offers the perfect blend of privacy, character, and opportunity. Set back from the road by a long driveway, the property creates a peaceful retreat just minutes from the heart of Lenox and outdoor destinations like October Mountain State Forest and Kennedy Park. Inside, the home is ready for its next chapter with spacious and inviting living areas including a formal living room, dining room, kitchen, and a cozy family room with gas fireplace and slider access to the private backyard. A sunroom off the kitchen is perfect for seasonal enjoyment. The first-floor primary bedroom features a connected full bath with convenient hall access, while upstairs offers two additional bedrooms, an office space, and another full bathroom. A two-car garage located under the home provides direct access to the basement and additional storage or workshop potential. Full of warmth and well cared for through the years, this property is ready for its next owners to reimagine and make it their own.

Pine Needles--Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest, and a rare level of privacy and provenance. Arrival. Approached via a long private drive, the property unfolds gradually—passing a sun-kissed meadow, through a grove of majestic pines, past a stunning carriage house, before arriving at an inviting courtyard. The house itself is beautifully sited to capture natural light and frame the sweeping mountain and pastoral views. Entry--A double-door entry opens to a gracious reception hall with original tile flooring and sightlines through French doors to the central living room and terrace beyond. Just off the entry is a coat room with period hooks and hardware, as well as a cozy sitting room with fireplace and built-in shelves. The central living room, paneled in rich wood, is anchored by a fireplace and opens to the view through a wide picture window and two sets of French doors leading to a stone terrace. West Wing--Formal and informal rooms radiate from the center of the home. The western wing includes a spacious living room, a library tucked beneath a vaulted studio, and a striking Persian-themed room adorned with carved woodwork, decorative tile, and intricate architectural details, providing an atmospheric space for reading, conversation, or quiet escape. Above, the vaulted studio with exposed beams and skylights offers an inspiring space for art, music, or quiet retreat. East Wing--The east wing centers around a chef's dream kitchen, thoughtfully tucked to one side for privacy, with direct access to a classic butler's pantry. The pantry connects to the kitchen, the formal dining room, and an airy summer dining space that opens to a loggia, offering an elegant progression for entertaining that bridges indoors and out. Sleeping Quarters--The second and third floors are devoted primarily to bedrooms, retaining the character of the original layout. Two sleeping porches, both located on the upper levels of the west wing, provide a nostalgic and tranquil way to enjoy the Berkshire air. Some of the bedrooms were originally designed for staff, while others, particularly those with the best views, served as guest or family quarters. Grounds and Outbuildings--Outdoor spaces are equally compelling, with lawns and mature plantings surrounding the home. A wide open meadow along the drive amplifies the sense of arrival and serenity. A pool built into the natural bedrock and fed by a spring provides a private and picturesque place to swim, echoing the home's seamless blend with the surrounding landscape. Additional structures include a striking two-story carriage house, distinguished by its dramatic arched entry and distinctive proportions. The lower level retains original horse stalls, a nod to the estate's equestrian past, while the upper level features a character-rich apartment offering opportunity for personalization. A detached garage with another apartment offers further accommodations for extended family, guests, or staff. The estate is well suited for a private compound or multi-generational retreat. Legacy--This is a rare opportunity to own one of Lenox's great legacy properties--where natural beauty, architectural significance, and enduring charm come together just minutes from the cultural heart of the Berkshires.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.