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39 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$386,500
3 BD | 3 BA
Residential - Single Family

Nestled in a quiet cul-de-sac in one of the area's most desirable neighborhoods, this beautifully maintained 3-bedroom, 2½-bath home offers the perfect combination of comfort, space, and location. Inside, you'll find beautiful hardwood floors and a thoughtfully designed floor plan ideal for everyday living and entertaining. A Spacious kitchen granite counters, cherry cabinets, newer appliances and a breakfast bar. Large sunroom overlooking the backyard offers the perfect place to relax, with plenty of natural light. Charming front porch adds to the home's inviting curb appeal and provides the perfect place to enjoy the quiet rhythm of the cul-de-sac. With its ideal location, inviting spaces, and effortless livability, this home isn't just a place to live-it's a place to truly feel at home.


39 Photos
ROBERTS & ASSOC. REALTY, INC
$389,900
2 BD | 2 BA
Residential - Single Family

Easy living in this move-in ready contemporary in southeast Pittsfield! Stylishly designed with a flexible floor plan. Enter into a light-filled living space with built-in cabinetry in the entry, spacious oversized eat-in kitchen that that opens to a large rear deck. Kitchen with quartz island/ stainless appliances. Oversized first floor bath with laundry. Additionally find a den/sleeping space with French doors for privacy. Primary suite is the entire upper level and features deep soaking tub. Many options for the finished lower-level walk-out recently enhanced with custom built-in storage. Efficient propane heat/hot water, this is a gem not to be overlooked. Convenient to all Berkshire locations, this like-new home is a must-see for full or part-time living!


47 Photos
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


25 Photos
REAL BROKER
$399,000
3 BD | 2 BA
Residential - Single Family

Welcome home to this move-in ready Becket ranch, set back from the road on nearly an acre and surrounded by a park-like, fully fenced setting. Designed for easy one-level living, this inviting home offers 3 bedrooms, 2 full baths, gleaming wood floors, and an updated eat-in kitchen with direct access to the back deck, perfect for everyday living and entertaining. Relax on the covered front porch, enjoy the spacious yard, or take advantage of the oversized attached 2-car garage with plenty of room for storage. Conveniently located just minutes from Jacob's Pillow, the Mass Pike, Lee Premium Outlets, and all the Berkshires have to offer. Whether you're looking for a year-round home or a Berkshires getaway, 2305 Jacobs Ladder Road is ready to welcome you home!


39 Photos
SIGNATURE ASSOCIATES
$399,900
3 BD | 2 BA
Residential - Single Family

Beautiful newly remodeled 3-bedroom Cape. Nothing to do but move right into this home. New roof, new siding, new windows, gutters, all exterior and interior doors. Updated kitchen with new appliances, new driveway with bluestone front steps, electric car charger in heated garage, large family room in basement and so much more. OPEN HOUSE SATURDAY 8/1 10:00AM-11:30am


58 Photos
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. New sewer line this month Solar Panels are owned and for hot water only


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.


41 Photos
STONE HOUSE PROPERTIES, LLC
$425,000
8 BD | 4 BA
Multi-Family

Turnkey Investment Opportunity in a Prime Pittsfield Location! Discover this meticulously renovated four-family property where every detail has been thoughtfully updated to deliver strong returns and low-maintenance ownership for years to come. Updates completed in 2024 include: roof, siding, windows, decks/egresses, wiring/service/panels including owners' meter, four new heating systems, four new water heaters, kitchens/baths, LVP flooring, refinished wood floors and tile, plumbing,doors/trim sheetrock paint etc. Each unit is serviced by its own brand-new gas heating system and water heater, providing efficiency and convenience for both owners and tenants.


36 Photos
THE KINDERHOOK GROUP
$430,000
4 BD | 2 BA
Residential - Single Family

Move in ready! New roof and gutters in 2026, maintains original details but has been thoroughly updated. Located on a quiet, tree lined street, 81 Northumberland offers the kind of lifestyle one dreams about. Imagine walking your children to the nearby elementary school, stopping in for fresh pastries at the local bakery, grabbing a coffee on the way home, or enjoying an evening stroll through the established Southeast neighborhood. With a warm, inviting home and everyday conveniences just minutes away, this is more than a place to live - it's a place to build lasting memories.


43 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$469,000
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.


36 Photos
LAMACCHIA REALTY, INC
$469,900
4 BD | 2 BA
Residential - Single Family

Welcome to 30 Lexington Parkway, an exceptionally cherished home in one of Southeast Pittsfield's most coveted neighborhoods. Brimming with timeless character, warmth, and pride of ownership, this impeccably maintained 4-bedroom home blends classic charm with everyday comfort. The inviting living spaces feature a stunning fireplace, hardwood floors, spacious eat-in kitchen, screened-in porch surrounded by the meticulously cared-for private backyard. A finished basement offers room to grow, while flexible spaces adapt effortlessly as a home office, library, studio or gym. Complete with a 2-car garage and conveniently located near parks, recreation, schools, dining, shopping, downtown, and the Berkshires renowned arts and cultural attractions. Come home to a place where memories are made!


49 Photos
MOCKINGBIRD REAL ESTATE
$479,000
4 BD | 3 BA
Residential - Single Family

Beautifully maintained 4-bedroom, 2.5-bath Colonial set on a quarter acre lot with privacy and curb appeal. Enjoy a spacious floor plan featurning a wood-burning fireplace, natural gas heat & hot water and newer replacement windows throughout, including new living room windows in 6/2026. The primary suite offers his-and-hers closets and a private bath. The finished lower level adds valuable living space with a family room, bar area, surround sound and separate storage room with built-in cabinets. Relax outdoors on the deck with a new awning (2026), framed by an arbor & private setting. Additional highlights include metered water, an attached 2-car garage with auto openers and rear storage room. Move-in ready and ideal for everyday living and entertaining!


39 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$490,000
3 BD | 2 BA
Residential - Single Family

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 cooks kitchen and dining room, ample fire placed living room w/ built-ins galore. First floor 1/2 bath, & period details & charm that cannot be replicated today. Upstairs, 3 sizable bedrooms, & a fully renovated bathroom w/ Italian marble counters, tiled walk-in shower & radiant heat. The partially finished lower level features another bedroom for extended family and guests. A large two car garage was added, with exceptional loft storage space above. Be ready to fall in love!


37 Photos
COMPASS MASSACHUSETTS , LLC GB
$495,000
4 BD | 3 BA
Residential - Single Family

Spacious split-level home in Dalton offering three levels of living space and a functional floor plan. Features include an updated kitchen with granite countertops and newer stainless appliances, beautiful hardwood floors, a home office or den and three generously sized bedrooms, including a primary suite with an updated private bath, plus an additional full bathroom. Enjoy central A/C throughout the main living areas for added comfort. Step outside to the expansive deck overlooking the large backyard, perfect for entertaining, relaxing, or outdoor activities. A two-car attached garage adds everyday convenience. Additional highlights include an 8-year-old roof with solar panels and a newer hot water heater. Ideally located close to schools, parks and shopping.


52 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$515,000
3 BD | 4 BA
Residential - Single Family

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.


53 Photos
NOCHER REALTY
$539,000
3 BD | 2 BA
Residential - Single Family

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 newer 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!


32 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$539,000
3 BD | 2 BA
Residential - Single Family

Embrace the beauty of the Berkshires from this thoughtfully updated home, ideally situated on a sought-after street across from Onota Lake. Large windows fill the home with an abundance of natural light, highlighting the warmth and classic character found throughout. The many improvements include an updated kitchen, gorgeous wood flooring that creates an inviting connection to the spacious living room. A fireplace surrounded by contemporary built-in shelving brings a welcoming space boasting seasonal views of the backyard. The dining room with its original built-in cabinetry adds a cozy space for gathering. The newly finished basement offers nearly 1,000 square feet of bonus space with another fireplace, perfect for entertaining, work and/or play space or whatever your heart desires.


58 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$549,900
4 BD | 3 BA
Residential - Single Family

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.


51 Photos
Lamacchia Realty, Inc. - Dalton
$549,900
4 BD | 2 BA
Residential - Single Family

Welcome to 551 Tamarack Road! A beautifully updated and maintained Cape-style home, nestled on 1.28 acres in picturesque Pittsfield, MA!This charming 4-bedroom,2-bath residence boasts a perfect blend of modern amenities and classic charm. Step inside to discover a spacious, light-filled living area, ideal for gatherings and relaxation.The eat in kitchen features contemporary finishes and ample storage, seamlessly connecting to the dining area. Enjoy the convenience of 2 well-appointed bathrooms and generously sized bedrooms, perfect for family and guests.Outside, the expansive yard offers endless possibilities for outdoor activities, gardening, or simply enjoying nature.Meticulously maintained and set in a peaceful setting, this home is a true gem just waiting for you to make it your own!

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