49 Bow Wow - A Gilligan Brothers Masterpiece on 30+ Acres!Set on over 30 acres of stunning meadows, mountain, pond access, and forest, the Gilligan family home at 49 Bow Wow Rd comes to the market for the first time.In the second half of the 20th century, the Gilligan Brothers name was synonymous in southern Berkshire County with a quality built home. Founded by three brothers - Matthew, William, and Earl - in the 1940s, Gilligan Brothers homes were often a showcase for the ingenuity and craftsmanship of their founders. And perhaps no home better illustrates their innovative streak than Matthew's family home at 49 Bow Wow Road. Built in 1941 for his family - and retained by them to this day - 49 Bow Wow was stylistically and functionally ahead of its time.

An opportunity to curate a spectacular 10 acre parcel located on the NY/CT border with majestic views to the East and the West. The property is partially cleared and is board of health approved with an existing 4 bedroom septic, electric service, and well. There is currently a 1 bedroom home which could serve as a guest cottage for your three bedroom home or it could be raised and you can build your 4 bedroom dream home. The location is private and quiet and nestled within an area of prime estates, farms and stunning pastoral vistas. Minutes to the pristine town of Sharon, Ct and Amenia, with Metro North just a short drive. Property like this, in a pin-point perfect location is extremely hard to come by.

Incredibly lush and private 80 acre haven with a beautiful, spacious log home, and separate studio apartment above the 2-car garage. Great open living spaces look out onto a mature landscape of gardens and fruit trees. The first floor primary suite opens onto an arbor covered patio and has a second floor sitting room/office. Fabulous screened porch for outdoor living and dining. Two more bedrooms and a bath on the second floor. Nice kitchen and baths throughout. Large partially finished basement offers a great spot for a workshop, gym, media room or kid space. Perfect place to welcome friends and family, or, just relax and enjoy the silence.

Sophistication in the country. Vast open views and fields abound where you can soak up the calm vibe of the country while being a stones throw to cultural venues, fine restaurants, shops, farmers markets, skiing and so much more! This custom built home on 5+ acres welcomes you to swim in the gunite pool. Enjoy your primary suite on the first floor with large walk-in closet and full bath; an eat-in-kitchen with two dishwashers, gleaming quartzite countertops, double wall ovens, a Wolf cooktop and range- a true home chef's dream; the great room where dining and living are centered around the fireplace; a powder room; laundry and craft room; and mud room complete the first floor. 2 guest BR's and a large bath upstairs. Full basement could be finished. Close to the Berkshires!

Majestic oak trees line the road and driveway to this home which ends surrounded by perennial gardens and gorgeous stone work. The stone steps and patio, the timber framed entry and beautiful contrast colors are just the right amount of drama for this colonial farmhouse. Although this home is a spacious home, from the second you enter you feel wrapped in it's warmth and coziness. Picture the snow beginning to fall as the fire is burning in the woodstove insert in the the brick fireplace of the living room. Or settle in for a homemade meal in the dining room next to the wood burning antique oven where the homeowners have actually cooked Thanksgiving dinner. The kitchen is lined with understated, shaker style built ins some with glass paned cabinets which provide lots of storage

Nestled at the end of Brett Rd at the base of bear mountain. This 29-acre parcel includes a charming home with rolling hills, a natural pond, staggered wooded plots leading way to large open hay fields for agriculture or development. The 3-story home includes 3 bedrooms 2 baths. All the bedrooms are downstairs with an island kitchen and large open space on the main floor. The main floor features high ceilings, wood grained walls, slider doors, bay windows and access to wrap around deck. Vast stunning views from the deck feature Bear Mountain all the way to Butter Nut. This property has dual zoning for industrial, commercial residential and agriculture. Property has recently been tested and failed to title 5 Owner acknowledges this is a contingency that shall be addressed prior to closeing

Nestled in the picturesque landscape of New Marlborough, Massachusetts, lies a captivating 1790 dairy farm, boasting an enchanting blend of history and contemporary artistry. This sprawling 94-acre estate features a dynamic terrain, adorned with a sheer rock face, streams, woods, meadow, marsh, beaver pond, stone walls, and a cascading waterfall. Seamlessly integrated into this idyllic setting is a large barn, art studio, and a residence brimming with original details and modern touches. The main house, with its formal front door, welcomes you into a gracious central hall, leading to multiple rooms for entertainment, dining, work, and socializing. The home features four bedrooms, two full bathrooms, two half baths, and four working fireplaces, all warmed by a brand new new furnace.

Easy one level living in Alford; this hip roofed modernized home sits on 14 acres encompassing the Alford Brook. Light/Bright open living, kitchen and dining area makes for the perfect space to spend your days. Wide hall from main entrance has a primary suite with laundry, a den and two guest rooms (or office and guest room). Off the main living space is another full bath. Large wraparound deck on the south side with sunken hot tub and a vegetable garden separating a small deck off the primary. The acreage goes back with a meandering woodland path to the brook and beyond. Awesome oversized attached garage.

Three house compound with direct water front on East Lake, outside of Rhinebeck NY. This is a rare opportunity to acquire a waterfront compound with a strong history of rental income. The cottages have the old world charm of an Adirondack family camp, with modern updates and conveniences. Each home has its own private hot tub and screened in porch.

GREAT STOCKBRIDGE-LENOX HOME with POOLFor TANGLEWOOD + STOCKBRIDGE BOWL (lake) fans - stroll to the Music Shed at Tanglewood in just over 5 minutes, or 10 minutes to YOUR DEEDED ACCESS AT THE BOWL for picnics or kayaking! The back yard is your own summer resort! This 2,829 sq ft home has been substantially renovated & improved since it was purchased in 2018. It now features all the coveted features one seeks in a BERKSHIRE GETAWAY OR FULL-TIME HOME: pool (w/ new liner & systems); beautifully landscaped, very private backyard, patio, fire pit, hot tub & space for outdoor games; screened porch; 1st floor primary suite with fireplace; new kitchen & new great room with gas fireplace since 2018 + 3 ENSUITE BEDROOMS & 5 baths, office/den/add'l sleeping space + a bonus basement area.

IMPRESSIVE 1840's TIMBER FRAME BARN CONVERSION with large open living spaces and exposed beams, has the perfect location! Outstanding construction blends old with new, built by a premier local timber framer D. Lanoue, with modern amenities which include a chef's kitchen, fully renovated bathrooms, A/C, new granite front steps, new roof, and complete with a Level 2 EV charger. The lower level with walkout, makes a great recreation area, with separate workroom and lots of storage. The fenced yard is bordered by woods, affordingtotal privacy as you enjoy time relaxing on the deck. A must see property, with Skiing and athletic center close by, town center and Lake Mansfield just a short stroll away.

Ideally situated in the heart of downtown Stockbridge, this 1860 colonial home has been stylishly updated and is move-in ready. The stunning first floor has three spacious adjoining living areas, including a central dining area and a family room with fireplace. The renovated kitchen has a chef's range and a large island perfect for gathering around. In the rear of the first floor is one of the home's two primary en-suite bedrooms, both with gas fireplaces. Take the back or front staircase to the second floor, which has the second primary en-suite bedroom, a central sitting area, and three more bedrooms, each with their own bathroom. A light filled loft/office and a vaulted-ceiling media room are found at the rear of the second floor - a perfect place for work or entertainment.

A remarkable offering of this restored 18th century Georgian home built in 1764 on almost 4 acres with the possibiilty of an additional building site as part of the listing price; with an early barn and shed opposite the Clark Art Institute. Once located on Main St where the College President's house now sits, it was moved by oxen to its current location in 1800. (RRBrooks.)Restoration efforts follow the Deerfield tradition of interior feather-edged sheathing and paneling, wide pine board flooring and a large colonial cooking fireplace with adjacent beehive oven in the keeping room. 4-5 bedrooms/3.5 baths.

An idyllic setting on 8.34 acres w/panoramic views of lush meadows and protected land. With frontage on the Konkapot River, this is a serene retreat just 15 min from Great Barrington and the rolling hills of Litchfield County. The one level home has a thoughtful layout with a dedicated primary wing and 2 guest bedrooms conveniently located on the opposite side of the house. The heart of the home is the impressive great room, complete with radiant-heated floors, vaulted ceilings and a jaw-dropping stone fireplace. Large windows and doors, newly installed, frame the heavenly surroundings from every room including the open, bright kitchen w/soapstone countertops. Practicality meets style in the contemporary 2-car garage. Improvements include a newer septic system, roof and propane generator.

Spacious five-bedroom, move-in ready condo with high-quality finishes located in the Cottages at Barrington Brook. This warm and inviting end-unit enjoys a quiet, elevated corner of the community. Beautiful views from almost every room of the condo. Open living/dining/kitchen area with high ceilings, blush maple custom flooring, propane fireplace, and crown molding. Also enjoy the views and tranquil Berkshire days from the attached deck and screened-in porch. Thoughtfully designed kitchen with stainless appliances, honed granite countertops, and tumbled marble backsplash. The main level also includes the large primary bedroom with en-suite bathroom and gas fireplace, as well as two additional bedrooms with shared bathroom. Oversized, walk-out lower level with

Spacious five-bedroom, move-in ready condo with high-quality finishes located in the Cottages at Barrington Brook. This warm and inviting end-unit enjoys a quiet, elevated corner of the community. Beautiful views from almost every room of the condo. Open living/dining/kitchen area with high ceilings, blush maple custom flooring, propane fireplace, and crown molding. Also enjoy the views and tranquil Berkshire days from the attached deck and screened-in porch. Thoughtfully designed kitchen with stainless appliances, honed granite countertops, and tumbled marble backsplash. The main level also includes the large primary bedroom with en-suite bathroom and gas fireplace, as well as two additional bedrooms with shared bathroom. Oversized, walk-out lower level with

Always wanted to own a piece of history, but also want peace of mind? This 1900's grand colonial has been thoughtfully renovated to keep the charm of yesterday, but the comforts of today. As you pull down the street, take time to notice the community that surrounds, minutes from downtown Northampton. Walking up the steps, you'll immediately fall for the welcoming oversized porch. Original features blend magically with luxurious updates. Follow the gleaming hardwoods & allow the natural light to guide you into each space, starting with a home office, elegant living & dining room, through the butler's pantry, & into the heart of the home, the kitchen. Picture your friends & family gathering & note that space is abundant. Don't miss the wine room, 6 bedrooms, & 3.5 bathrooms. Welcome Home!

This impressive New Marlborough property offers spectacular views from almost every room. With the perfect blend of country charm and modern living, this sprawling 4 BR, 3 BA home sits on over 3 acres, and is a sanctuary of peace and serenity. Step inside to discover pristine comfort that flows effortlessly, with every detail meticulously curated. Natural light streams through the windows - filling the spacious kitchen and sunlit rooms with warmth. The thoughtful layout includes a kitchen with granite countertops, stainless steel appliances, fresh, updated cabinets, eat-in kitchen area and adjoining dining room. The main floor also includes a spacious living room with gas fire place, office space and sliders to the lovely and peaceful bluestone patio. The second floor includes the

Welcome to this winery and tasting room located in the beautiful southern Berkshires! This business/farm is located right on Rt 7 which is considered the ultimate New England road trip. Capture tourists year round with nearby Tanglewood, the botanical gardens, Butternut ski resort and so much more! This spacious post and beam building consists mainly of two large rooms both with lofts. One, currently a tasting room with a wrap around loft, floor to ceiling windows for abundant light, a dramatic center staircase and french doors leading to the patio and outdoor space. The second room is currently an event center with loft. The tiled lobby has access to storage and a handicapped bathroom. The opportunity exists to live on site with the attached apartment; kitchen, full bath, small

This delightful 18th century farmhouse transports you to a more simple and carefree time. Comfortable, bright spaces abound, both inside and out. A large living room features a beautiful fireplace and a wall of windows overlooking the property. The tasteful, modern kitchen integrates beautifully with the home's lovely historic details. Charming dining room with windows on two sides. A wonderful screened porch runs the length of the north wing, overlooking the lovely 6+ acre grounds with colorful gardens and lawns that roll down to the Roe-Jan Kill, known for its trout fishing. On first level, there's an en suite bedroom, plus a guest suite with sitting room and its own separate entrance. Upstairs, two more inviting bedrooms share a hall bath.