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40 Photos
MACCARO REAL ESTATE
$399,000
3 BD | 2 BA
Residential - Single Family

Escape the hustle and bustle of city life and embrace the tranquility of this Charming Cape style home nestled on a picturesque 5-acre oasis. Located on a quiet road, this property offers the perfect blend of peaceful living and modern convenience.Two spacious barns await your livestock, making it easy to indulge in the ranch life you've always dreamed of. And with the town public beach just a stone's throw away, you can seamlessly transition from tending to your animals in the morning to enjoying a refreshing swim in the afternoon. Not a farmer? No problem! Explore the potential of 2-3 building lots on this expansive property. Simply check out the parcel maps. Close to Jacobs Pillow, Otis Reservoir, Big Pond, Otis Ski Lodge, and much more.


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BIRCH PROPERTIES
$399,000
3 BD | 2 BA
Residential - Single Family

Enjoy peaceful country living in this 3-bedroom, 2-bath home set on 8.6 scenic acres along the Umpachene River and surrounded by abundant wildlife. The property offers endless potential for gardening, recreation, or creating your private retreat. Solar panels are included and will be paid off at closing, providing long-term energy savings. Conveniently located near the Southfield Store, The Old Inn on the Green, the Mill River General Store, York Lake, and Umpachene Falls, this home blends rural tranquility with easy access to local favorites. Being sold as is.


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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


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ALTON & WESTALL REAL ESTATE AGENCY, LLC
$399,900
3 BD | 2 BA
Residential - Single Family

Nestled in the heart of downtown Cheshire, this beautifully updated New England farmhouse blends classic charm with modern comforts. Featuring a convenient first-floor bedroom and full bath, plus two additional bedrooms and a second full bath upstairs. The recently renovated kitchen boasts granite countertops, abundant cabinet space, stainless steel appliances, and an abundance of natural light. Enjoy Berkshire summers relaxing on the spacious back decks or lounging on the shaded front porch, all with new composite decking and railings. Located within walking distance to the scenic Ashuwillticook Rail Trail and less than a mile from Cheshire Lake. New septic system installed in 2022. Current owner has done extensive upgrades and improvements. See full list under Documents.


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$399,900
2 BD | 2 BA
Residential - Condo/Townhouse

Experience mountainside luxury at this stunning ski condo located within the Berkshires premier ski destination, Jiminy Peak Resort! Four seasons of fun, adventure, relaxation and scenic vistas await. An ideal retreat for ski enthusiasts and outdoor lovers alike. Amenities to keep everyone entertained, such as the high-speed-quad lift, mountain coaster, alpine slide, tennis, heated swimming pool, sauna and hot tubs just to name a few. An exceptional resort indeed!


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HART REALTY
$419,900
4 BD | 3 BA
Residential - Single Family

Beautiful views and move-in condition! This home has a new kitchen with SS appliances, stone countertops, tile back splashes and slider to the 2 tiered deck overlooking Noble farm fields. Relax and take in nature's beauty! There are all new floors, interior and exterior paint, and extreme low temp high efficiency heat pump/Air conditioning. Updated 2.5 bathrooms and a 2 car garage make this home everything that you need.


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SIGNATURE ASSOCIATES
$429,400
4 BD | 2 BA
Residential - Single Family

Lovely, meticulously maintained home in southeast Pittsfield offers spacious living. Attractive kitchen with large dining area leading to deck. Generous yard with fenced area for pets or kids, a garden area, large shed. There is an ''in-law'' arrangement in the lower level that has living room, bedroom or dining room, a den or dining or bedroom, kitchenette, full bath and door to the garage.Three bedrooms on first floor with nice closets, and there is a full bath. 2 car garage with work area. Come and see this home! Open house 10/25 10:30-12:30


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JIMINY REALTY
$450,000
2 BD | 2 BA
Residential - Condo/Townhouse

Amazing opportunity to own a ski vacation home right in the heart of Village Center is this totally turnkey 2 bedrooms 2 full baths unit with an outside balcony. Private parking spot. Private ski locker. No stairs. 10 foot ceilings throughout. Crown molding. Easy access to the slopes.


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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!


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LAMACCHIA REALTY, INC
$465,000
5 BD | 3 BA
Residential - Single Family

OPEN HOUSE Sat 11/01/25 11am-12:30pm. This stunning 5-bedroom, 3-bath farmhouse was fully renovated from top to bottom in 2020, offering 2,800 SqFt of stylish, move-in-ready living space in one of Southeast Pittsfield's most desirable neighborhoods. Situated on a generous corner lot, the home makes a striking first impression with its inviting wraparound front porch. A circular driveway provides ample parking and is complimented by a detached one-car garage. Step through the front door into a spacious foyer with sleek hardwood floors throughout the open concept main level. The dining room has enough space for memorable meals and entertaining, while the chef's kitchen is outfitted with stainless steel appliances, a natural gas range, quartz & granite countertops, center island and French


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$469,000
3 BD | 2 BA
Residential - Single Family

Tucked away in the desirable, low-tax community of Richmond, Massachusetts, this 3-bedroom, 2-bathroom ranch, surrounded by higher-priced properties, offers comfortable single-floor living. The open-concept living area, filled with natural light, includes a recently updated kitchen and features quartz countertops, quality stainless appliances, and ample counter space. The master suite includes a newly updated bathroom. Two additional spacious bedrooms offer flexibility for guests or a home office. A privately owned solar array provides net-zero energy, combining eco-conscious living with cost savings. Located just 4 miles from Tanglewood, the Berkshires' premier cultural attraction, 5 miles from Lenox, the region's culinary hub, 4 miles from West Stockbridge, and 5 miles from Balderdash C


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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


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BISHOP WEST REAL ESTATE
$489,000
5 BD | 3 BA
Residential - Single Family

Welcome to 321 High Street, Dalton! This spacious home offers the perfect balance of New England charm and modern comfort. Located across from Pine Grove Park, it features inviting curb appeal with well-maintained landscaping and a generous backyard. You'll find light-filled rooms with newly refinished hardwood floors, a spacious living room and an updated kitchen with a stunning cathedral ceiling, granite countertops, and an eat-in bar. The home offers 5 bedrooms and 3 bathrooms, including a primary bedroom with a walk-in closet and ensuite bathroom. The property has been extensively updated with energy-efficient improvements such as a new roof, solar panels, and heating system. This home offers easy access to parks, schools, and shopping. Don't miss your chance to make this home yours!


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RED HORSE REAL ESTATE
$494,900
3 BD | 2 BA
Residential - Single Family

Nestled between forest and garden in the serene, secluded Crystal Pond neighborhood, this bright and breezy home offers rustic charm, serenity and convenience, & central A/C.The open concept floorplan seamlessly merges the dining, kitchen areas into a vaulted great room that boasts threewalls of windows, and skylights. Two bedrooms, new bath and laundry on the first floor, with a beautiful summer screened porch. The primary is on the second floor, offering a small office area and bath attached. Lower level has an extra-long garage and a playroom for more living space. Short walk to private beach and pond. So Close to all Berkshire cultural venues. With in 5 miles Hiking, Becket Beach, the Art center, Appalachian trail, skiing, restaurants. Available w/ contemporary neutral furnishing.


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STREAMLINE COMMUNITIES
$495,000
1 BD | 1 BA
Residential - Condo/Townhouse

Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including the Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, fitness center, interior bike storage, package delivery room, dog wash and on-site professional management.


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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.


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LAMACCHIA REALTY, INC
$519,900
4 BD | 3 BA
Residential - Single Family

Welcome to this beautifully appointed & pristinely maintained residence that combines timeless character with modern upgrades. Situated on a desirable corner lot, offering a fully fenced-in yard. This spacious home features generously sized rooms throughout, offering comfort & elegance at every turn. The stunning kitchen is equipped with stainless steel appliances, soapstone countertop, quartz island and classic backsplash. A formal dining room flows seamlessly into the side porch, overlooking the serene side yard, perfect for entertaining. The expansive living room boasts a stacked stone wood-burning fireplace and built-ins. Just off the living room, a cozy sitting area with an electric fireplace provides a perfect spot for an office or a reading nook.


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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.


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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.


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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.

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