Discover your dream retreat in this stunning log home, nestled on 37 acres of breathtaking land that adjoins over 1,000 acres of serene state forest. This oasis offers an unmatched blend of tranquility and natural beauty, allowing you to escape from the hustle and bustle of everyday life. Imagine sipping your morning coffee on the wrap-around deck, soaking in the picturesque mountain views. Indulge in the ultimate relaxation experience with a soak in your wood-fired hot tub or a rejuvenating session in your outdoor sauna. Step inside and be captivated by the charming open floor plan. The chef's kitchen is a culinary enthusiast's dream, featuring a large island, elegant granite countertops, and a high-end Viking stove, perfect for entertaining guests or creating culinary masterpieces.

Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an open concept kitchen and family room with cathedral ceilings, where sliders lead seamlessly to a large rear deck overlooking a spacious, flat, and fenced backyard; ideal for gatherings, play, or quiet relaxation amid mature landscaping and beautiful gardens.

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 Fame (open floor plan) contemporary home features 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. Ready to move right in? With relatively low inventory level, particularly in Monterey, this listing is a lucky strike extra. Schedule your showing today.

Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open common spaces. The primary bedroom has wood flooring, walk-in fitted closet and tastefully renovated en-suite bath with custom finishes. Included on the main level is the charming half bath, garage with storage and laundry room. The second floor features a large loft flex space with oversized closet, two guest bedrooms and stunning full bath. The lower level walkout is

Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful surroundings. Conveniently located just minutes from Sheffield village, Canaan (CT), and Great Barrington, this versatile property works beautifully as a full-time residence, vacation retreat, or investment opportunity in the heart of the Berkshires. This is a new build, and taxes have not yet been determined.

Architectural gem with lots of glass perched like a treehouse on the backside of Monument Mountain. The open, mid-century modern home was built in 2012 for maximum light, efficiency, and provides glittering views through the trees of the Housatonic River! 2 bedroom, 2 full baths-both ensuite + central AC, and a Scandinavian soapstone wood stove, permit included! Minutes from hiking trails, Taft Farm, Berkshire Mountain Bakery and downtown GB. Also close to town schools, Butternut, Tanglewood, and other Berkshire cultural centers. So quiet, yet close to everything. Design by AIA recognized architect Steve Dietemann.

This brand new just completed contemporary is located in a quiet prime in-town location just moments from the heart of town. This stunning new home gleams with hardwood floors, stainless steel appliances, and provides the latest in heating, air-conditioning comfort. Boasting over 1,700 square feet of stylish living space, including first floor primary bedroom suite, two additional bedrooms, two full and one half baths, and a spacious, insulated two-car garage. This lovely move-in perfect home is nestled on a compact level easy care .2 acre parcel. All of this and offered way below cost. Here are some additional details you will want to review to find out just how exceptional this home is. Every inch of this home has been designed with comfort, energy efficiency, and elegance ... See More

Located in the desirable, gated community of Woodmont Estates, this thoughtfully updated home offers a timeless layout, flexible living spaces, and easy access to the best of the Berkshires. Inside, vaulted ceilings, expansive windows, and hardwood oak floors create a light-filled and inviting atmosphere, anchored by a gas fireplace and elegant details. The custom kitchen serves as the heart of the home, featuring maple cabinetry, granite countertops, updated finishes, and a layout that flows effortlessly into both formal and casual living spaces--ideal for everyday living and entertaining alike. The primary suite is a true retreat, complete with his and hers walk-in closets and a well-appointed bath designed for comfort and

Discover the perfect blend of comfort and charm with this stunning contemporary situated on two acres. There is a full-house Generac generator for comfort and peace of mind and central air. The great room is washed with natural light from the wall of windows and has a beautiful gas fireplace to provide additional warmth on cold Winter days. There is a circular flow into the spacious dining room and the updated kitchen making this home ideal for entertaining. A full bath and two charming guest bedrooms welcome visitors and offer opportunities for a home office. The oversized four-season sunroom offers magnificent light that takes in the picturesque landscaped surroundings and woodlands. It features an efficient gas stove for chillier days and screen inserts to help capture Summer breezes.

Open House Sunday, March 15th, 10:30 AM to 12:00 PM. Beautifully renovated 3-bedroom, 3.5-bath home offering 2,078 sq ft of thoughtfully updated living space. The home features a large open-concept kitchen and dining area, ideal for everyday living and gatherings, and a spacious living room with a centrally located wood-burning fireplace that creates a warm and inviting focal point. Modern finishes are found throughout, along with an attached two-car garage for added convenience.A large back deck provides an ideal outdoor space for entertaining or relaxing in the shade while enjoying the peaceful surroundings. The private backyard retreat also includes a pool, outdoor shower, and an additional half bath, providing ease and functionality when enjoying the outdoor amenities.

First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first level, is a charming screened porch for dining or just taking in the sounds of nature. An open deck on the backside of the main level awaits your enjoyment. The 2nd level contains two VERY large bedrooms Ensuite; both with walk-in closets along with more locations for maximizing the distant views. The finished lower/walkout level has a full bath for a possible 4th Ensuite and living space

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming gazebo and a generous deck, perfect for hosting gatherings or relaxing in your own outdoor oasis.The oversized garage provides ample storage and includes a versatile space above, ready for your expansion ideas. With rough plumbing and electrical already in place, customizing this area is effortless. Located 2 min from Monument Mountain Reservation and 6 min to Main Street.

BE THE FIRST TO LIVE IN THIS HOME!!! This thoughtfully designed contemporary home offers quality construction, energy efficiency, and a rare opportunity for customization--without the lengthy build process. Built with comfort and performance in mind, the home features spray-foam insulation in the walls and attic, fiberglass insulation between floors, energy-efficient windows, and Central Air/Heat system. The walkout basement provides excellent potential for future expansion of living space. The builders are open to conversations with buyers regarding modifications and finishing details, allowing you to personalize the home to suit your needs while moving into a substantially complete, quality structure. Driveway and landscaping will be installed in early Spring 2026.

A Stunning Three-Story Residence with Breathtaking Views for an Easy Care Lifestyle in the Berkshires.Majestic and magical perfectly describe this exquisite three-story mountain top home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community or work at home with glorious views of the Berkshire Hills.Prime Location for Nature and Culture.Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors.

Welcome to this newly remodeled 4,298 sq. ft. luxury residence, perfectly set on 1.53 acres of beautifully landscaped grounds. Built in 1998 and thoughtfully updated, this home blends timeless elegance with modern sophistication. Inside, the open and airy floor plan features 4 bedrooms and 3 1/2 bathrooms, designed for both comfort and style. The chef's kitchen boasts a Sub-Zero refrigerator, Wolf appliances, and a built-in Miele coffee machine, while the dining room is enhanced with custom-built-in fridge and freezer drawers--perfect for hosting. From the attached two-car garage, a custom mudroom with built-in shoe storage leads into a finished home gym outfitted with state-of-the-art equipment.

Your waterfront lifestyle begins at this Hayes Pond sanctuary. From sunrise paddles to sunsets savored from the deck, this home is your private four-season escape in the Berkshires. The modern, open interior is designed to celebrate the water, with soaring cathedral ceilings and a wall of windows that frames the stunning lake view. A cozy wood stove, bright sunroom, and a large deck provide perfect spaces for relaxing or entertaining. This 4-bedroom retreat includes a primary suite featuring a calming soaking tub. Your private, grassy shoreline is your personal gateway to the lake--perfect for launching kayaks, fishing, swimming, or the occasional bonfire. This is the ultimate waterfront escape, where every detail is focused on a life lived by the water.

Once the First Methodist Episcopal Church, built in 1898, this incredible 6,500 sq ft property has been thoughtfully reimagined as a two-family residence and offers unparalleled potential for an artist's dream live/work space. Located just a short walk from downtown on a 3/4 lot abutting an 18 acre nature reserve, this building is ideally positioned to offer both the tranquility of the Berkshires and proximity to its cultural and natural attractions.On one side, the 4,000 sq ft SoHo-style loft spans two levels, blending historic charm with modern luxury. With soaring ceilings, original exposed wood beams, and rich hardwood floors, this 4-bedroom, 5-bath residence provides spacious, light-filled living areas w/ cozy floating sitting nooks that overlook the expansive great room below.

Welcome to 221 Bailey Road in Lanesboro, MA., an exquisite ranch-style home offering approximately 4,200 sqft of luxurious living space. Nestled on 87 acres atop a mountain, this property provides unparalleled privacy and breathtaking views that enhance its serene atmosphere. The open-concept living area is perfect for entertaining, featuring abundant natural light and seamless flow between spaces. Energy efficiency is a hallmark of this home, ensuring comfort year-round while minimizing utility costs. Ample room for family and guests, this stunning residence combines modern amenities with the tranquility of nature. Some of the amenities this home offers a three car garage, heated in ground pool, owned solar and a cozy wood stove for those chilly Berkshire nights.

Discover a stunning oasis in this custom-built contemporary home, ideally situated in a picturesque and private setting. Enjoy tranquil views of a serene pond, beautiful gardens, and flourishing fruit trees, all while basking in an abundance of natural light. This home is a dream for those who love to entertain. The spacious dining room and inviting living room, complete with a cozy fireplace, provide the ideal backdrop for gatherings, complemented by three spacious decks that extend your living space outdoors. Culinary enthusiasts will delight in the oversized cook's kitchen, featuring charming terra cotta floors, premium appliances, a generous center island, and ample dining space. Retreat to the luxurious first-floor primary bedroom suite, which offers a large walk-in closet,

Discover comfortable & gracious living in this impeccably renovated home in Lenox. 4 BRs & 4 BAs approx. 4,000 sq ft of open, modern design. The entire home is filled w/sunlight & gleaming new red oak flooring & a sleek chef's kitchen outfitted with new Bosch appliances, quartz countertops & significant storage. Functional yet luxurious details throughout- from laundry on 2nd level to mini-split systems, fireplace & a sunroom that promises cozy comfort in all season. Step outside into your private natural oasis: enjoy gatherings w/ woodland views around the fire pit, on deck or patio. Newly finished lower level includes a living, dining & media room equipped with kitchenette & full bthrm. Set in one of Lenox's most desirable neighborhoods, this home provides privacy and convenience.