Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location -- where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room -- perfect for gathering with friends and family.

Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two spacious levels. Natural light fills the interior, highlighting beautiful wood floors throughout and adding to the warm, inviting atmosphere. Skylights bring even more light into the home, while the oversized deck provides an ideal setting for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. An oversized two-car garage offers generous parking and storage.

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.

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.

Sun Filled Historic Reproduction Home Built in 2004 seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living & entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee & evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Gt Barrington & Berkshire attractions.

Gracious, stately, and filled with distinct warmth, this impressive Colonial is a rare offering of exceptional scale and character. With more than 4,300 square feet, five bedrooms, two and a half baths, and an abundance of beautifully proportioned gathering spaces, the home offers an extraordinary sense of presence while remaining remarkably welcoming. Original detail remains beautifully intact, including exquisite wood trim, handsome hardwood floors, a grand stairway, and elegant bay windows. Huge windows and wonderful natural light illuminate the large, gracious rooms throughout the day, highlighting the craftsmanship and timeless beauty of the home.

Cross the charming historic-style covered bridge and enter a world of privacy, nature, and endless possibilities. This remarkable 94-acre sportsman's estate offers river frontage on the Farmington River, expansive woods, trails, and room to roam. At the heart of it all is a spacious split-level home with 3 bedrooms and 2.5 baths, featuring fresh paint, new flooring, and a new roof. A 5-bay barn/garage provides incredible space for vehicles, equipment, hobbies, and toys. A separate mobile home offers flexible additional space for a studio, guest quarters, office, or creative retreat. Whether you're seeking a private Berkshire escape, outdoor adventure, or simply a place where the woods are truly your own, 132 North Main Road is a rare opportunity to own your very own Hundred Acre Wood!

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.

Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout. The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's kitchen is thoughtfully designed with quartz countertops, custom cabinetry, and seamless flow into the dining and living spaces--perfect for both everyday living and entertaining. Custom built-ins add character and functionality, while an inviting den or home office on the main level provides flexible space for work or relaxation. Guests will appreciate the privacy of well-appointed en-suite bedrooms.

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings.

A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Rental income? This property has a very nice history of rental income! Who could ask for anything more? Call for a showing today

Nestled in the center of Williamstown, just steps from Williams College, this stunning two-story Colonial stucco home offers timeless charm and modern comfort. Built in 1907, this 4,100 sq. ft. residence features five spacious bedrooms, three full baths, and one half bath. Set on 1.35 picturesque acres, the property boasts a large post-and-beam barn, a beautifully covered stone patio, and breathtaking western views of the Taconic Mountains. The expansive, level backyard is adorned with mature gardens and majestic old-growth trees, creating a serene and private retreat. Don't miss this rare opportunity--call today for your private showing!

Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive building materials. Distinctive circular towers, curved walls, arched windows and premium natural finishes harmonize with the surrounding natural landscape. The grand foyer opens to an expansive kitchen, living, & dining space anchored by a striking Finnish soapstone wood stove and marble fireplace. A sun-filled breakfast room leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

Move-in ready and beautifully upgraded, freestanding home offers the ease of one-level living paired with over 4,600 sf over three finished levels. Four br, 4.5 bat and a walkout lower level. Live at the desirable Miraval golf/resort campus. Hardwood floors flow throughout the main living area, anchored by a striking double-sided fireplace wi stone hearth connecting the living and family rooms. Custom shades throughout add a polished, designer touch. Rear deck offers magnificent views of October Mountain. Upper level includes open loft, private office, 2 br with en-suite baths. Lower level extends the living space significantly, ideal for guests with bedroom, bath, media/exercise room, glass sliders to the outside. Short level walk to pool, golf, fitness, restaurants. Luxury living!

Spectacular Homestead! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 pristine acres with stunning views, mountain paths, and stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36'' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark

Tullar Farm is a rare opportunity to own a remarkable piece of Berkshire history--where timeless architecture, modern comfort, and natural beauty come together across 67+/- park-like acres in South Egremont. With three distinctive residences, a mature specimen tree farm, spring-fed pond, wooded walking trails, and captivating distant mountain views, the estate offers an extraordinary sense of privacy and place, while remaining just moments from restaurants, shops, and the many cultural and recreational offerings of the Berkshires. At the heart of the property is The Tullar House, a substantial 6-bedroom, 5,000+ square-foot antique Dutch Gambrel dating to 1761 and reported to be the second-oldest house in Egremont. Carefully preserved while thoughtfully adapted for modern living, the

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary is awaiting buyers final finishes and offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook--creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. SEE LIST OF ITEMS TO BE FINISHED IN DOCUMENTS.