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!

Charming home brimming with character and far more space than meets the eye! A lovely front porch with mahogany floors welcomes you to gracious living and dining spaces, wood floors throughout, and a stately fireplaced living room. The updated kitchen features an abundance of cherry cabinetry, plus a first-floor laundry, half-bath, den, and a useful office addition. Upstairs offers three ample bedrooms--including a primary with his/hers closets--and an updated bathroom with a walk-in shower. The walk-up attic provides additional storage or could easily be finished. Outside, find a detached one-car garage, large back deck and a great fenced-in back yard perfect for pets and fun. Sidewalks to town; minutes to Laurel Lake and Lenox. A well loved and cared for home, ready for its next chapter!

Discover the timeless appeal of this beautifully renovated mid-century modern split-level home, thoughtfully designed across four spacious levels. Offering two bedrooms and two full bathrooms, this unique property features flexible living space with the potential for a third bedroom, home office, family room or hobby space to suit your needs. The stunning living room showcases soaring vaulted ceilings, hardwood floors, expansive windows and a french door leading to the deck, creating an open and inviting atmosphere. Situated on two scenic acres with breathtaking mountain views, this property offers the perfect blend of privacy and tranquility. Recent and extensive renovations provide a stylish move-in ready

ADAMS! Dynamite Berkshire Land. Bordering Greylock Glen Land into Greylock Mountain State Reservation. 1,000's & 1,000's acres of direct access to preserved forestlands & fresh water brooks, waterfalls & ponds. A nature enthusiast dream getaway. Enjoy it all right from your own 83 acres - hike, bike, hunt & snowmobile directly from your own property. Direct access to a vast network of protected trails including the Appalachian Trail. Simply enjoy the wilderness & use for basic camping or build your own mountain paradise. Enjoy Mt. Greylock Views. Located close to town for all the in-town amenities. Easy access North into North Adams, Williamstown & Southern Vermont and South to Cheshire, Lanesboro, Pittsfield, Lenox & Stockbridge. Only about 40 minutes to I-90 connection.

Privacy, space, and the beauty of the Berkshires come together at 125 Town Hill Road. Set on nearly 3 wooded acres in the peaceful town of Sandisfield, this 4-bedroom, 3-bath contemporary offers a private retreat surrounded by nature. The home features comfortable living spaces, a screened porch, spacious deck, finished walk-out lower level, and a private tennis court. Enjoy the serenity of country living while being conveniently located near lakes, hiking, skiing, restaurants, galleries, and the charming towns of the southern Berkshires. A special setting for a year-round home or Berkshire getaway.

: Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare Theatre Company, museums, Housatonic River and more.

'ON THE HILL' Cozy 4 bedroom 1925 Cape, HOUSE BEING SOLD ''AS IS'' WALK TO TOWN AND LAKE MANSFIELD. Living room with mini split, custom built cabinets in DR, Large primary bedroom with mini split, large family room, OPEN FRONT PORCH WITH VIEWS. BACK YARD PATIO FOR COOK OUTS. Attached 1 car garage, TOWN WATER AND SEWER. So much charm, house needs updating. DONT MISS THIS GEM !!

Rare 22-acre wooded parcel offering exceptional scale and privacy in scenic Egremont. With over 700 feet of continuous road frontage, the property delivers easy access and versatile building site options--ideal for a private multi-structure compound, a substantial country estate, or thoughtful division. The acreage features mature hardwood canopy, rolling topography, and established trails throughout, providing complete rural seclusion just minutes from South Egremont village, Catamount Mountain Resort, and downtown Great Barrington. A versatile South County land holding built for quiet country living.

Rare 22-acre wooded parcel offering exceptional scale and privacy in scenic Egremont. With over 300 feet of continuous road frontage, the property delivers easy access and versatile building site options--ideal for a private multi-structure compound, a substantial country estate, or thoughtful division. The acreage features mature hardwood canopy, rolling topography, and established trails throughout, providing complete rural seclusion just minutes from South Egremont village, Catamount Mountain Resort, and downtown Great Barrington. A versatile South County land holding built for quiet country living.

Welcome to 1350 Massachusetts Ave -- a distinctive North Adams property offering space, character, and a rare combination of indoor and outdoor amenities. With 4 bedrooms, 1.5 bathrooms, and an expansive lot, this home offers room to live, entertain, relax, and make it your own. A true highlight of the property is the two-level wrap around deck, creating an exceptional outdoor living space that connects the home's porch and garage. Whether you're hosting summer gatherings, enjoying a quiet morning coffee, or spending evenings outdoors, this unique setup provides an abundance of usable space and multiple areas to enjoy.

DON'T JUDGE A BOOK BY IT'S COVER! This is a must see. Beautifully renovated from 2020-2025, this 3-bedroom, 2-bath Ashmere Lake cottage offers an ideal blend of modern updates and timeless lake-house appeal. The open living, kitchen, and dining layout provides bright, flexible space, complemented by an enclosed front porch for additional seasonal enjoyment. Located just a short walk to the private association beach, this property also features an indoor wood stove and an inviting outdoor firepit area, making it a perfect year-round or seasonal getaway.

Welcome to your own private slice of the Berkshires! Nestled on 3.09 picturesque acres in the town of Cheshire, MA where taxes are low and land is beautiful. This beautifully maintained 3- bedroom, 2 bath home offers the perfect blend of comfort, privacy and natural beauty. From the moment you arrive, you'll appreciate the pride of ownership this well kept property. The inviting home features spacious living areas, comfortable bedrooms with the primary having a balcony to relax on. Step outside and discover what truly makes this property special. The expansive yard is beautifully landscaped, providing plenty of space for gardening and recreation, or simply relaxing while enjoying the peaceful surroundings.

Great opportunity to be close to downtown Lenox on a quiet side street! This Lenox duplex with separate utilities includes lots of updates for a move-in ready, or rent-ready experience. Hardwood flooring in much of the space, first floor laundry on each side, updated baths and kitchens. One side is 3 bedrooms; the other side contains 2. Town water/sewer; close walk to the bus line.

This well-maintained mixed-use property offers excellent flexibility for both commercial and residential use. The building is currently configured as two separate units. The first floor features a bright commercial space with large front-facing windows that provide excellent visibility and natural light--ideal for office or retail use. The space includes a private bathroom, dedicated heating and air conditioning, and a water filtration system for added convenience. The second floor offers a comfortable three-bedroom residential unit with a full bathroom, an open-concept kitchen and dining area, and attractive wood flooring throughout. The property is equipped with two separate heating systems to efficiently serve each unit. Additional highlights include ample parking in front and back.

Wonderful opportunity to own 19 acres in Stockbridge for your dream home! The parcel features acres of deciduous trees with an abundance of peacefulness and tranquility. Gentle upward slope from the street then levels off. Providing several options for building. Freestanding fireplace/chimney remains from a former homestead. Norman Rockwell Museum, Chesterwood and Berkshire Botanical Gardens down the street. Charming downtown Stockbridge within 3 miles. Close proximity to Tanglewood, Lenox and Great Barrington. Presently in Chapter 61 for tax benefits. Sellers to complete a perc test upon accepted offer.

The drive to this beautiful parcel takes you off the main road, past farms, cottages, and estates—all within a mile or two. Hidden away in one of the most scenic parts of Monterey and surrounded by larger holdings and hundreds of acres of conserved, trust-protected land, this property offers peace and privacy rarely found. The land is mostly level before gently sloping down to a brook on the east and a stream and pond to the south. Located just down the road from the Gould Farm Harvest Barn and the beloved Roadside Store Café, this is a great area for walking a dog, on the surrounding roads or on nearby hiking trails. With conservation lands and established homes all around, this is a truly exceptional and enduring setting.

STOREFRONT/OFFICE/RETAIL/COMMUNITY SPACE ALSO WITH A 2-3 BEDROOM APARTMENT. ALL SEPERATE UTILITIES. PLENTY OF PARKING AVAILABLE FRONT AND BACK.

Spacious 2+ bedroom, 3-bath end-unit condo in Mountainside Hemlock Village. Fully furnished and turnkey, with parking at the door and a short walk to the slopes. Strong rental history and excellent investment potential.

Country Living at its best! Discover the perfect blend of space, comfort and opportunity with this large 4-bedroom, 2-bath home on 10 acres (consisting of two 5-acre lots). The welcoming layout includes a first floor bedroom and a convenient first floor laundry, making daily living easy and accessible. The great room boasts cathedral ceilings, creating an open and airy feel, perfect for gatherings. The spacious kitchen features ample counter space and cabinetry. Upstairs are three more bedrooms and a full bath. Need even more room? Theres an unfinished room over the 3-car garage just waiting for your finishing touches. Outside is a large fenced backyard with plenty of room for gardens, play and pets.

Beautiful ranch with attached garage and inground pool with new fence! Upon entering the home you will be welcomed by a cozy living room with wood burning fireplace. The kitchen is open to the dining area, which has sliders to the newer Trex deck with electric awning, backyard and pool. The primary bedroom offers two closets and private primary bathroom with walk-in shower. There are 2 additional bedrooms and full bathroom, for a total of 3 bedrooms and 2 baths. Vinyl siding, vinyl replacement windows, city water/sewer and a new high efficiency heat & hot water system complete this home! Plus there are two sheds! This home sits on 0.71 acres, and the adjacent 0.53 lot is also being included, for a total of 1.24 acres in the beautiful town of Lenox, just minutes from Tanglewood and town!