luxury real estate for sale Pittsfield, United States

Located in Southeast Pittsfield, this well-maintained Colonial offers timeless charm, thoughtful updates, and a floor plan that feels just as functional today as it did when it was built. Hardwood floors run throughout the home, and the inviting living room is anchored by a wood-burning fireplace with a bright sunroom just beyond--perfect for a home office, reading nook, or additional living space. The kitchen features granite countertops, cherry cabinetry, stainless steel appliances, and plenty of workspace, while the formal dining room provides the ideal setting for everyday meals or entertaining. Just off the kitchen, a mudroom and full bath create a convenient everyday entrance with direct access to the backyard. Upstairs, you'll find three bedrooms, including a spacious primary bedroom, along with a full bathroom. Step outside to enjoy a deck and patio overlooking the fully fenced backyard, offering a private space to relax, garden, or entertain. Two storage sheds provide plenty of room for tools and outdoor equipment, while the detached two-car garage is a standout feature with epoxy floors and a recently updated driveway. From the beautifully maintained interior to the meticulous outdoor spaces, this is a home where pride of ownership is evident throughout. Move right in and enjoy everything this Southeast Pittsfield neighborhood has to offer.

Immaculate, adorable, expansive, well-maintained 2500 sq ft ranch. 4 bedrooms 3 bathrooms, open living room, and dining area with fireplace. Bright eat-in kitchen, a sunny 3-season porch with a newer deck. This home sits on a 1/2-acre lot in a quiet, tucked away neighborhood. There's a full walkout lower level with family room, fireplace, bar, full bathroom, and dining area which leads to a back patio and a nice, open backyard area. Home has lots of storage. New chimney, garage door, and side deck are just some of the upgrades. Close to shopping, downtown, theaters, Lake Onota and schools.

Set on an oversized corner lot at the end of a quiet dead-end street, this bright renovated 3-bedroom, 2-bath home offers an impressive amount of outdoor space in a neighborhood setting. The expansive yard is the standout feature, with established gardens, mature trees, a firepit area, open lawn space, and a fenced section for pets. Inside, the home has been thoughtfully updated throughout. The bright eat-in kitchen features new appliances, stylish finishes, and a generous pantry. The main level also includes a living room, first-floor bedroom, full bath, and a three-season porch. Upstairs you'll find two additional bedrooms, a home office, a renovated full bath, and a covered porch overlooking the neighborhood. The lower level provides laundry and storage space, while the detached garage offers additional room for tools, equipment, and seasonal items. The established gardens, firepit, and oversized yard are what make this property special, creating a home that feels welcoming and well-loved.

Welcome to this well maintained 3-bedroom, 1-bath home tucked away at the end of a quiet side street, offering privacy, convenience, and a beautiful connection to nature. Inside, hardwood floors run throughout most of the home, reflecting years of attentive care and pride of ownership. Step outside to a spacious, fully fenced backyard featuring a deck with a remote-controlled retractable awning, perfect for relaxing or entertaining. Abutting protected land through Berkshire Natural Resources Council, this property offers easy access to hiking trails leading to The Boulders and beyond. A move in ready home in a peaceful setting that you'll love coming home to.

Experience the perfect balance of grand-scale architecture and tranquil nature in this stunning 6,000+ sq. ft. modern Colonial. Nestled on 3.42 manageable acres within a private enclave near Onota Lake, this 5-bedroom, 5.5-bath estate offers sweeping meadow views just minutes from the world-class arts of Tanglewood and The Clark. The entry is marked by dramatic dry-laid stonework, leading into an interior defined by soaring heights. The heart of the home is a two-story living room featuring vaulted ceilings and a floor-to-ceiling stone fireplace. The expansive living space of the great room flows effortlessly into a gourmet chef's kitchen equipped for high-end entertaining with dual refrigerators, double wall ovens, and a center island cooktop with a built-in griddle. High-top island seating allows for social cooking and a sizable breakfast area flanked by a wall-to-wall credenza—ideal for buffet-style hosting. The home's floor plan thoughtfully blends communal areas with distinct privacy across three levels. The main level is designed for complete convenience and the primary suite is a true sanctuary. It features a private egress to the pool and a hidden back staircase leading to a secluded loft—perfect for a library or reading nook overlooking the suite. The upper level offers a sweeping gallery balcony overlooking the great room, leading to four spacious bedrooms. This includes two private ensuites and two additional bedrooms serviced by a full bath and a dedicated laundry room. The lower level is an entertainment hub featuring a home theater, gaming space, gym, full bath, and a secondary egress for easy garage access. The fully-fenced backyard makes for a resort-style oasis. Host movie nights on the expansive deck, or relax by the heated inground pool and custom-finished patio. The designer firepit is anchored by a unique stone compass inlay, and a poolside full bathroom ensures guests never need to track water through the main house. For the automotive hobbyist or enthusiast, a high-end, three-bay attached garage is professionally finished with epoxy floors, industrial-style metal cabinets, and an EV charger. You will also find a massive, 50x40 detached shop with four bays and oversized doors. Whether for housing a car collection, an RV, or a professional art studio, the possibilities of this space are endless. Embrace the Berkshire landscape in a home where every detail has been considered. Whether you are heading out for fine dining or staying in to enjoy your private oasis, Blythewood Estates offers a lifestyle of unparalleled peace and sophistication.

Be wowed by this southeast sleeper that presents as a traditional-style colonial where you'll be pleasantly surprised by all the upgrades. This home offers custom luxury features and stylish finishes with exceptional indoor-outdoor living. 145 Leona is modernized inside and out. It is situated on a unique lot with a welcoming front porch, spacious side lawn ideal for play plus a bonus hilltop wooded retreat. You get the best of all worlds here. Begin your tour inside with the awe-inspiring heart of the home, a beautifully designed kitchen with quality cabinetry, top-of-the-line Bosch appliances, marble counters, and a sleek tile backsplash that blends artistic symmetry with everyday function. The centrally placed coffee-bar buffet is perfect for morning coffee, casual entertaining, or signature summer cocktails with friends and neighbors. Radiant heated floors add cozy comfort throughout the family room, kitchen and everyday dining area. The mudroom features an updated Kohler half bath/powder room, laundry, and entry from the garage. The dining area and fireplaced family room overlook the full-span TREX deck and 2 goshen stone patios with a firepit--an ideal setting for s'mores, campfires, and memorable evenings outdoors. The east-side backyard lawn is perfect for outdoor sports and a swing set. A stairway built into the hillside leads up to the wooded hilltop and your own backyard forest escape, complete with a stand of trees, picnic table, hammock, and tent area for at-home adventures. As the night wanes and it's time to wander indoors, you will discover a beautiful sweeping circular staircase leading you to the bedroom level. Enjoy four bedrooms and two updated custom finished baths. Choose the designer deep soaking Kohler bathtub to soak and unwind, creating a luxury spa experience before slipping into the freshly carpeted cozy bedroom of your choice. The primary suite is queen-sized for comfort ensuring a restful ending to your day with the soothing water in motion rain shower experience in the designer bath which also has a radiant heated floor. Start the day with a spacious well planned walk in closet and enjoy the central locale for a quick and easy morning commute to school and work. Updated mechanicals complete the quality and value of this home with a lower level family room and an abundance of storage. Everything you need is ready for you to move right in. Join this welcoming neighborhood and the Friends of Leona community, where you can enjoy the perfect blend of comfortable living, nearby parks, city conveniences, and two levels of outdoor space on a manageable wooded home site. This home is a treasure to be discovered.

Pride of ownership resonates through this distinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut Street near the esteemed Pittsfield Country Club and Upstreet Cultural District, and just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character, boasting five bedrooms and two and a half baths, thoughtfully improved over the long term owners' commitment to preservation and restoration. This prominent manor style home may be coupled with the neighboring guest house which features 3 bedrooms and 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends, or caregivers.

Charming, move-in ready side hall Colonial, a true ''dollhouse!'' Welcome home to this absolutely stunning, meticulously maintained side hall Colonial nestled in a super quiet, peaceful neighborhood. Combining classic charm with a long list of modern, high-ticket upgrades, this home is the definition of a turnkey property and is ready for its next chapter. Step inside to find a warm and inviting living space featuring a cozy wood-burning fireplace, perfect for chilly evenings. Classic hardwood floors run throughout the home, currently protected by brand new, plush carpeting that offers a fresh feel while preserving the beautiful wood underneath. The beautifully updated kitchen and dining area flow seamlessly together, creating an entertainer's dream space that is sure to please your guests. Through the sliding glass doors off the dining area, you will discover your own private outdoor oasis. The brand new deck overlooks a quiet, beautifully landscaped backyard that offers a peaceful escape from the daily grind. It is the ultimate setup for summer BBQs, morning coffee, and refreshing afternoon dips in the sparkling above-ground pool. The screened porch is another magnificent amenity to cozy up and read in the afternoon or sip cocktails in the evening. Beyond its picture-perfect aesthetic, this home offers incredible peace of mind with major mechanical upgrades designed to last for years to come. The property boasts a durable new metal roof, a high-efficiency wall-hung furnace, and a brand new hot water heater, saving you from any hidden, immediate expenses. From its exceptional curb appeal to its pristine, thoughtful interior, this home is simply a dollhouse that you have to see to believe. Properties this well-maintained do not stay on the market long, so schedule your private tour today before this gem is gone!

This well-maintained multi-unit property presents an exceptional opportunity in the heart of Pittsfield's thriving Downtown Cultural District. Offering spacious units with strong rental appeal, the property combines classic character with important updates including newer siding, a high-efficiency natural gas heating system and a new roof in 2021. A unique feature of the property is the versatile third unit, formerly utilized as a commercial storefront, which may offer future mixed-use potential with the appropriate permitting--ideal for investors, entrepreneurs, or those seeking added income flexibility. Rare for downtown living, the property also includes generous off-street parking. Located just moments from restaurants, shopping, entertainment, public transportation, and the city's cultural attractions this property offers convenience, visibility, and long-term potential in one of downtown's most desirable locations. Whether you're looking to expand your investment portfolio or explore owner-occupancy possibilities, this is an opportunity not to be missed.

Spacious and thoughtfully designed, this executive ranch located on coveted Mountain Drive offers the perfect balance of comfort and functionality. Featuring three bedrooms and three full bathrooms, the home's expansive layout provides room to gather, relax, and spread out with ease. At the heart of the home, a generously sized living room with a wood-burning fireplace creates a warm and inviting gathering space. The eat-in kitchen is equipped with stainless steel appliances, granite countertops, and ample cabinetry, making meal preparation a pleasure. A versatile additional living space, complete with a second fireplace, offers endless possibilities like a cozy den, family room, or formal dining room. The oversized mudroom serves as a practical everyday entry and includes laundry, a full bathroom, and direct access to the backyard. Tucked away at the rear of the home, the primary suite provides a peaceful retreat with privacy from the main living areas. Two generously sized bedrooms and a full bathroom are thoughtfully situated alongside the primary suite. A cozy nook is perfect for a large storage closet or office space. The attached two-car garage provides convenient access to the home and ample space for vehicles, storage, and outdoor gear and an unfinished basement offers additional storage or workshop space, providing flexibility for hobbies and future expansion. Outside, enjoy a private setting with room to relax, garden, or entertain. Ideally located in one of Pittsfield's most sought-after neighborhoods, this well-maintained home combines generous living space, timeless appeal, and a floor plan designed for the way people live today.

Completely renovated in 2021, this thoughtfully updated 2-bedroom, 1-bath home offers easy, low-maintenance living with a fresh, modern feel throughout. With 747 square feet of efficiently designed space, every inch has been maximized for comfort and functionality. The interior features updated finishes, an inviting layout, and abundant natural light, creating a warm and welcoming atmosphere. The kitchen and living areas flow seamlessly, making the home feel open yet cozy--perfect for everyday living or entertaining. Ideally located just minutes from downtown Pittsfield and the vibrant Cultural District, you'll enjoy convenient access to local dining, shopping, arts, and entertainment. Whether you're looking for a primary residence or an investment opportunity, this property offers value and accessibility in a central location.

Set just off the shoreline of Onota Lake and accessed by a private bridge, this approximately 1.25-acre island offers a kind of ownership that is seldom available in the Berkshires. Surrounded by water, the property creates a natural sense of separation and calm, with broad lake views and a level of privacy that is difficult to replicate without sacrificing accessibility. Here, the experience is distinctly your own, yet the mainland is always within easy reach. The existing residence is positioned to take full advantage of the setting. A vaulted living space with a loft above, two fireplaces, and expansive windows and sliders bring in light and water views throughout the day. A covered porch extends directly toward the lake, offering a simple, immediate connection to the outdoors. Nearly every room engages the water in some way, reinforcing the feeling of being fully immersed in the landscape. For many, the true value here lies in the land itself. An island of this scale, with direct access and generous shoreline, presents a rare opportunity to shape a long-term vision in a setting that stands apart from more typical waterfront properties. Centrally positioned within the Berkshires and convenient to the region's cultural and outdoor destinations, the property offers a balance of seclusion and accessibility that is rarely achieved.

Set on a corner lot in a well-established neighborhood, this home offers a practical layout, thoughtful updates, and plenty of outdoor space. This 2-bedroom, 1.5 bath split-level home features hardwood floors throughout the main living spaces and bedrooms, creating a warm and cohesive feel. The kitchen opens directly into the dining room, offering an easy flow while overlooking the spacious backyard with a laundry and half bathroom right off the side entrance for convenience. The lower level offers excellent potential for partial finishing--ideal for additional living space, a home office, gym, or recreation area. Outside, the large backyard provides ample room for entertaining, gardening, or play, and the detached one-car garage adds convenience and storage. Well-maintained and full of opportunity, this home combines comfort, charm, and future potential in a desirable setting.

Set on Aspen Way in Pittsfield, this well-maintained condo offers a practical layout and easy, low-maintenance living in a desirable community. The main level welcomes you with an open living area featuring a gas fireplace, flowing into a spacious dining area. The kitchen is positioned at the back of the home and is finished with stainless steel appliances and granite countertops, with a slider that opens directly to the deck--an easy extension for outdoor dining or relaxing. The primary suite offers a spacious retreat with a large en-suite bathroom and walk-in closet, while two additional bedrooms share a full bath. Designed for one-level living, the first floor also includes laundry for added convenience. Additional features include a two-car attached garage and a full unfinished basement, offering ample storage and the potential to create additional living space such as a family room, game room, or home gym. A clean, functional condo with a strong balance of space, convenience, and future potential, all in a convenient Pittsfield location.

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas. Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous outdoor activities of the Berkshires. Please note that home must be minimum 3000 sf, with design and construction of home subject to HOA approval. With additional adjacent lots available to create an expansive, custom estate, this location represents the ultimate destination—privately situated yet perfectly connected to everything the region has to offer.

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas. Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous outdoor activities of the Berkshires. Please note that home must be minimum 3000 sf, with design and construction of home subject to HOA approval. Additional adjacent lots available to create an expansive, custom estate, this location represents the ultimate destination—privately situated yet perfectly connected to everything the region has to offer.