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Currently listing 881 sales properties. |
| Found 45 Listings | Sort: |
28 Photos COMPASS MASSACHUSETTS , LLC GB |
$329,000
4 BD |
3 BA
Residential - Single Family Discover the charm of downtown living in this Colonial home located in the heart of West Stockbridge. This home features four bedrooms, two full baths, kitchen, living room, dining room and a deck overlooking the river. In addition to the main living area the property also includes an in-law or studio apartment with it's own kitchen and bathroom. With a nice flat yard for outdoor activities, outdoor shed for extra storage and backing up to the picturesque Williams River makes this a wonderful opportunity. |
3 Photos DALTON TOWN & COUNTRY ASSOC, INC |
$425,000
4 BD |
2 BA
Residential - Single Family 4 Bedroom 1.5 bath brick cape on over half acre lot, wood floors throughout, fireplace, newly painted, dining room, eat in kitchen, one car attached garage, breezeway, family room in basement.Includes separate 720 square foot ranch with 2 bedrooms, 1 bathroom on property, front porch, vinyl siding, separate utilities |
45 Photos WILLIAM PITT SOTHEBY'S - LENOX |
$450,000
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 (2025). |
35 Photos Compass Massachusetts, LLC |
$499,000
3 BD |
3 BA
Residential - Single Family An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility. |
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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37 Photos 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. |
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. |
55 Photos COHEN & WHITE ASSOCIATES |
$599,000
3 BD |
3 BA
Residential - Single Family Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area. Additionally there is an attached first floor In-law apartment with living room, kitchen, bedroom and full bath. Included with the house is a multi level barn with electricity. Lovely setting to relax on the back deck and take in the views or stroll into town to enjoy the cultural amenities This gem has great potential and is ready for the new owners vision |
41 Photos PIRETTI REAL ESTATE |
$624,900
2 BD |
2 BA
Residential - Condo/Townhouse This caterpillar has become the most beautiful butterfly....you have to see it to believe! The most tastefully done unit, gutted and re-built to perfection with all high end fixtures, floors, layout, appliances and functionality. New ebony stained hardwood floors, gorgeous kitchen with stainless steel counters, marble island and back splash, Viking appliances, loads of cabinetry and access to the gorgeous deck for 3 season living. Beautiful master suite with an adjoining study, plus a whole bedroom suite with full bath and study on the lower walk out level. The cut stone fireplace in the living room is magnificent and the placement of rooms affords plenty of privacy for guests and owners alike. This unit is truly unique, a labor of love, and awaiting its next discerning owner! |
58 Photos DIGRIGOLI REAL ESTATE |
$844,000
6 BD |
4 BA
Residential - Single Family This exceptional home is ideally located within walking distance of the town center and Williams College. Set alongside protected conservation land, the property offers a rare blend of convenience, privacy, and natural beauty and is also located in a highly desirable Williamstown neighborhood. The property has direct backyard access to Lower Linear Park walking trails, the Mohican Trail bike path, a public tennis court, a nearby dog park, and river recreation areas, all just a few minutes' walk away.The home features a spacious and private backyard, secluded from the street, which provides a peaceful setting. The yard is beautifully framed by mature landscaping and is complemented by mountain views of the Appalachian Range, which can be enjoyed from a large deck. SEE MORE TAB |
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50 Photos BIRCH PROPERTIES |
$845,000
4 BD |
4 BA
Residential - Single Family Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated, blending original character with contemporary upgrades. Post and beam construction adds warmth and architectural texture, while a sleek gas fireplace anchors the open living and dining areas. The updated kitchen is ideal for gatherings both casual and festive. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two additional bedrooms and a full bath complete the |
73 Photos WILLIAM PITT SOTHEBY'S - LENOX |
$889,900
5 BD |
4 BA
Residential - Single Family Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved over this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregiver |
56 Photos WILLIAM PITT SOTHEBY'S - GT BARRINGTON |
$899,000
3 BD |
4 BA
Residential - Single Family Experience the pinnacle of refined living in this reimagined masterpiece, meticulously renovated by a premier local design/build firm, Wingate Ltd. Spanning three levels and 2,748 square feet of bespoke living space, 549 Shunpike Road offers a rare blend of architectural drama and modern efficiency, situated on one of the most scenically stunning corridors in all of Berkshire County.The Setting: Scenic Sanctuary - Your journey home begins along a road celebrated for its breathtaking beauty. The drive leading to Shunpike Road is a quintessential Berkshire landscape, dotted with historic family dairy farms, rolling open pastures, and sweeping views of dramatic mountain vistas. This property offers a front-row seat to the changing seasons and the quiet majesty of the New England countryside |
79 Photos LAMACCHIA REALTY, INC |
$995,000
4 BD |
4 BA
Residential - Single Family Welcome to one of Southeast Pittsfield's most coveted neighborhoods, where this exceptional Colonial seamlessly blends timeless elegance with modern luxury. Offering 4 bedrooms and 3.5 baths, the home showcases a simply stunning interior highlighted by a chef's kitchen with Omega cabinetry and commercial-grade appliances. Expansive windows bathe every room in natural light, creating effortless indoor-outdoor flow. Outside, unwind to unforgettable sunsets from the private backyard abutting Canoe Meadows, complete with a large wraparound deck, in-ground swimming pool, and pool house. The finished walkout lower level features a second kitchen, full bath, home gym, and generous recreation space ideal for teens, guests, or extended stays. A truly rare offering in an irreplaceable setting. |
20 Photos WILLIAM PITT SOTHEBY'S - GT BARRINGTON |
$998,000
4 BD |
4 BA
Residential - Single Family Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond, just minutes away, this home is a haven for those who crave both serenity and adventure.Where Modern Elegance Meets Natural Beauty A Grand Welcome - A wraparound deck, inground pool, and upper balcony invite you to take in the forested surroundings, framed by black aluminum railings and Trex boards built for beauty and longevity. |
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48 Photos WILLIAM PITT SOTHEBY'S - LENOX |
$999,999
6 BD |
9 BA
Residential - Single Family Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room, a library, and a large cook's kitchen with eat-in area and pantry. Three period fireplaces add warmth and charm. Outside, mature trees frame open meadow, with room for gardens, games, and long summer evenings. The setting is remarkably convenient. Tanglewood, Lenox, Stockbridge, and downtown Lee are a short drive, and access to Route 7 and the Mass Pike keeps weekend trips simple. |
92 Photos WILLIAM PITT SOTHEBY'S - LENOX |
$1,050,000
6 BD |
5 BA
Residential - Single Family A Stunning Three-Story Residence with Breathtaking Views for an Easy Care Lifestyle in the Berkshires.Majestic and magical perfectly describe this exquisite three-story mountain top home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community or work at home with glorious views of the Berkshire Hills.Prime Location for Nature and Culture.Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors. |
13 Photos WILLIAM PITT SOTHEBY'S - LENOX |
$1,245,000
4 BD |
4 BA
Residential - Single Family Introducing Green River Meadows, a new luxury development that prioritizes healthy, sustainable living--ideal for those seeking an eco-friendly lifestyle without sacrificing luxury. Nestled alongside the Green River in Williamstown, just a short distance from the prestigious Williams College and surrounded by the cultural richness of the Berkshires, this community offers an exceptional lifestyle in a prime location.These to-be-built homes reflect a deep commitment to sustainability, seamlessly blending innovative design with environmental stewardship. Built using Passive House principles, the homes are designed to achieve optimal energy efficiency through superior insulation, triple-pane windows, airtight construction, and continuous fresh air ventilation, |
68 Photos BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY |
$1,395,000
4 BD |
4 BA
Residential - Single Family This quintessential turn of the century antique home, built in 1909, is in immaculate condition. Set just outside the charming village abutting desirable Pine Crest Hill Rd, the property provides privacy with beautiful gardens and landscaping and stunning views of pasture and mountains, 3 miles to downtown Great Barrington, in low-tax Egremont. The main residence features 4 spacious bedrooms, 3.5 baths, two cozy fireplaces, tall ceilings, and light, bright, airy spaces that create a welcoming atmosphere. A separate guest house with two bedrooms, currently in need of some TLC, adds to the versatility of the estate. The grounds span 11 gorgeous, sub-dividable acres, presenting future possibilities for a family compound. Conveniently located near Berkshires attractions. |
42 Photos WILLIAM PITT SOTHEBY'S - GT BARRINGTON |
$1,395,000
5 BD |
4 BA
Residential - Single Family Embrace the epitome of Berkshires luxury in this newly constructed residence, poised on a serene cul-de-sac with community pool privileges. Spanning an impressive 4,200 square feet, this home is a stone's throw from the bustling heart of Great Barrington. Step under the elegant covered portico and into the grandeur of a cathedral great room, where a cascade of natural light streams through expansive windows, offering tranquil woodland views & access to a cozy screened porch. Designed for the ultimate in sophistication and convenience, the open floor plan unites the living, dining, & kitchen spaces, creating an idyllic setting for hosting soirees or savoring quiet moments.With Ski Butternut & a plethora of year-round activities at your doorstep, adventure & leisure await! Move in ready! |
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