99 houses for sale in 01244

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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

Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, providing flexible space for guests, hobbies, or a home office. This home has seen many updates since 2019, including a new furnace, oil tank, front siding, and all new windows on the front of the house. Beautiful hardwood floors were added in the living room, dining room, and first-floor bedrooms, while the kitchen, laundry room, and den feature durable new laminate flooring. Additional highlights include a walk-out basement. With some updating, this home has tremendous charm and potential - a wonderful opportunity to create your dream space while enjoying the character and generous layout this property already offers. All

3 BR 2 Bath Home with tons of storage and lots of space. Great opportunity for a small homestead or someone looking for a home with shope space and outbuilding. BEING SOLD AS IS

Set on four private acres along a quiet stretch of road near the Housatonic, this is a property that keeps to itself. No sightlines from the neighbors, no road noise to speak of, just the sound of the brook that runs through the back of the yard. This is a place built for quiet enjoyment, and the land delivers it in full. The gardens are the kind that take decades to get right, and someone got them right. The driveway is lined with rhododendrons that light up every spring, and from there the whole landscape is paced to bloom straight through summer. Fruit trees, azaleas, perennials, blueberries, raspberries. Walk it in July and you understand: this wasn't landscaping, it was devotion. And for all that's established, there's still room to put your own touch. Inside, the first floor opens up and flows, with wood floors throughout and a wood-burning fireplace that anchors the whole space. A full bath sits on the main level. Upstairs, the primary has its own en suite, and the other two bed

Step into the timeless character and charm of this remarkable historic property, built in 1750 and set on four picturesque acres. Blending centuries-old craftmanship with thoughtfully updated modern amenities, this special home offers a rare opportunity to enjoy historic living without sacrificing today's comforts. The home features three classic farmhouse bedrooms including a first-floor primary with a fireplace. There are two modern bathrooms, each tastefully updated with tile showers and one with a jetted tub. The bright, open kitchen is warm and inviting, with beautiful light-wood counters, counter-height coffee bar and ample space for hosting and creating. The dining area accommodates a large farmhouse table, perfect for family gatherings. Beautiful wide-plank wood floors, abundant natural light, thoughtful updates, and a tranquil setting make this home delightful as is-or the perfect canvas to create your dream country retreat. The property continues to impress with a deck and st

Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a legendary head start for a premier stable, a grand creative studio, or an architectural centerpiece for your new estate. The property is directly abutted by conservation land, ensuring your privacy and pristine views are preserved forever. T

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently located on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth and craftsmanship of another era. 16 rooms, 5 bedrooms, multiple baths and 4 fireplaces, the home features beautiful wide-board floors, period details, sun-filled rooms and gracious proportions. A large three-season porch and welcoming front deck extend the living spaces and add to the home's timeless village appeal. With its rich history, wonderful scale and multipurpose zoning offering intriguing possibilities, this is a property ready for its next chapter-an opportunity to preserve its past while creating a home for generations to come. There is something truly special about a home that has been part of a village for more than two centuries. Built in 1819, this iconic Sheffield antique stands near the historic town center and predates the

Spacious 4-bedroom 1+1/2 bath Cape with several useful storage buildings and a convenient 2 car attached garage. Heated sunroom with sliding windows, Eat in kitchen with access to back patio, Livingroom with knotty pine paneling and wood burning stove. FIRST FLOOR has 2 bedrooms, full bathroom with walk in shower, LR, kitchen and sunroom. UPSTAIRS has two bedrooms and a half bath. Large wood stove in the basement. Oil furnace for entire house. Passing Title V

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 72 acres surrounding the house include a screened hut overlooking a private beaver pond, a stream, and paths through the woods

Set on four private acres along a quiet stretch of road near the Housatonic, this is a property that keeps to itself. No sightlines from the neighbors, no road noise to speak of, just the sound of the brook that runs through the back of the yard. This is a place built for quiet enjoyment, and the land delivers it in full. The gardens are the kind that take decades to get right, and someone got them right. The driveway is lined with rhododendrons that light up every spring, and from there the whole landscape is paced to bloom straight through summer. Fruit trees, azaleas, perennials, blueberries, raspberries. Walk it in July and you understand: this wasn't landscaping, it was devotion. And for all that's established, there's still room to put your own touch. Inside, the first floor opens up and flows, with wood floors throughout and a wood-burning fireplace that anchors the whole space. A full bath sits on the main level. Upstairs, the primary has its own en suite, and the other two bed

Enjoy the peace and privacy of country living on this spacious 1.75-acre property, beautifully set back from a quiet country road. The level backyard offers plenty of room to relax, entertain, and enjoy the outdoors, with established fruit trees, blueberry and raspberry bushes, a fire pit, and a deck overlooking the expansive yard. A hot tub adds the perfect touch for unwinding at the end of the day. This raised ranch features 3 bedrooms and 2 full baths, with a comfortable and functional layout. The main level boasts brand-new laminate flooring throughout, new exterior doors, and a bright kitchen equipped with new appliances, abundant cabinetry and counter space, plus a convenient breakfast bar. The spacious primary suite offers his-and-her closets and a private full bath featuring featuring double sinks and a relaxing garden tub. Laundry is conveniently located on the first level. Outside, the property offers a 22' x 24' garage with an additional carport on the backside, providing pl

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

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

Move right into this beautifully renovated mid-century Cape, where modern updates blend seamlessly with timeless charm. Designed for easy single-floor living, this bright and airy home features an open-concept kitchen, dining, and living area that creates an inviting space for both everyday living and entertaining. The living room is highlighted by a soaring cathedral ceiling and abundant natural light, enhancing the home's spacious feel.The thoughtfully designed layout includes a private primary suite with an en suite bath,offering comfort and convenience. French doors open from the living room to a rear deck overlooking a fire pit area, creating the perfect setting for outdoor gatherings, relaxing evenings, and enjoying the surrounding landscape.Ideally located just minutes from downtown Great Barrington, Ski Butternut, and the public boat launch at Lake Buel, this move-in-ready home provides easy access to the best of the Berkshires, from outdoor recreation to dining, shopping, and

This recently renovated cottage, set on 4 woodland acres in beautiful Monterey enjoys close proximity to Lake Garfield, for boating and swimming, and plentiful hiking trails throughout the town. With 750 square feet of bright, clean, efficient living space, and a large detached garage, the cottage is the perfect Berkshires getaway. Recent upgrades include a spacious deck, interior painting, a refurbished bath and partially fenced back yard. Truly a little gem in the woods! Offered fully furnished. Move in for the Summer!

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

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. Tucked away in a completely private setting yet just minutes from town, this exceptional property is approximately two minutes from Sheffield's Cobble and the Appalachian Trail, offering easy access to hiking, nature, an

Welcome to 19 Buckingham Lane, a completely turnkey, beautifully curated waterfront retreat designed by internationally acclaimed interior designer Jess Cooney of Jess Cooney Interiors. Offered fully furnished, this newly renovated home sits directly on the shores of Lake Garfield and features four bedrooms and three baths across three levels. Soft earth tones, richly textured wood finishes on floors, walls and ceilings, and elegant stone surfaces create a relaxed yet sophisticated atmosphere for lakefront living. Tucked into a private cove, it offers exceptional peace and seclusion while the expansive deck provides the perfect setting for entertaining with sweeping water views. And if you don't own a boat, you're in luck-one is included with the

Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is offered with 3 business rentals and 2 apartments creating a living and income opportunity

Perched on a hill overlooking a scenic valley road, this 4-bedroom Dutch Gambrell offers a secluded country setting just a few minutes from town. This vibrantly-designed home opens into a handsome petrol-green kitchen with polished concrete floors and an ample dining area framed by French doors. The kitchen/dining area flows into an inviting living room anchored by a herringbone tile propane fireplace, a warm gathering space for family and friends. Just off the living room the 1st floor primary suite is a cheerful retreat with it's own striking classic black-and-white tiled bath with glass shower surround. Upstairs 3 guest bedrooms, a full bath and an upstairs playroom/lounge offer plenty of room for guests to relax. On the basement level there are two unheated semi-finished spaces for exercise and Media viewing. The lush back yard features a beautiful stone patio and hot tub. An attached 2-car garage with EV charging completes the package. Easy access to hiking, swimming, and everythi

Nestled among spectacular rhododendrons that burst into bloom each spring, this architect-designed contemporary home offers a seamless blend of natural beauty and timeless mid-century modern inspiration. Designed byarchitect Andrew Daland, the residence features expansive windows that frame peaceful pastoral views and fill the home with natural light. Designed for comfortable one-level living, the main floor includes the primary living spaces, while the lower level provides exceptional accommodations for family and guests with two bedrooms each with en suite full baths, and a spacious family room. The open-concept great room boasts a cathedral ceiling, a fireplace, built-in bookcases, and flows effortlessly into the kitchen. Additional highlights include a screened gazebo, an attached two-car garage, and the opportunity to purchase the abutting 10-acre parcel with a stream, offering enhanced privacy and recreational possibilities. Home and adjoining acreage are available together for a

Nestled among spectacular rhododendrons that burst into bloom each spring, this architect-designed contemporary home offers a seamless blend of natural beauty and timeless mid-century modern inspiration. Designed byarchitect Andrew Daland, the residence features expansive windows that frame peaceful pastoral views and fill the home with natural light. Designed for comfortable one-level living, the main floor includes the primary living spaces, while the lower level provides exceptional accommodations for family and guests with two bedrooms each with en suite full baths, and a spacious family room. The open-concept great room boasts a cathedral ceiling, a fireplace, built-in bookcases, and flows effortlessly into the kitchen. Additional highlights include a screened gazebo, an attached two-car garage, and the opportunity to purchase the abutting 10-acre parcel with a stream, offering enhanced privacy and recreational possibilities. Home and adjoining acreage are available together for a

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26

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