Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an open concept kitchen and family room with cathedral ceilings, where sliders lead seamlessly to a large rear deck overlooking a spacious, flat, and fenced backyard; ideal for gatherings, play, or quiet relaxation amid mature landscaping and beautiful gardens.

Set in a small country neighborhood, this stunning 4 Bedroom is perfect for entertaining friends and family. The 1st floor includes an open kitchen and dining area with granite countertops and high ceilings, a cozy sunken living room with propane fireplace, and a spacious first floor bedroom suite. Sliding French doors throughout the 1st floor bring in plenty of light and lead onto a 50' mahogany deck overlooking the back yard. The 2nd floor offers a large primary bedroom suite with walk-in closet, and two additional bedrooms sharing a full bath with laundry. The insulated third floor with high ceilings provides potential for an extra 1620 square feet of living space.

Escape to an exceptional Post & Beam Berkshire Retreat nestled on the east side of Jiminy Peak Mountain Resort. Set on 25+ acres for seclusion and privacy, eat, play & live in this 4 bedroom, 2.5 bath chalet-style home with countless modern updates. Spectrum was recently added for everyday internet and tv streaming, as well as 5 new high-efficiency mini split air conditioning/heating units for those steamy Summer, and cold Winter, nights. New granite countertops and GE Cafe and Bosch stainless appliances in the recently refurbished kitchen are a true cook's delight. An open living concept, under a soaring 25 foot ceiling, creates multiple gathering spaces from the huge sectional to the plentiful island seating, and floor to ceiling dining room window frames the outdoors inside.

One of the largest condo units available @ 34 Bridge St. Just minutes from the movies, shopping and restaurants. Views facing east mountain to enjoy the sunrise. Beautiful morning light. Open floor plan with Juliette Balcony. Primary bedroom with private bathroom with double sinks. Both bedrooms include remote darkening shades. Stackable laundry and ac in unit. Includes plenty of storage with one dedicated parking spot. Come and enjoy easy living in town.

Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful surroundings. Conveniently located just minutes from Sheffield village, Canaan (CT), and Great Barrington, this versatile property works beautifully as a full-time residence, vacation retreat, or investment opportunity in the heart of the Berkshires. This is a new build, and taxes have not yet been determined.

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry.

To Be Built - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 2.14-acre lot (MLS # 248343), featuring a private well, 3-bed septic design, and underground electric. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 3.59-acre lot (MLS # 248344), installed private well, perc test/soil evaluation complete, and underground electric in place. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.

HIGHLY MOTIVATED SELLER! Set atop a gentle hill along a quiet, winding county road, this charming New England saltbox home offers a rare blend of timeless elegance and modern comfort. Set atop a gentle hill along a quiet, winding county road, this charming New England saltbox home offers a rare blend of timeless elegance and modern comfort. Built in 1995 by a skilled contractor as a spec project, the home was thoughtfully customized to suit a relaxed yet refined lifestyle. With two spacious bedrooms, a cozy den that doubles as a convenient ground-floor guest bedroom, and three full bathrooms, the home strikes the perfect balance between form and function.From the moment you step inside, you'll be welcomed by a warm and inviting ambiance. The traditional dining room flows seamlessly in

Located in the desirable, gated community of Woodmont Estates, this thoughtfully updated home offers a timeless layout, flexible living spaces, and easy access to the best of the Berkshires. Inside, vaulted ceilings, expansive windows, and hardwood oak floors create a light-filled and inviting atmosphere, anchored by a gas fireplace and elegant details. The custom kitchen serves as the heart of the home, featuring maple cabinetry, granite countertops, updated finishes, and a layout that flows effortlessly into both formal and casual living spaces--ideal for everyday living and entertaining alike. The primary suite is a true retreat, complete with his and hers walk-in closets and a well-appointed bath designed for comfort and

Custom built home! Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French doors lead to an inviting screened porch/sunroom. Large private deck overlooking patio with firepit and meticulous lawn. Large mudroom/office. Beautiful living room with bay window, cozy den/family room with wood burning fireplace. Large first floor full bathroom with washer/dryer hook-up. Thoughtful design throughout.

Discover the perfect blend of comfort and charm with this stunning contemporary situated on two acres. There is a full-house Generac generator for comfort and peace of mind and central air. The great room is washed with natural light from the wall of windows and has a beautiful gas fireplace to provide additional warmth on cold Winter days. There is a circular flow into the spacious dining room and the updated kitchen making this home ideal for entertaining. A full bath and two charming guest bedrooms welcome visitors and offer opportunities for a home office. The oversized four-season sunroom offers magnificent light that takes in the picturesque landscaped surroundings and woodlands. It features an efficient gas stove for chillier days and screen inserts to help capture Summer breezes.

Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian stands as a true architectural gem, nested amid lush gardens and beautifully landscaped grounds. From its distinctive urn shaped columns to its twin towers, gables and wrap around porch, every detail reflects the grace and grandeur of a bygone era - balanced perfectly with thoughtful modern updates. Sweeping lawn with private patio and mature plantings. Currently configured as a two family residence, the layout offers easy conversion back to a magnificent single-family home, making it ideal for a grand Berkshire retreat, full time residence, or multi-generational living. Inside you will find historical character, original millwork & trim, and updated kitchens & baths. Whether you're seeking a stately

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

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A beautiful heated swimming pool and a dedicated tennis court provide endless recreation. The expansive grounds, located at the end of a quiet road, guarantee unmatched privacy. Plus, a large solar array and new heating system drastically cuts utility costs. Enjoy total seclusion while being in the middle of everything that makes Great Barrington one of the most desirable towns in the Berkshires.

GORGEOUS LOW MAINTENANCE HOME IN LOW TAX EGREMONT. A move-in ready opportunity, just minutes to the NY & CT borders AND Great Barrington. This home is ready for occupancy just in time for Ski Season. Wonderful chef's kitchen with open plan Living/Dining. The upper level hosts a grand primary en- suite, with a dedicated office space and seating area, AND its own screened porch. Two additional Bedrooms and full Bath provide total comfort for family and guests. The expanded deck, fire pit and level yard great for family & friends. Two car attached garage, Generator, and meticulously maintained grounds. Custom shed, has studio or play house potential. Dog fenced area. Hy's Fried, Egremont Barn & Catamount Ski area minutes away. Trains 20 minutes away.

Your dream oasis awaits! Nestled on 19.2 private, bucolic acres, this meticulously maintained 3-4 bedroom/3 bath log home is being offered with numerous upgrades, all within the past 3 years. 1st floor features an open floor plan with hardwood floors, vaulted ceilings, an abundance of natural light, along with the convenience of a 1st floor laundry and full bath. 2nd floor is home to a generous loft, spacious primary bedroom w/ensuite bath, 2 additional bedrooms and full bath. Entertain year-round on your new trex deck and throughout manicured grounds; enjoy N.E. winter nights fireside by your new gas fireplace and bluestone/cultured stone hearth! All representations are from the seller or public source; broker has not verified same. Recommended buyer independently verify all information.

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.

This thoughtfully designed contemporary home offers quality construction, energy efficiency, and a rare opportunity for customization--without the lengthy build process. Built with comfort and performance in mind, the home features spray-foam insulation in the walls and attic, fiberglass insulation between floors, energy-efficient windows, and Central Air/Heat system. The walkout basement provides excellent potential for future expansion of living space. The builders are open to conversations with buyers regarding modifications and finishing details, allowing you to personalize the home to suit your needs while moving into a substantially complete, quality structure. Driveway and landscaping will be installed in early Spring 2026.