Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped backyard featuring a built-in grill, hot tub and plenty of space to relax or gather with family and friends. A rare opportunity to enjoy privacy, comfort, and an exceptional Lenox location.

Historic 9-Unit Bed & Breakfast | ±10,560 SF on ±0.33 Acres Exceptional opportunity to own a beautifully maintained three-story historic bed & breakfast offering approximately 10,560 square feet on a ±⅓-acre lot. Within walking distance to the downtown theater/business district. This well-appointed property features nine unique guest suites, each with private baths and kitchenettes, blending classic charm with modern amenities. Large parking lot in the rear of the property also offers a separate right of way directly onto East Housatonic St. Guests are welcomed through an elegant entry foyer, leading to inviting common spaces including a parlor, formal dining room, and fully equipped common kitchen. The first floor also includes two spacious guest suites.

Beautifully maintained 4-bedroom, 4.5 bath home located in one of Lenox's most desirable neighborhoods. Thoughtfully designed floor plan featuring a spacious living room with vaulted ceiling and abundant natural light. The well-appointed kitchen offers granite countertops, stainless steel appliances, and comfortable dining area overlooking the private backyard. Generous first-floor primary suite provides convenience and privacy, while three additional bedrooms and well-appointed baths offer ample space for family and guests. A versatile den/home office and finished lower-level family room add flexibility for today's lifestyle. Enjoy outdoor living from the screened porch and stone patio surrounded by mature landscaping. Conveniently located just minutes from downtown Lenox and Tanglewood.

This iconic building has been home to one of the Berkshires most beloved businesses for over 50 years. Built in 1731 as the Egremont Tavern stage coach stop, it was expanded in the 1960s. The 2.2 acre lot provides substantial parking. The historic front section offers unique features like stone floors and exposed beams and fireplaces. The rest of the building consists of a series of lovely rambling spaces with rustic elements on the main and lower levels, and two rental apartments upstairs (one 3/1, one 1/1). This property offers a buyer an extraordinary opportunity: own an incredible income producing property in the bustling town of South Egremont.

Discover this breathtaking timber-frame home sited on a peaceful and private 10-acre park-like setting central to the Berkshires. Redesigned by architect Pam Sandler, who added a vaulted great room ceiling, a welcoming front porch, a spacious screened porch, and a 3-car garage. Featuring a first-floor en-suite primary bedroom, a generous living & dining area anchored by a commanding fieldstone fireplace, and a well-planned kitchen with all stainless appliances. Three upstairs bedrooms have ample closet space, and the basement family room with a wood-burning stove offers a cozy winter retreat. This eco-friendly home features a newly built barn, solar panels, and heat-pump climate control. There is so much to experience in this beautifully updated home, just 10 minutes from Tanglewood.

Welcome to this exceptional Kruzel Built custom residence, where timeless craftsmanship meets thoughtful modern design. Perfectly appointed and meticulously maintained, this stunning home offers luxurious living with every detail carefully curated for comfort, style, and functionality. Step inside to discover an expansive open floor plan filled with natural light, elegant finishes, and seamless flow throughout the main living spaces. The beautifully designed great room features a cozy gas fireplace, creating a warm and inviting atmosphere ideal for both everyday living and entertaining. The kitchen opens effortlessly to the dining and living areas, making gatherings feel both intimate and spacious. The first-floor primary suite serves as a private retreat, complete with a generous wa

Dreaming of your own private sanctuary? 30+ acres await exploration! Enter between two stone pillars and the long winding driveway will take you past woodland glades, open spaces, mature tree stands, manicured lawns and a magnificent spring-fed swimming quarry! Acres of open cleared land afford additional usage options. Cedar log home, one-owner custom built. Large wrap-around deck and long covered porch; great for summer entertaining! Inside you'll enjoy over 2000 sf of relaxed country living. Great room with vaulted ceiling, massive stone fireplace. Open kitchen w. granite counters and island w seating. Two first floor bedrooms and full bath. Upper level with spacious primary suite and an open loft with fireplace. Finished walk-out lower level w. 2 car garage. Truly one-of-a-kind!

Set in the heart of the Berkshires of Lee, Mass, this beautifully maintained 4-bedroom home captures the essence of Berkshire living with panoramic, elevated views for all 4 seasons that will leave you speechless; particularly in Autumn, when views in the Berkshires explode with color. A 4th oversized garage below the house is the perfect place for all of your toys. Inside, the home offers 3 finished levels of flexible living space designed with an open concept. The 1st floor primary suite provides the ease of one-level living and features a newly renovated bathroom with walk-in shower, creating a spa-like retreat with tasteful tile finishes.

Own a piece of Williamstown history with this beautifully preserved Greek Revival modern farmhouse, set along the Green River on just under 20 picturesque acres. This exceptional property offers a rare combination of historic charm and modern comfort, with ample acreage for farming or livestock, ponds, barns, an in-ground pool, and more. The main residence features 5 bedrooms and 4 bathrooms, while the attached guest house offers 2 bedrooms and 2 bathrooms, providing flexibility for extended family, guests, or multi-generational living. Step inside this timeless home to discover thoughtful modern upgrades designed for everyday living. A spacious mudroom at the rear entrance keeps daily life organized, while the stunning kitchen—complete with stainless steel appliances, granite countertops

Special Berkshire retreat on 25 private acres in Harrington Woods with beautiful views. Offering 5,400 sq ft, this 4-bedroom, 4-bath home features oversized rooms and high ceilings. The main level includes a recently renovated chef's kitchen, expansive primary suite with walk-in closets, guest room/office, library with built-ins, dramatic living room and a 400 sq ft screened porch. The walkout lower level offers two additional bedrooms, exercise room, family room, professional pool table, sauna and steam shower. Additional highlights include an oversized 2-car garage with Level 2 EV charger, 12x24 storage shed, and a 30-panel solar array with a transferable utility credit. HOA amenities include tennis, pickleball and a heated seasonal pool. Minutes to Otis Ridge and Great Barrington.

Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort. Property Highlights 5 Bedrooms | 4 Full Baths + 1 Half Bath** Complex rebuild from the ground up** - preserved nod to the town's heritage with a fresh, modern interior Chef's Kitchen** - high-end appliances, ample prep space, and thoughtful layout for entertaining Radiant Floor Heating** - in entry Dual Fuel Heat throughout High Velocity Central Air Conditioning** - efficient, quiet climate control Solid Heavy Doors with Emtek Hardware** - substantial, timeless feel with premium finishes 4-Season Porch**

Experience the beauty of Berkshire lakefront living on beautiful Pontoosuc Lake, where breathtaking sunrise views, peaceful waters, and exceptional privacy create the perfect year-round retreat. Nestled in the heart of the Berkshires, this beautifully remodeled home blends luxury, comfort, and thoughtful design, ideal for both everyday living and entertaining by the lake.

Set across 30+ pristine Berkshire acres, this property offers sweeping westerly mountain views, gently rolling fields, and Cone Brook running the length of the land to Shaker Mill Pond. With approximately 2,000 feet of frontage on Swamp Road, the possibilities are wide open: farming, equestrian use, a private estate, or potential subdivision into 6+ buildable lots.Two substantial barns, both equipped with electric and water, are already in place, offering immediate utility and flexibility. The setting is both scenic and convenient & just minutes to the village of West Stockbridge. A short drive to Tanglewood and Lenox, and within easy reach of ski areas.Additionally, a 1950s four-bedroom, two-bath home with a heated basement sits along the road frontage, ready for

A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent century-old oak tree, and follow the gentle brook that borders the property. This remarkable landscape offers a rare combination of privacy, natural beauty, and accessibility. Create an incomparable estate overlooking the mountains, or take advantage of the property's three ready-to-build lots to establish a family compound nestled among meadows and woodland. Whether envisioned as a private retreat,

Nestled among spectacular rhododendrons that burst into bloom each spring, this architect-designed contemporary home offers a seamless blend of natural beauty and timeless mid-century modern inspiration. Designed byarchitect Andrew Daland, the residence features expansive windows that frame peaceful pastoral views and fill the home with natural light. Designed for comfortable one-level living, the main floor includes the primary living spaces, while the lower level provides exceptional accommodations for family and guests with two bedrooms each with en suite full baths, and a spacious family room. The open-concept great room boasts a cathedral ceiling, a fireplace, built-in bookcases, and flows effortlessly into the kitchen. . . .

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

Well maintained and set in a prime Egremont location, this home is perched above the Egremont plain with open views. Quiet and private, yet just minutes to downtown Great Barrington, Egremont and everything the Berkshires has to offer. The main level is bright and welcoming, with an open living space centered around a wood-burning fireplace. A first-floor library adds a quiet, separate space; ideal for a home office while the kitchen connects directly to the deck, creating an easy flow for indoor/outdoor living and a perfect spot to take in the views. The upper level features three bedrooms, including a primary ensuite, along with a full bath and an additional den that can easily serve as a lounge or office. The lower level offers a full in-law apartment complete with it

Situated at the top of vibrant Railroad Street, this property offers exceptional visibility in a bustling location, making it an ideal spot for retail stores, restaurants, cafes, or office spaces. The building features two spacious stories and a full basement, providing ample room for various business operations. With high ceilings that create an airy atmosphere and windows on three sides that flood the interiors with natural light, the space feels open and inviting. This is a remarkable opportunity to establish your business in the heart of Great Barrington, surrounded by the excitement and energy of a thriving community.

LOCATION, LOCATION, LOCATION. This terrific home is in low-tax Egremont, setback from road, & is a short walk to French Park which sports new tennis/pickleball courts, a playground, hiking trails, a basketball court, and a dog park. The town also features two of the more popular restaurants in the Berkshires. But, what about the house? This well maintained 4 bedroom/3 bathroom home is wheelchair accessible, and meticulously maintained. There is an in-apartment that might be rented as an apartment or a professional office. Ever been inconvenienced by a power outage? Not at this house because it has a 10kW generator. Worried about roof conditions? Not a concern at this house. The steel roof should be good for another 40 to 50 years. Schedule a showing today! SEE MORE...