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27 Photos
JIMINY REALTY
$499,900
3 BD | 2 BA
Residential - Condo/Townhouse

Looking for a corner unit at JJ's lodge? This 3 bedroom 2 full bath unit is literally steps away from the private locker room and walk out to the Berkshire Express. Beautiful distant Mountain vistas and views of the bunny hill where you can watch your kids learn how to ski and snowboard all from your private balcony! Multiple beds for family and friends. The unit has central AC and Heating with an electric fireplace for ambiance and looks. This unit is close to all the amenities like the summer pool, winter slopes, hiking trails, bars and restaurants. This one will not last long...


41 Photos
ALTON & WESTALL REAL ESTATE AGENCY, LLC
$499,900
4 BD | 3 BA
Residential - Single Family

Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System(BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious living room featuring a wood-burning fireplace and French doors that open to a private deck overlooking the park-like backyard. A separate study offers space for work or reading, while a dedicated laundry room, half bath, and entry to the attached two-car garage add convenience.


6 Photos
LANCE VERMEULEN RE, INC

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.


6 Photos
LANCE VERMEULEN RE, INC

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.


6 Photos
LANCE VERMEULEN RE, INC

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.


6 Photos
LANCE VERMEULEN RE, INC

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.


11 Photos
LANCE VERMEULEN RE, INC

Settle into the quiet charm of the Windemere Lake community with this 6.607-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake--a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.


41 Photos
EQUINE HOMES REAL ESTATE, LLC
$500,000
3 BD | 2 BA
Residential - Single Family

Two homes on almost 5 acres! Have you always dreamed of living a sustainable, homesteading life with your family and extended family? This property makes generational living possible! The ''cabin'' is 2,106 sq ft with updated bathrooms, mainfloor laundry, 2 fireplaces with wood and pellet stove inserts, primary bedroom with large cedar lined walk in closet. Impressive P&B exposed wood throughout the home adds character and a rustic feel. Second home is 1728 sq ft has updated bathrooms, 2 fireplaces, updated kitchen and large bedrooms. Both homes are surrounded by gardens, fruit trees and some open pasture. A barn on the property can be converted for livestock or can be used as a workshop and potting shed. 6.51 acres across the street may also be available.


47 Photos
COHEN & WHITE ASSOCIATES
$500,000
3 BD | 3 BA
Residential - Single Family

Let's imagine extreme privacy for a moment, yet your loved ones are simply a three minute walk away or a quick drive; because each one has their own home! With connecting roads this home is 1 of 3. This home has a hot tub, 3 fireplaces and a garage for winter parking. A parcel on Indian lakes is also an attractive feature that is available. This will give you access to the tennis court and the lake itself. This home has a bedroom on the first level. The laundry is conveniently located on the 2nd level between the other 2 bedrooms. Extra Living space is found in the lower level and direct access to the garage is very convenient. An amazing deck with an exterior fireplace makes for a lovely ambiance. It is easy to get to and from the nearby majoring cities.


19 Photos
RED HORSE REAL ESTATE, LLC
$519,000
1 BD | 0 BA
Residential - Single Family

Unique Opportunity! Lakefront on Center Pond. Original lake cabin built circa 1950 set on .79 acres with 100 feet of lake frontage. Located within 25 feet of the lake the structure will require extensive renovations. The cabin does have electricity and will need well and septic. Great spot and well worth the effort!


45 Photos
NOCHER REALTY
$519,900
4 BD | 3 BA
Residential - Single Family

Step inside and be greeted by an inviting and light-filled interior. Offering 4 bedrooms and 3 baths, the thoughtful, open-flow floor plan is an entertainer's delight, ensuring guests are always part of the conversation, whether gathered around the large kitchen island or relaxing in the main living space.The versatility of two separate living rooms is a rare find, offering endless possibilities for a growing family, multi-generational living. Perfect entertaining space offered in the rear yard with patio fire pit and custom he/she shed. Amazing greylock views year round! Close to downtown and the local rail trail, just tucked away on a double lot nearing a full acre.


43 Photos
LAMACCHIA REALTY, INC
$524,900
4 BD | 3 BA
Residential - Single Family

OPEN HOUSE Sat 7/5/25 11a-12:30p Welcome to your private escape in the heart of the Berkshires on a quiet country road. This expansive ranch-style home offers ample space for large family gatherings, house guests or entertaining. Enjoy the ease of one-level living with a bright, open floor plan and a grand brick fireplace anchoring the spacious main living area. The home features four spacious bedrooms and two updated full bathrooms along with a back deck and screened-in back porch overlooking the woodlands. The lower level offers even more flexibility with a private entrance, an additional bedroom, full bath and convenient kitchenette - perfect for guests, in-laws or potential rental income. There is also a large unfinished room with a second fireplace and walk-out access to


20 Photos
JIMINY REALTY
$525,000
3 BD | 2 BA
Residential - Condo/Townhouse

This beautiful three-bedroom two-bathroom condo is located in JJs Lodge in middle of it all. Spacious, immaculately clean and appointed with all the comforts of home - gaming, games, Ski locker, plus more! Walk out the lodge door to high-speed quad lift - you can't get any closer at Jiminy Peak to the mountain! This place offers all season fun in the Berkshires. Jiminy Peak has family fun and summertime pools and hot tubs. Master bedroom En Suite with Queen size bed. Deep jetted tub and shower. Second bedroom with Queen size bed. Third guestroom with two twin over full size bunk beds. Plentiful closet space and dresser space for settling in during your stay. Second bathroom has deep jetted tub and shower. This is your opportunity to own your own ski lodge condo.


53 Photos
COHEN & WHITE ASSOCIATES
$525,000
4 BD | 3 BA
Residential - Single Family

This home is ready for its new owner. A complete professionally remodeled interior. New Septic System, New insulation, New Windows, New Kitchen and Appliances, Freshly Painted, Fiber Optic Internet available, New gravel Driveway, New Boiler, New hot water heater, Brand new LED lighting within the entire home. New tile work in the the 2 full baths. Laundry conveniently located on the same level as the bedrooms. No detail has been overlooked. You will not be disappointed with this remodeled home.


37 Photos
LANCE VERMEULEN RE, INC
$525,000
3 BD | 1 BA
Residential - Single Family

Tucked away in a walkable east-side neighborhood of Great Barrington, this custom 3-bedroom bungalow is anything but ordinary. From the moment you step inside, the care and creativity in every corner are impossible to miss--handcrafted woodwork, thoughtful built-ins, and artful finishes infuse the home with a personality all of its own.The inviting and cozy open floor plan make everyday living feel effortless, while abundant natural light fills the spaces. At the heart of the home, the kitchen stands out with its custom copper countertops, reclaimed wood shelving, and clever storage solutions for functionality.Step outside to your own private oasis: a fully fenced yard with seven 20-foot no-till garden beds, ready for your homesteading dreams or a vibrant


19 Photos
Www.HomeZu.com
$525,000
4 BD | 4 BA
Residential - Single Family

This is a spacious house with generously sized rooms 5 minutes from town. 4 bedrooms with 1 full bath, 2 3/4 baths and one powder room. First floor has kitchen, living room, dining room, pantry, laundry and a generous master suite with sitting area, office space and full bath. Second floor has 3 bedrooms, one with ensuite 3/4 bath. Lots of closets and plenty of storage space with basement storage or workshop area. New 16k oil burning furnace in 2025. for hot water baseboard heat. New septic to be installed by seller this fall.Charmingly surrounded by neighbor's barns, with a nice .45 acre parcel with lawn or ready for your own garden. Screened in porch, patio and fire pit are perfect for summer in the Berkshires.


16 Photos
JIMINY REALTY
$525,000
3 BD | 2 BA
Residential - Condo/Townhouse

Experience the pinnacle of slope-side living in this 3-bedroom, 2-full bathroom ski-on/ski-off condo. Boasting 1,133 sq. ft. of meticulously designed living space, this mountain retreat offers unparalleled convenience and comfort. Step directly from the lodge onto the trails, maximizing your time on the slopes and eliminating transportation hassles.Inside, you'll find an inviting atmosphere with a focus on seamless indoor/outdoor living. The fully equipped kitchen features ample storage for all your culinary needs. Relax by the cozy [mention fireplace type, e.g., electric] fireplace after a day of adventure, or step out onto your private balcony/patio to enjoy breathtaking mountain views.


24 Photos
STONE HOUSE PROPERTIES, LLC
$525,000
3 BD | 2 BA
Residential - Single Family

Are you or your clients searching for a private, picturesque property with endless potential? This three-bedroom, two-bath contemporary home is ready to be reimagined into a modern retreat. Sited at the end of a quiet cul-de-sac on a tranquil 3-acre lot, the setting offers exceptional privacy and natural beauty. Inside, you'll find hardwood floors, abundant natural light, and an open layout that welcomes creative transformation. Whether you're looking for a full-time residence or a weekend escape, this property presents a rare opportunity to craft something truly special. Enjoy easy access to the Harlem Valley Rail Trail, ideal for biking and walking, and benefit from the home's prime location--perfectly positioned between Hudson and Great Barrington. Outdoor adventure, small-town charm, d


48 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$525,000
4 BD | 3 BA
Residential - Single Family

This well-cared-for colonial home has been cherished by the same owners for over seven decades and is ready to welcome its next chapter. The first floor offers a spacious layout with a large kitchen, dining room with access to a seasonal porch, a living room featuring a wood-burning fireplace, a family room with half bath, and a four-season sunroom surrounded by windows overlooking the backyard.Upstairs, the primary bedroom impresses with double closets and a vaulted ceiling, complemented by three additional bedrooms and a full bathroom. The fully finished basement provides valuable extra living space with a laundry room, 3/4 bath, and game room.Recent updates include a new roof (2021), heating system (2023), and refinished floors with fresh paint.


4 Photos
FAIRGROUND REAL ESTATE
$525,000
4 BD | 2 BA
Multi-Family

Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, blending classic charm with modern comfort.Step inside to discover a welcoming floor plan with ample natural light, hardwood floors, and period details. The kitchen and living areas are perfect for entertaining or relaxing with family. Upstairs, the bedrooms offer privacy and comfort, with plenty of storage throughout. Warm and efficient forced hot water heating.

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