Found 77 Listings

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36 Photos
LAMACCHIA REALTY, INC
$399,000
3 BD | 1 BA
Residential - Single Family

Pride of ownership shines throughout this well-cared-for property offering lake rights and a long list of meaningful improvements spanning nearly two decades. Inside, you'll find a home that's been continuously upgraded with a remodeled kitchen and bathroom, updated windows, including a bright bay window in the living room. Both the boiler and roof have been replaced. The three-season room adds flexible living space and connects seamlessly to the back porch--perfect for relaxing or use as a home office. The entry ramp leads into a mud room that connects the house, garage and back porch.


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MACCARO REAL ESTATE
$409,000
2 BD | 2 BA
Residential - Single Family

Designer style one level living garden bungalow with beautiful Berkshire bucolic pastoral and mountain views! Easy living and low maintenance with 2 bedrooms and 2 full bathrooms, conveniently located on the Lenox/Pittsfield line. Beautifully renovated with open floor plan, spacious living room, beautiful kitchen and dining room w/amazing views. Primary bedroom leads to back deck with large primary bathroom. Pastoral views from front deck and October Mountain views from large back deck. Beautifully landscaped. Cottage potting shed, cedar fence and much more. Convenient to Tanglewood and all cultural and recreational venues the Berkshires has to offer! Natural gas heating system and central air. Turnkey home!


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CARRIAGE HOUSE REAL ESTATE
$409,000
3 BD | 2 BA
Residential - Single Family

Perched on a gentle hill, this charming ranch offers the perfect blend of comfort and privacy. Surrounded by woods in the backyard, you'll enjoy peaceful views and the beauty of the nature right outside your door. This inviting home features three spacious bedrooms and two full baths, providing plenty of room for family and guests. With its quiet setting and warm, welcoming layout, this hilltop retreat is ideal for anyone looking to enjoy simple living with a scenic backdrop.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$425,000
2 BD | 2 BA
Residential - Condo/Townhouse

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail--from the textured walls to the light pouring in at all hours--creates a sense of romance and possibility.The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest.


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HELEN MULLANY REAL ESTATE, LLC
$465,000
3 BD | 3 BA
Residential - Single Family

Multi-family in a convenient location, walking distance to town and shopping, bus line nearby.Well maintained. The perfect location, walking distance to restaurants and shopping, public transportation nearby.


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MACCARO REAL ESTATE
$489,000
4 BD | 2 BA
Residential - Single Family

Welcome to this solid, well-built four-bedroom, two-bath raised ranch, built in 1969 and nestled in a wonderful neighborhood just minutes from beautiful Laurel Lake. The main living area features a beautiful brick fireplace anchored in the center of the room, hardwood floors throughout the first floor, offering warmth and timeless appeal. This home provides a functional and flexible layout with a large kitchen/ dining area and a finished lower level that includes an additional fireplace and bar, ideal for a recreation room. Separate office and finished laundry room, two car garage is conveniently located underneath. Deck overlooking the large fenced in backyard creates a great space for relaxing or hosting gatherings. A solid home with great bones, waiting for you to make it your own!


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BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
$495,000
4 BD | 2 BA
Residential - Single Family

This Cape is nestled in the pines on East St. Lenox. It features 4 Bedrooms, 2 Full Baths, New Kitchen and appliances, Primary Bedroom on the first floor, Relax in the Four season Sunroom, Beautiful Hardwood floors, Finished Basement, ( New Roof, New Windows, exterior paint 2025 the Boiler and Oil tank replaced in 2022 ). Conveniently located; it's just around the corner from Routes 7 & 20 ( Pittsfield / Lenox Rd ) where you'll find everything you need from shopping to dining and access to all of the Arts, Entertainment and Attractions of living in the Berkshires.


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WILLIAM RAVEIS REAL ESTATE
$495,000
3 BD | 2 BA
Residential - Single Family

This thoughtfully updated home blends warmth, comfort, and history. An amazing front porch welcomes you before you even step inside, and the short walk to downtown or quick drive to the lake offers an easy, connected Berkshire lifestyle. Inside, bright and inviting rooms and beautiful wood floors create a natural sense of warmth, while the layout makes everyday living feel effortless. Flexible spaces adapt to your needs whether that's a home office, playroom, studio, or additional lounge area. With many updates throughout, the home feels modern and refreshed while still honoring its original character. A property that balances charm with convenience!


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LAMACCHIA REALTY, INC
$498,000
3 BD | 2 BA
Residential - Single Family

Beautifully updated and well-maintained 3-4 bedroom split level home nestled in a peaceful lake community on a RARE DOUBLE LOT with partial views of Pontoosuc Lake. Features include hardwood floors throughout, rich cherry wood cabinetry, granite countertops, quality Anderson windows and sliding patio door that blend timeless style with everyday functionality. Step out from the kitchen onto the Trex deck just off the dining area that is perfect for outdoor dining or relaxing. The home also features an attached 2 car garage and the convenience of a full bath on each level. Just a short walk to the lake to drop in a kayak or a motorized boat at the community boat ramp. Mature perennials and a new trex covered front porch add to the charm of this turn-key home. Click on the virtual tour tab.


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ALDEN COUNTRY REAL ESTATE SERVICES
$499,000
6 BD | 3 BA
Residential - Single Family

A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and laundry room. A separate 25' x 50' building, originally built in 1990 as an antique shop, now features a recently updated spacious 2 bedroom bungalow apartment currently rented for $1,700 mo. Additional space includes a large 3 bay workshop / garage for projects or other income uses. Close to Sheffield Green, Library, Dewey Hall, 10 min to GB or CT. House needs updating, but well worth the effort!


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SIGNATURE ASSOCIATES
$499,500
2 BD | 2 BA
Residential - Condo/Townhouse

Birchwood Village in Lenox! Conveniently located near the center of Lenox, Tanglewood and Miraval. This home offers two upstairs bedrooms, a great room with vaulted ceilings and a fireplace, a large kitchen/dining space, walk out flex space downstairs, deck and an attached garage.


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


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$535,000
4 BD | 3 BA
Residential - Single Family

Escape to this stunning four-bedroom contemporary retreat, nestled on 4.7 serene acres along a quiet country road. The open-concept living area boasts soaring cathedral ceilings, rich hardwood floors, and French doors that lead to an expansive upper deck. The sleek kitchen features stainless appliances, quartz countertops, and a bay window with picturesque views of the wooded backyard. The luxurious primary suite showcases double closets, a jetted tub, double sink vanity, and spacious tiled shower. 2 additional bedrooms on the upper level share a bathroom with a full tub and separate tiled shower. The second level offers flexibility with a 4th bedroom or office and a full bathroom, flowing seamlessly into the expansive 35-foot family room with French doors to the lower deck.


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LAMACCHIA REALTY, INC
$539,900
5 BD | 4 BA
Residential - Single Family

Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous counter space leading to the bright living room. Another feature on the first floor is that there is an option for private living quarters/in-law suite with its own entrance. The large primary suite offers a cozy fireplace, two walk-in closets, and an en suite bath with shower and jetted tub. Additionally, there is a first-floor laundry off the two-car garage, and an extra room great for an office.


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ASHMERE REALTY, INC.
$545,000
4 BD | 2 BA
Residential - Single Family

Nestled on a serene private 5.52 -acre lot with a picturesque brook running through, this beautifully updated brick ranch offers the perfect blend of comfort, style, and nature. Located in desirable Dalton, this home features 4 spacious bedrooms with a versatile office space ideal for remote work -- and 2 full bathrooms. Step into the heart of the home with a chef's kitchen with stunning granite countertops, ideal for cooking and entertaining. Recent updates include a new roof (2018), new furnace (2025) and fresh paint throughout, giving the home a warm, bright and welcoming feel. The finished lower level provides a generous family room perfect for gatherings with a wood burning fireplace insert, along with laundry hookups and a two-car garage tucked beneath the house.


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

Nestled in the peaceful hills of Becket, this charming ranch offers the perfect Berkshire escape as winter fades into spring. Imagine enjoying fresh mountain air, morning coffee with birdsong, and quiet wooded views just outside your door. Surrounded by tall pines and serene forest, the setting provides wonderful privacy and calm. Inside, the easy single-level layout features an open living area and a kitchen perfect for relaxed weekend breakfasts or gathering after a day outdoors. Located a short drive from Otis Ridge, Bousquet Mountain, and Jiminy Peak, you'll enjoy year-round recreation--from late-season skiing to spring hikes. Ideal as a full-time home or seasonal retreat, this Becket gem is ready for peaceful mornings and relaxing evenings.


51 Photos
MACCARO REAL ESTATE
$569,900
4 BD | 2 BA
Residential - Single Family

Introducing the Beautiful Spacious Ranch in a Great Neighborhood! Easy Living at Its Finest! Key Features:- Prime Location: Close to Main St.- Impeccably Maintained & Beautifully Updated- Stylish Granite Countertops for a Touch of Elegance- Lower Level Living Area/In-Law Unit, Extra Space for Guests or Rental Income Opportunity, Second Kitchen with Cozy Eat-In Area, Spacious Living Room for Entertaining, Large Bedroom & Full Updated Bathroom with Walkout Access.


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COHEN & WHITE ASSOCIATES
$585,000
2 BD | 3 BA
Residential - Condo/Townhouse

MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry closet. The second level features the primary bedroom with en suite full bath, walk in closet and bonus loft space; Guest bedroom and en suite full bath. Association beach rights to the Stockbridge Bowl, tennis courts, indoor pool, gym and hiking paths. All of this while being conveniently located near Tangelwood, Lenox Village and many cultural attractions here in the Berkshires.


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ROBERTS & ASSOC. REALTY, INC
$599,900
3 BD | 2 BA
Residential - Single Family

Location is everything with this light-filled contemporary ranch on Prospect Hill. Ready for quick occupancy! Five minutes from downtown Stockbridge or to Tanglewood and so close to the town beach on Stockbridge Bowl. This three bedroom, two bath home has been lovingly cared for. Living room and dining with hardwood floors, built-in shelving and built-in storage. Quality updates in the primary bath. Almost two acres of land with garden shed, many perennials and raised vegetable garden beds. Bonus features: spacious attached two car garage, back-up generator, first floor laundry for truly one-level living. The three-season sunroom and outdoor deck add to the charm of this Stockbridge home that's priced to sell!


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PAULA MCLEAN REALTORS INC.
$600,000
3 BD | 3 BA
Residential - Condo/Townhouse

Welcome to 5D Lakeside at Foxhollow - a beautifully updated 3-bedroom, 3-full-bath condo offering the perfect blend of modern comfort and classic Berkshire charm.Enjoy seasonal views of sparkling Laurel Lake from your enclosed summer porch, the ideal spot for morning coffee or evening gatherings. Inside, you'll find a thoughtfully updated kitchen and baths, a cozy wood-burning fireplace, and generous living space designed for both relaxation and entertaining. This sought-after community offers a wealth of amenities including an outdoor pool, Har-Tru tennis courts, and private water frontage on Laurel Lake -- complete with kayak and canoe storage for easy days on the water. Perfectly situated just minutes from Lenox, Stockbridge, Tanglewood &, Jacob's Pillow.

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