Berkshire County MA Homes for Sale

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  /25

  $579,900

  • 3 Beds
  • 4.5 Baths
  • 5,640 Sq Ft

  168 Elm St, Pittsfield, MA 01201

  Welcome to this exceptional mixed-use building that combines residential and commercial opportunities in one of the most sought after areas in Pittsfield .This property features 3 great apartments and two storefronts, making it ideal for investors or entrepreneurs looking to capitalize on a vibrant local community. The building offers 3 one bedroom apartments, 2 units will be delivered empty for

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  168 Elm St, Pittsfield, MA 01201
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  /27

  $285,000

  • 2 Beds
  • 3 Baths
  • 1,770 Sq Ft

  2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240

  If you are looking for location, Rolling Hills is the place to be. Just minutes from Tanglewood, Shakespeare & Company, skiing, arts, and all of the Culture the Berkshires has to offer. This unit is right across from the Clubhouse/Pool/fitness room. This unit has 2 bedrooms, 3 baths, additional family room on the lower level and newer appliances. Enjoy the Tennis/pickle ball courts or take swim

  Toni Marie Gage SIGNATURE ASSOCIATES

  2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
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  /38

  $850,000

  • 18,000 Sq Ft

  40 Pecks Rd, Pittsfield, MA 01201

  Don’t be late for this redevelopment opportunity! 18,000 Sqft on 1.1 Acres. Structurally sound property offers a rare opportunity to transform a historic space into a vibrant new community. Preliminary estimates suggest the potential for 12 residential units, with ample room for parking and green space. Featuring solid brick construction. Expansive windows, high ceilings, and open floor plans,

  Xavier Cruz Fathom Realty

  40 Pecks Rd, Pittsfield, MA 01201
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  /58

  $4,995,000

  • 7 Beds
  • 8 Baths
  • 13,261 Sq Ft

  319 Under Mountain Rd, Lenox, MA 01240

  Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

  Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  319 Under Mountain Rd, Lenox, MA 01240
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  /6

  $70,000

  • 12 Beds
  • 5 Baths
  • 4,032 Sq Ft

  48 Brown St, Pittsfield, MA 01201

  Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only. All offers considered.

  Xavier Cruz Fathom Realty

  48 Brown St, Pittsfield, MA 01201
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  /28

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  303 Lakeshore Dr, Sandisfield, MA 01255

  Experience the ultimate in lakeside living with this stunning 4-bedroom, 2-bath home in the coveted Otis Wood Lands community. This property offers a perfect blend of comfort and entertainment, featuring spacious sun-filled rooms and a sprawling deck ideal for relaxation and gatherings. Enjoy the convenience of a fully furnished home, complete with game room favorites like pool and air hockey

  

  Gary Fuls Jr

  RE/MAX TRANSITIONS

  (413) 884-5511

  303 Lakeshore Dr, Sandisfield, MA 01255
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  /12

  $170,000

  • 6 Beds
  • 2 Baths
  • 2,128 Sq Ft

  242 Wahconah St, Pittsfield, MA 01201

  Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd & 48 Brown st

  Xavier Cruz Fathom Realty

  242 Wahconah St, Pittsfield, MA 01201
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  /17

  $99,000

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  49 Access Rd Unit 3b, Windsor, MA 01270

  This charming and rustic seasonal lake cottage, rebuilt in 2011 with structural enhancements, replacement windows, and a large side deck, is a cozy retreat nestled on 1.24 wooded acres by Windsor Pond. The interiors are adorned with knotty pine, giving it a warm and inviting feel harkening to an era past. With two comfy bedrooms, a wood stove to keep you warm on chilly nights, a spacious screened

  

  Lisa Carroll

  Delap Real Estate LLC

  (413) 741-2269

  49 Access Rd Unit 3b, Windsor, MA 01270
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  /70

  $995,000 Open Sat 2:30PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,844 Sq Ft

  257 W Mountain Rd, Lenox, MA 01240

  Nestled in the heart of the Berkshires, 257 W Mountain Road offers a rare blend of luxury and tranquility. This exquisite property is set on a serene, tree-lined road just minutes from downtown Lenox and Tanglewood. With refined finishes, spacious living areas, and walls of windows framing the lush landscape, every detail reflects elegance and comfort. The landscaped grounds feature stone patios,

  Nicole Moore KELLER WILLIAMS REALTY

  257 W Mountain Rd, Lenox, MA 01240
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  /37

  $699,000

  • 3 Beds
  • 2.5 Baths
  • 1,828 Sq Ft

  92 Hancock Rd, Williamstown, MA 01267

  OPEN HOUSE: SATURDAY, NOV 1ST from 2:00pm - 3:30pm. Don't miss a rare opportunity to own this charming ranch-style home nestled in the tranquil countryside of South Williamstown. Set on over three picturesque acres with almost 900 feet of frontage on the scenic Green River, this spacious 3-bedroom, 2.5-bath home offers the perfect blend of comfort and privacy, yet conveniently just 5 miles from

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  92 Hancock Rd, Williamstown, MA 01267
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  /31

  $945,000

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft

  18 Creamery Rd, Great Barrington, MA 01230

  Nestled on 6.6 peaceful acres, this beautifully renovated country Cape offers exceptional privacy just minutes from town. Set well back from the road, the home enjoys a quiet, convenient location surrounded by mature trees and gardens.Inside, a spacious dining room features a striking stone fireplace, while the large living room showcases wood floors that extend throughout. Every detail has been

  Allison Rada STONE HOUSE PROPERTIES, LLC

  18 Creamery Rd, Great Barrington, MA 01230
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  /40

  $249,900

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft

  33 Hancock Rd, Williamstown, MA 01267

  This charming property is being sold as-is and offers the perfect opportunity for someone to bring their own finishing touches. While it could benefit from modern updates, it features a recently upgraded alternative grey water system with over $30,000 invested. 2-bedroom, 2-bath single-family home with 1,071 sqft of living space on a 6,098 sqft lot. Built in 1900, this home features a newly

  Alex King Lock and Key Realty, Inc

  33 Hancock Rd, Williamstown, MA 01267
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  /4

  $850,000

  • Land
  • 18.46 Acres
  • $46,045 per Acre

  0 Northwest Hill, Williamstown, MA 01267

  Located on a quiet country road, this 18.5-acre parcel offers beautiful mountain views, privacy, and a peaceful setting. Just minutes from Williams College, the Clark Art Institute, and town amenities, it's the perfect place to create your ideal retreat in the heart of the Berkshires. The property is under Chapter 61A.

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  0 Northwest Hill, Williamstown, MA 01267
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  /27

  $630,000

  • 4 Beds
  • 3 Baths
  • 1,950 Sq Ft

  245 Clubhouse Dr, Otis, MA 01253

  Fantastic 4 BR Otis Wood Lands Contemporary situated at the end of a cul-de-sac close to all community amenities! This spacious home has great spaces for family and friends. Price includes furniture. Community amenities include pool, tennis/pickleball courts, fitness room, playground, lodge, lake and beach. New septic in 2023, new hot water heater 06/2025, new roof 2003. $4,000 reserve fund fee

  Emily Piacquadio LANCE VERMEULEN RE, INC

  245 Clubhouse Dr, Otis, MA 01253
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  /40

  $579,000

  • 3 Beds
  • 2 Baths
  • 2,418 Sq Ft

  16 Iroquois St, New Ashford, MA 01237

  Newly built in 2025, this stunning ranch offers modern comfort and quality craftsmanship throughout. Featuring a spacious master suit, walk in closet and tiled shower with porcelain floors and lighted mirrors. Engineered Outlast floors, 10' ceilings, solid wood interior doors and recessed lighting add style and durability. Enjoy the warmth of spray foam insulation for year-round comfort,

  Janet Benoit Janet L. Benoit

  16 Iroquois St, New Ashford, MA 01237
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  /16

  $799,000

  • 11 Beds
  • 10.5 Baths
  • 2,016 Sq Ft

  3949 Jacobs Ladder Rd, Becket, MA 01223

  A unique lakefront cedar home with 8 room motel. many possibilities.Approximately 2.7 acres with over 500 ' lake frontage on Beautiful Greenwater Pond . Close to Appalachian trail and many Berkshire cultural and recreational venues.

  Anthony Caropreso MACCARO REAL ESTATE

  3949 Jacobs Ladder Rd, Becket, MA 01223
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  /24

  $550,000

  • 5 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  867 Notch Rd, Cheshire, MA 01225

  A charming, spacious Colonial with privacy, and lovely grounds. Breathtaking mountain views. Built in 2005 and set on 7.25 acres, this 5-bedroom, 4.5-bathroom residence offers 3,307 square feet of living space. Two primary suites, one up and one down. The open-concept kitchen flows seamlessly into a great room, perfect for entertaining. This home does need work but is priced accordingly. Make

  Marnie Garzone THE KINDERHOOK GROUP

  867 Notch Rd, Cheshire, MA 01225
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  /63

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 3,292 Sq Ft

  2017 Monterey Rd, Otis, MA 01253

  Modern Elegance Meets Tranquil Nature on the Clam River - a short ride to Gt Barrington on the Monterey Line! Tucked away on a private drive that gracefully winds over the scenic Clam River, this meticulously maintained residence is a hidden gem offering the perfect blend of sophistication and natural beauty. From the moment you arrive, the approach sets the tone--a tree-lined driveway leads to a

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  2017 Monterey Rd, Otis, MA 01253
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  /49

  $949,000

  • 1 Bed
  • 1.5 Baths
  • 3,810 Sq Ft

  30 Great Barrington Rd, West Stockbridge, MA 01266

  The renovation of this 1930's Cape Cod by a master craftsman and his designer wife into the stunning modern day Contemporary it is today, while preserving some of the original highlights,is nothing short of a design miracle. The immense Great Room with the 60 foot wall of glass overlooking the terraced stone wall that leads to a stream and pine forest is the focal point of this special home. The

  Cortney Dupont COHEN & WHITE ASSOCIATES

  30 Great Barrington Rd, West Stockbridge, MA 01266
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  /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
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  /2

  $69,900

  • Land
  • 0.87 Acre
  • $80,123 per Acre

  0 Iroquois St, New Ashford, MA 01237

  Beautiful lot, partially cleared, nestled in a lake community. Perfect building lot for your dream home!

  Jordan Romeo 413 REAL ESTATE

  0 Iroquois St, New Ashford, MA 01237
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  /24

  $695,000

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft

  80 Taconic Ave Unit 3, Great Barrington, MA 01230

  Welcome to Oakwood Condominium. A one car garage comes with unit. Plenty of additional parking. Lovely inground well manicured pool. Beautiful outdoor landscaping and sitting area. Private deck attached to unit for outdoor entertaining. This unit has been renovated over the years with updated kitchen with eat in nook area. All new windows and sliding doors. Gorgeous primary bathroom with radiant

  Suzann Ward HOUSATONIC REAL ESTATE

  80 Taconic Ave Unit 3, Great Barrington, MA 01230
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  /77

  $4,995,000

  • 5 Beds
  • 5.5 Baths
  • 5,002 Sq Ft

  764 E Hill Rd, New Marlborough, MA 01230

  WHERE THE WORLD FALLS AWAYAt the top of East Hill Road in the Southern Berkshires, East Hill Farm stretches out over 227 acres of unspoiled beauty: forest, meadow, pond, pasture, and sky . One of the most storied and visually captivating estates in the region, it offers not just land, but peace. Not just privacy, but purpose.At its heart stands a 1798 Federal home, built when John Adams was

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  764 E Hill Rd, New Marlborough, MA 01230
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  /66

  $430,000

  • 3 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  47 Gale Ave, Pittsfield, MA 01201

  Exceptional opportunity: Fully renovated three-bedroom main residence with guest cottage...FULL DELEADING COMPLIANCE!!! This special property offers owner-occupied living and additional income. The fully renovated main residence with the separate guest cottage provides ample space for various living arrangements. Both homes are move-in ready!

  Brandon White COHEN & WHITE ASSOCIATES

  47 Gale Ave, Pittsfield, MA 01201
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  /54

  $649,000

  • 5 Beds
  • 2.5 Baths
  • 2,750 Sq Ft

  168 Main St, Sheffield, MA 01257

  Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

  Tony Segalla LANCE VERMEULEN RE, INC

  168 Main St, Sheffield, MA 01257
• 

  

  /23

  $523,995

  • Land
  • 10.02 Acres
  • $52,279 per Acre

  0 Swamp Rd, Richmond, MA 01254

  This 10-acre parcel in scenic Richmond, available for the first time in generations, offers a rare chance to build your dream home in the heart of the Berkshires. Surrounded by open farmland and natural beauty, this property provides a peaceful and inspiring setting for a country retreat or a year-round residence. The land features gently rolling meadows filled with wildflowers and native

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  0 Swamp Rd, Richmond, MA 01254
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  /39

  $440,000

  • 2 Beds
  • 2 Baths
  • 1,683 Sq Ft

  5 Windflower Way, Williamstown, MA 01267

  Welcome to your dream condo located at 5 Windflower Way. This beautifully updated residence offers a blend of comfort & convenience, making it a perfect place for those seeking low maintenance. The well-equipped kitchen features modern appliances, quartz countertops, a beautiful, tiled floor, & ample cabinets. This condo includes 2 generously sized bedrooms, and two bathrooms. The attached

  Jessica Rizzo LAMACCHIA REALTY, INC

  5 Windflower Way, Williamstown, MA 01267
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  /38

  $249,000 Open Sun 10AM - 11PM

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft

  1052 Beaver Pond Meadows, Hancock, MA 01237

  Price Reduction!Charming 3-Bedroom Country Condo Escape the hustle and embrace the tranquility of country living with this beautifully maintained 3-bedroom, 2-bathroom condo, nestled in a peaceful rural setting. Perfect for families, retirees, or weekend getaways, this home offers a perfect blend of comfort, style, and natural beauty.Spacious Open Floor Plan: Enjoy a sun-filled living and dining

  Lisa Mendel BURNHAM GOLD REAL ESTATE, LLC

  1052 Beaver Pond Meadows, Hancock, MA 01237
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  /9

  $59,000

  • 4 Beds
  • 1.5 Baths
  • 2,244 Sq Ft

  477 Mohawk Trail, Drury, MA 01343

  Nestled along the scenic Mohawk Trail in Drury, MA, this 3.5-acre parcel offers a unique opportunity to build your dream home or getaway retreat in the heart of the Berkshires. While the existing structure is likely a teardown, the land itself boasts natural beauty, privacy, & convenient road frontage. Just minutes from Savoy Mountain State Forest, Mohawk Trail State Forest, and the Western

  Laiken Rapisarda LAMACCHIA REALTY, INC

  477 Mohawk Trail, Drury, MA 01343
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  /60

  $419,900

  • 3 Beds
  • 2.5 Baths
  • 2,093 Sq Ft

  144 Kittredge Rd, Pittsfield, MA 01201

  Welcome to 144 Kittredge Road in Pittsfield, Massachusetts! This charming brick 3-bedroom, 2.5-bath ranch-style rambler offers a perfect blend of comfort and convenience. Step inside to find an inviting open floor plan featuring a spacious living area bathed in natural light, ideal for both relaxation and entertaining. The well-appointed kitchen boasts ample counter space, making meal prep a

  Doug Collins LAMACCHIA REALTY, INC

  144 Kittredge Rd, Pittsfield, MA 01201
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  /79

  $1,360,000

  • 3 Beds
  • 2.5 Baths
  • 3,443 Sq Ft

  28 Main Rd, Lee, MA 01238

  THEY DON'T BUILD HOUSES LIKE THIS ANYMORE.They don't build love at first sight anymore, either. But Sky Hill Farm - a genuine 1798 Federal colonial in Tyringham Valley - has been creating that exact feeling for over two centuries.In 1912, Adele LeBourgeois Chapin wrote about first arriving here at dusk, walking through high grass to the old front door with its worn stone steps and feeling the

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  28 Main Rd, Lee, MA 01238
• 

  

  /20

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,449 Sq Ft

  841 Moberg Rd, Becket, MA 01223

  Charming 3BR/2B home in popular Indian Lake Estates. Sunny great room and expansive decks welcome you to this cozy home. Screened porch for al fresco dining and a Vermont Castings wood stove for toasty winter get-togethers. Community offers two (non-motorboat) lakes with beaches and tennis courts. Excellent location with easy access to Jacob's Pillow Dance Festival, Tanglewood and most other

  Jeff Wilkinson STONE HOUSE PROPERTIES, LLC

  841 Moberg Rd, Becket, MA 01223
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  /30

  $695,000

  • 3 Beds
  • 6 Baths
  • 4,044 Sq Ft

  1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222

  Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is

  Tony Segalla LANCE VERMEULEN RE, INC

  1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
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  /62

  $1,330,000

  • 16 Beds
  • 10 Baths
  • 8,870 Sq Ft

  6 Manville St, Great Barrington, MA 01230

  A prime investment opportunity in the heart of downtown Great Barrington. This 10-unit residential property features a desirable mix of six spacious two-bedroom apartments and four one-bedroom units. The two-bedroom apartments are particularly appealing, all offering private balconies and fireplaces, with three of these premium units also including formal dining rooms and Jack-and-Jill style

  Tony Segalla LANCE VERMEULEN RE, INC

  6 Manville St, Great Barrington, MA 01230
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  /37

  $600,000

  • 6 Beds
  • 5 Baths
  • 3,502 Sq Ft

  53 Mahaiwe St, Great Barrington, MA 01230

  A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to

  Tony Segalla LANCE VERMEULEN RE, INC

  53 Mahaiwe St, Great Barrington, MA 01230
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  /58

  $690,000

  • 3 Beds
  • 5 Baths
  • 2,786 Sq Ft

  233 Algerie Rd, Becket, MA 01223

  Let's imagine extreme privacy for a moment, yet your loved ones are simply a three minute walk away or a quick drive; because each one has their own home! With connecting roads this home is 3 of 3. This home is the larger of the 3, Sitting at 2786 Sq. Ft. 3 Bedrooms, 3 Full Bathrooms, a spacious Great Room Perfect for entertaining. A completely finished lower level, currently being used as a game

  Cristian Sanchez COHEN & WHITE ASSOCIATES

  233 Algerie Rd, Becket, MA 01223
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  /47

  $349,900

  • 5 Beds
  • 2 Baths
  • 2,120 Sq Ft

  127 Gamwell Ave, Pittsfield, MA 01201

  Tucked away at the end of a quiet cul-de-sac, this spacious five bedroom, two bathroom home offers 2,020 square feet of living space along with additional space in the basement. As you enter the home, you will notice hardwood floors throughout the main level that features three of the bedrooms, laundry, and one full bathroom. The bright living area flows easily into the dining room that connects

  Cory Evangelisto NOCHER REALTY

  127 Gamwell Ave, Pittsfield, MA 01201
• 

  

  /31

  $589,000

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

  70 Main St, Great Barrington, MA 01230

  Charming 1790 Historic Home in the Heart of South EgremontNestled on a beautifully landscaped 0.8-acre lot in the heart of the village, this 4-bedroom, 2-bath home blends timeless charm with modern convenience. Built in 1790 it features wide plank floors, built-ins, and a fireplace with a historic Dutch oven.Enjoy local access to shops and dining, with scenic hiking at Jug End Reservation just

  Judi Panzano HOUSATONIC REAL ESTATE

  70 Main St, Great Barrington, MA 01230
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  /54

  $1,185,000

  • 4 Beds
  • 2.5 Baths
  • 2,180 Sq Ft

  119 Hayes Pond Rd, Otis, MA 01253

  Your waterfront lifestyle begins at this Hayes Pond sanctuary. From sunrise paddles to sunsets savored from the deck, this home is your private four-season escape in the Berkshires. The modern, open interior is designed to celebrate the water, with soaring cathedral ceilings and a wall of windows that frames the stunning lake view. A cozy wood stove, bright sunroom, and a large deck provide

  Tony Segalla LANCE VERMEULEN RE, INC

  119 Hayes Pond Rd, Otis, MA 01253
• 

  

  /27

  $935,000

  • 4 Beds
  • 4 Baths
  • 2,280 Sq Ft

  21 East St, Stockbridge, MA 01262

  Nestled in the heart of the Berkshires, this spacious Colonial on 14+ acres offers privacy, potential, and long-term value. With only two owners, it's been well cared for and currently functions as a private residence and doggy daycare. Updates include the kitchen, baths, carpets, back deck, and landscaping--while still leaving room for added equity. Features include solar panels, well water, a

  Brianna Boffoli NON-MEMBER / RECIPROCAL

  21 East St, Stockbridge, MA 01262

Showing Results 441 - 480, Page 12 of 18