Welcome home to this beautifully maintained and thoughtfully cared-for residence, ideally situated on one of Southeast Pittsfield's most desirable dead-end streets. Offering exceptional curb appeal, mature landscaping, and a peaceful garden-like setting with a wonderfully private backyard, this charming home showcases quality craftsmanship, timeless character, and pride of ownership throughout. Designed for both everyday living and entertaining, the spacious sunroom is filled with natural light and overlooks the backyard, creating the perfect place to relax or gather with family and friends. Step outside to enjoy the inviting in-ground pool, private patio, and tranquil outdoor setting.

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!

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.

Spacious single-level living in Woodmont Estates! Set on 3.04 acres across two lots, this 3,400 sq. ft. home offers 4 bedrooms, 2.5 baths, an updated kitchen, renovated primary bath, custom library, private office, four-season sunroom with newer Andersen windows, and a large bonus room with endless possibilities. Recent improvements include a repaired retaining wall and tree removal that opened up the front entry, bringing in more natural light and enhancing curb appeal. Enjoy mature landscaping, seasonal water views, a brook, sunrise views, protected land beyond, central air, natural gas heat, and a full walkout lower level with abundant storage and future potential.

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!

Brand new construction at Berkshire Country Meadows! Must see this 2000 sf single-family condo is now ready for immediate occupancy! With the ease of one-level living, you'll enter into a great room with hardwood flooring, gas fireplace and bathed in natural light. Fully applianced kitchen with large work island. This unit features 3 bedrooms, 2 baths, central a/c, natural gas heat. Multi-purpose den/library/office space off the living area. You'll find a large screened porch off the back for summer enjoyment. Spacious unfinished lower level offers expansion possibilities. Established condo community with pool, tennis, and a clubhouse with fitness center. Around the corner from Pontoosuc Lake, close to skiing and centrally located to all cultural attractions.

Brand new construction at Berkshire Country Meadows! This 2000 sf single-family condo is now ready for immediate occupancy. With the ease of one-level living, you'll enter into a great room with hardwood flooring, gas fireplace and bathed in natural light. Fully applianced kitchen with large work island. This unit features 3 bedrooms, 2 baths, central a/c, natural gas heat. Multi-purpose den/library/office space off the living area. You'll find a large, screened porch off the back for summer enjoyment. Spacious unfinished lower level offers expansion possibilities. Established condo community with pool, tennis, and a clubhouse with fitness center. Around the corner from Pontoosuc Lake for boating/swimming, nearby skiing and centrally located to arts and culture.

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.

This 12.84-acre parcel offers excellent versatility with Multi zoning, making it ideal for commercial or residential projects. Centrally located near shopping and public transit, the wooded lot features distant views. Key Features: Size: 12.84 Acres (559,310 Sq. Ft.) of uncleared, wooded land. Zoning: Multi, accommodating a wide range of development plans. Utilities: Electricity and cable are available at the street; there is currently no water or sewer connected. Prep Work: An existing curb cut and available engineering plans provide a head start for the new owner. Location: High-traffic area situated off Lenox Rd, abutting several commercial properties.

This 12.84-acre parcel offers excellent versatility with Multi zoning, making it ideal for commercial or residential projects. Centrally located near shopping and public transit, the wooded lot features distant views. Key Features: Size: 12.84 Acres (559,310 Sq. Ft.) of uncleared, wooded land. Zoning: Multi, accommodating a wide range of development plans. Utilities: Electricity and cable are available at the street; there is currently no water or sewer connected. Prep Work: An existing curb cut and available engineering plans provide a head start for the new owner. Location: High-traffic area situated off Lenox Rd, abutting several commercial properties.

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.

Great opportunity to design your 2000 sq ft free-standing condo home at Berkshire Country Meadows! This is one of only three remaining homesites in this established condo community. Select from a several floor plans with contemporary design, featuring one-level living. Primary suite, one-two additional bedrooms, central a/c, gas heat, screened porch, two car garage. On-site amenities include pool, tennis, clubhouse with fitness center. Centrally located to all Berkshire attractions and right around the corner from Pontoosuc Lake. HOA fee is $520.00 per month

Great opportunity to design your 2000 sq ft free-standing condo home at Berkshire Country Meadows! This is one of only three remaining homesites in this established condo community. Select from a several floor plans with contemporary design, featuring one-level living. Primary suite, one-two additional bedrooms, central a/c, gas heat, screened porch, two car garage. On-site amenities include pool, tennis, clubhouse with fitness center. Centrally located to all Berkshire attractions and right around the corner from Pontoosuc Lake. HOA fee is $520.00 per month.

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.

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.

Investment opportunity near downtown Pittsfield. This renovated 7,904-square-foot commercial building is situated on approximately 0.72 acres in the Downtown Creative District and is currently leased to an established daycare/school operator through August 2031. The property generates an annual base rent, plus documented reimbursements for real estate taxes, insurance, and water/sewer expenses. The building offers approximately 3,952 square feet on each of two levels, with an open, adaptable layout suitable for educational, nonprofit, institutional, professional, or community-oriented uses. Improvements include central HVAC, replacement windows, sprinkler and fire-alarm upgrades, and extensive interior renovations. An elevator provides convenient access between floors.