Just over the hill from Tanglewood, down a quiet country road, this year-round Richmond retreat blends privacy, rustic character, and expert craftsmanship. The heart of the home is the vaulted great room, where exposed beams, a loft balcony, and a wood stove create a warm gathering space that flows seamlessly into a beautifully crafted three-season porch with interchangeable glass and screen panels overlooking the woodland. Thoughtfully designed to preserve the home's original rustic charm, the spacious primary suite is a private retreat featuring vaulted ceilings, a sitting area with a gas stove, an ensuite bath with a soaking tub, and laundry. Wraparound decks further extend the living space outdoors, embracing the natural landscape. The walk-out lower level provides excellent storage

Beautifully tucked away in one of Pittsfield's most established neighborhoods, this stately 5-bedroom, 5-bath home is a rare offering filled with warmth, character, and endless potential. From its gracious proportions to its timeless architectural details, this is a home that makes a lasting impression. Sun-filled living spaces, generously sized rooms, and a thoughtful layout provide the perfect balance of elegance and everyday comfort. Whether you're gathering with family, entertaining friends, or simply enjoying a quiet evening at home, there's room for every occasion. Rich in original character and beautifully maintained, this home also offers an exciting opportunity for its next owner to add their own style and create something truly extraordinary.

Located in one of Southeast Pittsfield's most sought-after neighborhoods, this well-maintained home offers a versatile layout, great natural light, and comfortable living spaces designed to fit a variety of needs. The open living, dining, and kitchen area creates an easy flow for everyday living and entertaining, while two first-floor bedrooms and a full bath provide the convenience of single-level living. A recently added sunroom brings in even more natural light and offers the perfect spot to relax and enjoy the changing seasons. A mudroom, laundry room, and half bath just off the attached two-car garage add everyday functionality and convenience. Upstairs, two additional bedrooms and a full bath provide plenty of room for family or guests, while the finished basement offers valuable

Step out your back door and onto the mountain--this unique slopeside condo offers direct access to skiing and hiking trails right from your backyard. Offering 2,750 sq. ft., this beautifully updated 3-bedroom, 2½-bath home features a gas fireplace and refreshed kitchen with quartz countertops, subway tile backsplash, and GE Profile appliances. Updates include newer carpeting and paint, California Closets, and USB/USB-C outlets. The unfinished basement offers generous storage, home gym or future living space and is stubbed for plumbing. Enjoy peaceful mountain surroundings and a community pool in warmer months. Just a short drive from Lenox and Tanglewood, with easy access to dining, shopping and the best of the Berkshires.

Step out your back door and onto the mountain--this unique slopeside condo offers direct access to skiing and hiking trails right from your backyard. Offering 2,750 sq. ft., this beautifully updated 3-bedroom, 2½-bath home features a gas fireplace and refreshed kitchen with quartz countertops, subway tile backsplash, and GE Profile appliances. Updates include newer carpeting and paint, California Closets, and USB/USB-C outlets. The unfinished basement offers generous storage, home gym or future living space and is stubbed for plumbing. Enjoy peaceful mountain surroundings and a community pool in warmer months. Just a short drive from Lenox and Tanglewood, with easy access to dining, shopping and the best of the Berkshires

Dramatic Price Reduction creates opportunity for updates and remodel. Gracefully situated on a gentle sloping hillside street this distinctively designed, quality built, multi-level home offers distant neighborhood mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home to embrace privacy, natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined residence is a private enclave offering 4-5 bedrooms, 3 full bath, masterfully landscaped set on 1.5 acres with unique tree selection, blooming shrubs and pollinator flowering perrenials. Just 10 minutes to the culture, cuisine and art offerings of Lenox especially the sounds of Tanglewood. Minutes to all that is Berkshire while being immersed in renowned peaceful

Beautifully situated atop a hill on Crofut Street, this brick Georgian-style home blends timeless architecture with thoughtful updates. The owners have preserved its original beauty and distinctive architectural details while making improvements for modern living. Featuring five bedrooms and two and a half baths, the home offers generous space in a convenient Central Berkshires location. It's within walking distance of the Colonial Theatre, the Amtrak station, and other public transportation, as well as close to downtown Pittsfield and local restaurants. Lenox and Tanglewood are also nearby, offering scenic beauty and live music. Enjoy classic character, a lovely hilltop setting, and easy access to the arts, dining, and transportation in the Berkshires.

Welcome to life on beautiful Pontoosuc Lake, where breathtaking sunrise views and year-round waterfront living await. This charming, move-in-ready home offers the perfect combination of comfort, thoughtful updates, and low-maintenance living in a truly special lakefront setting. The open and airy living room features soaring vaulted ceilings, expansive windows that capture stunning lake views, abundant natural light, and a cozy gas fireplace, creating a warm and inviting space to relax or entertain. The well-designed floor plan includes spacious first-floor bedrooms with generous walk-in closets, updated bathrooms, newer flooring, Anderson windows, skylights, and multiple heating zones for added comfort.

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.

Set within one of the Berkshires most coveted communities, 9 Eastbrook Lane is a masterclass in refined living, where thoughtful design meets impeccable care. Beautifully and intentionally sited, this distinguished residence offers 5 bedrooms, 3 full and 2 half baths across a gracious, light-filled layout designed for both elegant entertaining and everyday comfort. The stunning kitchen showcases rich maple cabinetry, a premium Viking range, dual refrigerators and exceptional workspace, perfectly suited for the discerning cook. The renovated primary bathroom evokes a true spa experience, blending luxury and serenity with timeless finishes. Every detail has been meticulously maintained, from the seamless indoor-outdoor flow to the expansive Trex decking ideal for al fresco gatherings.

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.

Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate first floor office with French doors for privacy. The first-floor primary suite boasts a walk-in closet and en suite bath while the walkout lower level expands the living space with a generous family room, two additional bedrooms, full bath and private patio. With 4 bedrooms, 4 full baths, and exceptional space throughout, this home is simply gorgeous and ready to enjoy. Clubhouse, pool, tennis.

Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate first floor office with French doors for privacy. The first-floor primary suite boasts a walk-in closet and en suite bath while the walkout lower level expands the living space with a generous family room, two additional bedrooms, full bath and private patio. With 4 bedrooms, 4 full baths, and exceptional space throughout, this home is simply gorgeous and ready to enjoy. Clubhouse, pool, tennis.

Gracious, elegant, and designed for living well, this exceptional center hall Colonial offers timeless character, beautiful mountain views, and an abundance of space. The welcoming entrance is accented by exquisite English stained glass, with wood floors flowing throughout the home. Five bedrooms and 3.5 baths provide room for family and guests, while grand living and dining rooms are perfect for entertaining. A spacious family room offers a more relaxed gathering space. The primary suite features cathedral ceilings and beautiful mountain views. Outside, covered patios and decks overlook a spectacular in-ground pool, gazebo, and bathhouse--creating a private setting for summer entertaining and relaxation. Thoughtful updates include a 2016 roof, 2023 driveway, and appliances updated 2023-26

Find Your North Star in the Berkshires! The pinnacle of value priced $250,000 below appraised value and $450,000 below assessed value! A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom su

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 8.94-acre lot (MLS #248342), featuring a private well, installed septic system, underground electric, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. 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.

A remarkable turn-of-the-century Colonial where timeless architecture, meticulous care, and gracious proportions come together beautifully. Set against a backdrop of sweeping Berkshire views, the home captures a sense of elegance and permanence rarely found today. Rich in character yet beautifully suited to modern living, this is a home that feels as extraordinary as its setting. and cutting-edge modern comfort. Designed for both entertaining and intimate family life, this c1930, 6800 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately

A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark