Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated, blending original character with contemporary upgrades. Post and beam construction adds warmth and architectural texture, while a sleek gas fireplace anchors the open living and dining areas. The updated kitchen is ideal for gatherings both casual and festive. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two additional bedrooms and a full bath complete the

Located in the desirable, gated community of Woodmont Estates, this thoughtfully updated home offers a timeless layout, flexible living spaces, and easy access to the best of the Berkshires. Inside, vaulted ceilings, expansive windows, and hardwood oak floors create a light-filled and inviting atmosphere, anchored by a gas fireplace and elegant details. The custom kitchen serves as the heart of the home, featuring maple cabinetry, granite countertops, updated finishes, and a layout that flows effortlessly into both formal and casual living spaces--ideal for everyday living and entertaining alike. The primary suite is a true retreat, complete with his and hers walk-in closets and a well-appointed bath designed for comfort and

Unique home overlooking Mount Greylock range. Early morning, afternoon and evening sun fill this 4 bedroom 2.5 bathroom, open floor plan home with light all year round.The entire first floor has been renovated and now has an open floor plan with a new doublesided propane fireplace. Opportunity for single floor living exists since primary bedroom and laundry are on first floor in addition to a half bath and mudroom. Exiting the kitchen you enter a three season sun room with a door to the deck. Second floor consists of 3 bedrooms, a full bathroom and a walk in attic. Recent improvements include new wall to wall carpetingBasement has three areas, a workout room, a finished family room and storage/mechanical area are on unfinished side.

A stunning and modern contemporary home that is MOVE IN READY. It is situated privately on 4 acres, in a wooded, tranquil setting. The home, with 3 bedrooms and 3 bathrooms, has been fully and tastefully renovated in the past 12 years. The main floor features high ceilings, abundant windows, open kitchen with soapstone counters, dining area, and living room, all with scenic wooded views; perfect for entertaining or simply enjoying the natural surroundings. On the second floor...... see ''more''

First time on market in almost 50 years. Located on the north end of Gt. Barrington at Belcher Square is this exceptional opportunity. Boasting two curb cuts, one on Rt 7 aka Stockbridge Rd and the other on Rt 23 aka State Rd. This property is ready for new owners. Situated on .47 +/_ acres are two buildings. At 215 State Rd is a post and beam two story barn with one story additions on two sides. Two garage doors for ease of access. There is a 1/2 bath (cold water only). Utilities are town water, town sewer, 200-amp fuses, natural gas hot air furnace. The second building contains three rental units. Upstairs at 8A Stockbridge Rd is a three-room apartment with galley kitchen and full bath. Heat is oil fired hot water. Electric is 200-amp circuit breakers. Main level at 8 Stockbridge Rd

Located on a quiet country road, this 18.5-acre parcel offers beautiful mountain views, privacy, and a peaceful setting. Just minutes from Williams College, the Clark Art Institute, and town amenities, it's the perfect place to create your ideal retreat in the heart of the Berkshires. The property is under Chapter 61A.

The owners are retiring so this is an opportunity for a new generation to take over this 3 acre parcel with a two large buildings, Was a winery. One building is a beautiful tasting room with a kitchen and two half baths. The other is a heated and air conditioned storage room. See the grapevines and the beautiful scenery. Bring your friends, sit in the gazebo and enjoy the local wine . Minutes to town, Stockbridge and Lenox. Around the corner from Butternut Ski area. Could easily be a full fledged winery again or there are so many possibilities.

Custom built home! Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French doors lead to an inviting screened porch/sunroom. Large private deck overlooking patio with firepit and meticulous lawn. Large mudroom/office. Beautiful living room with bay window, cozy den/family room with wood burning fireplace. Large first floor full bathroom with washer/dryer hook-up. Thoughtful design throughout.

Private Log Cabin Retreat on 18+ Acres with River Frontage -Escape to your own slice of secluded Berkshires with this classic log cabin set on over 18 private acres. Surrounded by nature, this home offers peaceful living with unmatched charm and character.A welcoming wrap-around porch invites you to relax and take in sweeping views of the property. Inside, the main floor features a dining room, a kitchen with access to a bath, and two inviting living areasone opening to a large sunroom, perfect for enjoying the scenery year-round.The lower level offers a cozy living room, bedroom with bath, utility space, and a versatile hobby room with its own fieldstone fireplace. In total, the home boasts 4 bedrooms, 3 baths, and 6 stunning fieldstone fireplaces that create a warm,

Discover the perfect blend of comfort and charm with this stunning contemporary situated on two acres. There is a full-house Generac generator for comfort and peace of mind and central air. The great room is washed with natural light from the wall of windows and has a beautiful gas fireplace to provide additional warmth on cold Winter days. There is a circular flow into the spacious dining room and the updated kitchen making this home ideal for entertaining. A full bath and two charming guest bedrooms welcome visitors and offer opportunities for a home office. The oversized four-season sunroom offers magnificent light that takes in the picturesque landscaped surroundings and woodlands. It features an efficient gas stove for chillier days and screen inserts to help capture Summer breezes.

LOOKING FOR A COUNTRY ESTATE IN THE FOOTHILLS OF THE BERKSHIRES? This spectacular 6,460 sf custom built Colonial home has just been completed and has additional unfinished space over the attached 5 car garage, perfect for car enthusiasts! This spectacular property is set on nearly 5 picturesque acre and sits beside the Worthington Golf Club! Quality throughout w/gorgeous maple hardwood flooring, 8 bedrooms, 6 full custom baths, soaring 10ft ceilings on all 3 levels, exquisite Caesarstone quartz kitchen w/island & farmers sink, spacious 2 room primary suite w/walk-in closet, lots of recessed lighting, second kitchen would make a great pub style hangout, 2 decks (one oversized wrap deck,) new roof, freshly painted exterior & brand new septic! Additional land available!

Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian stands as a true architectural gem, nested amid lush gardens and beautifully landscaped grounds. From its distinctive urn shaped columns to its twin towers, gables and wrap around porch, every detail reflects the grace and grandeur of a bygone era - balanced perfectly with thoughtful modern updates. Sweeping lawn with private patio and mature plantings. Currently configured as a two family residence, the layout offers easy conversion back to a magnificent single-family home, making it ideal for a grand Berkshire retreat, full time residence, or multi-generational living. Inside you will find historical character, original millwork & trim, and updated kitchens & baths. Whether you're seeking a stately

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.

Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must haves' to enjoy in this recently updated property. Steps away from the shoreline of Lake Mansfield and a simple stroll to downtown Great Barrington's many coffee shops, restaurants, bakeries and theaters, this property is the perfect move in ready home!

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just 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 over this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregiver

Discover a rare opportunity to own 181 extraordinary acres in the picturesque town of Adams. Available for the first time, this expansive property features an ideal blend of open meadows, rolling hills, mature woodlands and stunning views - perfect for nature lovers, outdoor enthusiasts, or visionary developers. The land boasts gently sloping topography from east to west, creating a dynamic landscape rich in wildlife and diverse ecosystems. Property borders Savoy Mountain State Forest to the east, providing direct access to hundreds of acres of protected land. Extensive frontage on East Hoosac Street and additional right-of-way access from East Road opens the door to potential development. Priced at just under $5,000 per acre, this is a unique opportunity in the heart of the Berkshires.

An exceptional commercial opportunity on busy Route 7 at the Sheffield-Great Barrington line, this 7.29-acre property offers over 1,000 feet of frontage and unmatched visibility. Formerly a GMC dealership and auto repair shop, the site includes a 5,540 sq ft garage with five oversized service bays and heavy-duty power--ideal for automotive, fleet, or light industrial use. An additional storage building on-site expands functionality.The expansive paved lot can accommodate over 100 vehicles, making it ideal for dealerships, rentals, or display. The location benefits from steady traffic, close proximity to tri-state area schools & businesses, and easy access to downtown Great Barrington's shops, restaurants, and cultural venues.

PANORAMIC VIEW, PRIVACY AND A STUNNING CONTEMPORARY is waiting to become your country sanctuary. As you drive up the long, private driveway, you feel your shoulders relax and then..peaceful thoughts take over as you soak in the sweeping south west view at the top of your private hill. The multi-level design of this home offers living with peace and tranquility for both gathering and quiet time alone, all while capturing the nature surrounding you on 5+ acres. Main level bedroom with private deck, full bath, office, cozy den and open kitchen/dining with direct access to the attached 3 car heated garage for convenience, dramatically opens to the Great Room in one direction and the primary bedroom with fireplace and newly designed luxurious ensuite bath with another guest bedroom and bath on

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. This sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.