Just over the hill from Tanglewood, down a quiet country road, this year-round Richmond retreat blends privacy, rustic character, and expert craftsmanship. The heart of the home is the vaulted great room, where exposed beams, a loft balcony, and a wood stove create a warm gathering space that flows seamlessly into a beautifully crafted three-season porch with interchangeable glass and screen panels overlooking the woodland. Thoughtfully designed to preserve the home's original rustic charm, the spacious primary suite is a private retreat featuring vaulted ceilings, a sitting area with a gas stove, an ensuite bath with a soaking tub, and laundry. Wraparound decks further extend the living space outdoors, embracing the natural landscape. The walk-out lower level provides excellent storage

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office,

Welcome to this beautifully maintained ranch home situated in a very desirable neighborhood. This 2 bedroom 2 bath home will surprise you with all its extra living space. The kitchen and bathroom have been nicely updated in the last couple years. The large 4 season sun room is cozy and flooded with light. The large finished basement allows for lots of flexibility, with 1 large family area and 2 separate rooms to use as you see fit. You will love spending time in the private backyard with mature landscaping and gorgeous perennial gardens. Enjoy summers in the above ground pool with an attached deck. Windows are new, roof is less than 10 years old. There is 100 amp electric, efficient gas heat and a pellet stove. This home is ready for you to move right in and enjoy!

Rare opportunity to own a beautifully restored Berkshire cottage at 17 Main Street, perfectly situated in the vibrant heart of downtown Lenox. This remarkable property, originally built in 1883 and once the residence of Gilded Age shipping magnate John Schermerhorn, combines historic elegance with modern comfort. The home underwent a comprehensive renovation between 2021 and 2025, including a new 30-year roof, upgraded electrical and plumbing, 8.5 renovated bathrooms, custom millwork, and restored original hardwood floors. The gourmet kitchen features a Viking 8-burner oven, KitchenAid designer dishwasher, and commercial-grade refrigeration--ideal for private entertaining or everyday living. All systems are new, including a four-zone HVAC and seven mini-splits for year-round comfort.

This charming and move-in ready home invites you to settle into an easy Berkshire lifestyle. The first floor offers the comfort of one-level living, with a bedroom, full bath, laundry, and welcoming living spaces, while the second floor provides additional bedrooms and room for guests. Recent updates include an updated electrical service, refreshed interiors, and a beautiful enclosed porch made for slow mornings and quiet evenings. Just moments from shopping and dining, with downtown Lenox minutes away, Bousquet Mountain Ski Resort & Sports Center 4 minutes away, and Tanglewood about 10 minutes away. Spend your days exploring scenic trails, discovering local favorites, or enjoying the beauty of the Berkshires in every season.

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,

Rare Lakeside Opportunity on Shaw Pond! Incredible opportunity to make this 3-bedroom, 2-bath property your own on the shores of beautiful Shaw Pond. This handyman special needs TLC but offers tremendous potential in a truly rare location. Enjoy lakeside living with the Berkshires right at your doorstep. Whether you're looking for a weekend getaway, investment property, or a home to renovate and customize, this property offers the chance to create something special in an unbeatable setting. Bring your vision and unlock the potential!

Welcome to this spacious 2,784-square-foot home located in the charming town of Cheshire, Massachusetts! offering 3 bedrooms and 1.5 baths, this property provides plenty of room to spread out, entertain, and enjoy all the comforts of home. Inside you will find a generous living room perfect for relaxing or gathering with family and friends. The finished basement adds even more versatile living space, featuring a wet bar and two separate entertainment areas- ideal for hosting game nights, watching the big game, or creating your own recreation space. Outside, the property offers a very large deck for entertaining, relaxing or grilling also a unique combination of outbuildings, including a large barn, garage, shed. Come discover all this home has to offer!

Move right into this beautifully maintained home featuring hardwood floors in great condition and a cozy, inviting living room. The versatile layout offers a convenient first-floor bedroom, two bedrooms upstairs, and space with the potential for a fourth bedroom or office. The home includes a classic 1950s kitchen and a back deck overlooking a very private backyard. Best of all, enjoy total peace of mind with a New roof and exceptional care shown throughout!

The Ultimate Vermont Mountain Sanctuary: Discover total serenity at the end of a winding gravel road. Encircled by 37 acres of pristine woods, a natural pond, and sprawling lawns, this impeccably maintained contemporary estate offers complete isolation from the outside world. Located in peaceful Stamford, you are just minutes from Premier Vermont skiing boating, and hiking, as well as the world-class dining, theater, and art of the Massachusetts Berkshires. The Great Room Experience: Ascent to the 2nd level and prepare to be breath-taken. The spectacular great room features soaring 18-ft cathedral ceilings, rich all-wood finishes, and a magnificent stone fireplace. A towering wall of glass frames panoramic views of the tree-covered mountains. Step onto the massive 20x29 deck to experi

Offered for the first time in 40 years, this White Pines condo is a rare opportunity to own a residence within one of Stockbridge's most storied properties. Rich with musical history, both White Pines and this particular residence have fascinating ties to local and international music scenes. Filled with natural light, this gracious two-bedroom, two-bath condominium offers generous living spaces and an inviting, easy flow. The beautiful great room is the heart of the home, with two distinct sitting areas and a dedicated dining space--ideal for both relaxed everyday living and entertaining. A large primary suite provides a private retreat, while the second bedroom and full bath offer flexible space for guests or creative pursuits.

Welcome to 34 School Street in Lee, the Gateway to the Berkshires! Walk to downtown shops, restaurants, and local attractions from this spacious 8-room, 4-bedroom, 2-full-bath home. Freshly painted throughout, this inviting home features beautiful hardwood floors, first-floor laundry, and a versatile floor plan offering the possibility of a first-floor bedroom. Enjoy two enclosed porches, one in front and one in back, providing additional space to relax. An oversized two-car garage offers plenty of room for vehicles, storage, or hobbies. A separate fenced yard is ideal for pets, young children, or outdoor enjoyment. Convenient to interstate highways, cultural attractions, and all the Berkshires have to offer. A wonderful combination of location, charm, and flexibility!

Investor and contractor opportunity! This two-story colonial is being sold strictly as-is and is ready for a complete transformation. The exterior gives you a head start with vinyl siding and replacement windows, while the interior awaits a full renovation and your personal touch. Bring your vision: restore it as a single-family or explore the potential to convert to a two-family, subject to town approval. This is a great project for flippers, builders, or investors, looking to add value!

Nice three acre lot on a classic New England dirt road. Pretty lot with a stone walls running along a level building area overlooking a small valley. excellent perc rate from a 2001 perc test.