luxury real estate for sale Pittsfield, United States

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.

Set along the highly sought-after Parkways in Southeast Pittsfield, this classic center hall offers the perfect blend of timeless character and thoughtful modern updates. Bathed in natural light, the home enjoys peekaboo views of Bousquet Mountain and a beautifully landscaped setting that changes with the seasons. The main level features a spacious front-to-back living room anchored by a wood-burning fireplace, with those mountain glimpses and views of the private backyard. Just beyond, a four-season sunroom creates an easy extension of living space, with direct access to the outdoors and a partially covered pergola--ideal for relaxing or entertaining. On the opposite side of the home, a formal dining room flows into the updated kitchen, finished with quartz countertops and large pantry. A half bath completes the first floor. Upstairs, the primary suite offers a comfortable retreat with its own en suite bath, while two additional bedrooms are well-sized and share a full bathroom. Additional highlights include an attached one-car garage, Tesla charger, and a yard that truly caters to garden enthusiasts, with mature plantings, space for raised beds, and a dedicated storage shed. Do not miss this one!

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.

Welcome to 27 Morgan Street, a bright and inviting home tucked away on a quiet dead-end street in Pittsfield. Natural light fills the main living spaces, highlighting gleaming wood floors and creating a warm, easy feel. The first floor offers a circular layout with a spacious, light-filled living room. Upstairs features three well-sized bedrooms and a full bath. Enjoy a charming front porch and a fenced backyard that offers a comfortable sense of space, along with a one-car garage and off-street parking. A well-rounded home in a peaceful setting, just minutes from everything Pittsfield has to offer.

Set within one of Pittsfield's most established and desirable neighborhoods, this beautifully maintained Colonial blends timeless character with carefully curated updates. From the moment you enter, a gracious living room sets the tone--anchored by a gas fireplace, framed by classic built-ins, and finished with gleaming hardwood floors that carry throughout. The formal dining room offers an elegant setting for entertaining and transitions seamlessly into the thoughtfully renovated kitchen. Designed with both style and function in mind, it features quartz countertops, updated appliances, and a clean, sophisticated aesthetic. A versatile first-floor room, currently used as an office, offers flexibility for a fourth bedroom. A well-appointed half bath adds a touch of personality with its distinctive, design-forward wallpaper. Upstairs there are three well-proportioned bedrooms including one with a delightful sleeping porch--an inviting nod to the home's classic New England roots. A full bath serves the second floor, while the finished third-floor attic presents exceptional bonus space, ideal for a private studio, playroom, or creative work-from-home space. Additional highlights include a newer roof on both the main house and garage, updated electrical systems, a one-car garage, a thoughtfully designed patio for outdoor entertaining, and an additional half bath in the basement. A rare offering in Southeast Pittsfield--where classic architecture, modern updates, and attention to detail come together in a location that remains consistently in demand.

At $375,000, it's rare to find this kind of space, condition, and flexibility in the heart of Pittsfield. Set just off North Street, 84 Elizabeth Street offers 2,788 square feet of recently updated living space with a layout that actually works. The first floor flows effortlessly from room to room, with a bright, updated kitchen, formal dining area, two connected living spaces, and the kind of details you don't often see at this price point, including original pocket doors that bring character without sacrificing openness. A mudroom and first-floor laundry add everyday convenience right where you want it. Upstairs, the bedrooms are all generously sized, and the bathrooms have been thoughtfully renovated with a clean, modern feel. The updates here aren't surface level, they've been done throughout the home in a way that makes it feel move-in ready from day one. A spacious pantry, multiple storage options, and two outbuildings give you flexibility beyond the main house. One includes a private garage bay with additional storage, while the second is a larger barn-style structure shared with the neighboring property, ideal for equipment, hobbies, or overflow. Prepaid solar panels add real long-term value, helping offset future utility costs. If you've been looking for true square footage, updated interiors, and a walkable in-town location without stretching your budget, this is a standout opportunity.

Welcome to 42 Lexington Parkway, a beautifully maintained Colonial tucked into one of Southeast Pittsfield's most desirable neighborhoods. Offering over 1,800 square feet of living space, this home is larger than it appears and is filled with thoughtful updates throughout. A freshly painted exterior and exceptional curb appeal make this a home you'll love coming back to. A beautiful, wide, and gracious foyer sets the tone as you enter. Inside, the main living area is spacious and inviting, centered around a classic wood-burning fireplace, perfect for cozy evenings. Sun-filled rooms, a flexible den/sunroom, and a generous layout create an ideal setting for both everyday living and memorable gatherings. Elegant French doors, featured throughout the main living area, add charm and seamlessly connect the living room to the back deck. The home features three bedrooms and two and a half baths, including a large primary with an ensuite bath and a charming window seat. The updated kitchen offers new stainless steel appliances, a breakfast nook, and a pantry, blending style and functionality for everyday living and entertaining. Numerous recent improvements add to the home's turnkey appeal, including a new Klaus roof (with new plywood) installed in 2023. The finished lower level offers additional flexible space with a half bath, ideal for a playroom, media room, or home office. Step outside to a beautifully landscaped, fenced-in backyard designed for enjoyment in every season. Mature plantings, perennial gardens, a fire pit, and a deck provide the perfect backdrop for summer evenings and crisp fall nights. Additional highlights include an expanded one-car detached garage and a location offering easy access to the best of the Berkshires, just a short walk to local favorites for coffee, ice cream, and baked goods, and minutes from world-renowned cultural attractions, including Tanglewood, MASS MoCA, The Clark Art Institute, and Norman Rockwell Museum.

Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an open concept kitchen and family room with cathedral ceilings, where sliders lead seamlessly to a large rear deck overlooking a spacious, flat, and fenced backyard; ideal for gatherings, play, or quiet relaxation amid mature landscaping and beautiful gardens. A heated sunroom extends year round enjoyment, while the layout offers remarkable versatility with five bedrooms, including two primary suites. The first floor primary features a walk-in closet and en suite bath, while the second floor primary also offers an en suite and double closets, complemented by additional second floor bedrooms. A finished, heated area in the expansive basement adds valuable bonus space, and practical comforts include first floor laundry, three zone natural gas heat, town water and sewer, and a two car attached garage with loft storage above. Thoughtful, inviting, and designed for both everyday living and entertaining, this is a home that truly delivers a lifestyle.

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.

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. 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.

Spacious and adaptable, this Pittsfield home offers exceptional flexibility for today's lifestyle. The first floor features a sun-filled living room with hardwood floors and a bay window, a generous kitchen with an island and large dining area, and a mudroom with convenient first-floor laundry. A full bath and two bonus rooms on the main level provide versatile options for home offices, guest space, or additional bedrooms, allowing for the ease of one-level living if desired. Upstairs, a large landing creates the perfect spot for a home office or play area, while the primary bedroom boasts a walk-in closet and private exterior balcony. Three additional bedrooms and a full bath complete the second floor. Outside, enjoy a fenced-in backyard, one-car garage, solar panels, and a location just minutes from parks, shopping, and dining.

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.

Conveniently located just moments from downtown Pittsfield, this 3-bedroom, 1-bath home offers a straightforward, well-designed layout that works for everyday living. The open kitchen and dining area act as the center of the home, with plenty of space to gather, entertain, or simply move through your day with ease. An enclosed front porch creates a welcoming entry and adds flexible living space. Off the kitchen, a mudroom provides practical functionality and leads directly to the back deck through sliding doors, making the transition to outdoor space feel easy and natural. Upstairs, three bedrooms offer comfortable accommodations with the flexibility to suit a variety of needs, whether for guests, workspace, or additional living. Set in a location that keeps you close to downtown Pittsfield, Berkshire Medical Center, and Pontoosuc Lake, this home offers convenient access to local dining, shopping, and outdoor recreation without sacrificing day-to-day ease.

Offering an abundance of space and flexibility, this expansive Cape is ready for its next chapter. The first floor features a spacious kitchen, dining room overlooking the backyard, inviting living room, full bathroom, and an oversized primary suite complete with two separate rooms and abundant closet space -- ideal for a private sitting area, home office, or dressing room. Upstairs, you'll find two generously sized bedrooms and an additional full bathroom. Recent updates include a newer roof and heating system, offering peace of mind for years to come. The unfinished basement provides excellent storage and endless possibilities for a workshop, hobby space, or future finished living area. Conveniently located just minutes from downtown Pittsfield, Pontoosuc Lake, shopping, and nearby biking and hiking trails, this home combines everyday convenience with plenty of room to grow.

Old Farm Lane, Lot #26 offers the perfect blend of wooded privacy and neighborhood community, while being tucked away on a quiet cul-de-sac. Utilities are in place with public sewer, private well, underground electric and gas. This lot borders the Pittsfield State Forest and offers close proximity to other year-round activities. It is also a short drive to the cultural hubs of Lenox, Williamstown, and North Adams. Privately located with access to everything.

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.

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.

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.

This sweet and charming 3 bedroom, 1.5 bath Colonial blends timeless character with thoughtful updates throughout. Set on a spacious, fully-fenced yard, the property offers plenty of room to relax, garden, entertain, or play, along with a welcoming 3-season enclosed porch perfect for enjoying quiet mornings or summer evenings. Inside, the living and dining rooms feature beautifully refinished hardwood floors that bring warmth and charm to the home, while a walk-up finished attic provides valuable bonus space for storage, hobbies, or future possibilities. Recent improvements have enhanced both the functionality and appeal of the property, including a newer electrical service, a newer sewer line, insulation upgrades, and the addition of a brand new half bath. Fresh interior paint, refinished flooring throughout much of the home, and updates to the bathrooms create a clean, refreshed feel while still preserving the home's classic Colonial style. Outside, updated porches, painted shutters and trim, landscaping, and stonework add to the home's curb appeal and inviting presence. With so much of the work already completed, this is a wonderful opportunity to move right in and enjoy!

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.