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Berkshire County MA Homes for Sale with Pool

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  • 24 Alpine Trail, Pittsfield, MA 01201
    24 Alpine Trail, Pittsfield, MA 01201
    24 Alpine Trail, Pittsfield, MA 01201
    /44

    $629,500

    • 4 Beds
    • 4.5 Baths
    • 3,081 Sq Ft

    24 Alpine Trail, Pittsfield, MA 01201

    Welcome to your Berkshire retreat! This spacious 4-bedroom, 5-bath condo at The Pines of Bousquet is a rare corner unit filled with natural light and sweeping views of the bunny ski slope--right in your backyard. Whether you're watching skiers in the winter from your office nook on the second floor, or enjoying peaceful greenery in warmer months from your screened porch, this home offers

    Tanya Shepardson LAMACCHIA REALTY, INC

    24 Alpine Trail, Pittsfield, MA 01201
  • 157 Maple Grove Dr, Pittsfield, MA 01201
    157 Maple Grove Dr, Pittsfield, MA 01201
    157 Maple Grove Dr, Pittsfield, MA 01201
    /27

    $255,000

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft

    157 Maple Grove Dr, Pittsfield, MA 01201

    Welcome to easy, one-level living in this 3-bedroom ranch, nestled in the sought-after southeast section of Pittsfield. The property features vinyl siding, modern appliances, and on-demand hot water. Outside you will find a fully fenced-in yard ideal for relaxing or entertaining. Enjoy summer days on the expansive deck or take a dip in the above-ground pool. Two storage sheds provide space for

    Jessica Rizzo LAMACCHIA REALTY, INC

    157 Maple Grove Dr, Pittsfield, MA 01201
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /48

    $5,775,000

    • 5 Beds
    • 8 Baths
    • 9,400 Sq Ft

    Unlisted Address

    Nestled in the heart of Alford, Massachusetts, this extraordinary 35.6-acre Berkshire County estate offers unparalleled privacy with sweeping western Catskill Mountain views and direct access to conservation land. The impressive 9,400 sq ft main residence, built in 2003 and comprehensively updated beginning in 2020, features 4 bedrooms, 5 full baths, and resort-caliber amenities throughout its

    Elyse Morris ELYSE HARNEY REAL ESTATE

    Unlisted Address
  • 880 East St Unit 1A, Lee, MA 01238
    880 East St Unit 1A, Lee, MA 01238
    880 East St Unit 1A, Lee, MA 01238
    /38

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,405 Sq Ft

    880 East St Unit 1A, Lee, MA 01238

    Desirable end unit at October Mountain Village in Lee, MA, offering a serene and picturesque setting. This unit is a short stroll to the tennis courts and community pool. The open-concept living and dining areas feature laminate flooring and a charming two-sided wood-burning fireplace, shared with the vaulted family room. Two skylights and a ceiling fan bring abundant natural light and airflow.

    Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    880 East St Unit 1A, Lee, MA 01238
  • 171 Lake Shore Dr, Otis, MA 01253
    171 Lake Shore Dr, Otis, MA 01253
    171 Lake Shore Dr, Otis, MA 01253
    /70

    $895,000

    • 3 Beds
    • 2 Baths
    • 1,567 Sq Ft

    171 Lake Shore Dr, Otis, MA 01253

    Welcome to this exceptional 3-bedroom, 2-bathroom lakefront retreat w/an in-ground pool,located in the highly sought-after Otis Woodlands community. Perfectly situated on OWL Lake, this home offers a rare combination of natural beauty, modern upgrades, and an array of resort-style amenities, making it the ideal country escape or full-time residence.Step inside to an open-concept living area with

    Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

    171 Lake Shore Dr, Otis, MA 01253
  • 140 Hancock Rd, Pittsfield, MA 01201
    140 Hancock Rd, Pittsfield, MA 01201
    140 Hancock Rd, Pittsfield, MA 01201
    /55

    $5,499,500

    • 8 Beds
    • 6.5 Baths
    • 6,986 Sq Ft

    140 Hancock Rd, Pittsfield, MA 01201

    Welcome to an extraordinary opportunity on the shores of Pontoosuc Lake. This remarkable estate sets a new standard for lakefront living in Pittsfield and beyond, offering a rare combination of luxury, scale, and setting.With over 18,700 square feet of total space, including an impressive amount of garage space suitable for car collectors or hobbyists, this home provides room to live, relax, and

    Cameron Volastro STONE HOUSE PROPERTIES, LLC

    140 Hancock Rd, Pittsfield, MA 01201
  • 33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    /52

    $765,000

    • 5 Beds
    • 4.5 Baths
    • 3,381 Sq Ft

    33 Alpine Trail, Pittsfield, MA 01201

    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

    Cortney Dupont COHEN & WHITE ASSOCIATES

    33 Alpine Trail, Pittsfield, MA 01201
  • 9201 Mountainside Dr, Hancock, MA 01237
    9201 Mountainside Dr, Hancock, MA 01237
    9201 Mountainside Dr, Hancock, MA 01237
    /25

    $659,000

    • 4 Beds
    • 3 Baths
    • 2,122 Sq Ft

    9201 Mountainside Dr, Hancock, MA 01237

    Turnkey ski home at Jiminy Peak—New England’s premier mountain resort under 2.5hrs to NYC & Boston. Steps from the slopes, it offers 2 living rooms, a fireplace for cozy winter evenings, master bedroom with ensuite jacuzzi, deck overlooking forest and mountain, and ample parking. Enjoy heated pools, hot tubs, tennis courts, onsite dining from the Mezze Hospitality Group, the convenience of an

    Derek Greene The Greene Realty Group

    9201 Mountainside Dr, Hancock, MA 01237
  • 19 Aspen Way, Pittsfield, MA 01201
    19 Aspen Way, Pittsfield, MA 01201
    19 Aspen Way, Pittsfield, MA 01201
    /41

    $965,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 3 Baths
    • 4,024 Sq Ft

    19 Aspen Way, Pittsfield, MA 01201

    Live the lifestyle you deserve in this stunning 4-year-young detached single family condominium offering over 4,000 square feet of luxury! This 3-bed, 3-bath home features a gourmet kitchen with quartz counters, custom cooktop and hood and double ovens. Perfect for the Chef of the family. The home gym with sauna, and a spacious walkout lower level with game room and bar is the perfect space for

    Victoria Standring LAMACCHIA REALTY, INC

    19 Aspen Way, Pittsfield, MA 01201
  • 258 Sandisfield Rd, New Marlborough, MA 01230
    258 Sandisfield Rd, New Marlborough, MA 01230
    258 Sandisfield Rd, New Marlborough, MA 01230
    /61

    $2,995,000

    • 5 Beds
    • 8 Baths
    • 5,508 Sq Ft

    258 Sandisfield Rd, New Marlborough, MA 01230

    Magnficent Modern Farmhouse designed by CRISP ARCHITECTS and custom built for the owner. Estate grounds, quiet elegance and privacy. Main House, Guest House and Pool House on 10 Acres. The Main House was designed to offer soaring ceilings and plenty of natural light. The Den w/ Fireplace will be your ideal retreat, and the dine-In Kitchen will please any gourmet. First floor Primary Bedroom w/

    Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    258 Sandisfield Rd, New Marlborough, MA 01230
  • 9074 Mountainside Dr, Hancock, MA 01237
    9074 Mountainside Dr, Hancock, MA 01237
    9074 Mountainside Dr, Hancock, MA 01237
    /25

    $390,000

    • 2 Beds
    • 2 Baths
    • 1,035 Sq Ft

    9074 Mountainside Dr, Hancock, MA 01237

    Your Ultimate Year-Round Escape Awaits at Jiminy Peak!Move-in ready, adventure-ready! This pristine 2-bed, 2-bath end-unit condo at Jiminy Peak Mountain Resort isn't just a home--it's your passport to four seasons of Berkshires fun.Ideally located just 30 minutes to Tanglewood in Lenox, 20 minutes to the Clark in Williamstown, and 10 minutes to the base of Mount Greylock, this mountain retreat

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    9074 Mountainside Dr, Hancock, MA 01237
  • 76 Corashire Rd, New Marlborough, MA 01230
    76 Corashire Rd, New Marlborough, MA 01230
    76 Corashire Rd, New Marlborough, MA 01230
    /41

    $925,000

    • 4 Beds
    • 3 Baths
    • 2,362 Sq Ft

    76 Corashire Rd, New Marlborough, MA 01230

    Did you dream of someday living in a log cabin? Maybe it was surrounded by field and woods with a river running through it. Did it have a spacious porch and deck for a rocking chair or two? Of course, it had a fireplace or maybe even six. In your dreams it had 4 bedrooms and 3 baths and a brick floored sunroom. A storage barn? Pool? Absolutely! Well, dreams do come true because your dream

    Deborah Mielke CORASHIRE REALTY

    76 Corashire Rd, New Marlborough, MA 01230
  • 1786 S Undermountain Rd, Sheffield, MA 01257
    1786 S Undermountain Rd, Sheffield, MA 01257
    1786 S Undermountain Rd, Sheffield, MA 01257
    /17

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 2,408 Sq Ft

    1786 S Undermountain Rd, Sheffield, MA 01257

    Classic 3-Bedroom Cape with Pool - Perfectly positioned between NW Connecticut and Sheffield, MA in the Berkshires. Sheffield is the oldest Town in Berkshire County - the township was purchased in 1724 from Chief Konkapot and other Stockbridge Native Americans. This bright, lovely 3-Bedroom Cape features a beautiful, heated pool, a Bedroom and Full Bath on the Main Floor, 2 Bedrooms and another

    Juliet Moore ELYSE HARNEY REAL ESTATE

    1786 S Undermountain Rd, Sheffield, MA 01257
  • 116 Brush Hill Rd, Great Barrington, MA 01230
    116 Brush Hill Rd, Great Barrington, MA 01230
    116 Brush Hill Rd, Great Barrington, MA 01230
    /48

    $3,750,000

    • 4 Beds
    • 4.5 Baths
    • 5,300 Sq Ft

    116 Brush Hill Rd, Great Barrington, MA 01230

    Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

    Mark Rosengren LANCE VERMEULEN RE, INC

    116 Brush Hill Rd, Great Barrington, MA 01230
  • 14 Alpine Trail Unit 14, Pittsfield, MA 01201
    14 Alpine Trail Unit 14, Pittsfield, MA 01201
    14 Alpine Trail Unit 14, Pittsfield, MA 01201
    /29

    $692,000

    • 4 Beds
    • 3.5 Baths
    • 3,296 Sq Ft

    14 Alpine Trail Unit 14, Pittsfield, MA 01201

    Welcome to your dream mountain retreat! This stunning end unit in a community of 96 units offers an unparalleled lifestyle for outdoor enthusiasts. With effortless access to ski trails right from your back screened-in porch, you can hit the slopes at Bousquet Mountain anytime you desire.Spanning over 3,200 square feet, this 4-bedroom, 3.5-bath condo has a spacious three-level layout. Step inside

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    14 Alpine Trail Unit 14, Pittsfield, MA 01201
  • 16 East Rd, Adams, MA 01220
    16 East Rd, Adams, MA 01220
    16 East Rd, Adams, MA 01220
    /36

    $465,000

    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    16 East Rd, Adams, MA 01220

    Your dream home awaits! Open house 7/19, 10am-12 noon. This meticulously cared-for residence offers move-in-ready living with something for everyone. The downstairs flows beautifully, ideal for gatherings, and boasts a stunning formal dining space, along with a convenient first-floor half bath & laundry. The large open kitchen features beautiful granite countertops. As you explore, notice the

    Shannon Regan KRG - Key Realty Group

    16 East Rd, Adams, MA 01220
  • 9253 Mountainside Dr, Hancock, MA 01237
    9253 Mountainside Dr, Hancock, MA 01237
    9253 Mountainside Dr, Hancock, MA 01237
    /24

    $540,000

    • 3 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    9253 Mountainside Dr, Hancock, MA 01237

    Featured in The Boston Globe's ''8 Homes in the Berkshires for Your Ideal Winter Getaway'' -- this updated and move-in ready condo at Jiminy Peak is the ultimate four-season escape. Whether you're looking for a full-time home, weekend retreat, or high-performing rental, this property checks every box. Set along the slopes of Jiminy Peak Mountain Resort, this spacious unit offers easy access to

    THE KAHN TEAM BISHOP WEST REAL ESTATE

    9253 Mountainside Dr, Hancock, MA 01237
  • 15 East St, Stockbridge, MA 01262
    15 East St, Stockbridge, MA 01262
    15 East St, Stockbridge, MA 01262
    /16

    $1,800,000

    • 40 Beds
    • 20 Baths
    • 30,000 Sq Ft

    15 East St, Stockbridge, MA 01262

    Located in a Sngle Family zoned area on a desirablle, private parcel consisting of nine total buildings with an in-ground pool amongst other amenities. Property is available for sale, lease or equity investment by new partners. This is an amazing property on the border of Stockbridge and Lenox with close proximity to Albany / Hartford / I-91. Many opportunities for possible hotel, B&B, family

    Tim Damon Mercury Real Estate

    15 East St, Stockbridge, MA 01262
  • 181 Bridges Rd, Williamstown, MA 01267
    181 Bridges Rd, Williamstown, MA 01267
    181 Bridges Rd, Williamstown, MA 01267
    /26

    $397,000

    • 3 Beds
    • 1.5 Baths
    • 1,464 Sq Ft

    181 Bridges Rd, Williamstown, MA 01267

    Experience the perfect blend of historic charm and modern convenience in this beautifully-renovated home. Featuring 2 spacious bedrooms upstairs and a versatile 3rd bedroom or bonus room/office downstairs, along with 1.5 updated bathrooms, this light-filled house boasts a brand-new kitchen that harmonizes contemporary functionality with the farmhouse's vintage allure. The inviting open floor plan

    Gary Fuls Jr RE/MAX Transitions

    181 Bridges Rd, Williamstown, MA 01267
  • 105 Harrington Rd, Otis, MA 01253
    105 Harrington Rd, Otis, MA 01253
    105 Harrington Rd, Otis, MA 01253
    /69

    $650,000

    • 4 Beds
    • 3.5 Baths
    • 3,204 Sq Ft

    105 Harrington Rd, Otis, MA 01253

    Nestled on over 7 acres of serene,wooded greenery,this meticulously maintained home offers a separate cottage where your friends and family can stay with comfort and privacy.Located in the highly sought-after community of Harrington Woods, this property provides a peaceful country setting w/ access to community amenities,including a pool & tennis/pickle ball courts.Inside,the home boasts an open

    Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

    105 Harrington Rd, Otis, MA 01253
  • 792 Middle Rd, Clarksburg, MA 01247
    792 Middle Rd, Clarksburg, MA 01247
    792 Middle Rd, Clarksburg, MA 01247
    /40

    $425,000

    • 4 Beds
    • 2 Baths
    • 1,740 Sq Ft

    792 Middle Rd, Clarksburg, MA 01247

    Welcome home to this spacious Ranch/Rambler home with 4 bedrooms and two full bathrooms. Vaulted ceiling in the living room. The floor plan conveniently flows well through the kitchen and dining room. The kitchen has a penincela with seating. Off the dining room is a slider out to the large deck that also connects to the swimming pool. The lower level has a bonus/family room with a bar. Two car

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    792 Middle Rd, Clarksburg, MA 01247
  • 113 Brush Hill Rd, Great Barrington, MA 01230
    113 Brush Hill Rd, Great Barrington, MA 01230
    113 Brush Hill Rd, Great Barrington, MA 01230
    /72

    $4,290,000

    • 4 Beds
    • 4.5 Baths
    • 5,800 Sq Ft

    113 Brush Hill Rd, Great Barrington, MA 01230

    THE GOAT......This exceptional Berkshire minimalistic sensation has been architecturally designed to maximize the open floor plan concept while being mindful of private work/play spaces. A showpiece with 12+ acres of privacy surrounds you while the panoramic western views in every season bring you peace and calmness. The walls of glass integrate nature and the tranquil spellbinding views with

    Mary Jane White COHEN & WHITE ASSOCIATES

    113 Brush Hill Rd, Great Barrington, MA 01230
  • 305 Shadow Ln, Sandisfield, MA 01255
    305 Shadow Ln, Sandisfield, MA 01255
    305 Shadow Ln, Sandisfield, MA 01255
    /41

    $575,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 1,864 Sq Ft

    305 Shadow Ln, Sandisfield, MA 01255

    This beautiful 3-bed, 3-bath home in the Otis Wood Lands offers modern comforts in a serene setting. The property boasts a screen porch, sun deck, and 2 wood burning fireplaces! The sunlit great room, with floor-to-ceiling windows, is perfect for entertaining with its open concept living room, dining area, and kitchen. The large primary suite features a wood burning fireplace, walk-in closet, and

    Sarah Dixon LANCE VERMEULEN RE, INC

    305 Shadow Ln, Sandisfield, MA 01255
  • 71 Blunt Rd, Great Barrington, MA 01230
    71 Blunt Rd, Great Barrington, MA 01230
    71 Blunt Rd, Great Barrington, MA 01230
    /49

    $1,999,000

    • 6 Beds
    • 6 Baths
    • 4,850 Sq Ft

    71 Blunt Rd, Great Barrington, MA 01230

    Artist Retreat / Family Compound! This very special property has a lot more to offer than anything on the market with three separate living/working spaces all thoughtfully designed for inspiration and comfort! Completely remodeled from top to bottom, the main house has three bedrooms, three bathrooms and featuring in-floor radiant heat under reclaimed ancient teak floors. There is a first floor

    Ryan Lane Gilcrest Properties

    71 Blunt Rd, Great Barrington, MA 01230
  • 12 Alpine Trail, Pittsfield, MA 01201
    12 Alpine Trail, Pittsfield, MA 01201
    12 Alpine Trail, Pittsfield, MA 01201
    /53

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,381 Sq Ft

    12 Alpine Trail, Pittsfield, MA 01201

    This well-maintained end-unit condo in the Pines at Bousquet offers 2,381 sq ft and seamlessly blends comfort and style. It features 3 bedrooms and 2.5 bathrooms, including a 1st-floor primary ensuite. The spacious layout boasts vaulted ceilings that fill the space with natural light, complemented by beautiful hardwood floors and an outdoor deck. Additionally, there is a cozy interior balcony and

    Marc Bellora LAMACCHIA REALTY, INC

    12 Alpine Trail, Pittsfield, MA 01201
  • 54 Egremont Plain Rd, Great Barrington, MA 01230
    54 Egremont Plain Rd, Great Barrington, MA 01230
    54 Egremont Plain Rd, Great Barrington, MA 01230
    /26

    $629,000

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    54 Egremont Plain Rd, Great Barrington, MA 01230

    Great New England farmhouse with really nice views. Common rooms are amply sized and the kitchen great room is perfect for many different activities. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many extras - structural renovations in 2004, central air, in line generator, in ground pool, screened porch and so much charm. Nice 3.89 acre parcel with detached

    Katie Williams STONE HOUSE PROPERTIES, LLC

    54 Egremont Plain Rd, Great Barrington, MA 01230
  • 390 Tamaridge Rd, Great Barrington, MA 01230
    390 Tamaridge Rd, Great Barrington, MA 01230
    390 Tamaridge Rd, Great Barrington, MA 01230
    /31

    $5,995,000

    • 5 Beds
    • 6.5 Baths
    • 5,890 Sq Ft

    390 Tamaridge Rd, Great Barrington, MA 01230

    STUNNING LONG VIEWS, RARE 330+ ACRE PARCEL, ABUTS CONSERVATION LAND! Total seclusion and privacy, bucolic countryside with some open meadows and wooded hillside. Once a grand Berkshire estate, the property is comprised of the main Tudor style residence with indoor pool, shingled barn, Dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. The buildings are all

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    390 Tamaridge Rd, Great Barrington, MA 01230
  • 56 Crooked Hill Rd, Great Barrington, MA 01230
    56 Crooked Hill Rd, Great Barrington, MA 01230
    56 Crooked Hill Rd, Great Barrington, MA 01230
    /53

    $3,150,000

    • 5 Beds
    • 4.5 Baths
    • 5,238 Sq Ft

    56 Crooked Hill Rd, Great Barrington, MA 01230

    Alford Stunner! Exceptionally Designed Turnkey Home with Mountain Views!Completed in 2006, this 5200+ sq ft architect-designed home comes to the market for the first time. Meticulously curated materials, interior designer finishes, and a high-end build culminate in this showpiece home on 19.3 acres, with gunite pool and pool house.Upon entry, this home exudes warmth, style, and comfort - the

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    56 Crooked Hill Rd, Great Barrington, MA 01230
  • 37 Corey Rd Unit 844, Hancock, MA 01237
    37 Corey Rd Unit 844, Hancock, MA 01237
    37 Corey Rd Unit 844, Hancock, MA 01237
    /22

    $350,000

    • 2 Beds
    • 2 Baths
    • 1,006 Sq Ft

    37 Corey Rd Unit 844, Hancock, MA 01237

    Here is a unique opportunity to own a large and bright 2 bedroom/2 bath condo in the Paul Major Welcome Center. It is steps to the lifts as well as other amenities like restaurants and shopping. The unit has its own storage locker, parking space and owner's closet for your convenience. This unit features really beautiful views of the mountains and the ski slopes. Primary bathroom has double sinks

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 844, Hancock, MA 01237
  • 5 Aspen Way Unit 17, Pittsfield, MA 01201
    5 Aspen Way Unit 17, Pittsfield, MA 01201
    5 Aspen Way Unit 17, Pittsfield, MA 01201
    /20

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    5 Aspen Way Unit 17, Pittsfield, MA 01201

    Great opportunity to custom design your 2000 square foot free-standing condo home at Berkshire Country Meadows! This is one of only a few remaining sites in this established community. Close to Pontoosuc Lake and centrally located for all Berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    5 Aspen Way Unit 17, Pittsfield, MA 01201
  • 813 East St, Lenox, MA 01240
    813 East St, Lenox, MA 01240
    813 East St, Lenox, MA 01240
    /75

    $2,895,000

    • 7 Beds
    • 9 Baths
    • 6,578 Sq Ft

    813 East St, Lenox, MA 01240

    Don't miss seeing the beautiful renovation just completed on this lovely Lenox Contemporary on almost 5A of privacy...enjoy incredible outdoor living spaces including an in-ground Gunite pool, Pavilion with outdoor kitchen and pool house with living space, kitchen, outdoor and indoor showers and even an outdoor TV! A real STAYCATION! The main house boasts lovely common spaces in the open floor

    Mary Jo Piretti PIRETTI REAL ESTATE

    813 East St, Lenox, MA 01240
  • 1373 Boardman St, Sheffield, MA 01257
    1373 Boardman St, Sheffield, MA 01257
    1373 Boardman St, Sheffield, MA 01257
    /61

    $2,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft

    1373 Boardman St, Sheffield, MA 01257

    The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1373 Boardman St, Sheffield, MA 01257
  • 37 Corey Rd Unit 843, Hancock, MA 01237
    37 Corey Rd Unit 843, Hancock, MA 01237
    37 Corey Rd Unit 843, Hancock, MA 01237
    /26

    $429,900

    • 2 Beds
    • 2 Baths
    • 1,004 Sq Ft

    37 Corey Rd Unit 843, Hancock, MA 01237

    Totally turnkey opportunity for a beautifully updated unit in the heart of Village Center. Located on the second floor of the Welcome Center building, this much-loved unit offers two spacious bedrooms, two full bathrooms, a well-equipped kitchen, washer dryer, dedicated parking spot and private ski locker. Walk out your front door to skiing, dining, hiking, gym, hot tubs and pools. Staying in?

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 843, Hancock, MA 01237
  • 45 Forest St, Lee, MA 01238
    45 Forest St, Lee, MA 01238
    45 Forest St, Lee, MA 01238
    /41

    $1,499,900

    • 12 Beds
    • 7 Baths
    • 7,956 Sq Ft

    45 Forest St, Lee, MA 01238

    This stunning 6-family home sits on 1.5 acres, just a couple minutes away from the Lee Outlets, a convenient location with easy access to the Mass Pike. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and primary bedroom on the the 1st floor, and 3 bedrooms

    Maria Liccardi Lamacchia Realty, Inc.

    45 Forest St, Lee, MA 01238
  • 41 Bulkley St, Williamstown, MA 01267
    41 Bulkley St, Williamstown, MA 01267
    41 Bulkley St, Williamstown, MA 01267
    /42

    $695,000

    • 4 Beds
    • 4 Baths
    • 2,806 Sq Ft

    41 Bulkley St, Williamstown, MA 01267

    In-town Victorian with loads of space inside and out. Built in the 1880s and then restored and expanded since, this charming home will embrace you with character and delight you with the location offering convenience and privacy. With 4 bedrooms and 3 full baths, including 1st floor primary suite plus full bath, and kitchenette in the converted barn, this wonderful home offers a wide variety of

    Paul Harsch Harsch Associates

    41 Bulkley St, Williamstown, MA 01267
  • 37 Corey Rd Unit 862, Hancock, MA 01237
    37 Corey Rd Unit 862, Hancock, MA 01237
    37 Corey Rd Unit 862, Hancock, MA 01237
    /27

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,130 Sq Ft

    37 Corey Rd Unit 862, Hancock, MA 01237

    Looking for a corner unit at JJ's lodge? This 3 bedroom 2 full bath unit is literally steps away from the private locker room and walk out to the Berkshire Express. Beautiful distant Mountain vistas and views of the bunny hill where you can watch your kids learn how to ski and snowboard all from your private balcony! Multiple beds for family and friends. The unit has central AC and Heating with

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 862, Hancock, MA 01237
  • 885 Washington Mountain Rd, Washington, MA 01223
    885 Washington Mountain Rd, Washington, MA 01223
    885 Washington Mountain Rd, Washington, MA 01223
    /41

    $1,800,000

    • 22 Beds
    • 21 Baths
    • 9,018 Sq Ft

    885 Washington Mountain Rd, Washington, MA 01223

    The Possibilities are endless! Family Compound & Retreat ! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl

    Joy Salvini RE/MAX Compass

    885 Washington Mountain Rd, Washington, MA 01223
  • 77 Seekonk Cross Rd, Great Barrington, MA 01230
    77 Seekonk Cross Rd, Great Barrington, MA 01230
    77 Seekonk Cross Rd, Great Barrington, MA 01230
    /66

    $6,850,000

    • 5 Beds
    • 3.5 Baths
    • 3,474 Sq Ft

    77 Seekonk Cross Rd, Great Barrington, MA 01230

    Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/

    Elvia Gignoux WILLIAM PITT SOTHEBY'S - SALISBURY

    77 Seekonk Cross Rd, Great Barrington, MA 01230
  • 148 Maple Ave Unit 28, Great Barrington, MA 01230
    148 Maple Ave Unit 28, Great Barrington, MA 01230
    148 Maple Ave Unit 28, Great Barrington, MA 01230
    /15

    $798,700

    • 2 Beds
    • 2 Baths
    • 1,141 Sq Ft

    148 Maple Ave Unit 28, Great Barrington, MA 01230

    Nestled amidst the picturesque embrace of Great Barrington, where the harmonious blend of nature and small-town charm unfolds, The Laurel beckons you into a realm of opulence and refinement. As you step inside, a grand two-story glass atrium lobby welcomes you with a breathtaking display of contemporary design and lavish furnishings. Lush plants and waterfalls adorn the walls, seamlessly

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    148 Maple Ave Unit 28, Great Barrington, MA 01230
  • 148 Maple Ave Unit 26, Great Barrington, MA 01230
    148 Maple Ave Unit 26, Great Barrington, MA 01230
    148 Maple Ave Unit 26, Great Barrington, MA 01230
    /15

    $753,200

    • 2 Beds
    • 2 Baths
    • 1,076 Sq Ft

    148 Maple Ave Unit 26, Great Barrington, MA 01230

    Nestled amidst the picturesque embrace of Great Barrington, where the harmonious blend of nature and small-town charm unfolds, The Laurel beckons you into a realm of opulence and refinement. As you step inside, a grand two-story glass atrium lobby welcomes you with a breathtaking display of contemporary design and lavish furnishings. Lush plants and waterfalls adorn the walls, seamlessly

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    148 Maple Ave Unit 26, Great Barrington, MA 01230

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