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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.


70 Photos
MOCKINGBIRD REAL ESTATE
$525,900
6 BD | 3 BA
Residential - Single Family

Beautiful, spacious 6 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated kitchens with granite counters and stainless steel appliances. Ample room for the kids and pets to play in the fully fenced in backyard with playset. Enjoy relaxing in the hot tub on the lower level while have shelter from the upper deck! This gorgeous home has all you could need! Surveillance cameras are active outside in the front & back of home.


39 Photos
NOCHER REALTY
$529,900
4 BD | 2 BA
Residential - Single Family

One level living with loads of extra features. Located conveniently in Richmond and close to Tanglewood, Norman Rockwell Museum, Bartlett's Orchard, and much more! Exterior features mature trees for privacy, fresh exterior paint, a new roof, new deck, screened-in porch, and 1.6 acres of land. Interior offers hardwood floors throughout with a recently renovated kitchen and bathrooms. With four bedrooms and two bathrooms the layout offers enough space for comfortable living with an open and bright living room that features skylights and a vaulted ceiling. Along with a separate bedroom/bathroom that could be used as in-law space. Basement is finished with a large family room, laundry, and multiple storage spaces. Ductless mini-splits for efficient heating and A/C. Truly a hidden gem!


30 Photos
JIMINY REALTY
$530,000
2 BD | 3 BA
Residential - Condo/Townhouse

New to the market a large end unit in Mountainside Hemlock Village a 2+ bedrooms (sleeping loft) 3 full bathrooms on 3 levels of living. This end unit has lots of windows and space for the larger family. Park your car right out front and walk into your ski vacation condo. Great rental history if you decide you want to rent. The condo is sold fully furnished and is turnkey. Great location on lower mountainside. Just walk over to the slopes. This will not last long...


44 Photos
NOCHER REALTY
$539,900
4 BD | 2 BA
Residential - Single Family

Welcome to this spacious 4-bedroom, 2-bathroom home offering 1,865 sq ft. of comfortable living space on a generous 1.42 acre lot in the beautiful town of Cheshire. This property features a bright and inviting layout, well-sized bedrooms, and ample room for everyday living or entertaining. New vinyl siding, gutters & awnings added in the most recent years. Enjoy the privacy and outdoor possibilities that come with an expansive lot & beautiful Trex deck leading to the above ground pool. Perfect for gardening, recreation or simply taking in the peaceful surroundings. A wonderful opportunity to own a versatile home in a serene Berkshire County location. Schedule your showing today!


43 Photos
LANCE VERMEULEN RE, INC
$540,000
3 BD | 2 BA
Residential - Single Family

Tucked along a winding country road, this 3 bedroom Cape feels worlds away from everything--yet close to all that makes the Berkshires & Hudson Valley special. Set on two wooded acres where light filters through old maples and the seasons feel close at hand, it's a home that invites you to slow down and breathe. Step inside and you'll sense the calm immediately. The living room gathers around a wood-burning fireplace--an easy place to land after a day exploring Beebe Hill or Harvey Mountain's trails just minutes away. The four-season heated sunroom stretches toward the lawn, its wide windows framing birds, snowfalls, and every shade of green in between. The kitchen has been thoughtfully updated opening naturally into the dining area so cooking and conversation flow together.


34 Photos
BERKSHIRE LISTINGS
$547,700
3 BD | 2 BA
Residential - Single Family

Experience a peaceful Berkshire fall from this inviting ranch-style home in the quiet hills of Becket. Surrounded by vibrant foliage and towering pines, this single-level retreat offers warmth, comfort, and nature at your doorstep. Enjoy scenic hikes and crisp fall days now, then gear up for winter fun with Otis Ridge, Bousquet Mountain, and Jiminy Peak just a short drive away. With a fully equipped kitchen, open living space, and year-round outdoor adventure nearby, this cozy home is the perfect Berkshires getaway.


4 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Prime Commercial Development Parcel on Route 20. Corner Parcel. Almost a full Acre. Comprised of 2 Lots. High traffic count,. Zoning allows for several uses.(note: Property delineation lines on photographs are approximations only.)


32 Photos
BIRCH PROPERTIES
$549,000
2 BD | 1 BA
Residential - Single Family

Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The setting is exceptional, stroll just minutes to the Red Lion Inn, cafes, shops, and the library; at the end of the street, pick up beloved local trails toward Laura's Tower for quick nature escapes. A manageable 6,970 sq ft lot keeps weekends free for play, gardening, or launching out to the Berkshires' cultural highlights: Tanglewood, Norman Rockwell Museum, Naumkeag, and more.


62 Photos
PAULA MCLEAN REALTORS INC.
$549,000
4 BD | 4 BA
Residential - Single Family

Welcome to 100 Northumberland Road - Storybook Berkshire Retreat where timeless charm meets exceptional space and possibility. Located in south east Pittsfield this home sits on .44 acres offering an inviting blend of elegance, comfort & room to grow. Inside, generous living spaces, sun filled rooms, rich architectural details and thoughtful updates create an environment perfect for both everyday living and unforgettable gatherings. 4 bedrooms, 4 bathrooms, expansive common area's featuring a grand living room with fireplace, formal dining room and quiet den this home offers endless flexibility. Host holidays with ease, celebrate milestones, or simply enjoy peaceful evenings. Each room feels like a backdrop for future traditions to be cherished.


51 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$549,000
3 BD | 2 BA
Residential - Single Family

Welcome to this meticulously maintained and lightly lived-in private country home, set at the end of a quiet cul-de-sac on a scenic country road. Situated on nearly 4 acres and backing up to the Farmington River Wildlife Management Area, this one-owner home offers privacy, natural beauty, and modern comfort in equal measure.Boasting nearly 2,500 sq ft of finished living space, this bright and airy home features a thoughtfully designed open floor plan with cathedral ceilings and hardwood floors throughout the main level. The heart of the home is the stunning great room, filled with natural light and anchored by a cozy propane stove, perfect for gathering with family or relaxing in solitude.The spacious main-floor primary suite includes a full bath, while additional guest bedrooms


28 Photos
NON-MEMBER / RECIPROCAL
$549,000
3 BD | 1 BA
Residential - Single Family

Welcome to your dream lake house! Charming seasonal cottage w/knotty pine walls + lofted ceilings, recently added skylights + all new Pella windows + doors, creating a light-filled living space w/epic views. Main room includes nostalgic original kitchen w/formica counters, built-in stovetop, + new retro refrigerator. Dining area + living room include large original stone fireplace - a beautiful centerpiece for the room. Rinnai propane heater provides back up heat for chilly nights. Split level second floor includes three spacious bedrooms + 1 full bath. Off kitchen is large screen porch w/both trex + stone floors. Each room in house is oriented towards the beautiful, 122 acre Norwich Lake - with pristine waters for FISHING, boating and swimming!!


47 Photos
BERKSHIRE LISTINGS
$549,000
3 BD | 2 BA
Residential - Single Family

Don't miss this unique historic property -- truly a GEM! Ready for quick rental income and perfect to enjoy as spring arrives. A wonderful second home to share with family! Imagine a short stroll to downtown Lenox for coffee, a quiet dinner, and a beautiful night at Tanglewood under the stars. Just one street from downtown and steps from St. Ann's Church, this 1,700 sq. ft. bungalow blends charm with comfort inside and out. With a strong rental history (up to $16,000 in summer income), could be a ideal turnkey furnished investment or personal retreat. Enjoy 2025 tax breaks, settle in for the 2026 Tanglewood season, and explore Lee, Stockbridge, or Great Barrington. Embrace the arts this summer!


39 Photos
STONE HOUSE PROPERTIES, LLC
$549,900
3 BD | 4 BA
Residential - Single Family

Spacious split foyer with addition of a year-round heated Florida room featuring inground, heated, fiberglass pool, hot tub, its own granite kitchen, full bath, & Tiki bar, making it ideal for hosting gatherings; or cover the pool and the entire floor with an already existing truss floor system when not using the pool..has 2 egresses, for a great guest/in-law space that can be closed off to the main home. Enlarged, Primary bedroom includes a full bath, walk-in closet and sliders to sneak out to the pool area. Glass room has gas, ceramic tiled fireplace and the main dining room has a field stone fireplace (for cozy New England days). All 3 bedrooms are very large with closet space. There are many extra storage closets throughout the home, as well as an oversized 2 car garage.


27 Photos
BARB HASSAN REALTY INC PITTSFIELD OFFICE
$549,900
3 BD | 3 BA
Residential - Single Family

Welcome to this beautifully maintained home located in a private setting in the town of Lanesborough with wonderful mountain views. This spacious 3-bedroom, 2.5-bathroom home offer a perfect blend of classic charm and modern comfort, inviting and bright interior featuring a thoughtfully designed floor plan, including a stunning kitchen with granite countertops & great center island and gorgeous flooring throughout...ideal for everyday living and for entertaining. The first-floor laundry adds convenience, while the generous living and dining areas provide plenty of space to gather with family and friends. First floor offers 1 bedroom and 1 full bath, while the 2nd floor offers two generous sized bedrooms each with walk in closets and another full bath. This one is a real charmer.


50 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$549,900
3 BD | 3 BA
Residential - Single Family

Classic country charm awaits you in the foothills of Cheshire Massachusetts and escape home to privacy and serenity in northern Berkshire to live and play in the great outdoors. Enjoy hiking out your door and follow the Appalachian Trail even reach Mount Greylock, bike ride north and south on the Ashuwillticook Trail exercising and exploring the beautiful farmlands and countryside as you immerse yourself in nature for miles and miles. Stay home and escape on your very own 4.5 wood acres for foraging mushrooms and enjoying your fairytale woodland animals with a trail camera in the comfort and warmth of this Berkshire traditional country colonial. Experience quality craftsmanship with wood paneled walls and ceilings blended beautifully with a country pallet of colors on sheet rocked walls


11 Photos
Compass Massachusetts, LLC

The drive to this beautiful parcel takes you off the main road, past farms, cottages, and estates--all within a mile or two. Hidden away in one of the most scenic parts of Monterey and surrounded by larger holdings and hundreds of acres of conserved, trust-protected land, this property offers peace and privacy rarely found. The land is mostly level before gently sloping down to a brook on the east and a stream and pond to the south. Located just down the road from the Gould Farm Harvest Barn and the beloved Roadside Store Cafe, this is a great area for walking a dog, on the surrounding roads or on nearby hiking trails. With conservation lands and established homes all around, this is a truly exceptional and enduring setting.

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