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58 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$399,000
3 BD | 2 BA
Residential - Single Family

A rare find: 3 Bedroom colonial home with a picturesque pond for endless enjoyment. Dining under the stars in your private backyard oasis and waking up to breathtaking views and gentle melodies of nature. Discover the magic where memories are waiting to be made. Anderson windows and doors. A brick chimney with a wood stove adds seasonal warmth to the living room. The back porch entices you to come relax or entertain while listening to the babbling brook and a serene view of the pond. The rolling field across the paved street provides plenty or privacy. The convenience to work from home is made easy with fast fiber optics and Windsors low taxes. 39 minutes to Northampton and


27 Photos
HELEN MULLANY REAL ESTATE, LLC
$449,000
3 BD | 3 BA
Residential - Condo/Townhouse

EXCEPTIONAL CORNER UNIT! Bright and inviting 3 Bedroom, 2.5 Bath town house offering the perfect place to live, in the heart of Great Barrington. Designed for comfort & style, these light filled rooms showcase a beautiful distant mountain view. With the warmth of wood floors throughout, the spacious open plan is perfect for entertaining, and a new HVAC system has been added for year round comfort. The lower level is bonus space for recreation, bunk room or office. Plenty of storage, with walk out to a private seating area and gently sloped lawn. There is a one car detached garage. Rose bushes and thoughtfully designed landscaping create a welcoming setting. Conveniently located and move-in ready! Many Berkshire cultural attractions nearby, minutes to restaurants, shopping & skiing.


43 Photos
HOUSATONIC REAL ESTATE
$449,000
3 BD | 2 BA
Residential - Single Family

Nestled in Sheffield Village on 8+ acres, this charming New England farmhouse blends rustic character with modern comfort. Featuring 3 bedrooms, 2 baths, wood floors, beams, Great Room with a gas stove offers a warm inviting space Enjoy a country kitchen with a pantry. Screened in porch with outdoor patio, gardens, and two sheds for storage or hobbies. Perfect as a private sanctuary or Airbnb, this property combines timeless charm, tranquil surroundings, and great potential.


34 Photos
LAMACCHIA REALTY, INC
$449,900
2 BD | 1 BA
Residential - Single Family

Tucked away on a quiet country road just minutes from downtown Great Barrington, this charming single-level ranch offers the perfect Berkshire retreat. Set on two private acres, the home is surrounded by mature trees and natural beauty- with nearby access to trails. Step inside to a bright interior featuring a spacious living room anchored by a beautiful stone fireplace. The kitchen offers crisp white cabinetry, and modern countertops. Two bedrooms and a full bath complete the main level. Whether you're seeking a full-time residence or a peaceful getaway, 245 Long Pond offers all the charm and abuts preservation land conveniently located near Tanglewood, theaters, and more.


11 Photos
LANCE VERMEULEN RE, INC

Settle into the quiet charm of the Windemere Lake community with this 7.166-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.


37 Photos
COMPASS MASSACHUSETTS , LLC GB
$455,000
3 BD | 2 BA
Residential - Single Family

Live in the center of Great Barrington with a private backyard of almost 3 acres on the river! This renovated farmhouse has an inviting kitchen with cozy wood stove, first floor primary suite and 2 spacious bedrooms with a shared bath on second floor. Beautiful wide-plank floors and built-ins preserve this home's history. A solar rooftop system, fully owned, brings energy efficiency and electricity credits. Front porch, back deck and two car garage with second story and an EV charger complete this in-town gem!


44 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$470,000
2 BD | 3 BA
Residential - Single Family

A charming 1900's farmhouse, thoughtfully renovated for modern living, just over the Lenox line in Pittsfield. Set on 1 acre with sweeping views of the Berkshire Hills, the property also includes a two-car garage, workshop, and small horse barn. Relax in the shaded garden nook beneath the pergola, or enjoy the eat-in kitchen at the back of the home with views of fields and hills. Includes a full bath on first floor. Upstairs, you'll find two spacious bedrooms, each with its own bathroom. All this just minutes from Lenox Center and Tanglewood. Truly a quiet country retreat with easy access to all the Berkshires has to offer.


25 Photos
MONARCH REALTY, INC.

ADAMS! Dynamite Berkshire Land. Bordering Greylock Glen Land into Greylock Mountain State Reservation. 1,000's & 1,000's acres of direct access to preserved forestlands & fresh water brooks, waterfalls & ponds. A nature enthusiast dream getaway. Enjoy it all right from your own 83 acres - hike, bike, hunt & snowmobile directly from your own property. Direct access to a vast network of protected trails including the Appalachian Trail. Simply enjoy the wilderness & use for basic camping or build your own mountain paradise. Enjoy Mt. Greylock Views. Located close to town for all the in-town amenities. Easy access North into North Adams, Williamstown & Southern Vermont and South to Cheshire, Lanesboro, Pittsfield, Lenox & Stockbridge. Only about 40 minutes to I-90 connection.


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WILLIAM PITT SOTHEBY'S - LENOX
$475,000
4 BD | 3 BA
Residential - Single Family

Welcome to your dream getaway in Otis Woodlands, one of the Berkshires' premiere private communities. This beautiful home offers the perfect blend of rustic elegance and modern comfort, ideal for year-round living or a serene weekend escape.Nestled among the trees, this spacious 4-bedroom, 3-bathroom home features a dramatic great room with vaulted ceilings and exposed beams, complemented by a 2020 custom kitchen with quartz countertops--perfect for entertaining. Enjoy the outdoors from the expansive wraparound screened porch, ideal for relaxing or dining al fresco.The upper level boasts a private primary suite with skylights, a full bath, and an open loft area. The main floor includes a bedroom with an en suite bath, while the lower level offers two additional bedrooms


39 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$475,000
3 BD | 3 BA
Residential - Single Family

Experience the charm of country living in this comfortable home, situated in the peaceful town of Charlemont, on Wilder Brook. The property includes a spacious barn, formerly a cabinet workshop, and an additional outbuilding for gardening tools or chickens. Enjoy hosting gatherings in the large kitchen and dining room, or relax in the expansive open living area. Upstairs, you'll find three roomy bedrooms and two bathrooms, providing plenty of space for everyone. Perfect for outdoor enthusiasts, this home is just minutes from mountain biking, ziplining, the mountain coaster, and downhill skiing at Berkshire East, as well as world-class fishing and tubing on the beautiful Deerfield River. Seize this opportunity to make this remarkable property yours!


23 Photos
HOUSATONIC REAL ESTATE
$495,000
4 BD | 2 BA
Residential - Single Family

Open House 10-11-25, 11:00-1:00. Inside pictures to follow soon. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanicals. Freshly painted inside and out, this home is truly move-in ready. The stonework patio provides a picturesque setting with a fabulous screened porch. There is a convenient shed and generous oversized garage space. Ample storage throughout ensures all your needs are met. Discover the perfect balance of history and modernity in this delightful property.


53 Photos
COHEN & WHITE ASSOCIATES
$495,000
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.


31 Photos
BERKSHIRE BUYER BROKERS
$495,000
3 BD | 2 BA
Residential - Single Family

Contemporary cape with an open, single floor design combines charm and practicality on two private acres. The walk out lower level features an expansive family room with two additional rooms. Heated garage, central vac, Vt Castings wood stove, underground propane, whole house generator and a screened porch to observe the private, landscaped lawn and gardens. This beautifully designed, well constructed, easy maintenance home provides the perfect oasis for every season!


48 Photos
RED HORSE REAL ESTATE, LLC
$499,000
3 BD | 3 BA
Residential - Single Family

: Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare Theatre Company, museums, Housatonic River and more.


61 Photos
LAMACCHIA REALTY, INC
$499,000
4 BD | 3 BA
Residential - Single Family

Welcome to this beautiful custom-designed Colonial set on 7.01 peaceful acres in scenic Washington, MA. Need more? An additional 7.01-acre abutting parcel (Land MLS# 247018) is available for even more privacy or expansion potential! This spacious 4-bedroom home combines classic style with modern efficiency, featuring a high-efficiency heating system with central air and a desirable southern exposure--perfect for adding solar.Inside, you'll find a gorgeous kitchen with granite countertops, hardwood floors, and an open layout ideal for everyday living and entertaining. The luxurious primary suite offers a private retreat with an ensuite bath and walk-in closet. Highlights include three additional bedrooms, bright and airy living spaces, and a convenient two-car attached garage.


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.


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


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


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.


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

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