luxury real estate for sale Pittsfield, United States

Welcome to 100 Boyston Street Ext, an extensively updated Pittsfield home with every major element renewed for a warm, modern, turnkey feel. The first floor features a bright open layout, a brand new contemporary kitchen, and connected living and dining spaces. Two first floor bedrooms and a full bath add flexibility for single level living or guests. Upstairs primary suite with refinished hardwood floors and a renovated bath. The layout is functional and offers more space than expected. Major updates include a new roof, new heating and cooling with a heat pump, all new bathrooms, a new kitchen, new main level flooring, and refinished floors upstairs. Fully move in ready in a convenient Pittsfield location.

Maggie Gavin [email protected] 413-822-4580 WILLIAM PITT SOTHEBY''S - LENOX

Gracious colonial style home in the heart of the southeast historic neighborhood minutes to upstreet cultural art and theatre district with museums, galleries, theatres, eclectic dining, and more. This home awaits your finishing touches is search of a new homeowner with a sense of style and interior design to make this beauty the show piece it deserves to be. Abundance of living spaces on multi levels, finished attic for six bedrooms boasting three full baths and one half bath. Modern kitchen and primary bath give you the start you need. New hot water baseboard heating system and incredible front yard that is edged in custom cut marble for easy care maintenance. Lower level walk-out offers more space for exercise, crafting and workshop space. Incredible oversized yard for fun and enjoyment

Step out your back door and onto the mountain! This unique slopeside condo offers direct access to skiing and hiking trails right from your backyard. Offering 2,750 sq. ft., this beautifully updated 3-bedroom, 2½-bath home features a gas fireplace and refreshed kitchen with quartz countertops, subway tile backsplash, and GE Profile appliances. Updates include newer carpeting and paint, California Closets, and USB-A/USB-C outlets. The unfinished basement offers generous storage, home gym or future living space and is stubbed for plumbing. Enjoy peaceful mountain surroundings and a community pool in warmer months. Just a short drive from Lenox and Tanglewood, with easy access to dining, shopping and the best of the Berkshires.

Surprisingly spacious cape style home with beautiful hardwood floors, offering comfortable living for everyone. First floor blends traditional floorplan with certain wheelchair-access conveniences that make for easy one-level living. First floor kitchen sink access, two full baths, primary bedroom suite, inside and outside deck access with ramps. Upstairs enjoy three private bedrooms--great options for multi-generational shared living. Lovely southeast neighborhood close to the famous East Side Pizza, Lakewood Creamery and nestled between three parks to enjoy baseball fields, tennis courts, pickleball, basketball, tracks or nature near Goodrich Pond. Surround yourself with nostalgia and the good life.

Enjoy easy, turn key living in this spotless, beautifully maintained 3 bedroom, 1 bath ranch style home! Ideally situated in one of Southeast Pittsfield's most desirable neighborhoods, this classic residence combines quality construction, timeless appeal, and exceptional value. Beautiful hardwood floors extend throughout the thoughtfully designed main level floor plan. The warm and inviting living room features custom built in cabinetry, a cozy fireplace, and a picture window offering seasonal mountain views. The dining room features built ins and is complemented by a well appointed kitchen with stainless appliances. Three bedrooms include a generously sized primary bedroom with a walk-in closet. The living space extends naturally into the scenic three season sunroom, which offers direct access to the deck and overlooks the lovely, level backyard. The lower level provides abundant storage and includes a spacious area with excellent potential to create additional finished living space, a playroom, home office, or recreation area. Outside, enjoy the level backyard and outdoor deck, perfect for relaxing or entertaining. Central air conditioning, replacement windows and a convenient one car attached garage add to the comfort and practicality of this well maintained home. A wonderful opportunity to own a quality built property in a highly desirable Pittsfield location! Note: Total square footage excludes the three-season sunroom.

Gracefully situated on a gentle sloping hillside street this distinctively designed multi-level home offers distant and seasonal Berkshire mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home and grounds, you can embrace the vast privacy, open land and natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined residence is a private enclave offering 4-5 bedrooms, 3 full bath, masterfully landscaped set on 1.5 acres with unique tree selection, blooming shrubs and pollinator flowering perrenials. Just 10 minutes to the culture, cuisine and art offerings of Lenox especially the sounds of Tanglewood. Minutes to all that is Berkshire while being immersed in renowned peacefulness. Follow the gently curved stone stairway to the covered front porch and enter into an open and spacious entry with an intriguing glimpse of flowers exquisitely private. Be welcomed into a graciously sized formal living and dining rooms ideal for entertainment, memories and laughs to be shared. Relax in comfort and warmth of the brick fireplace fully framed with wall to wall windows balancing light while inviting the outdoors in. Adjoined to the expansive cooks kitchen topped with granite countertops, triple windows for full backyard viewing, and spacious everyday dining which leads to a private and expansive rear deck and screened sunroom. Step inside and ascend a half flight of stairs to the bedroom level, where four generously sized bedrooms offer both comfort and ample space. These rooms share a spacious full hall bath. The private, king-sized primary suite welcomes you each morning with cheerful and soothing sunrise views over the October Mountain ridgeline. Descend to the walk-out entry level, which features a versatile home office or guest suite, a third full bath, and a convenient shared laundry area all situated on the lower entry level close to the oversized two-car garage. The next lowest level remains unfinished, providing an excellent opportunity for large-scale storage, a workshop, or additional creative uses. This is a unique opportunity in this glorious Berkshire Summer market, situated close to Lenox for enriched entertainment, Pittsfield's Guido's Fresh Marketplace for gourmet, farm-fresh foods. Enjoy lake activities at Pontoosuc or Onota Lake within 20 minutes or indulge in hiking and mountain biking at October Mountain and kayaking or hunting at Canoe Meadows Wildlife Sanctuary. With incredible views at home and endless outdoor adventures nearby, this residence offers the best of Berkshire living.

Introducing 444 Pomeroy Ave, a true neighborhood icon! This one ticks all the boxes: Curb appeal to the max with mature perennial plantings, gracious front yard, private side yard with hot tub, and the true star of the show--the screened porch, which you won't want to leave in the summer. The home is spacious with a cook's kitchen and dining room, plus an ample, fire-placed living room with built-ins galore. First floor 1/2 bath and period details and charm that cannot be replicated today. Upstairs, 3 sizable bedrooms, and a fully renovated bathroom with Italian marble counters, tiled walk-in shower, and radiant heat. The partially finished lower level features another bedroom for guests. A large two car garage was added, with exceptional loft storage space above. Be ready to fall in love!

Welcome to this immaculately maintained two-family home--a turnkey property that meets today's timeless standards! This choice 2-family home beautifully balances sophisticated living with incredible versatility, making it an ideal match for owner-occupants, multigenerational families, or savvy investors alike. Including features you are sure to love: Modern Living: Bright, open floor plan living areas featuring fresh paint and updated appliances. Comfort and Convenience: Both units boast primary bedrooms with ensuite baths, large dedicated laundry areas, updated windows, and pristine ceramic-tile bathrooms. Flex Space: A partially finished basement offers the perfect canvas for storage, workshop, craft area, home gym, etc. Outdoor Oasis: Enjoy your morning coffee or warm evenings from the screened-in porch or private second-floor deck, all overlooking a backyard ideal for gardening and relaxing by the charming water fountain. Whether you are looking for rental income or a spacious multifamily retreat, this property offers an extraordinary lifestyle opportunity!

Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the formal dining room and a tastefully remodeled kitchen. Enjoy year-round tranquility in the heated four-season sunroom or relax in the separate main-floor den featuring a cozy gas fireplace and sliders leading out to the rear deck. A generous first-floor bedroom, full bath, and dedicated laundry room offer effortless single-level living convenience. Upstairs, find a sprawling primary suite with a walk-in closet, a second sizable bedroom, and a fully renovated full bath. The lower level expands your entertaining footprint with a heated family/recreation room and workout space, alongside a large unfinished workshop and mechanical storage area. Out back, the private half-acre lot creates a peaceful retreat complete with a custom storage shed, mature landscaping, and the gentle backdrop of Sackett Brook. Featuring an attached two-car garage, natural gas heat, and public utilities, this turnkey home offers suburban tranquility just minutes from downtown Pittsfield, Lenox, and all Berkshire cultural attractions.

Set within one of Southeast Pittsfield's most desirable neighborhood settings, 53 Greenings offers an exceptional blend of privacy, space, and effortless everyday living. Set on a beautifully landscaped 1.07-acre double lot, this spacious ranch style residence feels wonderfully secluded while remaining connected to the conveniences and amenities of the surrounding community. Mature landscaping, established flower beds, and expansive lawn create a truly park-like setting, an inviting backdrop for morning coffee, summer gatherings, or simply enjoying the quiet of home. Inside, 3,275 square feet of living space unfolds with an appealing sense of openness and flow. Spacious rooms, generous windows, and a freshly painted interior create a warm, welcoming atmosphere, while the open floor plan makes the home equally comfortable for relaxed living and entertaining. At its heart is a stunning chef's kitchen, thoughtfully designed with an amazing oversized island, stainless steel appliances, open shelving, and abundant cabinetry. Large windows and French doors fill the space with natural light while creating a wonderful connection to the rear yard and provide direct access to the expansive rear deck. It is a space that invites both cooking and conversation, with views toward the beautifully landscaped grounds beyond. The primary suite provides a private retreat of its own, complete with a spacious bedroom and en-suite bath. Throughout the home, two fireplaces add warmth and character, while a sunken formal living room provides an intimate space for gathering or quiet evenings. The finished lower level significantly expands the living possibilities, offering additional family and recreational space, a full bath, and versatile sleeping arrangements for guests or extended stays. Abundant storage throughout the home, including substantial lower-level storage, adds an appreciated layer of practicality. Outside, the grounds are as much a part of the property's appeal as the home itself. The expansive rear yard, mature plantings, flower beds, and surrounding greenery create a sense of tranquility that is increasingly rare, particularly within a neighborhood setting. A spacious two-car garage provides ample room for vehicles, equipment, and additional storage. Leased solar adds to the home's thoughtful blend of comfort and energy-conscious living. Numerous updates enhance the home's comfort and ease of ownership, including newer windows (2024), a new hot water heater (2025), freshly painted interiors, and a recently power-washed exterior and deck. The leased solar system is another attractive feature, providing an energy-conscious addition to the property. With its generous proportions, beautifully updated kitchen, private outdoor spaces, mature landscaping, and unusually appealing setting, 53 Greenings offers a rare opportunity to enjoy the best of both worlds: the privacy and feeling of a country retreat, paired with the convenience and community of an established Southeast Pittsfield neighborhood. This is a property best experienced in person!

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.

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.

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. 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.

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.

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.