127 apartments for sale in Cheshire town, Berkshire County Massachusetts

Enjoy carefree condo living in this charming historic home, where timeless character meets modern convenience. Beautiful hardwood floors and thoughtful updates blend seamlessly with the home's original charm, creating a warm and inviting atmosphere. Nestled in a peaceful community, this unique property is just a short stroll from downtown dining, local shops, art galleries, and cultural attractions. A rare opportunity to own a home that perfectly combines charm, comfort, and convenience. (Some photos have been virtually staged)

Fantastic Offer! Custom-designed and beautifully maintained one-owner residence offering 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm and Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community and the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens and music. A beautiful open floor plan features a totally upgraded kitchen with gas stone fireplace overlooking the woods. Adjacent screened porch opens to a private paver patio surrounded by native gardens. 1st floor en-suite bedroom provides an ideal 1-level living. Upstairs the spacious primary suite offers double closets, a beautifully appointed bath with quartz countertops, double sinks, generous linen closet, tile tub and shower. A 3rd en-suite bedroom plus another bedroom/office complete the upper level. Additional features include central A/C and Vac, coat closet, pantry, hardwood floor, custom glass shower doors, new HVAC and a 220-

If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood flooring, stack laundry in the unit, central a/c and natural gas heat. Off street parking, plenty of green space to enjoy nature in this in-town oasis. Conveniently located close to shopping, medical, public transportation and all cultural attractions. Priced well below assessment for immediate !

If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood flooring, stack laundry in the unit, central a/c and natural gas heat. Off street parking, plenty of green space to enjoy nature in this in-town oasis. Conveniently located close to shopping, medical, public transportation and all cultural attractions. Priced well below assessment for immediate !

Ideal for those seeking comfort, convenience, and low-maintenance living, this three-bedroom, two-bath condo in Greylock Village offers a thoughtfully designed layout featuring a primary bedroom on the main level. Manufactured wood floors flow throughout most of the home, and the attached garage provides easy, weather-free access. As an end-unit condo, enjoy exceptional privacy with no neighboring driveway, creating a peaceful, tucked-away setting. Central air conditioning and gas heat ensure year-round comfort. While cosmetic updates are needed, the home presents a wonderful opportunity to tailor the space to your taste in a sought-after community known for its ease of living and proximity to Williamstown amenities

Ideal for those seeking comfort, convenience, and low-maintenance living, this three-bedroom, two-bath condo in Greylock Village offers a thoughtfully designed layout featuring a primary bedroom on the main level. Manufactured wood floors flow throughout most of the home, and the attached garage provides easy, weather-free access. As an end-unit condo, enjoy exceptional privacy with no neighboring driveway, creating a peaceful, tucked-away setting. Central air conditioning and gas heat ensure year-round comfort. While cosmetic updates are needed, the home presents a wonderful opportunity to tailor the space to your taste in a sought-after community known for its ease of living and proximity to Williamstown amenities

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. Tucked away on the opposite side of the home, the serene primary suite features a walk-in closet and an airy en suite bath with a sleek, custom-tiled glass shower. Two additional bright bedrooms share a full bath, while convenient first-floor laundry completes this ideal

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

Discover townhome living in 160 Water St U:24, Williamstown, MA. Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling 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. #TownhomesWilliamstownMA #MillBuildingCondo

Welcome to easy, in-town living at sought-after One Colt Road in a charming neighborhood. This first-floor condominium offers the perfect blend of convenience and comfort, just a short stroll to Berkshire Museum, Colonial Theatre, local restaurants, and boutique shops. Featuring 2 bedrooms and 1 bath, the layout is both functional and inviting. A rare screened porch extends your living space, ideal for relaxing or entertaining, while additional outdoor space adds to the appeal. Enjoy low-maintenance living in one of Pittsfield's most desirable and walkable locations

Enjoy easy Berkshire living in this spacious end-unit condo at Greylock Village! Offering nearly 2,000 sq. ft this 3-bedroom, 2-bath home features soaring ceilings, abundant natural light, a cozy fireplace, first-floor primary bedroom, attached garage, and a functional layout ideal for year-round living or a weekend retreat. Community amenities include a pool, tennis courts, and beautifully maintained grounds. Just minutes from Williams College, The Clark, Williamstown Theatre Festival, MASS MoCA, Mount Greylock, and some of the Berkshires' best hiking, skiing, dining, and cultural attractions. Low-maintenance living in one of Williamstown's most desirable communities!

Slope-side living at Jiminy Peak with proven income potential! Located just steps from the ski slopes and very close to the year-round heated pool, this beautifully positioned one-bedroom suite offers the perfect Berkshire getaway and an exceptional short-term rental opportunity. Currently operated as a successful Airbnb/short-term rental, the unit generated approximately $17,162 in net income after expenses in 2025 and over $20,000 in 2024, making this an attractive option for both lifestyle buyers and investors seeking a turnkey four-season property. Unit 521 combines the charm of a cozy mountain retreat with the convenience of full resort amenities, including an outdoor heated pool, fitness center, sauna/steam room, on-site dining, front desk services, and tennis courts Exceptional opportunity to own a proven income-producing resort condominium at the base of Jiminy Peak Mountain Resort in the heart of the Berkshires. Located just steps from the ski slopes and very close to the year

Fantastic Offer! Custom-designed and beautifully maintained one-owner residence offering 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm and Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community and the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens and music. A beautiful open floor plan features a totally upgraded kitchen with gas stone fireplace overlooking the woods. Adjacent screened porch opens to a private paver patio surrounded by native gardens. 1st floor en-suite bedroom provides an ideal 1-level living. Upstairs the spacious primary suite offers double closets, a beautifully appointed bath with quartz countertops, double sinks, generous linen closet, tile tub and shower. A 3rd en-suite bedroom plus another bedroom/office complete the upper level. Additional features include central A/C and Vac, coat closet, pantry, hardwood floor, custom glass shower doors, new HVAC and a 220-

Enjoy easy Berkshire living in this recently updated, bright and inviting 2-bedroom, 950 sq. ft. top-floor condo. An oversized slider brings in an abundance of natural light and creates a more open, spacious feel. Set within a pet-friendly community, residents enjoy a gas BBQ/picnic area, children's playground, tennis and pickleball courts, heated pool and walking trails. Comfortable and convenient, this condo is ideal as a year-round home or Berkshire getaway The Berkshires is widely celebrated as 'America's Premier Cultural Resort' offering a unique blend of world class arts, historic estates, and scenic natural beauty. Close to shopping, dining, Tanglewood, and endless outdoor recreation, this is a wonderful opportunity to own in Lenox at an attractive value

Nestled in the highly desirable Stratton Hills community of Williamstown, MA, this rarely available ground-floor end unit offers an exceptional blend of modern comfort, privacy, and breathtaking Berkshire beauty. Surrounded by meticulously landscaped grounds and commanding mountain views, this serene retreat is designed for buyers seeking a low-maintenance luxury lifestyle in the heart of Williamstown. Bathed in natural light, the open living and dining area features a dramatic picture window that frames spectacular mountain vistas, creating a tranquil backdrop for everyday living and entertaining. The thoughtfully designed galley kitchen is fully applianced and highlighted by a unique serving window that opens directly to the patio, making outdoor dining and entertaining effortless. Step outside to your private, covered patio, a true extension of the living space. Complete with electric service and ambient exterior lighting, this inviting outdoor sanctuary overlooks lush lawns and stu

LISTING PRICE REDUCED TO REFLECT NEEDED TLC. Rarely available ground-floor end unit in desirable Stratton Hills, offering privacy, abundant natural light, and spectacular Berkshire mountain views. The open living/dining area features a dramatic picture window, while the fully applianced galley kitchen includes a convenient serving window to the private covered patio. Enjoy outdoor dining, morning coffee, or evening cocktails overlooking beautifully landscaped grounds. Two spacious bedrooms, full bath, in-unit laundry, two parking spaces, and lockable basement storage add everyday convenience. Residents enjoy a swimming pool and beautifully maintained grounds. Minutes to Williams College, The Clark Art Institute, dining, shopping, hiking, and all that charming Williamstown has to offer

Welcome to Churchill Crest, where timeless elegance, comfort and the beauty of the Berkshires comes together. Inside you'll find 1 bedroom 1 bathroom with spacious living room with wood burning fireplace, dining and kitchen. From the living room is a private deck. Under the main level is a private garage and lower level offers laundry. Community offers a heated inground pool with pavilion space for gatherings. So, whether you're searching for a full-time residence or a Berkshire Retreat 42 Churchill offers the perfect blend of charm with sophistication and convenience. Located minutes from downtown Pittsfield for shopping and dining to Berkshire Culture including Tanglewood, The Colonial Theatre and much more!

Slope-side living at Jiminy Peak with proven income potential! Located just steps from the ski slopes and very close to the year-round heated pool, this beautifully positioned one-bedroom suite offers the perfect Berkshire getaway and an exceptional short-term rental opportunity. Currently operated as a successful Airbnb/short-term rental, the unit generated approximately $17,162 in net income after expenses in 2025 and over $20,000 in 2024, making this an attractive option for both lifestyle buyers and investors seeking a turnkey four-season property. Unit 521 combines the charm of a cozy mountain retreat with the convenience of full resort amenities, including an outdoor heated pool, fitness center, sauna/steam room, on-site dining, front desk services, and tennis courts Exceptional opportunity to own a proven income-producing resort condominium at the base of Jiminy Peak Mountain Resort in the heart of the Berkshires. Located just steps from the ski slopes and very close to the year

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. Tucked away on the opposite side of the home, the serene primary suite features a walk-in closet and an airy en suite bath with a sleek, custom-tiled glass shower. Two additional bright bedrooms share a full bath, while convenient first-floor laundry completes this ideal

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

Discover single level living in 160 Water Street Home 203, Williamstown, MA. Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling 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. #BerkshiresLofts #WaterfrontCondoMA #WilliamstownMACondo

Experience lakeside living at its best in this beautifully maintained stand alone condo set directly on Ashmere Lake. The main floor offers easy one level living with three bedrooms, two full baths, a welcoming great room with propane fireplace, a sunny breakfast nook, and a formal dining area. Step from the primary bedroom or great room onto the rear deck or relax in the three season porch overlooking Ashmere Lake. The finished lower level is perfect for guests or extended living, complete with a kitchenette, full bath, bedroom, large gathering space along with enclosed under-stair storage. Walk out access to the patio. Ashmere Landings amenities include a heated pool, Har Tru tennis court, pickle ball court, and lake access with kayak storage and dock. A rare blend of comfort, privacy

IT DOESN'T GET ANY EASIER THAN THIS! Own this beautiful slope facing 1 bedroom loft condo situated above the ski rental shop. Only 2 units like this exist in the Village Center! Brand new slope side deck overlooking the Berkshire Express chairlift. Newly renovated kitchen and bathroom, and freshly painted. Owner replaced heating/cooling unit and washer/dryer. Fully furnished, including new queen-size mattress with pull out couch. Location. location. location

Experience the ultimate ski-resort getaway in this charming 1-bedroom, 1-bath, 500 sq. ft. condo. Perfectly sized for a personal retreat, weekend escape, or investment opportunity, this inviting unit features brand-new flooring throughout, giving the space a fresh, updated feel. Enjoy the convenience and lifestyle of resort living, with easy access to skiing, outdoor recreation, dining, and year-round activities. Whether you're looking for a mountain getaway or a low-maintenance vacation property, this condo offers comfort, convenience, and endless potential. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own

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