Found 39 Listings

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40 Photos
LANCE VERMEULEN RE, INC
$799,000
4 BD | 3 BA
Residential - Single Family

Nestled on a corner lot in the quaint village of Ashley Falls, this c. 1900 New England farmhouse blends timeless charm with modern comfort and energy efficiency. This completely renovated 4-bedroom 3-bath home preserves its classic allure with numerous modern upgrades and all new mechanicals. Step onto the white-washed front porch and into the front parlor, where a wood-burning fireplace and engineered oak floors greet you with warmth and character. The bright open kitchen/dining area with exposed original beams and vaulted ceiling invites gatherings of family and friends. Sliding doors offer sunshine from the south-facing patio. Rounding out the first floor is a spacious 1st-floor bedroom and full bath, plus a side entry mudroom.


44 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$825,000
3 BD | 3 BA
Residential - Single Family

This Old House enjoys 2002-2005 renovations by current owners. Berkshires, South County located in historic Sheffield's village center, an easy walk to Dewey Hall, library, bank, post office, convenient to local eateries. Large rooms, easy flow, classic period features; property zoned residential/commercial, ideal for professional practice, studio or workshop w/loft above oversized garage and/or business in open-spaced outbuilding with utilities. Close to GB shopping and bucolic back road cycling. Situated in Berkshires Rte. 7 valley, area is less prone to harsh snowfalls, main road plowed in winter for driving access. Small town ''feel'' with nearby culture, schools and a great, diverse community. A period home and more for a buyer with distinct tastes, needs and pride of ownership.


28 Photos
HOUSATONIC REAL ESTATE
$849,000
3 BD | 2 BA
Residential - Single Family

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 with warm wood floors that lead to a great room, and a stone fireplace creating an ideal space for relaxation and entertaining. Natural light pours in through sliding doors, to the in-ground Gunite pool. Separate building lot included. 3 car oversized garage with bonus rooms.


38 Photos
EQUINE HOMES REAL ESTATE, LLC
$895,000
1 BD | 2 BA
Residential - Single Family

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


40 Photos
EQUINE HOMES REAL ESTATE, LLC

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


31 Photos
LANCE VERMEULEN RE, INC
$995,000
4 BD | 3 BA
Residential - Single Family

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.


42 Photos
LANCE VERMEULEN RE, INC
$1,175,000
3 BD | 4 BA
Residential - Single Family

Experience the serenity of 594 Shunpike Rd. This cozy 2600 sq. ft. Gambrel-style home, set on 2.32 acres, has been meticulously & extensively renovated for modern living. Enter through a bright, open foyer & enjoy central air/heat, a full house generator, & new wood flooring. The home features all new kitchen, bathrooms, gas fire place, plumbing, electric, windows & more. The newly finished lower level w/ walkout offers additional living space. Relax on the spacious deck, surrounded by a beautiful clearing in the woods. The primary suite w/ a spa-like bathroom & walk-in closet. This property is ideal for year-round living, vacation home, or potential rental income. Located on a quiet country road, minutes from town, enjoy location for recreation & cultural attractions.


32 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$1,195,000
9 BD | 7 BA
Multi-Family

Investment opportunity in Sheffield. Set way back from the main road, this multi family dwelling awaits its new Stewards after almost 40 years in the same family. The property consists of 3 separate buildings, The main house with four 1 BR apts.In the rear of the main house is a semi attached 2 BR apt with its own separate entrance. You then have an additional 3 bedroom 2 bath home with 3 season room and rear garden. There is also a separate 2 bay garage with maintenance room. The grounds are beautifully manicured with flowering bushes and trees with lovely mountain views. Its really a little bit of paradise just off the beaten path yet close to everything. 15 minutes in Great Barrington, 10 minutes to N Canaan CT. This lovely Homestead is set on almost 13 secluded acres.


56 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,200,000
4 BD | 2 BA
Residential - Single Family

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.


44 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$1,300,000
3 BD | 2 BA
Residential - Single Family

An idyllic setting on 8.34 acres w/panoramic views of lush meadows and protected land. With frontage on the Konkapot River, this is a serene retreat just 15 min from Great Barrington and the rolling hills of Litchfield County. The one level home has a thoughtful layout with a dedicated primary wing and 2 guest bedrooms conveniently located on the opposite side of the house. The heart of the home is the impressive great room, complete with radiant-heated floors, vaulted ceilings and a jaw-dropping stone fireplace. Large windows and doors, newly installed, frame the heavenly surroundings from every room including the open, bright kitchen w/soapstone countertops. Practicality meets style in the contemporary 2-car garage. Improvements include a newer septic system, roof and propane generator.


44 Photos
LANCE VERMEULEN RE, INC
$1,375,000
4 BD | 3 BA
Residential - Single Family

Berkshire contemporary masterpiece - offering privacy, a Gunite pool and stunning mature landscaping with a meadow creating an estate-like feel. Inside you will find yourself drenched in sunlight streaming in from the wall of windows and looking over the westerly view. With glass doors leading to the large cedar deck from every room, you will always feel a connection to nature. Recently updated, the kitchen and baths are a continuation of the modern vibe. Featuring 4 bedrooms - including a first-floor primary suite with cathedral ceilings and a walk-in closet - you will find plenty of space to spread out. The highlight is the luxurious Gunite swimming pool with a built-in spa, perfect for relaxation and entertainment. In addition, the home features central A/C and a back-up generator.


48 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,495,000
3 BD | 4 BA
Residential - Single Family

This timeless and well-loved residence offers 3 spacious bedrooms and 3.5 luxurious bathrooms, all set against the backdrop of breathtaking views and spectacular sunsets. The beautifully landscaped property features a large variety of flora and charming stone walls and details, creating an inviting and serene atmosphere. Step inside the main living area, where you'll find a convenient mudroom with a half bath. The open-concept kitchen, dining, and living room boast a big glass wall that floods the space with natural light, complemented by the warmth of a wood stove. The den, with its elegant French doors, opens onto a large deck and a screened porch, perfect for entertaining or enjoying quiet moments outdoors.Upstairs, the main bedroom is a true retreat with big views, featuring..


39 Photos
ELYSE HARNEY REAL ESTATE
$1,650,000
4 BD | 5 BA
Residential - Single Family

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.


57 Photos
LANCE VERMEULEN RE, INC
$1,750,000
3 BD | 3 BA
Residential - Single Family

Welcome to Rannapo Road, and your forever home! Sitting at the crest of the hill, this home peers across the valley overlooking cornfields, 2 rivers and Mt Everett. With 17 workable acres and a horse barn, this equestrian property is a perfect opportunity to own your own gentleman's farm. Inside you will appreciate the open floor plan and fireplace while enjoying the views as they paint pictures in every window. The large primary en-suite bedroom boasts a Juliette balcony overlooking the valley - the perfect spot for morning meditation. Two additional bedrooms, an office and a den can be found throughout the home - including a first floor bedroom. Additionally, the home features a large bonus room above the garage with a separate staircase - plumbed for heat and ready to finish.


46 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$2,500,000
3 BD | 5 BA
Residential - Single Family

UNDERMOUNTAIN HOUSE. Nestled beneath majestic views of Mt. Everett, this stunning modern barn-style home floats above the landscape. A boulder strewn rain garden creates a covered bridge effect. Clad in ebony stained cypress and stone with a standing seam metal roof, this award winning house has wonderful privacy with views of a wildlife pond and a fruit orchard. The house has an open living/dining area with a wood-burning fireplace adjacent to a three season porch with its own wood-burning fireplace. The architects designed a pierced wood screen to separate the dining area from an intimate banquette in the kitchen, and to create the most marvelous lighting effect at night. An office, powder room, and a primary suite complete the first floor.


66 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$3,500,000
4 BD | 5 BA
Residential - Single Family

Welcome to The Factory - a gorgeous three bedroom, three bath loft that comes with a rather large 10,000 foot manufacturing or studio space, along with an executive office with its own bedroom, another full bath and a service kitchen. Essentially two separate living spaces within the commercial space. The loft space is extraordinary, featuring a huge common area with a glass garage door to a large screened porch and deck, and a Malm 360 fireplace. All bedrooms and baths are generous. The commercial space includes two offices and other ancillary rooms with lots of storage on the second level. Enjoy the one year old in-ground lounge pool, newer barn with a corral and the neighboring Appalachian Trail. Located in the Housatonic Valley with views of neighboring protected cornfields.


76 Photos
BERKSHIRE PROPERTY AGENTS, LLC

Over 10,000sf of studio or manufacturing space available along with two extraordinary living spaces available under the same roof in the General Business District of Sheffield, MA. The large work space is conjoined with an large and exciting three bedroom, three bath loft with a glass garage door to a huge screened porch and deck overlooking a new in-ground lounge pool and another executive office with more sleeping space. Views over the Appalachian Trail land and protected cornfields to the south and Berkshire Hills to the east all in proximity of Great Barrington, MA and Salisbury, CT. It's a beautiful and convenient location in the middle of the Housatonic Valley for a true live/work situation.


39 Photos
ELYSE HARNEY REAL ESTATE
$7,500,000
11 BD | 6 BA
Residential - Single Family

This spectacular 85+/- acre property is a destination Educational Center. It offers a magnificent 1880 Manor House, with spectacular distant Views, a Pond, and 11 additional buildings which house an Auditorium, Group Meeting Areas, Breakout Private Offices, a Fitness Center, Pondside Cottage, huge Dining Hall with Commercial Kitchen, and accommodations in over 56 Guest Rooms. The land is made up of 70+/- acres in the Southern Berkshires and 15+/- abutting acres in Salisbury, CT - the entire CT side runs along Sage's Ravine. There are walking trails throughout the land and access to the Appalachian Trail. You will be smitten by this property and totally taken with the possibilities... Building and property tax details are for the Main house ONLY. Please contact agent for more details.


40 Photos
ELYSE HARNEY REAL ESTATE

Breathtaking Educational Facility, Residential Complex or Corporate Retreat This spectacular 85+/- acre property is a destination Educational Center. It offers a magnificent 1880 Manor House, with spectacular distant Views, a Pond, and 11 additional buildings which house an Auditorium, Group Meeting Areas, Breakout Private Offices, a Fitness Center, Pondside Cottage, huge Dining Hall with Commercial Kitchen, and accommodations in over 56 Guest Rooms. The land is made up of 70+/- acres in the Southern Berkshires and 15+/- abutting acres in Salisbury, CT - the entire CT side runs along Sage's Ravine. There are walking trails throughout the land and access to the Appalachian Trail. Details and taxes are only for the Main House, Please ask for details for all 12 buildings and total property.

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