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Modern & Contemporary Homes for Sale in Berkshire County MA

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  • /28

    $575,000

    • 4 Beds
    • 2 Baths
    • 3,218 Sq Ft

    303 Lakeshore Dr, Sandisfield, MA 01255

    Discover the epitome of lakeside living in this exceptional 4-bedroom, 2-bath home nestled in the desirable Otis Wood Lands community. This fully furnished residence seamlessly combines comfort and entertainment, featuring bright, spacious rooms and an expansive deck perfect for relaxation or hosting gatherings. Enjoy modern conveniences such as energy-efficient heat pumps, remote-controlled

    Agent Photo

    Gary Fuls Jr

    RE/MAX Transitions

    303 Lakeshore Dr, Sandisfield, MA 01255
  • /41

    $1,198,000

    • 4 Beds
    • 5 Baths
    • 3,584 Sq Ft

    210 Bailey Rd, Lanesborough, MA 01237

    Completed in 2022, this architecturally striking contemporary home on scenic Bailey Road offers panoramic views of the Mount Greylock Reservation and a thoughtful blend of modern design, energy efficiency, and connection to nature. Conceived by owners with a deep interest in wellness, sustainability, and environmental stewardship, the home was designed to maximize natural light, comfort, and

    Agent Photo

    Selina Lamb

    Birch Properties

    210 Bailey Rd, Lanesborough, MA 01237
  • /6

    $886,000

    • 3 Beds
    • 2.5 Baths
    • 4,516 Sq Ft

    69 Elmore Dr, Dalton, MA 01226

    NEW CONSTRUCTION. Opportunity to customize. Potential for multi-generational living. This elegant craftsman style home offers exceptional attention to finishes & architectural details. Open spacious open living room w/ fireplace has seamless access to covered deck & is continuously open to dining & kitchen. The kitchen boasts center island w/ seating, stone counters, stainless appliances,

    Agent Photo

    Nadine Hiser

    KRG - Key Realty Group

    69 Elmore Dr, Dalton, MA 01226
  • /33

    $698,500

    • 3 Beds
    • 2 Baths
    • 1,085 Sq Ft

    98 Loop Dr, Otis, MA 01253

    Classic lakefront cottage with frontage on quiet Benton Pond for swimming, kayaking canoeing and sailing, plus deeded rights to Big Pond for motorboating.. Four season contemporary Cape with an open plan featuring a window wall facing the lake and a brick fireplace. There are three bedrooms and two full baths plus a small loft. The screened porch is adjacent to the kitchen, convenient for al

    Jeff Wilkinson Jeff Wilkinson

    98 Loop Dr, Otis, MA 01253
  • /15

    $829,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,798 Sq Ft

    1 Marcy Rd, Otis, MA 01253

    New Construction!! Three bedroom contemporary chalet to be built on a 17 acre portion of the 1800's E.B. Palmer farm. Two owners in a construction company partnership bought the property 20 years ago with the idea that each would build a personal home on the acreage. Life changed. Now semi retired, they are contracting with a builder of quality manufactured homes to build modern, efficient homes

    Kim Bergland Red Horse Real Estate

    1 Marcy Rd, Otis, MA 01253
  • /56

    $995,000

    $255K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,447 Sq Ft

    6 Muddy Brook Cir, Great Barrington, MA 01230

    Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    6 Muddy Brook Cir, Great Barrington, MA 01230
  • /57

    $1,895,000

    • 6 Beds
    • 4.5 Baths
    • 4,139 Sq Ft

    176 W Center Rd, West Stockbridge, MA 01266

    A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With

    Randy Thunfors STONE HOUSE PROPERTIES, LLC

    176 W Center Rd, West Stockbridge, MA 01266
  • /66

    $1,395,000

    • 4 Beds
    • 4.5 Baths
    • 3,185 Sq Ft

    124 Egremont Plain Rd, Great Barrington, MA 01230

    This beautiful home was built in 2006, and updated in 2022. The house is situated on just shy of 5 Acres in the town of Egremont. The home is flooded with sun all day, rarely needing a light on in the house. Direct access to the Green River at the edge of property to cool off on those hot summer days. A new central AC system was installed throughout home and apt A New backup generator, rain

    Lawrence Reilly THE KINDERHOOK GROUP

    124 Egremont Plain Rd, Great Barrington, MA 01230
  • /66

    $1,950,000

    • 5 Beds
    • 4 Baths
    • 3,404 Sq Ft

    415 Brewer Branch Rd, New Marlborough, MA 01259

    Set on 21.5 acres at the end of a long, winding private drive, this extraordinary residence is a true architectural gem--where art, landscape, and modern living converge. Originally designed by Robert McMahon and built by Lou Boxer and later reimagined through a contemporary project by Deborah Reiser of the award-winning RUR Architecture with Hird Design and Construction as the builder, the home

    Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    415 Brewer Branch Rd, New Marlborough, MA 01259
  • /74

    $1,875,000

    $50K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 3,462 Sq Ft

    26 Stonebridge Way, Lee, MA 01238

    A rare opportunity awaits! Own a developable mountain top in the Berkshires! Your 4B/2.5Bath home is 10 years young with custom kitchen and baths. An unobstructed view of Goose Pond and beyond, it's a 56 acre sanctuary mostly comprised of Oak and Mountain Laurel forest with trails. Enjoy a 40 mile view to Mt. Greylock and views of October Mt. State Park, and boating on Goose Pond (@1/2 mile to

    Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

    26 Stonebridge Way, Lee, MA 01238
  • /39

    $1,575,000

    • 3 Beds
    • 2.5 Baths
    • 2,348 Sq Ft

    347 Pine Rd, Otis, MA 01253

    Discover an extraordinary lakefront opportunity on Otis Reservoir featuring a combination of amenities rarely found in a single package. Combined with the lower lot, enjoy 62 feet of direct waterfront, a super rare grandfathered boathouse dock with electricity and electric lift, a waterfront bathhouse with living room, heated garage, dedicated hot tub room with fireplace, and a floor plan

    Adam Rovithis Real Broker MA, LLC

    347 Pine Rd, Otis, MA 01253
  • /5

    $1,650,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,545 Sq Ft

    79 Woodmere Rd, Becket, MA 01223

    Pre-Construction: Step into a brand-new construction home designed to bring together modern comfort, generous space, and the natural beauty of the Berkshires. The heart of the home is an expansive open kitchen, dining, and family room area made for entertaining, slow mornings, and everyday living, complete with a walk-in pantry and seamless access to the rear deck. A separate study and additional

    Jarvid Cortes Keller Williams Realty Evolution

    79 Woodmere Rd, Becket, MA 01223
  • /34

    $799,000

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

    15 Cherry Hill Dr, Pittsfield, MA 01201

    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

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    15 Cherry Hill Dr, Pittsfield, MA 01201
  • /33

    $1,300,000

    • 4 Beds
    • 5 Baths
    • 3,060 Sq Ft

    201 Chanterwood Rd, Lee, MA 01238

    Set in the heart of the Berkshires of Lee, Mass, this beautifully maintained 4-bedroom home captures the essence of Berkshire living with panoramic, elevated views for all 4 seasons that will leave you speechless; particularly in Autumn, when views in the Berkshires explode with color. A 4th oversized garage below the house is the perfect place for all of your toys. Inside, the home offers 3

    Susan Calkins STONE HOUSE PROPERTIES, LLC

    201 Chanterwood Rd, Lee, MA 01238
  • /19

    $885,000

    • 2 Beds
    • 3 Baths
    • 1,753 Sq Ft

    856 Barnum St, Sheffield, MA 01257

    Modernist retreat in a pastoral Berkshire setting-an artful sanctuary where design, landscape, and light exist in quiet harmony. Designed by acclaimed architect Deby Reiser, this light-filled two-bedroom, three-bath home blends refined urban modernism with the stillness of the countryside. Set along a quiet dirt road beside Moon In The Pond Farm, (an eco-conscious farm) a landscape of grazing

    Elyse Morris Elyse Harney Real Estate

    856 Barnum St, Sheffield, MA 01257
  • /47

    $2,295,000

    • 4 Beds
    • 5 Baths
    • 4,345 Sq Ft

    169 Mount Hunger Rd, Monterey, MA 01245

    ENJOY STUNNING VIEWS FROM EVERY ROOM OF LAKE GARFILED, THE CONNECTICUT HILLS AND THE CATSKILL MOUNTAINS. THIS BRIGHT SUNFILLED HOME SITUATED HIGH UP ON MT HUNGER RD HAS OVER 700 ACRES OF LAND TRUST LAND DIRECTLY ACROSS THE ROAD TO ENJOY MANY HIKES. A FOUR BED ROOM HOME WITH MORE STORAGE SPACE THAN YOU COULD WISH FOR COMES WITH FIVE FULL BATHROOMS, ONE OF WHICH IS IN THE GUEST APARTMENT ABOVE THE

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    169 Mount Hunger Rd, Monterey, MA 01245
  • /42

    $1,100,000

    • 4 Beds
    • 3 Baths
    • 2,055 Sq Ft

    13 Hayes Pond Rd, Monterey, MA 01245

    EXCEPTIONAL WATERFRONT RETREAT ON TRANQUIL HAYES POND!Nestled on over 3 private acres w/an extraordinary 650 feet of frontage on Hayes Pond,this exceptional waterfront retreat offers sweeping elevated views,a private dock, sandy beach, & direct access to swimming, kayaking, & fishing.Designed to embrace its stunning natural setting,the home features expansive windows & multiple outdoor living

    Thom Garvey William Pitt Sotheby's International Realty

    13 Hayes Pond Rd, Monterey, MA 01245
  • /88

    $3,550,000

    • 6 Beds
    • 7 Baths
    • 9,254 Sq Ft

    Unlisted Address

    The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal sitting area and spacious eat-in kitchen at the back, stunning central stairwell, cozy den/bar, and media room. Five comfortable bedrooms, including two luxurious primary suites. Every material, sightline, and design element has been curated with care

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    Unlisted Address
  • /60

    $5,245,000

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

    50 East Rd, West Stockbridge, MA 01266

    Set on 35.6 acres in the heart of Alford, this exceptional estate offers privacy, sweeping western views to the Catskills,and direct access to the Tom Ball Mountain Trail, abutting hundreds of acres of protected land. Located just minutesfrom Great Barrington and approximately 10 minutes to the Massachusetts Turnpike, the property combines seclusionwith convenient access to the region's top

    Elyse Morris ELYSE HARNEY REAL ESTATE

    50 East Rd, West Stockbridge, MA 01266
  • /81

    $3,995,000

    • 4 Beds
    • 4.5 Baths
    • 5,683 Sq Ft

    27 Hemlock Hill Rd, Great Barrington, MA 01230

    Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully

    Claire Pollart WILLIAM RAVEIS - BERKSHIRE

    27 Hemlock Hill Rd, Great Barrington, MA 01230
  • /19

    $819,000

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

    5 Aspen Way, Pittsfield, MA 01201

    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

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    5 Aspen Way, Pittsfield, MA 01201
  • /16

    $829,000

    • 3 Beds
    • 2.5 Baths
    • 1,798 Sq Ft

    Lot1 Marcy Rd, Otis, MA 01253

    New Construction!! Three bedroom contemporary chalet to be built on a 17 acre portion of the 1800's E.B. Palmer farm. Two owners in a construction company partnership bought the property 20 years ago with the idea that each would build a personal home on the acreage. Life changed. Now semi retired, they are contracting with a builder of quality manufactured homes to build modern, efficient homes

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot1 Marcy Rd, Otis, MA 01253
  • /35

    $549,900

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    1791 Algerie Rd, East Otis, MA 01029

    Beautifully refurbished home in the Berkshires with deeded rights to the White Lily Pond Association, offering access to a private beach, tennis and pickleball courts. White Lily Pond is a quiet lake ideal for canoeing, kayaking, paddleboarding, and trolling motors only. Renovated with quality craftsmanship throughout, the home features upgraded insulation, efficient propane heat, and inviting

    Suzanne Bergeron NAPLES REALTY GROUP, LLC

    1791 Algerie Rd, East Otis, MA 01029
  • /42

    $1,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,999 Sq Ft

    37 Kalliste Hill, Great Barrington, MA 01230

    Amazing custom-built countryside retreat in The Berkshires. Meticulously maintained since it was built in 1999, this unbeatable 3 BR 3.5 Bath contemporary is located in one of the most sought after neighborhoods in Great Barrington. Perfect for those seeking a serene tranquil setting or a weekend/summer getaway, this home offers a unique inviting layout & is the definition of quality! From the

    James Wood Coldwell Banker Realty - Boston

    37 Kalliste Hill, Great Barrington, MA 01230
  • /41

    $1,390,000

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

    71 Blunt Rd, Egremont, MA 01230

    A Truly Inspired Berkshire Retreat. The perfect home to relax, create, and be inspired, this remarkable Egremont property offers an exceptional blend of luxury, comfort, and creativity--truly unlike anything else on the market.The main residence features three spacious bedrooms and three full baths, enhanced by radiant in-floor heating beneath stunning reclaimed ancient teak floors. The

    Ryan Lane GILCREST PROPERTIES

    71 Blunt Rd, Egremont, MA 01230
  • /8

    $985,000

    • 3 Beds
    • 3 Baths
    • 2,015 Sq Ft

    542 Water St, Williamstown, MA 01267

    Introducing Green River Meadows, a new luxury development that prioritizes healthy, sustainable living--ideal for those seeking an eco-friendly lifestyle without sacrificing luxury. Nestled alongside the Green River in Williamstown, just a short distance from the prestigious Williams College and surrounded by the cultural richness of the Berkshires, this community offers an exceptional lifestyle

    Danielle Giulian WILLIAM PITT SOTHEBY'S - LENOX

    542 Water St, Williamstown, MA 01267
  • /14

    $1,347,500

    $52K PRICE DROP
    • 16 Beds
    • 16 Baths
    • 8,608 Sq Ft

    14 Highland Ave, Pittsfield, MA 01201

    Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake!Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location--just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history.

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    14 Highland Ave, Pittsfield, MA 01201
  • /41

    $549,900

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft

    349 N Washington State Rd, Washington, MA 01223

    Completely renovated contemporary home on almost 10 acres of land. The home sits back from the road, offering tranquility and privacy. The 1st floor features 2 bedrooms and an additional room with a wood-burning fireplace which can be used as a recreation room or a 3rd bedroom. Downstairs you will also find a large laundry room with epoxy flooring, and full bathroom. The second floor offers an

    Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

    349 N Washington State Rd, Washington, MA 01223
  • /32

    $745,000

    $105K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,460 Sq Ft

    85 Main Rd, Monterey, MA 01245

    OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the main

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    85 Main Rd, Monterey, MA 01245
  • /57

    $2,400,000

    • 5 Beds
    • 5 Baths
    • 6,092 Sq Ft

    89 N Undermountain Rd, Egremont, MA 01258

    Welcome to Treetops. A long private driveway passing a large pond sets the scene for this impressive hilltop retreat with 6,000 square feet across three levels and seasonal views of the Taconic Hills. Built with wood hewn from trees on the property, including the distinctive stairway, the home offers a huge open-plan main level ideal for gatherings, along with an indoor pool, hot tub, sauna and a

    Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

    89 N Undermountain Rd, Egremont, MA 01258
  • /64

    $1,900,000

    • 5 Beds
    • 4.5 Baths
    • 4,500 Sq Ft

    355 Adsit Crosby Rd, New Marlborough, MA 01230

    Stunning contemporary nestled in tranquility. The main level boasts a gracious great room with cathedral ceilings, fireplace and walls of windows that wash the common spaces with natural light and bring nature in. Gourmet chefs kitchen with ample storage and dining room with direct access to the oversized porch that features a gas stove for the chillier days. First floor primary en suite with

    Cortney Dupont COHEN & WHITE ASSOCIATES

    355 Adsit Crosby Rd, New Marlborough, MA 01230
  • /50

    $1,500,000

    • 4 Beds
    • 3.5 Baths
    • 4,343 Sq Ft

    140 Beartown Mountain Rd, Monterey, MA 01245

    Set on 22 private acres, this Monterey retreat offers a peaceful escape from city and suburban life. Freshly painted this spring, it's near Lake Garfield and Monterey Town Beach, and across from Beartown State Forest. The bright, expansive home features four ensuite bedrooms, including a spacious primary suite, large entertaining areas, and cathedral & vaulted ceilings. Outdoors, enjoy a 16' x

    Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

    140 Beartown Mountain Rd, Monterey, MA 01245
  • /42

    $2,750,000

    • 2 Beds
    • 2.5 Baths
    • 1,183 Sq Ft

    327 Chester Rd, Becket, MA 01223

    Fabulous Estate Property with ponds, rushing streams, huge acreage and a gem of a house. The 220 acres abuts state forest and beautiful Walker & Spark Brooks both run through the property. The 2BR/2.5B home has lovely views of the pond and hills beyond, and was totally renovated to the highest standards in 2023 and 2024. Native stone fireplace, heart pine floors, new kitchen, baths, mahogany

    Jeff Wilkinson Jeff Wilkinson

    327 Chester Rd, Becket, MA 01223
  • /30

    $6,475,000

    • 9 Beds
    • 11 Baths
    • 12,968 Sq Ft

    250 Long Pond Rd, Great Barrington, MA 01230

    Experience a rare Zen-inspired retreat in the heart of the Berkshires, brilliantly designed to exist in harmony with its natural surroundings. Set on nearly 120 acres of protected land with striking rock outcroppings, sweeping mountain views, and frontage along the Williams River, this architecturally significant contemporary offers a true sense of privacy, tranquility, and escape- all just

    Elyse Morris Elyse Harney Real Estate

    250 Long Pond Rd, Great Barrington, MA 01230
  • /42

    $499,000

    • 2 Beds
    • 2 Baths
    • 2,084 Sq Ft

    283 Benton Hill Rd, Becket, MA 01223

    Nice 3 bedroom contemporary home set on over nine acres with Center Pond Brook flowing past the garden areas & through the back yard. The front porch opens onto the main kitchen & living areas with hardwood floors & cathedral ceilings. French doors lead to the sunroom overlooking the garden areas. The first floor primary bedroom features two walk in closets, built in dressers & desk. More built

    Kim Bergland Red Horse Real Estate

    283 Benton Hill Rd, Becket, MA 01223
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