127 apartments for sale in Cheshire town, Berkshire County Massachusetts

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly Views of October Mountain. Plenty of room for family and friends

Lovely Lenox Condo in the Beautiful Berkshires. Welcome home to this exceptional end-unit condominium at Rolling Hills in Lenox, offering a wonderful combination of comfort, privacy, scenic surroundings, and Berkshire lifestyle. This beautifully updated 3-bedroom, 3-full-bath residence offers approximately 1,552 square feet of living space with thoughtful improvements throughout. The inviting open living and dining areas are filled with natural light and feature beautiful unobstructed meadow views, creating a peaceful setting where you can enjoy nature, birds, and changing seasons from your private deck. The spacious living room provides an ideal gathering space, while the well-appointed kitchen features stainless steel appliances and open naturally to the main living areas. The versatile floor plan includes two bedrooms on the main level with two full baths. The lower level has a full bath with shower stall along with a room that could be used for a family room or an overflow sleeping

NO SHOWINGS WITHOUT LISTING AGENT APPROVAL - 2 bedroom end unit condo offering the rare ease of true one level living, tucked in Churchill Crest's most private and peaceful building. This special home feels like a quiet Berkshire sanctuary, with a thoughtful layout that flows comfortably and welcomes you the moment you arrive. It's ready for your vision, character allows you to shape the space to your own style. Outside, enjoy a sparkling pool, tennis court, and beautifully maintained grounds that enhance the sense of retreat. Private, serene, and wonderfully convenient. Easy to show and easier to fall in love

Perfect vacation or full-time Condo in a great spot at The Pines at Bousquet. Tons of year round activities at your finger tips in the Berkshires. This fabulous End unit has 3 stories of finished space including 5 Bedrooms, 4.5 baths, eat-in kitchen, large living room with gas fireplace and large den in lower level. An abundance of natural light throughout with tons of windows, a great feature for this end unit. A First floor Primary bedroom with en-suite full bath is a bonus. Other features include a screened in porch with an awesome view, lower patio perfect for your grill and entertaining and plenty of windows. Enjoy the 2021 renovations at Bousquet Mountain Complex, plenty of shopping close by and many cultural activities. This condo currently has tenants with a lease in place to Feb. 2028. See Realtor remarks for more details. Don't wait to see this Great Condo with monthly income in place

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no hassle management allows for time to enjoy all Jiminy Peak offers on a year round basis

Turnkey, fully furnished one-bedroom condo at the base of Jiminy Peak Mountain Resort! Whether you're seeking a personal Berkshire getaway, a low-maintenance second home, or an income-producing investment, this versatile property offers endless possibilities. Enjoy year-round recreation including skiing, snowboarding, mountain biking, hiking, dining, and resort activities just steps from your door. Conveniently located near the Berkshires' renowned cultural attractions, restaurants, and outdoor adventures. Use it for your own enjoyment, rent it short-term for added income, or enjoy the best of both worlds. Move right in and start enjoying everything this four-season destination has to offer

SELLER IS LOOKING FOR OFFERS. PERFECT FOR A FLIP. MAKE AN OFFER. Enjoy stunning views and low property taxes at Beaver Pond Meadows, private and quiet but close to all that Berkshire County's four seasons have to offer. This 3 bedroom 2 full bathroom townhouse features three levels of living area, with first-floor accessibility and multiple options for families. Three bedrooms and two full baths, living room with a wood floors and wood burning fireplace, and large loft area for home office or additional sitting area. Walk out to the deck with views of Beaver Pond. Private association pool and clubhouse, the complex is only minutes away from Jimmy Peak, but offers a quieter alternative to the more active Country Village

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly Views of October Mountain. Plenty of room for family and friends

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

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

Lovely Lenox Condo in the Beautiful Berkshires. Welcome home to this exceptional end-unit condominium at Rolling Hills in Lenox, offering a wonderful combination of comfort, privacy, scenic surroundings, and Berkshire lifestyle. This beautifully updated 3-bedroom, 3-full-bath residence offers approximately 1,552 square feet of living space with thoughtful improvements throughout. The inviting open living and dining areas are filled with natural light and feature beautiful unobstructed meadow views, creating a peaceful setting where you can enjoy nature, birds, and changing seasons from your private deck. The spacious living room provides an ideal gathering space, while the well-appointed kitchen features stainless steel appliances and open naturally to the main living areas. The versatile floor plan includes two bedrooms on the main level with two full baths. The lower level has a full bath with shower stall along with a room that could be used for a family room or an overflow sleeping

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no hassle management allows for time to enjoy all Jiminy Peak offers on a year round basis

Perfectly positioned in the heart of Jiminy Peak Mountain Resort, this stylishly updated two-bedroom, one-bath condominium offers the ultimate slopeside lifestyle. Just steps from the lifts, you'll enjoy effortless access to one of the region's premier ski destinations while retreating to a thoughtfully designed interior that blends comfort and modern appeal. The bright, open living space is ideal for relaxing after a day on the mountain, with tasteful updates throughout creating a move-in-ready experience. Beyond winter, Jiminy Peak Mountain Resort transforms into a vibrant four-season playground featuring hiking, mountain biking, and family-friendly attractions. Whether you're seeking a weekend escape, investment opportunity, or year-round retreat, this location delivers unmatched convenience and recreation. Secure your mountain getaway now and start planning your winter adventures while enjoying all the benefits of every season

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no hassle management allows for time to enjoy all Jiminy Peak offers on a year round basis

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

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

Beautifully maintained 2 bedroom, 2 bath condo, both bedrooms/ baths on main level with covered deck and beautiful views, finished lower level w/ laundry offers whole other level of space for office, hobbies, etc. Enjoy the clubhouse (gym, pool table, hot tub, sauna, kitchen/entertainment rm, local art hangings) out door POOL, TENNIS COURTS, walking TRAILS, community GARDENS, kayak storage, fenced dog PARK, EV charging stations. Perfect Berkshire location, CLOSE to all cultural destinations, Tanglewood, restaurants, shops, outdoor recreation! FIRST FLOOR condos like this are hard to find. RH is undergoing attractive and energy upgrades on the siding. This unit is priced to reflect the current siding assessment of@$250/month for 5 years. Monthly condo fee is $703. Buyer to verify

Enjoy effortless living in this beautifully renovated, move-in ready condo, perfectly situated between the vibrant energy of Pittsfield and the charm of Lenox center. This one-bedroom condo features brand new carpeting, generous closet space, and a modern kitchen with newer cabinetry and an updated bathroom. Natural light fills the living space, where sliding glass doors lead you to a private deck. Life at Lennox Heights is refreshingly simple. One monthly fee covers it all - heat, hot water, cable, internet, a private in-ground pool, tennis courts, exterior maintenance, landscaping, snow removal, trash removal, master insurance, road maintenance, town sewer, and public water. Just turn the key and you're home!

Spacious 2+ bedroom, 3-bath end-unit condo in Mountainside Hemlock Village. Fully furnished and turnkey, with parking at the door and a short walk to the slopes. Strong rental history and excellent investment potential

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

Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12'-16' tall ceilings, massive windows, exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-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 Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, gym, interior bike storage, package room, dog wash and on-site professional management. Approximately half a mile to shopping, dining, Williams College and one of the top collegiate golf courses- Taconic Golf Club and in close proximity skiing, hiking, rafting, museums and all the Berkshires has to offer.#CableMills #WilliamstownMA #BerkshiresLiving

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

Turnkey, fully furnished one-bedroom condo at the base of Jiminy Peak Mountain Resort! Whether you're seeking a personal Berkshire getaway, a low-maintenance second home, or an income-producing investment, this versatile property offers endless possibilities. Enjoy year-round recreation including skiing, snowboarding, mountain biking, hiking, dining, and resort activities just steps from your door. Conveniently located near the Berkshires' renowned cultural attractions, restaurants, and outdoor adventures. Use it for your own enjoyment, rent it short-term for added income, or enjoy the best of both worlds. Move right in and start enjoying everything this four-season destination has to offer

SELLER IS LOOKING FOR OFFERS. PERFECT FOR A FLIP. MAKE AN OFFER. Enjoy stunning views and low property taxes at Beaver Pond Meadows, private and quiet but close to all that Berkshire County's four seasons have to offer. This 3 bedroom 2 full bathroom townhouse features three levels of living area, with first-floor accessibility and multiple options for families. Three bedrooms and two full baths, living room with a wood floors and wood burning fireplace, and large loft area for home office or additional sitting area. Walk out to the deck with views of Beaver Pond. Private association pool and clubhouse, the complex is only minutes away from Jimmy Peak, but offers a quieter alternative to the more active Country Village

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

Step into this beautifully updated 3-bedroom, 3-bathroom with a lretreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and top-of-the-line stainless steel appliances, perfect for entertaining. The primary suite offers a spa-inspired bathroom with a walk-in shower. Outside, the meticulously landscaped, fenced-in patio provides a private sanctuary, complete with plenty of room for al fresco dining. Enjoy the convenience of being just a short walk from the slopes and local shops. Upstairs boosts a spacious loft

Discover the perfect mountain retreat in this beautifully maintained 2-bedroom, 2 full bath condo offering 1,030 square feet of comfortable living space. Ideally located just moments from the ski slopes, this home is a dream for outdoor enthusiasts and year-round adventurers. Enjoy easy access to a wide range of community amenities, including a heated pool, tennis courts, and beautifully maintained grounds. Whether you're hitting the slopes in winter, enjoying summer recreation, or simply unwinding in a peaceful setting, this condo offers the ideal blend of convenience and lifestyle. Perfect as a primary residence, vacation getaway, or investment property, this is your opportunity to own a slice of mountain living at its best

Motivated Seller! Welcome to Cable Mills, Williamstown's premier condo community, blending historic mill charm with modern living along the Green River. Unit 112 is a first-floor corner unit with 1 bedroom and 1.5 baths, featuring high ceilings, exposed brick and beams, and an open layout. Large windows fill the space with natural light and river views. Enjoy bamboo floors, ample storage, and a kitchen with granite counters, stainless steel appliances, and an eat-at island. The primary suite offers two closets, in-unit laundry, and a full bath. Includes central A/C and deeded covered parking. Amenities include a fitness center, lounge, riverwalk, and more. Close to Williams College, Taconic Golf Course, and Spring Street

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!