Just up the road from the world-renowned Jacob's Pillow Dance Center, this stunning architect-designed sanctuary sits on 14 sprawling acres with panoramic views of Greenwater Pond and the rolling valley beyond. At the heart of this masterfully crafted 1998 home is the great room with soaring vaulted ceilings centered on a magnificent oversized stone fireplace. This spectacular space is banked by a wall of glass windows and doors leading to an impressive 60-foot deck for a front row seat to dazzling sunsets. The great room flows seamlessly into a sleek and thoughtfully appointed kitchen, and a spacious dining room perfect for entertaining a crowd. The primary suite serves as a personal haven, featuring its own stunning vistas, dual primary baths, and a small office. The lower level...

Own a piece of Williamstown history with this beautifully preserved Greek Revival modern farmhouse, set along the Green River on just under 20 picturesque acres. This exceptional property offers a rare combination of historic charm and modern comfort, with ample acreage for farming or livestock, ponds, barns, an in-ground pool, and more. The main residence features 5 bedrooms and 4 bathrooms, while the attached guest house offers 2 bedrooms and 2 bathrooms, providing flexibility for extended family, guests, or multi-generational living. Step inside this timeless home to discover thoughtful modern upgrades designed for everyday living. A spacious mudroom at the rear entrance keeps daily life organized, while the stunning kitchen—complete with stainless steel appliances, granite countertops

Live, Love, & Play in Blythewood Estates priced favorable $250,000 less than assessed value for a quick sale to allow you enjoyment this beautiful Berkshire season. A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom suit

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 8.94-acre lot (MLS #248342), featuring a private well, installed septic system, underground electric, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.

Contemporary home built in 2012 on over 11 acres walking distance to Stockbridge center. Original house was taken down and this sun-drenched home was built on the saved footprint. Main floor has a small living area off the entry open to large kitchen and dining with sliders to the deck, primary suite with walk-in closet and deck access, 1/2 bath and access to the oversized garage. Second floor has vaulted ceilings, a large landing, second living area, 2 guest rooms with a hall bath and another primary suite. There are two porches off the second floor, one small off the primary and the other flanking the East side - covered for protected enjoyment. The Konakpot Brook winds through the back of the 11+ acres giving access to fishing and just relaxing by the water.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

A rare opportunity to experience a lakefront living on beautiful Lake Buel. This distinctive log cabin captures breathtaking water views from nearly every room and is filled with natural light. The dramatic great room features a soaring cathedral ceiling with exposed beams, rich wood floors, and a handsome fireplace, creating an inviting setting for both intimate gatherings and grand entertaining. Designed for effortless one-level living, the home offers four bedrooms and three full baths, including a private primary suite with en-suite bath, plus a dedicated office. A generous deck overlooks mature landscaping, the lake and private waterfront with dock which is an idyllic setting for morning coffee, and summer gatherings. A truly exceptional Berkshire lake retreat. A must see!

Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining.

Elevated Living - Inside and Out! Exceptional design and craftsmanship distinguish this stunning home. The single-level interior is warm, sophisticated and filled with natural light, with the kitchen, dining and living areas flowing together in one open space surrounded by specialty windows and French doors. Set on four private acres amid the highest peaks in South County, the home offers immediate access to premier hiking and protected lands. Locally sourced Massachusetts walnut floors, Scavolini cabinetry, Miele and Sub-Zero appliances, extensive custom woodwork, shoji-inspired glass sliding doors, and a dramatic stone fireplace wall speak to the quality and attention to detail throughout.

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

Magical Egremont setting. Step into timeless charm with the comfort and craftsmanship of a beautifully renovated 1860 home abutting Karner Brook. The brook flows just beyond the sitting room and deck overlooking the beautiful landscaping and bridge that leads to the garden and brand-new outbuilding. Offering three/four bedrooms, three bathrooms, and over 3,000 square feet, this distinctive property blends historic character with thoughtful modern upgrades, including cherry cabinetry, granite countertops, a Sub-Zero refrigerator, Viking six-burner range and hood, and two dishwashers. Wide-plank pine floors, beautiful woodworking, and a fireplace create inviting spaces throughout.

Nestled among spectacular rhododendrons that burst into bloom each spring, this architect-designed contemporary home offers a seamless blend of natural beauty and timeless mid-century modern inspiration. Designed byarchitect Andrew Daland, the residence features expansive windows that frame peaceful pastoral views and fill the home with natural light. Designed for comfortable one-level living, the main floor includes the primary living spaces, while the lower level provides exceptional accommodations for family and guests with two bedrooms each with en suite full baths, and a spacious family room. The open-concept great room boasts a cathedral ceiling, a fireplace, built-in bookcases, and flows effortlessly into the kitchen. . . .

Exceptional Federal style reproduction farmhouse located in a peaceful setting on a scenic country road. Offering 3-4 bedrooms, 3.5 bathrooms, beautiful hardwood and marble floors. The kitchen with Viking range, custom cherry cabinets, granite countertops and walk-in pantry opens to a family room with a brick Rumford fireplace. The formal dining room opens into the living room. There are French doors to a heated sunroom that connects to a barn/garage with 2nd floor great room and full bathroom. The grounds include a bluestone patio and Goshen steps to the home. Property setting has mature landscaping and perennial gardens. Adjacent undeveloped 2.5 acre lot included.

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings.

Entertainer's Delight! Tucked away in one of Sandisfield's most scenic settings, this quality-built log home offers over 4,600 sq.ft. of finished living space, plus an additional 2,000+ sq.ft. in the walkout basement ready for living, recreation, or storage. Crafted with exceptional materials, the home features soaring ceilings, expansive gathering spaces, and a warm, inviting atmosphere perfect for entertaining or everyday living. Multiple decks provide an ideal setting to dine, unwind, and enjoy the peaceful natural surroundings. Experience the perfect balance of privacy and convenience, just 20 minutes to Guido's and downtown Great Barrington, 30 minutes to Lenox and Tanglewood, and 15 minutes to Ski Butternut. A true Berkshire gem for year-round living, weekend retreat, or investment!

Experience upscale, maintenance-free living in desirable Devon Meadows, ideally located near Lenox and Stockbridge and just 5 minutes from Tanglewood and the many cultural and outdoor attractions of the Berkshires. This spacious luxury condominium features an open floor plan perfect for everyday living and entertaining. The first floor offers a primary bedroom suite, laundry, and a versatile fifth bedroom ideal for an office or den. Upstairs are three spacious bedrooms, two full baths, and a comfortable family room. Enjoy the privacy of a peaceful country setting with the convenience of being minutes from dining, recreation, shopping, and all that the Berkshires has to offer.

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

An incredible opportunity to surround yourself with privacy and exceptional views of Mt. Greylock. This amazing contemporary with detached guest house is sited on 4.5 acres. The main house offers 4 bedrooms, 2.5 bathrooms, kitchen with butler's pantry, granite countertops and modern appliances. The kitchen flows into the formal dining room w/wood burning fireplace and access to a covered deck. The living room with vaulted ceilings is enhanced by a floor to ceiling fieldstone propane fired fireplace and access to a large inviting deck. A hexagon barn was completely renovated into a delighful guest house with private deck, kitchen, bathroom, 1st floor bedroom and additional sleeping area on the 2nd floor. The property is enhanced by beautiful professional landscaping. Many Upgrades.

A remarkable turn-of-the-century Colonial where timeless architecture, meticulous care, and gracious proportions come together beautifully. Set against a backdrop of sweeping Berkshire views, the home captures a sense of elegance and permanence rarely found today. Rich in character yet beautifully suited to modern living, this is a home that feels as extraordinary as its setting. and cutting-edge modern comfort. Designed for both entertaining and intimate family life, this c1930, 6800 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully designed to meet the needs of modern living. These units feature elegant wood floors and come equipped with all necessary appliances, including dishwashers and in-unit laundry facilities. Central air conditioning ensures comfort year-round, while tiled double-sink bathrooms add a touch of luxury. Ample storage space is available in each unit, allowing residents to keep their living areas tidy.