756 properties for sale in Pittsfield city, Berkshire County Massachusetts

Welcome to easy single floor living in a highly desirable Southeast Pittsfield neighborhood! Built in 2003, this exceptionally well-maintained contemporary home features 3 spacious bedrooms, 2 full baths, soaring vaulted ceilings, and beautiful hardwood floors. The light-filled primary suite includes a private ensuite bath, while the enclosed 3-season room and front porch offer ideal spots to relax overlooking a low-maintenance yard. Complete with a brand-new roof, central air, a massive unfinished basement with endless potential, and city-maintained street access, this move-in-ready property is a standout Berkshire home!

Classic two family brick colonial with many possibilities! Including a front/rear porch, two separate yards on each side, and off street parking. Enter each side into a wide, open hallway with the original hardwood floors throughout. The left side has four bedrooms and one bathroom with potential for a second bathroom off the kitchen. The right side has been split into two smaller units with separate kitchens and bathrooms but originally was a three bedroom apartment. Each unit has its own heating, hot water, and electrical systems

Welcome to easy living at 691 Crane Ave, Pittsfield! This single-level ranch offers the perfect blend of convenience and peace of mind, highlighted by a 2-year-old roof and a two-car garage. Inside, you'll find a highly functional layout featuring fantastic space in the basement-an ideal setup for your favorite crafts, a home workshop, or weekend hobbies. Step out back to find a standout feature: a large, fully fenced-in yard that provides a wonderful private outdoor retreat. Nestled in a highly convenient location close to local shopping, dining, and schools, this move-in-ready home is designed for an effortless lifestyle. Don't miss this Berkshire gem!

Welcome to 1228 East St. A longtime family home filled with warmth, character and opportunity. Beautiful hardwood floors throughout much of the home. Updates include electric panel, blown in insulation, a new oil tank 2018 and new oil burner 2022. The spacious second floor kitchen area offers potential to create a two-family flat subject to city approval. A three-car garage offers extra space for storage, family vehicles or earning potential by renting out bays. Close to shopping, parks, recreation and everyday conveniences. This East st gem is full of possibilities. Schedule your showing today

A solid and versatile two-family flat located in Pittsfield's Newell Street neighborhood, 21-23 Newell St offers a great opportunity for owner-occupants, investors, or multi-generational living. This traditional New England multi-family home features two spacious units, each with private entrances. Just minutes to, Elm St Plaza, diners, restaurants, banks, variety store, and Ice Cream shop and more! Easy access to Downtown Pittsfield dining and shopping, Berkshire Medical Center, Local schools and parks, Cultural attractions like the Colonial Theatre and Barrington Stage, Easy access to Route 7 and Route 20

Beautifully maintained inside and out, this move-in ready 3-bedroom Ranch offers the perfect blend of comfort, updates, and outdoor living. Gleaming hardwood floors, abundant natural light, and a stunning floor-to-ceiling stone fireplace create a warm, inviting living space. The finished lower level with custom bar adds exceptional bonus space for entertaining, hobbies, or relaxing. Outside, enjoy an expansive composite deck overlooking a beautifully landscaped, fully fenced backyard with fire pit and storage shed. Recent improvements include a new transferable 50-year roof (2025), fence (2025), remodeled bath, finished basement, deck, updated flooring, and more. Every room reflects the pride of ownership this home has received. Simply unpack, settle in, and enjoy

Step into timeless elegance in this exceptional 6-bedroom, 3-bath historic residence, where classic architectural details blend seamlessly with thoughtful modern updates. Meticulously maintained and enhanced over the years, this one-of-a-kind home showcases the craftsmanship and character rarely found today. From the moment you enter, you'll be captivated by the grand, sun-filled rooms, gleaming hardwood floors, original built-ins, statement fireplaces, and exquisite stained glass windows that fill the home with natural light. With updated electrical, plumbing, boiler, sewer line and kitchen, this home is designed for everyday living and entertaining. Ideally located near downtown Pittsfield's cultural attractions this is a rare opportunity to own a piece of architectural history

Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped backyard featuring a built-in grill, hot tub and plenty of space to relax or gather with family and friends. A rare opportunity to enjoy privacy, comfort, and an exceptional Lenox location

Welcome to this charming and low-maintenance ranch offering 1,131 square feet of comfortable single-level living. Situated on a quiet street in a desirable Pittsfield neighborhood, this two-bedroom, one-bath home is just minutes from Onota Lake and Pontoosuc Lake, providing easy access to boating, fishing, swimming, and year-round outdoor recreation. Inside, you'll find a functional floor plan designed for easy living, with bright, welcoming spaces that make everyday living and entertaining effortless. Step outside and enjoy your morning coffee on the inviting front deck or relax on the side patio surrounded by beautiful perennial gardens and colorful landscaping. The backyard offers additional outdoor space complete with a storage shed for gardening tools and seasonal equipment

Great location in Southeast Pittsfield. Short walk to downtown Pittsfield. Lovely unit with hardwood floors in the Living room and Bedroom. Nice sized balcony (facing the morning sun) to relax on. Coin operated laundry just a few steps down into the lower level. Storage locker is available in an upstairs area through the door on the balcony. The unit sq footage is 617 and is recorded in the Marianne Inn Condominium Trust deed. PLEASE NOTE: THE ELECTRIC BILL FOR 2025 TOTALED $905.83.

Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00

Welcome to easy single floor living in a highly desirable Southeast Pittsfield neighborhood! Built in 2003, this exceptionally well-maintained contemporary home features 3 spacious bedrooms, 2 full baths, soaring vaulted ceilings, and beautiful hardwood floors. The light-filled primary suite includes a private ensuite bath, while the enclosed 3-season room and front porch offer ideal spots to relax overlooking a low-maintenance yard. Complete with a brand-new roof, central air, a massive unfinished basement with endless potential, and city-maintained street access, this move-in-ready property is a standout Berkshire home!

Welcome home to this beautifully maintained, ADA-compliant 3-bedroom, 1.5-bathroom ranch-style home, offering the perfect blend of comfort, accessibility, and modern efficiency. From the moment you arrive, you'll love the excellent curb appeal, featuring durable vinyl siding, updated vinyl windows, and a solar system to curb electric costs. Inside, the home boasts a wonderful, flowing floor plan bathed in abundant natural light. Designed for effortless single-level living, the thoughtful layout accommodates all needs with ease. Step outside into your own flat yard complete with a handy storage shed

PERFECT IN LENOX! This impeccably renovated Mid-Century Modern jewel has it all. Including a BIG VIEW! This 'down to the studs' interior rebuild including siding, windows, heating, electrical, plumbing, A/C with 2 zones and energy efficient LED lighting offers true main level living; three bedrooms, primary with walk in closet, open living/dining with stunning kitchen, main floor laundry, attached 2 car garage, sonos built in sound system and incredible natural light that envelops the panoramic view seen from every room; truly a move-in property. The location could not be more perfect. minutes to Miraval Resort for a little pampering, around the corner from beautiful Laurel Lake and of course minutes to the Village of Lenox and Tanglewood!

Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their timeless beauty. Recent improvements, including a new roof, providing peace of mind, while gas heat and central air conditioning ensure year-round comfort. Set in one of the area's most desirable neighborhoods and within a highly sought after school district, this property offers a truly special connection to its surroundings. The beautiful brook that flows through the backyard is the very feature for which Brookside Drive was named, creating a picturesque and tranquil setting that enhances the home's appeal. Enjoy the soothing sounds and natural beauty of the brook from your own backyard while appreciating the conve

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted

Step into timeless elegance in this exceptional 6-bedroom, 3-bath historic residence, where classic architectural details blend seamlessly with thoughtful modern updates. Meticulously maintained and enhanced over the years, this one-of-a-kind home showcases the craftsmanship and character rarely found today. From the moment you enter, you'll be captivated by the grand, sun-filled rooms, gleaming hardwood floors, original built-ins, statement fireplaces, and exquisite stained glass windows that fill the home with natural light. With updated electrical, plumbing, boiler, sewer line and kitchen, this home is designed for everyday living and entertaining. Ideally located near downtown Pittsfield's cultural attractions this is a rare opportunity to own a piece of architectural history

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!

Welcome to James Meadow! Tucked away in a peaceful, park-like setting, this beautifully refreshed end-unit offers the perfect blend of comfort and convenience. The bright main level features an open living and dining area with gleaming hardwood floors, fresh paint, and a cozy gas fireplace. The well appointed galley kitchen comes equipped with solid oak cabinetry and a convenient laundry closet with a stacked washer/dryer. Two generous bedrooms with large closets and a full bath complete this level. Upstairs, a versatile bonus loft space awaits-perfect for a home office, media room, or guest retreat. Brand-new carpet flows through both the loft and bedrooms. Outside, enjoy a the deck framed by lovely perennials. Complete with efficient natural gas heat, central air, and tasteful updates throughout, this beautiful home is entirely move-in ready. Schedule your tour today!

Welcome to this charming 4-bedroom, 2-bath home offering the perfect blend of comfort, updates, and extra living space. The updated kitchen and renovated first-floor bath provide modern style and convenience, while the finished lower level adds versatile space for a family room, home office, gym, or guest area. A bright and inviting sunroom fills the home with natural light and offers the perfect place to relax year-round. Outside, enjoy a spacious fenced backyard ideal for entertaining, pets, or play, along with an oversized garage providing ample storage and workspace. As an added bonus, the property includes deeded lake rights with private access to Onota Lake, giving you access to enjoy nearby water activities and scenic surroundings

Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00

Charming and well-maintained Cape offering 3 bedrooms and 1.5 baths in a desirable location just moments from Onota Lake. This inviting home features an open kitchen and dining area, creating a welcoming space for everyday living and entertaining. Full of character and warmth, the home also boasts a newly finished basement that provides additional living space perfect for a family room, home office, playroom, or gym. Thoughtfully cared for inside and out, this move-in ready property combines classic charm with modern functionality

Welcome to this stately raised ranch nestled in one of Pittsfield's most sought-after neighborhoods-Barkerville. Offering 1,896 square feet of thoughtfully designed living space, this home blends comfort, efficiency, and natural beauty in a truly special setting. Set on a cozy, private lot, the property is framed by mature evergreen trees, classic stone walls, and a peaceful brook flowing through the backyard. A grand entrance and custom walkway create a striking first impression, while the home abuts conservation land, providing direct access to scenic hiking trails and a serene, nature-filled backdrop year-round. Ideally located in the heart of the Berkshires, you're just minutes from world-renowned destinations including Tanglewood, the summer home of the Boston Symphony Orchestra as well as vibrant towns of Lenox, Great Barrington, Lee, Sheffield, Egremont, and Williamstown-all offering dining, shopping, arts, and outdoor recreation. Inside, you'll find an open-concept main level f

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and serenity. Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room. The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room. Enjoy the association pool, Bousquet Mountain next door and all of the

Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their timeless beauty. Recent improvements, including a new roof, providing peace of mind, while gas heat and central air conditioning ensure year-round comfort. Set in one of the area's most desirable neighborhoods and within a highly sought after school district, this property offers a truly special connection to its surroundings. The beautiful brook that flows through the backyard is the very feature for which Brookside Drive was named, creating a picturesque and tranquil setting that enhances the home's appeal. Enjoy the soothing sounds and natural beauty of the brook from your own backyard while appreciating the conve