Welcome to 221 Bailey Road in Lanesboro, MA., an exquisite ranch-style home offering approximately 4,200 sqft of luxurious living space. Nestled on 87 acres atop a mountain, this property provides unparalleled privacy and breathtaking views that enhance its serene atmosphere. The open-concept living area is perfect for entertaining, featuring abundant natural light and seamless flow between spaces. Energy efficiency is a hallmark of this home, ensuring comfort year-round while minimizing utility costs. Ample room for family and guests, this stunning residence combines modern amenities with the tranquility of nature. Some of the amenities this home offers a three car garage, heated in ground pool, owned solar and a cozy wood stove for those chilly Berkshire nights.

Imagine owning your own secluded sanctuary, where total privacy and tranquility are yours for the taking. This extraordinary property offers the rare opportunity to build your dream retreat on a breathtaking piece of land, untouched by the outside world. With 20-foot-tall mountain laurel trails leading to the top of a mountain with stunning views right at your doorstep, you'll have endless access to nature's beauty, all while remaining completely secluded.The land consists of 6 separate parcels, all being sold together, creating the perfect canvas for whatever you envision. Don't miss out on staking your claim to this hidden gem, an unparalleled escape !

14 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, and the Colonial Theater. Classic brick exterior and excellent off street parking. All units feature one bedroom and separate utilities. Coin-op laundry located on site for additional income.

Cable Mills, industrial mill buildings restored into beautiful homes with 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless appliances, granite countertops, gas ranges, generous closets and in home laundry. Cable Mills offers stunning views of the 'Purple Mountains' and the 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. #CableMills #WilliamstownMA #BerkshiresLiving #LoftStyleCondo

A thoughtfully designed home with south facing views on 3 acres. Constructed by a reputable local builder offering a perfect blend of luxury and privacy. Situated on the Canaan/New Lebanon line, it boasts breathtaking views and an in-ground pool ideal for relaxation and entertainment on the blue stone patio. Large first-floor primary suite provides a peaceful retreat, complete with large windows and freshly updated en-suite bath. Enjoy cooking in the large EIK that's open to the dining area. Relax after a meal by the fireplace in the living room. First floor half bath and laundry along with a gracious, welcoming mud room complete the first floor. Additional bedroom with bath and open landing on 2nd floor, PLUS a guest suite with kitchenette and bath with it's own private entrance!

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bedroom Title V, completed 4/

Gorgeous contemporary ranch home built in 2001, ideally situated on the North Adams/Williamstown line with breathtaking mountain views from every window. Sited on a 14 acre pastoral parcel, of which 6.9 acres are being placed in a conservation restriction, the home and landscape reflect the unique beauty of the Berkshires.This thoughtfully designed home offers convenient one-level living with three first-floor bedrooms, including a cozy primary suite featuring its own charming balcony. The main level also includes a large living/dining space with radiant heat and a beautiful fireplace, featuring an open, light-filled layout perfect for everyday living and entertaining. The lower level provides excellent flexibility with ample storage rooms, a two-car garage, and a finished bonus living

Historic 9-Unit Bed & Breakfast | +/-10,560 SF on +/-0.33 AcresExceptional 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.

A rare opportunity to own a well-established and respected auto parts store and full-service mechanic shop in the heart of Pittsfield. Located in a high-visibility, high-traffic area, this centrally situated property offers convenience, strong customer reach, and excellent brand recognition built over many decades.With over 11,000 square feet of space, the property features ample off-street parking, multiple service bays, dedicated retail areas, and offices for clerical and accounting functions. This well-organized layout supports efficient operations across both parts sales and mechanical services, including inspections, diagnostics, and general repairs.

A Nature-Lover's Haven Awaits Set on an expansive 94-acre stretch bordering the tranquil Tolland State Forest, this distinctive property combines unmatched privacy with exceptional natural charm. Envision life along the serene Farmington River, with hundreds of feet of stunning river frontage and your very own storybook-style covered bridge--an extraordinary hallmark of this countryside escape.Highlights Include:Vast Acreage: 94 acres of secluded, wooded beautyRiverfront Magic: Extensive frontage on the Farmington RiverSignature Feature: Historic-style covered bridge adds character and charm

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.

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

Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires.Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind.

An exceptional architect-designed home in the heart of the Berkshires, privately sited within the conservation landscape of Bishop Estates and just minutes from Tanglewood and the center of Lenox.Thoughtfully positioned to preserve complete privacy, the home is surrounded by protected natural beauty without neighboring homes in view. Expansive walls of glass frame sweeping meadow and mountain vistas, bringing the landscape into every principal room.Designed for comfortable everyday living and effortless entertaining, the flowing layout connects a galley kitchen to generous dining and living spaces filled with natural light.The primary bedroom suite offers a peaceful retreat with its own sitting room, while two additional bedrooms and a full bath provide inviting accommodations for ....

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly Views of October Mountain. Plenty of room for family and friends.

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 Highlights5 Bedrooms | 4 Full Baths + 1 Half Bath**Complex rebuild from the ground up** - preserved nod to the town's heritage with a fresh, modern interiorChef's Kitchen** - high-end appliances, ample prep space, and thoughtful layout for entertainingRadiant Floor Heating** - in entry Dual Fuel Heat throughout High Velocity Central Air Conditioning** - efficient, quiet climate controlSolid Heavy Doors with Emtek Hardware** - substantial, timeless feel with premium finishes4-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.

Discover comfortable & gracious living in this impeccably renovated home in Lenox. 4 BRs & 4 BAs approx. 4,000 sq ft of open, modern design. The entire home is filled w/sunlight & gleaming new red oak flooring & a sleek chef's kitchen outfitted with new Bosch appliances, quartz countertops & significant storage. Functional yet luxurious details throughout- from laundry on 2nd level to mini-split systems, fireplace & a sunroom that promises cozy comfort in all season. Step outside into your private natural oasis: enjoy gatherings w/ woodland views around the fire pit, on deck or patio. Newly finished lower level includes a living, dining & media room equipped with kitchenette & full bthrm. Set in one of Lenox's most desirable neighborhoods, this home provides privacy and convenience.

Nestled in picturesque Alford, this inviting four-bedroom, 4.5-bath home blends comfort and flexibility in a serene Berkshire setting. The first-floor primary suite features a private ensuite bath, ideal for easy living. Thoughtfully designed spaces offer room for guests, work, or hobbies, while seasonal views bring natural beauty indoors throughout the year. With low Alford taxes and a peaceful location close to all the Berkshires have to offer, this home is a rare and appealing find.

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