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.

8 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, schools, and parks. Low maintenance exterior with loads of off street parking. All units feature one bedroom/studio setups with separate heat and electricity. Coin-op laundry located on site for additional income.

Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full bath. This is perfect for a multi generational family. The basement has plenty of storage and a dry, carpeted rec room with a wet bar and a half bath. The grounds feature mature landscaping and privacy. The roof, skylights, and gas fireplace are newer (installed in 2016). Home is on a private street with a cul-de-sac and is within walking distance to BCC and the state forest. Bosquet and Jiminy Pe

Perfectly situated in a highly sought-after community just moments from the scenic waters of Pontoosuc Lake, and conveniently located near the main corridor connecting Williamstown and South County, this beautifully maintained, approximately 11-year-old standalone condo offers the ultimate rarity: the privacy of a single-family home with the effortless lifestyle of condo living. Inside, gleaming wood floors and abundant natural light flow through a thoughtfully designed layout. A welcoming living and dining area leads to a stunning chef's kitchen at the heart of the home. Just beyond, a cozy family room opens to a beautiful screened back porch, the perfect spot to bask in the afternoon sun after a morning by the lake.

Elegance Meets History on 1 Eaton Lane! Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield & only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a home with a story. The main house is a masterclass in classic architecture, featuring period details enhanced by thoughtful modern updates. High ceilings, gleaming hardwood floors, & charming front & back staircases ground the home in history, while the spacious layout provides endless room to breathe. The heart of the home is a sophisticated kitchen, featuring rich cherry cabinetry, new SS appliance

Welcome to this spacious and beautifully renovated 4 bedroom home in desirable Southeast neighborhood. With 3 full bathrooms and 1 half bath, this home provides plenty of room for family and guests. The open floor plan creates an inviting flow between the generously sized living spaces, while the renovated interior offers a fresh, modern feel. The impressive primary suite features a walk-in closet, bath, and its own loft area. Another bedroom also includes a loft area. The fully finished basement takes entertaining to the next level with a dedicated game room, movie theater room, and full bathroom--perfect for movie nights or game days. Sliders lead to a nice deck with screened room, hot tub and partially fenced yard. This move in ready home offers the versatility you're looking for!!

Beautiful early 1900's colonial farm house with deeded agricultural and horticultural rights offering 2,104 sq ft of classic charm on a picturesque 2.3-acre lot. This spacious 4-bedroom, 2-full-bath home is close to the state forest with access to mountain biking and hiking trails. The main level includes a bright living room, formal dining room, and a generous kitchen with great storage. High ceilings, original details, and large windows bring warmth and character throughout. Upstairs are four well-sized bedrooms and a second full bath, plus bonus unfinished space in the attic ideal for an office, studio, or playroom. Enjoy the expansive private yard with pastoral views and a pond. The back deck is perfect for outdoor dining or relaxing. Very private but also close to downtown.

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and serenity. Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room. The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room. Enjoy the association pool, Bousquet Mountain next door and all of the

Gracefully situated on a gentle sloping hillside street this distinctively designed multi-level home offers distant and seasonal Berkshire mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home and grounds, you can embrace the vast privacy, open land and 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 peacefulness.

Beautiful end-unit property featuring soaring ceilings and serene wooded views. The home offers open common spaces with excellent natural light, a screened porch, and a first-floor primary en suite. The second level includes two guest bedrooms, a full bath, and a loft overlooking the great room. Additionally, the lower-level walkout provides significant potential to be finished for extra living space. Residents can also enjoy the association's pool. This property is perfectly situated near Bousquet Mountain to enjoy the many cultural attractions here in the Berkshires.

This move-in-ready 4-bedroom, 2.5-bath Colonial in Southeast Pittsfield sits on over half an acre and blends classic charm with thoughtful updates. The welcoming chefs kitchen opens to a screened porch and flows into a generous dining room with built-in cabinetry, perfect for everyday living and entertaining. A light-filled living room anchored by a wood-burning fireplace creates a warm and inviting gathering space. Upstairs offers four comfortable bedrooms, two full baths, a large cedar closet, and abundant storage. A two-car garage and partially finished basement with a second wood-burning fireplace complete this exceptional home. Outside, the professionally landscaped, fully fenced backyard offers exceptional privacy and outdoor living space.

Discover the exceptional lakefront lifestyle in this beautifully renovated, move-in ready 2-bedroom, 2-bath residence on Onota Lake. Bathed in natural light, expansive walls of windows frame captivating water views from the living room, dining area, and kitchen, creating a seamless connection to the outdoors. A welcoming fireplace adds warmth and charm, while efficient mini-split systems provide year-round comfort. The spacious primary suite offers a private bath and a serene retreat. Outdoors, a lakeside deck, fire pit and private dock create an inviting setting for entertaining, boating, and relaxed Berkshire living. A truly special waterfront offering.

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.

Beautifully updated and maintained four bedroom, three and a half bath colonial. Spacious common areas washed with natural light make this home special. The main level boasts a large eat in kitchen, dining room, expansive living room with wood floors, family room with built ins and fireplace, separate laundry room, half bath, two car oversized garage and beautiful screened porch overlooking the landscaped large yard. The second level has three guest bedrooms, full bath and large primary bedroom with en suite and double closets. The finished lower level offers a media/flex room, office, bathroom and storage. This Convenient location is on the Southeast side of Pittsfield near Lenox and under 15 minutes to Tangelwood!

Set on 3.04 acres across two lots abutting protected land, this Executive Ranch is the only single-level home in the gated community of Woodmont Estates. 3,400 sq ft of expansive, easy living, featuring 4bd/2.5ba, a renovated primary bath, updated kitchen, and light-filled four-season sunroom w/ new Andersen windows. Designed for comfort & flexibility, the layout includes a private office, as well as a library w/ custom built-ins. Wide hallways & generously scaled rooms enhance the sense of space & accessibility. Enjoy sunrise views, a seasonal brook, beautiful gardens, & peaceful surroundings. Walkout lower level offers expansion potential. Natural gas heat, central air, central vac, radon mitigation, & major system upgrades already complete.

Berkshire Country Meadows single-family condo almost ready for occupancy. Seeking single level living? Compare this for value! 2000 sq ft, 3 br, 2 bath, central a/c, natural gas heat, gas fireplace hardwood flooring, screened porch, large basement offers expansion possibilities, and a two-car garage. Still time to make some custom finishes. Established condo community with pool, tennis, and clubhouse with fitness center. Around the corner from Pontoosuc Lake, close to skiing and centrally located to all cultural attractions.

Berkshire Country Meadows single-family condo almost ready for occupancy. Seeking single level living? Compare this for value! 2000 sq ft, 3 br, 2 bath, central a/c, natural gas heat, gas fireplace hardwood flooring, screened porch, large basement offers expansion possibilities, and a two-car garage. Still time to make some custom finishes. Established condo community with pool, tennis, and clubhouse with fitness center. Around the corner from Pontoosuc Lake, close to skiing and centrally located to all cultural attractions.

Set in a peaceful West Pittsfield neighborhood, 35 Meadow Ridge is a sophisticated contemporary home with spacious thoughtfully designed living. Soaring 12 foot ceilings and cherry hardwood floors welcome you inside. The main level features a family room with built-ins, living room with gas fireplace, dining room, eat-in kitchen and access to the outdoor deck. The second floor offers an expansive primary suite, 2 additional bedrooms, 2 full baths, and flexible fourth room for use as bedroom, den or gym.A finished walk-out basement includes a family room and ensuite bedroom adding valuable space. This versatile home offers exceptional comfort and flexibility.Moments from Pittsfield State Forest, Onota Lake, downtown dining and short drive to Tanglewood. This is Berkshire living at its best!

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally 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 by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!

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.