Don't miss this hard to find single floor living opportunity in the highly sought after town of Stockbridge. Offering nearly 2500 sq ft of thoughtful living space, this 3 bedroom, 2 full bath home blends main level convenience and genuine rustic warmth and modern versatility. Inside the home features multiple cozy heat sources for New England winters, including a classic wood burning fireplace as well as two seperate wood stoves. Outside, the property sits on almost 6 acres of private land just 3 minutes from downtown Stockbridge. Open lawn areas offer plenty of room for vibrant flower beds, rich vegetable gardens, or custom outdoor entertaining spaces. Complete with an oversized garage providing ample room for vehicles, storage or workshop. Close to everything the Berkshires offer.

Berkshires Luxury & New Lakeside Living. Enjoy distant lake and mountain views from each first floor room. This elevated ranch style home creates one level living with grand open sunfilled spaces. This floorplan features open floor plan capturing lakeviews from each room on the main living level. This beauty is what you have been waiting for - a brand new never lived in newly constructed home is ready for you to live and enjoy the Berkshires at it's best now. Expansive gourmet kitchen topped with quartz quality counters, stainless appliances, breakfast bar and oversized walk-in pantry. Dining room flows to living room with sliders leading to a glorious continuous wrap-around upper level deck. Custom wire railings enhance views and is oversized for outside dining and chaise lounging.

Nestled within a mixed use residential/commercial block this renovated space is ready for the next creative commercial endeavor. Rent the house and use the studio for art, office, store or Live and work all within walking distance to town center. Thoughtfully brought from a commercial office space to a 2 bedroom, 1.5 bath, bright open and airy living space with 5 parking spots and a nice size yard.

Light, airy & effortlessly inviting this 4 bedroom & 3 full bath home is made for Berkshire Living. Walls of windows & a sun filled sunroom bring the surrounding woodlands into nearly every room, while a brand new oversized deck sets the stage for long summer dinners & relaxing afternoons. A separate grilling deck offers the perfect spot for outdoor cooking & easy entertaining. Spacious interior rooms, abundance of natural light & multiple gathering spaces make this an exceptional year round retreat. Then there's the Otis Wood Lands lifestyle w/ an incredible array of amenities including a private lake, clubhouse, swimming pool, tennis/pickleball & playground. It's the perfect pairing of a beautiful home & a welcoming community offering everything you need to relax, play and entertain.

This Southfield home has been thoughtfully renovated and expanded, blending timeless New England charm with exceptional modern comfort. The stunning kitchen -- featured in Bon Appetit -- just received new stone countertops & sink. A gorgeous, wrap-around screened porch overlooks the entire backyard and stream. A renovated full bath creates the option of a primary suite on the first floor. A third-floor conversion (not included in the square footage) creates a magical hideaway for an office, fitness room or bonus guest space. Among the updates: all-new, multi-zone heating and cooling system, whole-house back-up generator, EV charger, and radiant heat in the kitchen floor. All that and you can roll out of bed for a short stroll to your morning coffee at the beloved Southfield Store.

The road ends here. At the end of quiet Old Quarry Road, still much as it felt 150 years ago, sits a circa 1840 farmhouse overlooking its own broad lawn, with sixty acres of woodland stretching beyond. Thoughtfully expanded over time, the original farmhouse and later addition are seamlessly integrated, yet retain separate entrances, giving everyone a little space of their own. Three bedrooms are in the original house, two more in the addition, and every bedroom has its own private bath. No sharing necessary. Multiple wood-burning fireplaces, two screened porches, an old tennis court and a stone wall between the dining and living rooms add to the story. Once a farm, now a home with history, land and possibility. The road ends here, but the rest is yours. Read on...

Immaculate Center Hall Colonial in one of Lee's most desirable neighborhoods. Beautifully maintained and move-in ready, this inviting home offers 3 bedrooms, 2.5 baths, plus a spacious game/bonus room. The first floor features a wonderful eat-in kitchen with granite counters and abundant cabinetry for the home chef, a large living room with fireplace, formal dining room, and gleaming hardwood floors. Upstairs, the en-suite primary provides a comfortable private retreat with two additional bedrooms. An attached two-car garage adds everyday convenience. Set on a beautiful residential street with a deck--perfect for grilling, morning coffee, or a glass of wine at the end of the day. Exceptionally well cared for plus, need more space, there is a walk out lower level waiting to be finished.

Set on 3.04 acres across two lots abutting protected land, this Executive Ranch is the only single-level home in the gated community of Woodmont Estates. 3,400 sq ft of expansive, easy living, featuring 4bd/2.5ba, a renovated primary bath, updated kitchen, and light-filled four-season sunroom w/ new Andersen windows. Designed for comfort & flexibility, the layout includes a private office, as well as a library w/ custom built-ins. Wide hallways & generously scaled rooms enhance the sense of space & accessibility. Enjoy sunrise views, a seasonal brook, beautiful gardens, & peaceful surroundings. Walkout lower level offers expansion potential. Natural gas heat, central air, central vac, radon mitigation, & major system upgrades already complete.

Immaculate and well-maintained contemporary home in an exceptionally convenient location set on 5+ wooded acres. Designed for easy living and low maintenance, this home offers an open floor plan with high ceilings, wood floors, and a beautiful fieldstone fireplace anchoring the main living space. The kitchen opens to another living area creating a comfortable flow for everyday living and entertaining. Enjoy the lovely screened porch and outdoor deck overlooking the natural setting. Three bedrooms and 3.5 baths, including guest quarters or apartment space for added flexibility. Large two-car garage. It is in a very private setting, but is also a short distance (walking distance) to the elementary and secondary schools. Easy transition for a first floor primary bedroom.

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!

Welcome to a custom-designed architectural haven where clean, modern design meets inviting warmth. Meticulously maintained and lightly lived-in, this spotless, move-in ready retreat offers the ultimate in effortless, single-floor living set against a backdrop of mature perennial gardens, custom walking paths, and complete privacy.Step through the inviting front porch into a bright, open-airy floor plan anchored by soaring ceilings, oversized windows, and rich bamboo floors that seamlessly bring the outdoors in. The heart of the home features a cozy gas fireplace and radiant-heated floors for year-round comfort. The chef's kitchen and main living spaces flow effortlessly onto an expansive wrap-around deck-perfect for alfresco dining while taking in views of the private grounds.

One of the Southern Berkshires' best-kept secrets! This private, family-friendly, four-season community is located near the shores of pristine 175-acre Noyes Pond, a non-combustion-motor lake. This large log cabin sits on 2 wooded acres with no neighbors, offering exceptional privacy. Enjoy evenings on the outdoor patio around the fire pit, making s'mores and creating memories with family and friends. The cabin is being sold with the recently purchased furnishings--everything stays, making this a truly turnkey retreat. The home features 4 bedrooms, 3 full baths, a 4-car garage, and an inviting open floor plan with beautiful vaulted, beamed ceilings. The spacious primary suite includes a walk-in closet. A large recreation room with a convenient back staircase provides additional space for

Located in Lee MA is a waterfront property a home built in 1880 and renovated in 1994. A bucolic location with views of rushing water and mountains. A perfect home for a variety of birds and established gardens. This 3500 sq. ft home offers an open floor plan that includes living room with fireplace, cooks kitchen with island and dining area. Main level includes a private bedroom and bath; screen porch, deck, laundry room/office, powder room, attached one car garage and office with separate entrance. The second floor offers 2 guest bedroom with private baths and PRIMARY with walk in closet, access to a Juliet deck and private studio space. Free standing single garage located at the rear of the property. This property has multiple uses!

Offered for the first time in more than forty years, this c.1880 residence presents a rare opportunity to own a substantial property on coveted Prospect Hill Road, one of Stockbridge's most desirable addresses. Set privately on 3.5 acres just moments from the center of Stockbridge, the property offers the increasingly rare combination of privacy, acreage, and location that defines some of the most sought-after luxury real estate in the Berkshires and Berkshire County.

Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate first floor office with French doors for privacy. The first-floor primary suite boasts a walk-in closet and en suite bath while the walkout lower level expands the living space with a generous family room, two additional bedrooms, full bath and private patio. With 4 bedrooms, 4 full baths, and exceptional space throughout, this home is simply gorgeous and ready to enjoy. Clubhouse, pool, tennis.

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion—with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision—be it modern apartments, stylish offices, retail space, or a dynamic studio. • Spacious and bright with 5,180 sq ft across two levels • Excellent bones

Embark on an entrepreneurial journey to be recreate one of the few lakefront dining spots left in the Berkshires! This exquisite property boasts a stunning waterfront restaurant nestled along the serene shores of Pontoosuc Lake, encompassing just over an acre of prime land. It is fully equipped with a liquor license, a lottery license, and a full commercial kitchen. Furthermore, the property offers exceptional potential for development, complete with direct access to the tranquil waters of the lake.

Introducing Green River Meadows, a new luxury development that prioritizes healthy, sustainable living--ideal for those seeking an eco-friendly lifestyle without sacrificing luxury. Nestled alongside the Green River in Williamstown, just a short distance from the prestigious Williams College and surrounded by the cultural richness of the Berkshires, this community offers an exceptional lifestyle in a prime location.These to-be-built homes reflect a deep commitment to sustainability, seamlessly blending innovative design with environmental stewardship. Built using Passive House principles, the homes are designed to achieve optimal energy efficiency through superior insulation, triple-pane windows, airtight construction, and continuous fresh air ventilation,

Originally the iconic Old Egremont Club, this site has been meticulously reimagined, offering a rare turn-key opportunity. The interior is magazine-worthy, featuring custom finishes and red-and-black checkered floors that set a cinematic, vintage-cool aesthetic. Behind the aesthetic lies a heavy-hitting commercial core fully overhauled in 2023, including new well, septic, 200-amp electric, and industry-best Henny Penny fryers. Situated in low-tax Egremont on the heavily traveled Route 23 corridor -- just moments from Catamount Mountain Resort and downtown Great Barrington. Lease-to-buy option available.

Perched on Mount Hunger is this lovely, private, contemporary four-bedroom, three-bath home located near Lake Garfield, of which there are winter views. The current owners added a huge, beautiful living/dining room with a fieldstone fireplace, cathedral ceiling and huge windows. The renovated kitchen has granite counters with a Viking cooktop and Bosch double wall ovens. A first floor primary suite is complimented by a den and a three-season porch. The second floor holds two guest bedrooms and a guest bath, while the lower walk-out level has a fourth bedroom, a family room, laundry and utility room and a storage room with built-in shelving. Located well off the road with air conditioning, an outdoor shower and fiber internet. A true Berkshire country home with the best town beach nearby.