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 full and 1 half bathrooms,A dramatic great room flooded with natural light,Three fireplaces, A charming three-season screened porch

A Landmark Berkshire Estate of Extraordinary Provenance. 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 and a rare opportunity to become the next steward of Berkshire history.

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County

EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for entertaining. A stunning wrought iron detail by Ivan Bailey enhances the staircase.. A media room with glass-paned sliders and built-in bookcases completes the exceptional living space. The first floor primary ensuite is a true retreat, boasting a soaring vaulted ceiling and two large walk-in closets. The second floor offers three additional bed rooms, and two full baths.

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main

Brookside Acres awaits your arrival, privately sited on 15 + acres, on one of the most scenic country roads in Richmond. This exquisitely renovated Contemporary offers a plethora of amenities for the person looking for a private retreat for a few or someone that likes to entertain and gather with a crowd. From the moment you enter your monitored driveway you realize Brookside Acres has it all; beautiful woodlands, acres of groomed lawn, established flower gardens, mature landscaping and the private stone pathway to the running stream side patio. Owned solar system, a whole house generator, a lighting system that lights up the house with an evening arrival, in ceiling sound speakers on the main level and pool area...no detail has been left undone.The interior of this 5 br, 5 bth

April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. MORE

Stunning Views! Exquisite Tudor-style stucco estate set on more than 18 breathtaking acres with panoramic views and a winding approach that creates an extraordinary sense of arrival. Bright, airy, and thoughtfully designed, this 5-bedroom, 5-bath residence blends timeless architecture with modern comfort and exceptional indoor-outdoor living. The heart of the home is a stunning great room featuring soaring ceilings, abundant natural light, and hardwood floors throughout. An open-concept layout flows seamlessly into the generous chef's kitchen, complete with a professional-grade gas range, spacious dining area, and direct access to the expansive deck overlooking the rolling landscape. The main-level primary suite offers privacy and convenience with a spacious bath and ....

As seen in Architectural Digest, this meticulously reimagined 1875 farmhouse compound unfolds across 11.5 lush acres on a quiet, bucolic dead-end country road, with protected views. Brought to life in collaboration with AD100 design firm Sachs Lindores and landscape design by Judy Murphy, the property is full of historic character with refined modern comfort. The compound includes a four-bedroom, four-bath main house, a one-bedroom, one-bath guest house and a large barn relocated from New York State. Outdoors, a private heated in-ground pool, gas-fired pizza oven and fire pit, orchard, fenced vegetable garden, and poolside outdoor shower create an idyllic country retreat. All systems were replaced in 2019, with high-speed internet and central A/C, just minutes from Great Barrington.

Set along the shores of beautiful Pontoosuc Lake, this extraordinary private estate captures the very best of Berkshire waterfront living. Enjoy sweeping lake and mountain views, a private dock, heated pool, outdoor kitchen and fire pits designed for unforgettable entertaining. Inside, open-concept living showcases the views, while a chef's kitchen with Wolf and Sub-Zero appliances anchors the home. Multiple private living quarters, a game room, loft and home office offer exceptional flexibility. Extensive garage and parking space provides room for cars, boats and recreational toys, while gated and fenced grounds offer privacy. Come for the views. Stay for the lifestyle. Make Pontoosuc Lake home.

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires.

Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a tennis court, guest house, swimming pool, gazebo, and gym shed to a three-level modern house evoking the New England barn. From the third-floor master loft suite with private terrace and kitchenette, a skylit central stair leads to the mid-level kitchen/dining room with fireplace nook, between stone patio and screened porch. An atrium living room includes cozy coffered-ceiling seating by a fireplace. A cherry-walled study with private porch, pass-through full bathroom, and family room complete the floor. Family or guests on the lower floor enjoy four bedrooms and three bathrooms, as well as laundry room and two-car internal garage.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back

Experience a rare Zen-inspired retreat in the heart of the Berkshires, brilliantly designed to exist in harmony with its natural surroundings. Set on nearly 120 acres of protected land with striking rock outcroppings, sweeping mountain views, and frontage along the Williams River, this architecturally significant contemporary offers a true sense of privacy, tranquility, and escape- all just minutes from downtown Great Barrington. Designed by renowned architect Steven Haas and constructed of steel, glass, concrete, and wood, the main residence is defined by dramatic volumes and German Sorpetaler door and window systems that dissolve the boundary between indoors and out.

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens.

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!

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.

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.