South Egremont MA Real Estate & Homes for Sale

Own a piece of history in this pristine setting. Charming 4 BR 3 BA home, situated on 11.95 acres adjacent to hundreds of preserved land on one of Southern Berkshires most revered scenic roads. The current owners have updated the property preserving the integrity by installing Marvin triple-glaze windows, cotton insulation, energy efficient heat pumps & 2-zone forced air furnace. The exterior has new cedar clapboard siding & metal roofs. The home includes a 4-car heated garage with ample space above, an in-ground salt water swimming pool, & custom post & beam barn. A stunning 2-story 1800 sq. ft. converted timber-frame barn/studio sits across the road, a perfect place to set up an art studio, or perfect for extended guests. With pastoral views to protected lands. SF includes house & barn.

Own a piece of History in this pristine setting. A Charming 4-Bedroom 3-Bathroom home situated adjacent to hundreds of preserved land on one of Southern Berkshires most revered scenic roads. The current owners have preserved and updated the property with Marvin triple-grazed windows, new cotton insulation, energy efficient heat pumps and 2-zone forced air furnace. The exterior has new cedar clap board siding and standing seam Metal roofs. The home includes a 4-car heated garage with ample space above, in-ground salt water swimming pool, and a custom post and beam barn. Additional acreage and converted timber-frame available.

Come and enjoy one-level living on approximately 16+ acres of picturesque, flat land with breathtaking mountain views and the tranquil sounds of a babbling brook. Nestled in a serene setting, this updated ranch-style home offers a perfect blend of modern amenities and timeless charm. Step inside to discover a thoughtfully designed layout with three spacious bedrooms and two newly renovated bathrooms, providing a comfortable and inviting retreat for residents and guests alike. The interior boasts a seamless flow and warm wood floors that lead to a great room ,stone fireplace creating an ideal space for relaxation and entertaining. Natural light pours in through sliding doors, to inground gunite pool. separate building lot included.

In 2021, The Freeman was transformed utilizing high-quality materials from an aging nineteenth-century estate to a clean and modern getaway and top-performing rental property. The main house, renovated to be 100% carbon-neutral, features six fireplaces, two dining rooms, a library, 1500sqft bluestone deck and more. The Freeman sits atop 40 acres of greenery to explore, containing a tennis court, four-acre vineyard, mountain views and a dock to access Harman Marsh Pond. Individuals, wedding parties, and corporate retreats alike have come to The Freeman to enjoy its secluded feel while being close to key Berkshire attractions like Catamount Ski Area, Bash Bish Falls, and downtown Great Barrington. This property is just over 100 miles from both Boston and New York City.

First time to the market, this beautiful property has all that you need to enjoy the Berkshire lifestyle. Custom built in 1994, this lovely home has a comfortable open floor plan. High cathedral ceilings, tall picture windows, and skylights let the light stream in. A large screened in porch flanked by two decks invite you to relax outside and take in the views. A first floor primary bedroom with an ample ensuite bath and a walk-in closet completes this level. The second floor has three spacious bedrooms, and two full baths, one ensuite. The lower level is partially finished, complete with a wine cellar, sliding doors to the yard, and access to a two car garage. A large yard with a private setting rounds out this idyllic escape, ready and waiting for its next loving owner!

Experience the quintessential village charm in this delightful Cape Cod-style cottage nestled in the heart of Copake, NY and picturesque Hudson Valley. Enjoy gatherings in the spacious great room featuring a welcoming gas fireplace, creating a perfect setting for relaxation and entertainment. Step out onto the charming screened porch, where you can savor the fresh air and tranquil surroundings, ideal for morning coffee or evening unwinding. Just a leisurely 2-hour drive from NYC.

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 library with built-in cherry cabinetry is the perfect spot to curl up with a good book, while the great room with its dramatic fireplace is an ideal space for hosting guests or enjoying a quiet evening at home. This property is the ultimate destination for anyone who loves the great outdoors. The swimming pool and tennis court provide terrific opportunities for recreation and fun. Hike, explore and connect with nature on the surrounding acreage, or on the nearby Appalachian Trail. There is plenty of space on the property to build a guest house or other additional structures to suit your needs. Whether you are seeking a peaceful retreat or an active lifestyle, this property is a remarkable opportunity--a once-in-a-lifetime opportunity to own a piece of paradise in the heart of the Berkshires.

This stunning and immaculate home offers a blend of modern comforts and classic charm in a picturesque location with beautiful views. The blend of Contemporary design with Cape Cod style creates a timeless aesthetic that combines elegance with functionality. The tasteful renovation shows quality craftsmanship and attention to detail. The abundance of natural light from eastern and western exposure creates a warm and inviting ambiance while showcasing the scenic views. Top-of-the-line appliances in the gourmet kitchen for those who enjoy cooking and entertaining. The four bedrooms and 3.5 baths provide space for family or guests, offering comfort and privacy. The stunning four-season sunroom with walls of glass offers a serene space to relax and enjoy the beauty of each season. See Supp This stunning and immaculate home offers a blend of modern comforts and classic charm in a picturesque location with beautiful views. The blend of Contemporary design with Cape Cod style creates a timeless aesthetic that combines elegance with functionality. The tasteful renovation shows quality craftsmanship and attention to detail. The abundance of natural light from eastern and western exposure creates a warm and inviting ambiance while showcasing the scenic views. Top-of-the-line appliances in the gourmet kitchen for those who enjoy cooking and entertaining. The four bedrooms and 3.5 baths provide space for family or guests, offering comfort and privacy. The stunning four-season sunroom with walls of glass offers a serene space to relax and enjoy the beauty of each season while connecting with the outdoors. The flow between the kitchen, living , and dining room allow for easy entertaining. Located just above the charming village with a general store, post office, and cafe, yet 3 miles to the bustling downtown of Great Barrington, the property is a perfect balance of tranquility and convenience. 26 Pine Crest Hill Road offers a lifestyle that combines luxury, comfort, and natural beauty, making it a fabulous choice for those seeking a peaceful yet sophisticated living environment in the southern Berkshire County area.

Perched at the edge of South Egremont, this stately 1900's structure offers the ideal confluence of residential home and business opportunity. The residence section is a meandering home that has four bedrooms and 2.5 baths, and is filled with sought-after details including post and beam framework throughout and a great room with cathedral ceilings, a roomy loft and a double-height wall of southern exposure windows that allow the sun to stream in. The adjacent commercial section is comprised of sprawling, expansive rooms on both floors, with an elevator for easy access. Its finished condition makes it ideal for a yoga studio, gallery, boutique, co-working space the only limits are its new owner's imaginations. And in a charming hamlet that already boasts Berkshire favorites including the popular restaurant The Old Mill, Kenver sporting goods and the South Egremont Spirit Shoppe, it's just waiting for the next beloved attraction.

Escape to tranquility in the Berkshires with this stunning 4000+ square foot residence boasting an open floor plan, 2 fireplaces, large sunroom, 2-car garage, formal dining and wrap-around front porch, offering both luxury and privacy. Featuring four bedrooms including a lavish primary suite with a fireplace, this home is designed for relaxation. Outside, a gunite pool and expansive stone patio create an idyllic retreat, complemented by a wall of glass overlooking the pool from the living space. Additional features include a finished basement and a third floor living room complete with a full bathroom and private office space, both providing additional space for recreation or relaxation. This is the perfect spot to embrace the epitome of New England living in this exquisite property.

Embrace the timeless elegance of this 1800s antique home nestled in the quaint village of Egremont. Offering a prime location, and situated on nearly 2 acres of lush, manicured grounds, this enchanting property offers a rare opportunity to own a piece of history in a picturesque setting. As you approach the residence, you'll be captivated by its historic charm and character, from the classic architecture to the meticulously maintained perennial beds and apple trees that adorn the landscape. A screened porch provides the perfect vantage point to admire the scenic views, along with the large carriage barn which provides additional storage and space. Inside, the home features 5 bedrooms with multiple inviting living spaces that beckon you to unwind and relax. Whether you're curling up with a good book in the charming library nook or gathering in one of the spacious and inviting rooms, every corner of this home exudes a sense of comfort. Large rooms offer plenty of space for living, dining, and entertaining. From the elegant hardwood floors to the historic details and period features throughout, every aspect of the home reflects a bygone era of craftsmanship and quality. Walking distance to the village, Less then 10 minutes to Great Barrington, and 15 minutes to Hillsdale NY.

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 to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+ year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by. Carriage lanterns, shutters adorned with intricate heart motifs, stately marble walkways, and stone walls all add to the sense of romantic history. Complementing this historic dwelling is a striking Timber Frame barn conversion crafted by a renowned local builder specializing in restoration. This 3,000+ sq ft 3-bedroom residence features a magnificent 2.5-story Great Room with hand-hewn beams, plastered walls, and natural light cascading in creating a warm and inviting atmosphere. Two walnut staircases flanking the walls add drama to the room leading to separate bedroom wings. The Primary is private and comfortable with sitting area, fireplace, and ensuite bathroom. The open-concept kitchen, dining, and living room layout complete with radiant heat flooring and a soaring fireplace seamlessly blends modern comfort with rustic charm. Breathtaking views of the pond are enjoyed from the common areas leading to a stunning stone patio. The generously sized first-floor Den/Office with a half bath and additional fireplace provides room for seclusion. A silo made into a rock-climbing gym adds a little whimsy to this impressive residence. Further enhancing the estate is a lovely carriage house with 1,000+ sq ft of living space with 2 bedrooms, a full kitchen with an open living and dining area, and 1 full bath; 3 garage stalls and a sweet potting shed. An impressive original working barn completes the property leaving room for the imagination. Tullar Farms' blend of meticulously kept grounds and accommodations creates a welcoming canvas for residents to express their own creativity and ideas. Situated on the border of New York and Connecticut and just a short drive from downtown Great Barrington, Berkshire School, Catamount Mountain Resort, and other Berkshire attractions, its prime location offers the best of both worlds - peaceful seclusion and easy access to amenities and activities. A perfect place for individuals looking to cultivate a unique living space while still being close to the vibrant offerings of the surrounding areas.

Quintessential historic waterfront property in the charming village of S. Egremont. This lovingly maintained, spacious antique home retains gorgeous period details -- wood floors, beautiful woodwork, original windows with vintage glass throughout. Country kitchen with pantry, washed in morning light. Fireplaces in dining and living rooms, large family room with French doors to spacious back deck for entertaining. Sun-filled artist studio (or office), quietly tucked away from the 3 large bedrooms upstairs. A generous wraparound front porch gets lovely evening light, while the large back deck is bathed in sun all day. The 1.7acre lot includes a large barn, expansive lawns, a picturesque woodland path, and a magical tree house. Karner Brook winds through the village and wraps around land

Nestled in beautiful Egremont, this New England farmhouse sits on 1.6 private acres and presents a unique opportunity to create your dream home! Restore the original farmhouse or start anew, this picturesque, serene location will amaze you. Outdoor activities and cultural venues are just minutes away such as Bash Bish Falls, Tanglewood, Norman Rockwell Museum, Catamount Adventure Park and the Appalachian Trail just to name a few! Whether you seek a full time residence or Berkshires retreat, this home offers an affordable option to experience living in the quaint town of Egremont. So many possibilities to reimagine this sweetheart of a farmhouse! Call today for a viewing.

49 Bow Wow - A Gilligan Brothers Masterpiece on 30+ Acres! Set on over 30 acres of stunning meadows, mountain, pond access, and forest, the Gilligan family home at 49 Bow Wow Rd comes to the market for the first time. In the second half of the 20th century, the Gilligan Brothers name was synonymous in southern Berkshire County with a quality built home. Founded by three brothers - Matthew, William, and Earl - in the 1940s, Gilligan Brothers homes were often a showcase for the ingenuity and craftsmanship of their founders. And perhaps no home better illustrates their innovative streak than Matthew's family home at 49 Bow Wow Road. Built in 1941 for his family - and retained by them to this day - 49 Bow Wow was stylistically and functionally ahead of its time. Take, for example, the massive stone fireplace and exposed beams in the family room - built with materials reclaimed from a nearby mill. Or, for instance, the sliding wall that opens (still to this day) the family room to the expansive porch with westerly views. Equally impressive, however, is the 30+ acre parcel of land Matthew Gilligan chose for his family home. It includes two multi-acre meadows, woodlands, pond access, and the western side and top of Little Johnny Mountain. Walking from the front to the rear meadow, observing huge 20+ ft boulders seemingly dropped from the heavens, one imagines a glacier carving through this little valley thousands of years ago. The rear meadow sits next to Little Johnny, and could be a spectacular second home site accessed by an existing farm road. The scramble up the side of Little Johnny brings you to a "table top" mountain with awe-inspiring view potential of Mount Everett and the valley below. From there, one can descend the southern slope to Sheffield's Town Park, which has a frisbee golf course, playground, and ball field. Or cross the meadow and return home via a trail system passing through the forest and a small brook. Kayak and water lovers can cross the road and have rights to the family's small "beach" on Mill Pond. The home's first floor features two beautiful living spaces, a kitchen with vintage custom cabinetry, a wood-paneled dining room, a bedroom and full bath. The upstairs includes three more bedrooms and a full bath divided into two sections. A cedar closet could be repurposed into an en-suite bath for the primary bedroom. The basement shows off the home's quality build, with high ceilings, updated systems, and a spot for a future wine cellar. Perfectly functional now, but also ready for its second-ever owner to update the bathrooms and kitchen to their personal preference. The home's "bones" and spectacular property will amply reward future investment. Two-car garage, high-speed Internet, several hobby farm outbuildings, updated electric panel, Buderus hot water heating system.

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.

Nestled in the Berkshires on a quiet road this 1958 Ranch with 3 bedrooms and 2 full baths on approximately 1+ acres is fully restored yet retains the warmth of its past with original wood floors and wood paneling. Updates include new kitchen, all new appliances, washer/dryer, windows, doors, septic, HVAC, insulation, electrical, plumbing, tile, and more. Partially finished basement with full bath. Storage shed/shop large enough for machines. Beautiful backyard, with flowering trees, mountain views and abundant wildlife. Close to charming town center, park and nearby schools. Whether you're looking to retire, raise a family, or gather for the weekends, this immaculate remodeled home offers the comfort of updated systems and the beauty of the natural scenery.

Location, location Location heated pool and tennis courtPerched on one of Hillsdale's most bucolic and quiet roads, everything about this 1800s cedar shingled property says, Welcome home.'' Its owners painstakingly transformed the center hall colonial, bringing more brightness to the first floor. The airy kitchen has granite counters, and includes a Viking stove and Miele dishwasher, and opens to a three-season porch with a Vermont Casting propane stove. The four bedroom home has 3.5 baths (including a 5x6' Whirlpool tub in primary bath, conveniently located on main floor with a door that leads to a quiet patio). The stately living room has a working fireplace, as does the primary bedroom. The meticulously maintained property includesd tennis court and heated swimming pool (with electrically-operated cover), rambling stone walls, and a quarter-acre pond. An abundance of spectacular trees (lilacs, tri-colored beech, Katsura, river birch, Japanese red lace leaf maple) grace the verdant yard, as well as a fenced-in vegetable garden and several perennial floral gardens designed by a landscape artist who trained at the NY Botanical Garden. The sprawling property (which has approval for subdivision) even includes three hiking paths that lead to Catamount ski trails, but calling this ski in/ski out would be apocryphal the property and the ski area are separated by a significant rise, so no concern for noise. Three-car garage, Five minutes from Hillsdale Center , 15 mins from Great Barrington. A unique find, indeed.

Welcome to this winery and tasting room located in the beautiful southern Berkshires! This business/farm is located right on Rt 7 which is considered the ultimate New England road trip. Capture tourists year round with nearby Tanglewood, the botanical gardens, Butternut ski resort and so much more! This spacious post and beam building consists mainly of two large rooms both with lofts. One, currently a tasting room with a wrap around loft, floor to ceiling windows for abundant light, a dramatic center staircase and french doors leading to the patio and outdoor space. The second room is currently an event center with loft. The tiled lobby has access to storage and a handicapped bathroom. The opportunity exists to live on site with the attached apartment; kitchen, full bath, small living space and an upstairs loft. The basement is large and excellent for storage. This post and beam was built with engineered Microlam beams for clear expanse in the basement and the ability to support heavy retail on the main level. There is also a fire protection system, alarm system, multi camera surveillance and 3 temperature zones. The business has both a wine license and food license. The land is 8 acres in 61A and can allow for a plethora of other business opportunities such as a farm to table restaurant, a farm stand, pick your own or a farm brewery. Also an opportunity for weddings, retail or indoor and outdoor events. There are currently two yielding vineyards approximately 2 acres total. The large parking lot can accommodate all your visitors! Is this your year to fulfill your dreams?

Classic American Farmhouse With Epic Views - Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views. Step inside to discover an extra-large chef's kitchen seamlessly connected to a delightful breakfast room, sunroom, and screened porch, each offering tranquil views of the pool and raised garden beds. The inviting living room, complete with a cozy fireplace, flows effortlessly into the dining area, creating an ideal space for entertaining.

Welcome to a slice of New England charm known for its rich history, scenic beauty, and vibrant community, Sheffield offers a quintessential Berkshires lifestyle with easy access to cultural attractions, outdoor recreation, and everyday conveniences associated with in-town living. Enjoy a picturesque setting offering a unique blend of historic elegance and modern comfort. Imbued with the timeless allure of Greek Revival architecture, this home boasts classic columns, symmetrical proportions, and refined details that evoke a sense of grandeur and sophistication. The heart of the home is the gourmet kitchen, equipped with custom cabinetry making it a chef's delight and the perfect space for culinary creations and gatherings. With three spacious bedrooms, including a luxurious primary suite, there is ample room for relaxation and rejuvenation. Featuring two and a half baths, each meticulously designed with modern fixtures and elegant finishes. Large windows bathe the interiors in natural light, creating a bright and inviting ambiance throughout the home.Enjoy the cozy fireplace in the spacious living room, perfect for chilly evenings with family and friends. From gleaming hardwood floors to crown moldings and designer lighting fixtures, every detail exudes quality craftsmanship and refined taste. Above the oversized 2 car garage, a beautifully finished loft awaits, offering endless possibilities as a home office, studio, or guest quarters. Adding to the versatility of this property is an unfinished outbuilding with electric and plumbing , ideal for either residential or commercial use. Whether you envision a charming guest cottage, a home gym, or a boutique storefront, the potential is limitless. Walk to the library, bank,Town Hall, Post Office and the many local eateries makes Sheffield the perfect location.

Lovingly Cared for Historic Home Dripping with Charm. Large and lovely kitchen with breakfast nook, formal dining, living room, cozy fire-placed den for cozy winter nights, powder room and you live in the inviting three season room off of the kitchen, it seamlessly offers the outdoors while relaxing with a morning coffee or glass of wine as the sun sets. The second floor has three generous bedrooms, a sitting room, and two full baths. Home also offers central air. Outside is a lush green lawn with beautiful flower gardens and a three car barn. The location is perfect, minutes to the Village of Sheffield and Great Barrington. Close to all of Berkshire Counties cultural attractions, music venues, restaurants and shops. A wonderful home waiting for its next chapter.

SHEFFIELD.....If you are looking for a rehab project, this is the property for you! A good amount of the demolition work has begun taking the interior down to bare bones leaving the layout pallet for your imagination. Just past Big Elm Brewery and the Sheffield Plastics along the train tracks, this 1900's colonial with hip roof is located on over an acre directly across from 70+ protected acres of Audubon Wildlife Sanctuary. Convenient location, minutes to Sheffield center to the north and CT to the south.

TO BE BUILT New Connecticut Country Your new dream home perched above Twin Lakes on 6+ acres in quaint Salisbury, Litchfield County. Featured in Architectural Digest Summer 2020. Built by design driven, eco conscience architects, StoneFox who focus on contemporary architecture with a strong sense of emplacement with a clean simple design with a sensitive approach to nature and the environment. If you've been waiting for the perfect home, it has arrived. You head up the sinuous driveway to an auto court. The house is sited to face the southwest to take in views of the Taconic range and winter and summer sunsets. The home features an open plan with a central room to gather yet also has cosy private areas to tuck away. No detail has been overlooked and the design combines luxury with an ease for comfortable living. This home is well designed, thoughtful and encompasses all you could want in a stunning country retreat. The main living space features the kitchen, dining and living room with multi slide glass doors that pocket into the wall on either side of an expansive opening that invites you to walk outside to enjoy nature and the view. On the first floor there is also a library and a guest bedroom with full bath, mudroom and powder room. Upstairs you will find the primary bedroom and bath plus two more bedrooms each with their own bath. The lower level offers more space for a gym and bathroom plus a laundry room. There is also a 2 car garage with another bedroom and bath above. Come visit a variation of the home to be built and make your own finish selections from a curated palette of materials prepared by the Architecture/ Design team. Please also visit to walk the land to take in the view to the distance, and imagine being surrounded by landscape inspired by nature. **LIST PRICE DOES NOT INCLUDE LANDSCAPING OR POOL PACKAGES.** **INTERIOR PHOTOS ARE AN EXAMPLE OF A FINISHED HOME**

NEWLY RENOVATED ESTATE COMPOUND for discriminating buyers on a quiet country road. TWO PARCELS COMBINED. This must-see, 7-building property was created exclusively with custom, high-end designer elements and imported materials in 2021-22. #71: MAIN HOUSE features 3 bedrooms, 2 1/2 baths, tiled fireplace, first floor primary BR, Club House/Guest House w/ kitchen (no stove), living room, loft office or BR, Pink House: office, doll house, extensive landscaping, heated gunite pool, pickleball court. #67: UNDER CONSTRUCTION: 6,000+/- POST & BEAM luxury 3-level, 3-BR home with inground pool and 2-BR Guest House privately set in the woods, UNIQUE TIMBER FRAME SANCTUARY w/Indonesian tub/fountain, antique fireplace, jeweled floor, koi pond.