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42 Photos
LAMACCHIA REALTY, INC
$389,000
3 BD | 2 BA
Residential - Single Family

Welcome to 1121 North St in Pittsfield. A well cared for home offering comfort, convenience and style. Classic style with some modern updates. Fully fenced backyard. Perfect for pets, gardening, entertaining or relaxing in your own private retreat. Unwind in the bright sunroom with its own gas fireplace for chilly evenings and winter days. The oversized garage opens to a mudroom. Updated kitchen and a half bath on the first floor. Wood floors in dining and living area. Easy access to routes in and out of the Berkshires. Just outside of downtown, yet close to medical facilities, shopping, dining, Pontoosuc Lake, outdoor recreation, cultural activities as well as local ski areas. Come experience the warmth, charm and lifestyle that make this a wonderful place to call home.


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WILLIAM PITT SOTHEBY'S - LENOX
$398,500
3 BD | 2 BA
Residential - Single Family

Pride of ownership shines throughout this beautifully updated ranch situated on a corner lot in a walkable, sought-after neighborhood, close to bike trails, hiking and shopping. This well maintained 3-bedroom, 2 full bath home features central air, a bright modern kitchen with Instaview refrigerator, double oven, 2 filtered water sites and a spacious dining area with cathedral ceiling. The beautifully renovated main bath features a spa style rain shower with dual heads, heated fan, tiled flooring and generous storage. This home offers hardwood floors and cedar closets throughout its comfortable, well-designed space.The private backyard features a pebble epoxy finished patio, a convenient electric awning and a charming stone fire pit for cool evenings, and entertaining


24 Photos
LAMACCHIA REALTY, INC
$399,500
3 BD | 2 BA
Residential - Single Family

Pristine Colonial located in desirable Southeast Pittsfield, featuring a newly renovated kitchen and updated half bath. This well-maintained home offers a wonderful, easy flow with three generously sized bedrooms. Enjoy the comfort of a cozy office just off the living room, along with a beautiful wood-burning fireplace. Truly move-in ready--just unpack and enjoy!


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RE/MAX COMPASS
$419,900
3 BD | 2 BA
Residential - Single Family

OPEN HOUSE SUN 5/10 11AM- 2PM.Pontoosuc Lake Community! A rare opportunity awaits in this sought after neighborhood. This home has hosted three generations of the same family, over 46 years. Many wonderful changes have occurred in as many years. With a ton more potential this 2 to 3 bedroom, 1-1/2 bath home is in need of some TLC. While not lakefront, it offers beautiful lake views from the amazing sunroom, balcony and pool decks, with a right of way just one lot over. New sewer line April '26, New pool pump '24, pool heater inoperable, porch roof '24, Main roof '18, Water main replaced '25, hot water tank is approx 3 years old.This home is being sold as-is, where-is. Bring your tools, ideas, and imagination!


47 Photos
SIGNATURE ASSOCIATES
$424,900
4 BD | 2 BA
Residential - Single Family

Enjoy this beautiful property on Williams St. Large yard consisting of 2 lots with pastoral views across the street. This 4 large bedroom, 1 full and 2 half bath home is just waiting for your interior decorating ideas Hardwood floors in most rooms, fireplace living room, large dining room. Central air conditioning, Basement partially finished, including 1/2 bath. New roof in 2020 and solar panels replaced. Updated electrical, furnace serviced 2/25. Sewer line to be replaced soon Solar Panels are owned and for hot water only


51 Photos
ROBERTS & ASSOC. REALTY, INC
$424,900
4 BD | 2 BA
Residential - Single Family

Step into style and comfort in this beautifully maintained move-in ready four bedroom, two-bath home in Southeast Pittsfield Conveniently located and perfectly positioned on a landscaped, fenced, corner lot. From the moment you enter the spacious hallway, you'll see gleaming hardwood floors that add warmth and character to every room. First floor includes timeless charm of a fireplaced living room, formal dining open kitchen and a family room with skylights. First floor bath w shower and bonus is a year-round heated sunroom on its own heat zone. Second floor features four generously proportioned light-filled bedrooms, updated full bath. Private rear patio, attached garage, Natural gas heat - four zones! Minutes to theater, restaurants and all of the Berkshire attractions.


34 Photos
PAULA MCLEAN REALTORS INC.
$425,000
2 BD | 3 BA
Residential - Single Family

Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom for ultimate comfort and privacy. Outside a 2 car garage great for snow days or storing an old vintage car! Ideally located close to Tanglewood, Ventfort Hall, Bousquet Mountain & Sport, The Colonial Theatre as well as wonderful restaurants, cafes, and shopping. A little something for everyone.


26 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$425,000
2 BD | 2 BA
Residential - Condo/Townhouse

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail--from the textured walls to the light pouring in at all hours--creates a sense of romance and possibility.The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest.


20 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$429,900
11 BD | 4 BA
Multi-Family

Income producing 3-family home with almost 4,000 SF of living space, featuring two 3 bedrooms/1 bath apartments and one 3 bedroom/2 bath apartment, each one with its own laundry hookups. All 3 apartments have lead compliance certificate!There are vinyl replacement windows, newer heating systems, newer roof done in 2022, and separate natural gas heat & hot water and electricity for each unit.Hall Place is a dead end street and the property sits on a large corner lot, offering plenty of parking and good yard space.This is a great income producing property with rents totalling $74,472/year. All apartments are rented through Section 8. *Interior photos shown are from 2025 before tenants moving in.


55 Photos
NOCHER REALTY
$449,900
4 BD | 3 BA
Residential - Single Family

Discover the perfect blend of modern style and effortless living in this stunning contemporary-style Ranch. Nestled on an expansive lot within one of Pittsfield's most sought-after neighborhoods, this home offers a rare combination of space, light, and a sophisticated layout. Sun-Drenched Interiors: light inviting windows throughout the home allow an abundance of natural light, creating a warm and vibrant atmosphere in every room. Spacious Living Features four generous bedrooms and two and a half baths, there is plenty of room for family, guests, or a dedicated home office.


37 Photos
Lamacchia Realty, Inc. - Dalton
$459,000
3 BD | 3 BA
Residential - Single Family

Welcome to sought-after Walden Village, where comfort and ease of living meet. This 3 bed, 2.5 bath unit is freshly painted and move-in ready. Gleaming hardwood floors enhance the main level, featuring a well-appointed kitchen w/ pantry and a desirable first-floor primary suite w/ full bath. Upstairs offers premium carpeting, two additional bedrooms, a full bath, and a versatile loft or home office. The unfinished lower level provides abundant storage or future expansion potential. Enjoy a rare screened porch, a one-car garage, and access to on-site pool and tennis. Perfect for low-maintenance living in a coveted community. Nearby Pontoosuc Lake is easily accessible by foot, bike, or car, and offers an enhanced lakefront park, picnic areas and a public boat launch. Ski, golf, dine nearby!


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$459,900
10 BD | 4 BA
Multi-Family

Income-producing four-family home with one unit vacant and 3 units rented out. Two of the tenants have Section 8 assistance. Whether you are an owner-occupant or an investor, this is a great opportunity! The vacant apartment is a spacious 3 bedroom/1 bath unit and has been tastefully renovated with new kitchen cabinets and quartz countertops, updated bathroom, flooring and freshly painted interior. The other 3 units each have 2 bedrooms/1 bath, however, can be used as a 3-bedrooms, since in addition to the two bedrooms, the units have separate dining and living room. There is a lovely front porch on the first floor and separate front porches for the upstairs units. The building features vinyl replacement windows, 4 new water heaters and great parking on the back.


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Lamacchia Realty, Inc. - Dalton
$469,000
3 BD | 3 BA
Residential - Single Family

Meticulously maintained and beautifully updated, this stylish 3 bedroom, 3 bath unit at highly sought-after Walden Village offers exceptional space, comfort, and convenience. The open-concept living, dining, and kitchen area is perfect for everyday living and entertaining, featuring quartz countertops, new appliances and flooring. A desirable first-floor primary suite includes a spacious bath and walk-in closet. Upstairs offers two additional bedrooms, an office/reading nook, and a full bath. The finished walkout lower level provides an ideal guest suite with a private patio, third full bath, laundry area, and abundant storage. Enjoy a new Trex deck, new heating system, and resort-style amenities including an onsite pool and tennis courts. Move-in ready and impeccably cared for.


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THE KINDERHOOK GROUP
$469,000
4 BD | 2 BA
Residential - Single Family

Rich in character and history, this beautifully maintained Colonial sits on land once belonging to Pittsfield's renowned Grey Tower Estate. Featuring original oak woodwork, decorative architectural leaded glass all which may have been salvaged from the estate. Move right in and relax on the expansive front porch with an iced tea in hand. As you walkthrough the quarter sawn oak doors there is plenty of light to greet you, Updated kitchen and baths a new roof, new gutters with guards, perennial gardens, sunroom, metered water, garage and carport, this exceptional home blends historic charm with modern comfort on the tree lined street of Southeast of Pittsfield. Enjoy the sunroom for reading and interior balcony for gazing at the stars all which is a step from the primary bedroom.


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WILLIAM PITT SOTHEBY'S - LENOX
$489,000
4 BD | 3 BA
Residential - Single Family

Immaculate, adorable, expansive, well maintained 2500 sq ft ranch. 4 bedrooms 3 bathrooms, open living room & 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 & dining area which leads to a back patio nice, open back yard area. Home has lots of storage. New chimney, garage door, side deck are just some of the upgrades. Close to shopping, downtown, theaters, Lake Onota and schools.


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JIMINY REALTY
$509,000
2 BD | 3 BA
Residential - Condo/Townhouse

A spacious end-unit condo in Mountainside Hemlock Village, offering 2+ bedrooms (including a sleeping loft) and 3 full bathrooms across three levels of living space. This bright, airy unit features abundant windows and ample room, making it ideal for larger families. Enjoy the convenience of parking right outside your door and stepping directly into your ski getaway. The property has a strong rental history, offering excellent investment potential. Sold fully furnished and turnkey, it's ready for immediate use. Ideally located on the lower mountainside--just a short walk to the slopes.


44 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$525,000
4 BD | 3 BA
Residential - Single Family

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.


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WILLIAM PITT SOTHEBY'S - LENOX
$525,000
4 BD | 3 BA
Residential - Single Family

Build to suit. This new construction modular home offers an open concept kitchen, dining & living room space, The home features grand, open, sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from every room on the main living level. 4 bedrooms 3 baths. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request.


71 Photos
MOCKINGBIRD REAL ESTATE
$525,900
6 BD | 3 BA
Residential - Single Family

Beautiful, spacious 6 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated kitchens with granite counters and stainless steel appliances. Ample room for the kids and pets to play in the fully fenced in backyard with playset. Enjoy relaxing in the hot tub on the lower level while have shelter from the upper deck! This gorgeous home has all you could need! Surveillance cameras are active outside in the front & back of home.


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HART REALTY
$539,000
4 BD | 5 BA
Residential - Single Family

This move-in home is a timeless classic with modern upgrades. Large nature lovers lot on an unheard of 1.3 acres in the sought after southeast neighborhood. New kitchen with stone counters and stainless appliances. Well appointed bathrooms, replacement windows, refinished impeccable hardwood floors, new concrete patio and garage floor. The 1st floor consists of a large living room with fireplace, a bedroom with private bath, a half bath, kitchen and dining room with gold chandelier. The enclosed and screened porch! The 2nd floor has a primary suite with it's own fireplace, private bath and walk-in closet. There are another 2 bedrooms and 1 bathroom with double vanities. The lower level has a large family room with fireplace, bar, half bath and a utility room

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