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.

The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked by 3,000-sq ft of stunning living spaces that seamlessly blend design, sophistication, comfort. From the glass walls that open to sweeping views, to its bespoke kitchen or design forward guest suite, every inch has been crafted to inspire. Host gatherings on the spacious screened deck, unwind by the 360 glass fireplace, find solitude in the ''Tower'' - and redefine living, creating, & thriving.

Seize this rare opportunity to complete a 55-unit expansion within an existing condo association. With a majority of infrastructure in place and high demand in the area, this semi-completed development offers exceptional return potential. Originally approved in 2002 as a 40B development, this project is ready to be picked back up where it left off. All current permits, site plans, and engineering documents on hand shall be transferred as part of sale, providing a streamlined path for completion. Don't miss the chance to capitalize on this ready-to-go project in desirable Great barrington.

Great Barrington Compound! Custom built salt box home situated the end of a town dirt road on 32 acres. Bear Town State Forest abuts the property. Heated gunite pool and stunning view of Monument Mountain. Enjoy established gardens including an apple orchard, lilies, peonies, etc. Main house with living room, library, dining room, eat in kitchen, laundry, two powder rooms, attached two car garage. Amenities include a screen porch, 4 wood burning fireplaces, wood floors and views! Second floor with 4 bedrooms, 2 baths, large primary bedroom with views, third floor with two additional bedrooms and full bath. A finished lower level for gym, ping pong, screening room. New oil -fired boiler and HWH Free standing 3 bdr. caretaker house A little piece of heaven!

Experience serene living at the end of a picturesque tree-lined driveway in a secluded family estate in the heart of West Stockbridge. Crafted as a berm home artfully built into the rolling hillside, this turnkey residence glows with natural light in its park-like setting. Ideal for both grand entertaining and quiet retreats, the multi-level home features over five bedrooms or flexible sleeping areas, 4.5 elegantly appointed bathrooms, a dedicated home office, a playroom, and more. The expansive great room overlooks a heated in-ground gunite pool and flows seamlessly onto three distinct blue stone patios, all set against breathtaking views of Tom Ball Mountain. Nestled on more than 25 acres, the property further includes your very own Har-Tru tennis court, a tranquil pond, and abundant

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a - see more

A rare, once in a lifetime opportunity to own an Original Berkshire Cottage! This spectacular property is situated on a 12-acre campus in Lenox, Overleigh was built in 1903 by Samuel Frothingham. Its history is detailed in the popular coffee table book ''The Berkshire Cottages-A Vanishing Era'', by Carole Owens. This property is located just 1.8 mi. from Downtown Lenox and within minutes to the most popular Berkshire attractions. Designed by Adams and Warren out of NYC and built by Joseph Clifford's Sons, a firm responsible for several cottage era constructions and renovations in Berkshire County. A rare find, this property has deep roots in being used as an academic setting for several diverse private residential schools and has been well maintained throughout the years.

A rare, once in a lifetime opportunity to own an Original Berkshire Cottage! This spectacular property is situated on a 12-acre campus in Lenox, Overleigh was built in 1903 by Samuel Frothingham. Its history is detailed in the popular coffee table book ''The Berkshire Cottages-A Vanishing Era'', by Carole Owens. This property is located just 1.8 mi. from Downtown Lenox and within minutes to the most popular Berkshire attractions. Designed by Adams and Warren out of NYC and built by Joseph Clifford's Sons, a firm responsible for several cottage era constructions and renovations in Berkshire County. A rare find, this property has deep roots in being used as an academic setting for several diverse private residential schools and has been well maintained throughout the years.

The historic Shipton Building, built in 1888, is a stylish cornerstone in the downtown Pittsfield business and cultural district. The four-story masonry facade on North Street has four storefronts with a total of over 60 commercial tenants. It is a very popular location for a mix of professional offices ranging from lawyers, designers and service organizations. There is consistent high occupancy and plenty of opportunity for rent escalations.The current owner bought the building in 2018 and has made many structural and cosmetic upgrades. All 131 windows have been replaced with high performance custom historic replicas. Common areas have all been upgraded to LED lighting and flooring is either new new carpet or converted to ceramic tile. A program has been started to replace gas HVAC

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 27 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the region's premier full-service equestrian facility.The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. Equestrian enthusiasts will revel in the compound's state-of-the-art amenities

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 27 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the region's premier full-service equestrian facility. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. Equestrian enthusiasts will revel in the compound's state-of-the-art amenities

225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Build your dream home with seclusion and privacy assured. Enjoy mountain views, spring fed ponds, endless pastures, and serene forested trails. An escape from the world and yet only minutes to town and a little over 2 hours to NY City & Boston. (* Additional Acreage may be available.)

225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Build your dream home with seclusion and privacy assured. Enjoy mountain views, spring fed ponds, endless pastures, and serene forested trails. An escape from the world and yet only minutes to town and a little over 2 hours to NY City & Boston. (* Additional Acreage may be available.)

225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Endless possibilities for the entrepreneur, builder or dreamer. Located a little over 2 hours from NY City, Greenwich & Boston. (* Additional Acreage may be available.)

225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Restore the Country Club, complete the Ranch or create something new. Endless Opportunity. Located a little over 2 hours from NY City & Boston. (* Additional Acreage may be available.)

The Birches....welcome to your new oasis in the Berkshires where every season is memorable. This magical compound has been architecturally redesigned & renovated using the finest materials offering all the modern amenities a buyer wants to live, play, relax and work from, surrounded by 20+ acres of privacy & far reaching protected views in all directions. This stunning contemporary has big open common areas for gathering, first floor primary en suite, guest bedrooms en suite and a private two bedroom guest quarters w/kitchenette, custom crafted wine room, and an exercise room all offering plenty of space for a large crowd or intimacy for a few. Just arrive with your suitcase and enjoy all this impeccably maintained estate has to offer; a beautiful gunite heated pool w/waterfall &

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, turn-of-the-century lake cottage with 530' of lake frontage including its own dock. Built in 1903, the Lakehouse denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and suites all with stunning, private bathrooms. The Lakehouse is exquisitely appointed and furnished with an eye toward showcasing the clean, graceful architectural details of the original lake cottage while adding modern ''creature comforts'' and ''cutting edge'' bathroom design. The Lakehouse is perfect for large families to gather for long weekends or extended vacations year 'round.

Experience the pinnacle of wellness living in this exquisite Canyon Ranch penthouse in Lenox, a beacon of luxury in one of the nation's most revered destinations. Crafted with meticulous attention to detail by William Caligari, this 3,300+ square foot sanctuary is a testament to high-end design and serene living. The residence boasts three generously sized bedrooms, each with its own ensuite bath, ensuring privacy and comfort. An additional half bath adds convenience for entertaining. The expansive great room serves as the heart of the home, with ample space for relaxation and social gatherings. The kitchen is a culinary artist's dream, perfect for crafting nutritious meals in line with the Canyon Ranch ethos of health and wellness. Three fireplaces add a warm ambiance to the residence.

AUCTION BIDDING OPEN! Bidding ends March 1st, 2025. Previously Listed $9,995,000. Current High Bid $5,500,000. Showings by Appointment. In the heart of the Hudson Valley, this expansive 133-acre estate Near Copake Lake, New York, epitomizes luxury and refinement. The property boasts serene water frontage on the 46-acre Chrysler Pond, lush woodlands, and farm facilities, all offering breathtaking mountain vistas. The handcrafted six-bedroom lodge, constructed with timber from British Columbia, spans over 8,000 square feet, featuring a chef's kitchen, an elegant dining room, and a grand living area with a commanding fireplace of local stone and vaulted beamed ceilings. Additional amenities include a breakfast nook, sunroom, outdoor kitchen, and a spa jacuzzi overlooking the Berkshire