luxury real estate for sale Great Barrington, United States

Welcome to Serenity Hill. This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires. Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind. The vaulted ceiling in the kitchen adds a sense of light and openness, while seamless transitions between the kitchen, dining area, and living room create a space that feels both cohesive and welcoming. A cozy wood-burning fireplace anchors the living room, adding warmth and charm to the heart of the home. With 3 bedrooms and 2.5 baths, every space feels intentional, comfortable yet refined rendering this home ideal for both everyday living and effortless entertaining. Thoughtful design choices enhance the home's warmth and inviting atmosphere. From the living room, multiple doors open onto a private back deck, creating a natural extension of the home's inviting flow. Beyond the deck, you'll find your own private sanctuary: a peaceful koi pond, an inviting in-ground pool, and a hot tub perfect for unwinding under the stars. Whether you're savoring quiet mornings in nature or hosting lively summer gatherings, this property offers the perfect balance of serenity and connection. This is more than just a home, it's a true Berkshire retreat, where timeless style shines in one of the area's most desirable settings.

Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings--a two-car garage and a garden house. The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined, restorative bath, and walk-in closet/dressing room. To the right, a spacious dining room, well-appointed kitchen, screened porch, and hallway to two bedrooms and full bath. The U-shaped floor plan embraces a secluded formal garden, reflecting pool with fountain, patio with pergola, and 40' lap pool. Completed in 1998, every element of the residence attests to architectural intelligence, superior craftsmanship, and love for the bucolic landscape. The high level of quality is evident in the visually commanding millwork, true stucco exterior, lath-and plaster walls in the principal rooms, east and south pergolas, west-facing screened porch, and sensitive choreography of space. With roots in the classical architecture of ancient Rome, this is a thoroughly modern dwelling replete with whole-house fan, air conditioning, generator, security system, 630-foot drilled well, and chef-ready appliances. The result is a home that feels both sculptural and deeply connected to its setting. With protected views, total privacy, and proximity to South County amenities (7 minutes to Guido's), this is a rare Berkshire offering -- serene, architecturally stunning, and eminently livable.

Offered fully furnished and ready to enjoy, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions. *Seller Financing may be available.

Perched high on Baldwin Hill! Set far back from the road on a beautiful 2.5-acre lot, this thoughtfully updated South Egremont residence offers a rare balance of scenic tranquility and unbeatable convenience. Positioned to capture sweeping mountain views, the property places you seconds from charming Egremont village, minutes from vibrant downtown Great Barrington, and right down the road from Prospect Lake and French Park. The owners have completed major updates so you can simply arrive and unpack. Recent improvements bring fresh energy throughout the home, including brand-new siding, new windows that flood the spaces with natural light, and a refreshed kitchen featuring new flooring and brand-new appliances. Outdoor living is seamlessly woven into the home's design. A lovely, quiet screened-in porch provides a private sanctuary to enjoy gentle breezes and peaceful mornings. Whether you are seeking a turnkey primary residence or an effortless Berkshire retreat, this Baldwin Hill gem places you moments from acclaimed dining, local parks, and cultural destinations. A distinctive property offering fresh updates and a setting that feels worlds away, yet sits close to everything that makes the region so desirable.

Discover a rare blend of modern functionality and classic charm in this meticulously-maintained Cape, ideally situated on over 3.5 private acres in the sought-after, low-tax town of Egremont. With a serene woodland backdrop, this bright and airy home offers an elevated living experience with open-concept flow and seamless indoor-outdoor integration. Thoughtfully designed with wheelchair accessibility at the forefront, this home features expansive, light-filled spaces including a chef's kitchen and open dining area, and a screened porch. Beyond the main living quarters, the lower level hosts a versatile apartment, perfect for guests or multi-generational living. Just moments from French Park and the cultural heartbeat of Berkshire County, this 4-bed, 3-bath home provides a private sanctuary without sacrificing proximity to the region's premier attractions.

OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This timber frame contemporary features an open floor plan with beautiful, wide-plank pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the main level and a wood stove on the lower level add warmth and charm. Move in ready! With a relatively low inventory level, particularly in Monterey, this listing is a rare gem.

This new-construction Craftsman Contemporary on private Terra Ferma Drive delivers sharp lines and bright living spaces. Anchored by vaulted ceilings and custom details, the open-concept layout flows directly to an expansive deck overlooking serene wooded wildlife. The five-bedroom, three-bath footprint provides a highly flexible layout for remote work, hosting, and modern living, supported by an attached two-car garage and a large yard, perfect for outdoor summer entertainment. Situated on a premier South Egremont cul-de-sac, the roadway connects directly to the Karner Brook Wildlife Management Area for instant trail hiking access, while keeping you minutes from Catamount skiing, Great Barrington, and low Egremont taxes. Clean, current, and highly efficient.

Offering the rare and coveted 'lake life' on Lake Buel, this unique property presents an extraordinary opportunity to establish your own Berkshire footprint on an expansive 2-acre parcel. Comprising 90% sun-drenched, open meadow, the large lot serves as the ultimate blank canvas with potential for a stunning architectural expansion, a custom family compound, or agricultural designs. While the existing cottage provides a peaceful, private retreat set back from the road, the true crown jewel is the property's dedicated lake access--offering the right to install your own private dock or boat slip on one of the Berkshires premier motorized lakes. Bring your vision to this exceptional property and start living the Berkshire lakeside dream today.

Perched high on one of Egremont's most desirable country roads, this exceptional estate offers breathtaking panoramic views stretching more than 30 miles across rolling meadows, mountain ranges, and Prospect Lake. Facing south and surrounded by approximately 15 private acres, the property combines natural beauty, privacy, and convenience just minutes from downtown Great Barrington and major Berkshire attractions. This contemporary residence was thoughtfully designed to capture the spectacular scenery from nearly every room. Soaring ceilings and sun-filled living spaces create a warm and inviting atmosphere throughout the home. The residence features 5 bedrooms, 5 and a half bathrooms, and a dramatic great room flooded with natural light. You will also find three fireplaces, a charming three-season screened porch, and: -fully finished walk-out lower-level with great views -heated gunite swimming pool with multiple entertaining areas -outdoor shower -attached two-car garage -high-speed internet -wine cellar with capacity for 1000 bottles Whether relaxing beside the pool, entertaining guests by the fire, or enjoying the ever-changing views from the porch, this property lives like a classic New England country estate while offering all the modern conveniences expected today. A rare opportunity to own a private Berkshire retreat with extraordinary views, timeless appeal, and unmatched access to the region's cultural and recreational attractions.

Perched atop a breathtaking ridgeline with some of the most extraordinary panoramic views in the Berkshires, this remarkable almost 18-acre estate parcel is one of only seven exclusive homesites within this private enclave. With the most recent neighboring estate having changed hands for $5.6 million, the property's exceptional pedigree and enduring value are unmistakable. Surrounded by more than 220 acres of permanently protected conservation land, the property offers unparalleled privacy, timeless natural beauty, and direct access to a protected greensward ideal for hiking, cross-country skiing, and year-round outdoor enjoyment. A handcrafted stone bridge spanning a tranquil woodland stream welcomes you to an expansive, level building site with coveted southeastern exposure, perfectly positioned to capture dramatic sunrises, rolling hills, forested vistas, and ever-changing Berkshire skies. The entrance, approach, dwelling site, and selective clearing have all been thoughtfully completed, providing an exceptional canvas for a world-class estate. The property spans two of the Berkshires' most desirable low-tax towns--11.2 acres in Egremont and 6.8 acres in Alford and borders New York State, offering the perfect blend of Berkshire culture, Hudson Valley charm, and convenient access to major metropolitan destinations. Perfectly situated in the heart of the Berkshires--home to Tanglewood, Jacob's Pillow, exceptional farm-to-table dining, boutique shopping, renowned cultural institutions, and endless outdoor recreation--the location balances complete privacy with remarkable accessibility. Hudson, New York, with direct Amtrak service to New York City, is nearby, while Manhattan's Upper West Side is approximately two hours away. Boston is just 2½ hours, Albany one hour, and Hartford 1½ hours. With an existing well, roughed-in driveway, excellent percolation, and permanently protected unobstructed views, much of the essential groundwork has already been completed. Opportunities of this caliber are exceedingly rare--a chance to create a legacy estate in one of the Berkshires' most coveted and thoughtfully planned settings.

Enchanting Egremont! Positioned on a beautiful 5.3 acre lot in Egremont, this solidly built home offers a rare combination of privacy and accessibility. A tree lined driveway leads to this peaceful Berkshire retreat, conveniently located with quick access to the Taconic State Parkway. Inside, you'll find over 2,500 square feet of living space highlighted by a dramatic living and dining room featuring a soaring two-story ceiling, skylights, an interior balcony, and a wonderful wood-burning fireplace. The spacious kitchen is complemented by a separate breakfast room with slider access to the outdoors, offering an ideal setting for everyday dining and entertaining. The home offers three spacious bedrooms and two full bathrooms, along with a versatile first floor den that can easily serve as a home office, guest room, or potential fourth bedroom. All three bedrooms feature slider access to the rear deck, creating a seamless connection to the surrounding landscape. Generous closet space throughout adds to the home's functionality. Enjoy front and rear decks, a beautiful natural setting, and seasonal mountain views. The property provides exceptional privacy while remaining close to Great Barrington and the area's amenities, recreation, dining and cultural attractions. A rare opportunity to own a private Berkshire retreat in one of Southern Berkshire County's most desirable locations.

Don't miss this hard to find single floor living opportunity in the highly sought after town of Stockbridge. Offering nearly 2500 sq ft of thoughtful living space, this 3 bedroom, 2 full bath home blends main level convenience and genuine rustic warmth and modern versatility. Inside the home features multiple cozy heat sources for New England winters, including a classic wood burning fireplace as well as two separate wood stoves. Outside, the property sits on almost 6 acres of private land just 3 minutes from downtown Stockbridge. Open lawn areas offer plenty of room for vibrant flower beds, rich vegetable gardens, or custom outdoor entertaining spaces. Complete with an oversized garage providing ample room for vehicles, storage or workshop. Close to everything the Berkshires offer.

Some land just feels right the moment you step onto it. This 2.5-acre parcel on River Road in prime Monterey has that quality, a generous level clearing that invites something to be built and loved here. With 550 feet of road frontage, the practical bones are exceptional. To the east and north, the property borders the Berkshire National Fish Hatchery, a working conservation landscape where trails thread through protected woodlands and the quiet restores. Across the road, the Konkapot runs. In spring, snowmelt fills it and you can hear it from the clearing. After a summer thunderstorm it rushes and tumbles, the sound filling the trees. Look closely in May and you may find old peonies pushing through the grass. A farmhouse once stood here. Something of it lingers.