1,266 properties for sale in Pittsfield city, Berkshire County Massachusetts

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Ideally located in the Downtown Arts District just off South Street, this two-family property offers an excellent investment opportunity. Fully renovated in 2007, the property features a total of 6 bedrooms and 2 1/2 bathrooms, with separate utilities for each apartment, paid by the respective tenants.The first-floor apartment offers 3 bedrooms, 1 1/2 bathrooms, and numerous updates throughout. The second-floor apartment features 3 bedrooms and 1 full bathroom, providing comfortable and functional living space.The property is serviced by public water and sewer and is equipped with two electric meters, two boilers, and two hot water heaters. Both apartments are heated with natural gas, with natural gas hot water as well. Conveniently located near Berkshire Medical Center, Berkshire Museum, The Colonial Theatre, Barrington Stage, schools, restaurants, shopping, and downtown attractions. Zoned business and residential, this property offers excellent investment potential in a convenient do

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

Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes a requisite annual resort membership with full access to Canyon Ranch's world-renowned wellness amenities. Just minutes from the Berkshires' acclaimed cultural attractions, fine dining and outdoor recreation, this is a rare opportunity to enjoy luxury, wellness and timeless design in one extraordinary home

Come enjoy the peace and quiet in this beautifully redone two-family property! This home has been completely updated from top to bottom, including New Roof and Siding, new walls, floors, and kitchen. Brand new fence for added privacy, a fully renovated basement with fresh concrete flooring, new water heaters, washer and dryer hookups on both floors, in addition, an upgraded electrical system. Whether you're looking for a comfortable home or a great investment opportunity, this property is move-in ready and built to last

Welcome to this beautifully renovated 3-bedroom ranch, perfectly situated on a quiet dead-end street in Southeast. This move-in-ready home features a brand-new roof, new windows, new flooring throughout, and a completely updated kitchen and bathroom. The thoughtful renovations offer a fresh, modern feel while maintaining the comfortable layout and easy living of a classic ranch. Outside, enjoy a fenced-in backyard-ideal for entertaining, gardening, pets, or relaxing. With major updates already completed and a peaceful location to call home, this property is a fantastic opportunity for buyers!

Cute as a button and move-in ready! This recently updated 3-bedroom, 1-bath bungalow offers the perfect blend of charm and comfort. The bright, inviting interior is complemented by a partially finished walk-out basement, providing flexible space for a family room, home office, or recreation area. Step outside to enjoy the back deck, ideal for relaxing or entertaining. Conveniently located in the heart of Berkshire County, you'll have easy access to shopping, dining, outdoor recreation, and everything the Berkshires have to offer. A wonderful opportunity for first-time buyers, downsizers, or anyone looking for a turnkey home! First showing is at the Open House Saturday 8/8 from 11-12:30

Welcome home to this charming and well-maintained three-bedroom, two-bath property located in a desirable neighborhood just moments from Allendale School, downtown Pittsfield, shopping, dining, and everyday conveniences. This inviting home offers a wonderful blend of character and comfort, featuring beautiful hardwood floors in excellent condition, vinyl replacement windows, and a cozy wood-burning fireplace that creates a warm and welcoming atmosphere. The updated kitchen offers excellent functionality, with all appliances included for the new owner's convenience. A standout feature of the home is the gorgeous sunroom addition, complete with soaring ceilings, skylights, and direct access to the backyard-an ideal space to relax, entertain, or enjoy the changing seasons year-round. Upstairs, you'll find spacious and oversized bedrooms offering plenty of room to spread out. Outside, the flat, fenced-in backyard provides a great setting for outdoor enjoyment, gardening, pets, or gathering

Welcome to this charming, updated ranch tucked into a quiet neighborhood and conveniently located near shopping and restaurants. Enjoy the ease of single-level living with thoughtful updates throughout. Recent improvements include an updated bathroom, new driveway (2026), siding and Trex deck (2025), and furnace (2018), with the roof replaced in 2011. Move right in and enjoy a comfortable home with a great combination of updates, convenience, and low-maintenance living

This charming Cape has been lovingly maintained and offers 3/4 bedrooms. The first floor features a bright and inviting living space, two comfortable bedrooms, and a full bathroom, making one-level living an option. The eat-in kitchen offers new appliances. Upstairs you'll find a third bedroom along with a versatile bonus room-perfect for a craft room, home office, playroom or guest space. With many recent upgrades throughout, this home offers true move-in-ready convenience and peace of mind for years to come. Outside, enjoy the attached screened-in carport, creating a wonderful three-season space for relaxing, entertaining, or enjoying summer. Conveniently located close to shopping, restaurants and all that Pittsfield has to offer !

Located in a desirable neighborhood in Southeast Pittsfield, this three-bedroom, 1.5-bath home offers comfort, versatility, and exceptional value. The main residence features spacious living areas, large primary bedroom with walk in closet and laundry room, and a functional layout designed for everyday living. A standout feature of the property is the attached first floor apartment with an additional bedroom, and additional bathroom, perfect for extended family, guests, rental income, or a private home office. The property also includes an insulated workshop/barn, providing ample space for hobbies, storage, equipment, or small business needs. Enjoy outdoor living in the fenced backyard, ideal for pets, gardening, entertaining, or simply relaxing in your own private retreat