The mid-century retreat you've been waiting for. This classic home sits on over 4 private acres, delivering the ultimate Berkshire lifestyle with a bright, open floor plan and two cozy fireplaces. With 4 bedrooms, 3 baths, a large office, and a sun room looking overlooking your oasis, the layout offers perfect flexibility for guests or remote work. Outside, your private resort features a heated swimming pool and a dedicated tennis or pickle ball court tucked at the end of a quiet road for unmatched seclusion. Modern upgrades including a large solar array and a new heating system drastically reduce utility costs. Experience total privacy while staying minutes from everything that makes Great Barrington a premier Berkshire destination.

Sitting right on the Lenox-Lee line, Katydid Cottage is one of the few freestanding homes at Fox Hollow - your own house, your own private patio, with Lenox and Tanglewood just up the road. It feels like a single-family home but comes with the ease of condo ownership, so your weekends go to the lake instead of the upkeep. The main floor is where this one really works. The kitchen is bright and open to a big dining room, and the living room has a gas fireplace for the cold months. The primary suite is on the first floor too, so you can live on one level if you'd prefer.

Perfectly poised and priced! This immaculately maintained four-bedroom residence, set on an acre of land, delivers three levels of sophisticated living space designed for both effortless entertaining and quiet sanctuary. The property balances a serene, retreat-like setting with beautiful mountain views and unparalleled convenience to local amenities and top-tier Great Barrington schools. The home is enveloped by a lush and mature landscape, offering a changing tapestry of flowering color and seasonal interest throughout the year. Cross the welcoming mahogany front porch an ideal vignette for morning coffee or evening relaxation into the expansive main level. The heart of the home is an open-concept great room featuring beautiful cherry wood floors, anchored by a warm fireplace, built-in

Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the living room, dining area and kitchen, highlighted by soaring beamed ceilings abundant natural light, and a gas fireplace. A bright sunroom to choose a book from its floor to ceiling bookcases. The deck overlooks the mature landscaping, pool, and pool house. The walkout lower level includes a second kitchen, providing space for guests. A Berkshire retreat just minutes from the cultural attractions!

Completely reimagined from top to bottom, 1790's Colonial blends historic New England character with modern luxury in a truly one-of-a-kind Berkshire setting. Located directly across from Pontoosuc Lake, the property offers stunning lake views, exceptional craftmanship and endless possibilities for live/work, business venture or investment in business/residential zone. Stunning kitchen featuring radiant heat, quartz countertops, high end appliances, oversized center island with dramatic full waterfall quartz sides flowing on every exposed edge. First-floor bath/laundry w/radiant heat. All three bathrooms have been fully renovated with spa like appeal and upscale design. Large living room/dining room, 1st floor bedroom with lake views, 2 sunporches all on main leve

Tucked away in one of Lenox's most desirable neighborhoods, this contemporary ranch has been completely renovated with no expense spared, offering effortless single-level living and a seamless connection to the outdoors. Vaulted ceilings, walls of glass, and an abundance of natural light create an open, inviting atmosphere, while nearly every room overlooks the beautifully landscaped, private backyard. Designed for both everyday living and entertaining, the thoughtfully planned floor plan centers around a stunning eat-in kitchen featuring quartz countertops, premium Thermador appliances and custom floor to ceiling millwork with an easy flow into the spacious living room with a gas fireplace, formal dining area, and an expansive sunroom with electric heat for extended seasonal enjoyment.

Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a private rear patio and deck. A welcoming cedar-decked front porch, French doors, and a heated two-car garage highlight thoughtful design. Basement level with High ceilings, and plenty of windows could be easily finished. Built with foam insulation and advanced mini-split climate systems, this home delivers modern efficiency in a serene Berkshire setting, convenient to CT and the Great Barrington.

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,

THIS is the one! Set on 1.53 beautifully landscaped acres, this 4BR, 3.5BA home delivers 4,298 sq ft of incredible living. The renovated chef's kitchen is what dreams are made of--Sub-Zero refrigerator, Wolf appliances, built-in Miele coffee maker, oversized island & custom cabinetry-plus built-in fridge/freezer drawers in the dining room. Cathedral-ceiling living room with fireplace, sunroom, dedicated office, dreamy laundry room & custom mudroom add to the wow factor. Outside, an expansive Trex entertaining deck is separate from the enclosed saltwater pool, with a fire pit, lush grounds & fruit trees beyond. The finished lower level adds flexible living/fitness space. Upstairs offers generous rooms ready for your personal touch. The price reflects the opportunity to make them your own.

Stunning architect designed space with soaring ceilings, floating staircases and numerous high-end features. Ideally situated on nearly 3/4 acre abutting an 18-acre nature reserve. Just a short walk to downtown Lee shops and restaurants. Lots of room for a pool, tennis court, and/or pickleball court. Minutes from the best places in the Berkshires. Great investment opportunity with the nearby $100 million Eagle Mill development. Lots of room with 4,000 square feet of living space plus a separate 2,500 square foot area with large stained glass windows to create a second dwelling unit, studio, chapel, gym, office, or entertainment extravaganza. Combining the best of new construction with old charm, you need to view this amazing space to experience its magnificence!

Rare offering of over six acres ''On the Hill'', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace.. porch-privacy-garage..open acreage bordered by woods.. walking distance to Main Street, Skiing and Lake Mansfield nearby... Five bedrooms, three baths. Formal living room. Plenty of room for expansion.

Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat along with 2.5 updated bathrooms.

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, Stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim all summer in your own pond. Pull a trophy buck in the fall. Hike to the peak and back country ski down in the wintertime. Be the first to catch a trout in your own private trout stream.

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

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.

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.

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly Views of October Mountain. Plenty of room for family and friends.

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.

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.

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.