Homes for Sale near Hillcrest Educational Centers

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  /58

  $1,395,000

  • 6 Beds
  • 3.5 Baths
  • 3,905 Sq Ft

  21 Stockbridge Rd, West Stockbridge, MA 01266

  Tucked away on a private 2.35-acre knoll, this beautifully updated residence offers a rare blend of antique charm and modern ease in one of the Berkshires' most sought-after villages. With six generously sized bedrooms, a chef's kitchen designed for entertaining, and multiple inviting living spaces with fireplaces, the home is ideal for gatherings or quiet retreats alike. A stunning contemporary

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 675-5317

  21 Stockbridge Rd, West Stockbridge, MA 01266
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  /50

  $845,000

  • 4 Beds
  • 3.5 Baths
  • 2,955 Sq Ft

  9 Castle Hill Rd, Stockbridge, MA 01262

  Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated,

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 269-8632

  9 Castle Hill Rd, Stockbridge, MA 01262
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  /53

  $2,649,000

  • 6 Beds
  • 6.5 Baths
  • 4,289 Sq Ft

  250 West St, Lenox, MA 01240

  Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 423-1264

  250 West St, Lenox, MA 01240
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  /5

  $998,000

  • Land
  • 9.1 Acres
  • $109,670 per Acre

  19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

  RARE LUXURY: READY-to-BUILD MODERNIST RETREAT on EXCLUSIVE PRIVATE POND minutes to TANGLEWOODWelcome to a once-in-a-lifetime opportunity in the heart of the Berkshires. Set on 9.1 acres approximately acres of pristine land, this exceptional estate parcel offers frontage on tranquil Lily Pond, a private, non-motorized body of water that ensures peace, privacy, nature and views. Comprising the

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 343-4919

  19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
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  /42

  $1,795,000

  • 4 Beds
  • 3 Baths
  • 7,027 Sq Ft

  17 East St, Lenox, MA 01240

  ICONIC STOCKBRIDGE BRICK FEDERAL ESTATEElegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Built in the 1830s, the Carter Estate has been artfully expanded and boasts over 5,400sf of light-filled, luxurious living space.As you enter through classic stone walls and manicured hedgerows, you'll be welcomed by sweeping

  

  Selina Lamb

  Birch Properties

  (413) 300-6860

  17 East St, Lenox, MA 01240
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  /6

  $395,000

  • Land
  • 3.3 Acres
  • $119,697 per Acre

  9 Wheatleigh Dr, Stockbridge, MA 01262

  RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

  

  Selina Lamb

  Birch Properties

  (413) 343-5283

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /6

  $395,000

  • Land
  • 3.3 Acres
  • $119,697 per Acre

  9 Wheatleigh Dr, Stockbridge, MA 01262

  RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 722-5098

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /48

  $875,000

  • 4 Beds
  • 2 Baths
  • 3,599 Sq Ft

  2507 State Rd, Richmond, MA 01254

  Welcome home! This magnificent 23-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. Enjoy walks, rides and cross-country skiing through woods and meadows on the maintained trails that meander through the 23 acres. A low-maintenance wild garden of

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  2507 State Rd, Richmond, MA 01254
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  /53

  $1,850,000

  • 4 Beds
  • 1.5 Baths
  • 3,084 Sq Ft

  1130 East Rd, Richmond, MA 01254

  ICE HOUSE HILL FARM. Richmond, MA There are properties with views in the Berkshires. Then there is Ice House Hill Farm270 degrees of sweeping, layered vistas, and exceptional distant views - guaranteed forever by 130 acres of land that can never be developed. The facts: Exceptional building parcel on one of the Berkshires most beautiful roads, commanding staggering views. | 143 total acres. |

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1130 East Rd, Richmond, MA 01254
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  /61

  $1,300,000

  • 4 Beds
  • 2 Baths
  • 2,548 Sq Ft

  18 Goodrich St, Stockbridge, MA 01262

  This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal,

  Robert Doerr LANCE VERMEULEN RE, INC., LENOX

  18 Goodrich St, Stockbridge, MA 01262
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  /18

  $1,260,000

  • 5 Beds
  • 4 Baths
  • 3,334 Sq Ft

  1574 Pleasant St, Lee, MA 01260

  Steeped in history and elegance, the Henry Billings Brown House (c.1815) offered at $1,260,000, is a rare Berkshire estate. This three-unit residence on the historic registry is a masterful blend of preserved history and refined updates for modern living. Anchoring its timeliness character are wide-plank floors, stately brick hearths, and marble sourced from the same quarries as the U.S. Capitol.

  Ashley Rose Compass

  1574 Pleasant St, Lee, MA 01260
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  /48

  $899,000

  • 6 Beds
  • 9 Baths
  • 4,652 Sq Ft

  560 Stockbridge Rd, Lee, MA 01238

  Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room,

  Lori Rose STONE HOUSE PROPERTIES, LLC

  560 Stockbridge Rd, Lee, MA 01238
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  /34

  $1,795,000

  • 4 Beds
  • 4 Baths
  • 3,524 Sq Ft

  1 Old Tree Farm Rd, Stockbridge, MA 01262

  Impeccably Renovated Stockbridge Country Retreat. Minutes from Stockbridge, Lenox and Tanglewood, in the heart of the Berkshires cultural corridor, a rare opportunity in a perfect setting on 4.16 level, landscaped acres. Surrounded by mature trees and curated gardens, this home blends classic design with modern updates, offering refined style throughout. White oak floors, three full baths, a gas

  Suzann Ward Housatonic Real Estate

  1 Old Tree Farm Rd, Stockbridge, MA 01262
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  /55

  $1,490,000

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  5 Glendale Rd, Stockbridge, MA 01262

  ''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming

  Martha Piper THE KINDERHOOK GROUP

  5 Glendale Rd, Stockbridge, MA 01262
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  /70

  $995,000

  • 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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  /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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  /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
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  /59

  $859,900

  • 4 Beds
  • 3 Baths
  • 2,732 Sq Ft

  135 East St, Lee, MA 01238

  Rustic Style Expansive Cape. Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French

  Lisa Kelley MACCARO REAL ESTATE

  135 East St, Lee, MA 01238
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  /27

  $349,000

  • 4 Beds
  • 3 Baths
  • 2,276 Sq Ft

  44 Main St, West Stockbridge, MA 01266

  Discover the charm of downtown living in this Colonial home located in the heart of West Stockbridge. This home features four bedrooms, two full baths, kitchen, living room, dining room and a deck overlooking the river. In addition to the main living area the property also includes an in-law or studio apartment with it's own kitchen and bathroom. With a nice flat yard for outdoor activities,

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  44 Main St, West Stockbridge, MA 01266
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  /17

  $3,850,000 Open Fri 11AM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  21A Interlaken Rd, Stockbridge, MA 01262

  Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  21A Interlaken Rd, Stockbridge, MA 01262
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  /40

  $419,000

  • 3 Beds
  • 1 Bath
  • 1,269 Sq Ft

  26 Lenox Rd, West Stockbridge, MA 01266

  1900's cottage set above the village of West Stockbridge. Open plan living with updated kitchen and bath, with laundry tucked in below the stairs and second floor has three bedrooms. Fenced yard creating a nice private space with wraparound deck. Shed at the back of the property providing a lovely additional space.

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  26 Lenox Rd, West Stockbridge, MA 01266
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  /60

  $1,695,000

  • 4 Beds
  • 4.5 Baths
  • 3,991 Sq Ft

  9 October Hill Dr, Lenox, MA 01240

  Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a

  Paula McLean PAULA MCLEAN REALTORS INC.

  9 October Hill Dr, Lenox, MA 01240
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  /43

  $495,000

  • 3 Beds
  • 1.5 Baths
  • 1,686 Sq Ft

  155 Laurel St, Lee, MA 01238

  This thoughtfully updated home blends warmth, comfort, and history. An amazing front porch welcomes you before you even step inside, and the short walk to downtown or quick drive to the lake offers an easy, connected Berkshire lifestyle. Inside, bright and inviting rooms and beautiful wood floors create a natural sense of warmth, while the layout makes everyday living feel effortless. Flexible

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  155 Laurel St, Lee, MA 01238
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  /40

  $1,995,000

  • 10 Beds
  • 10.5 Baths
  • 11,608 Sq Ft

  55 Crystal St, Lenox, MA 01240

  Perched atop a gentle hill with distant Berkshire views, this distinguished former Lenox school building known as ''Crystal Hill'' has been thoughtfully converted into 10 residential apartments plus one office space.The historic masonry structure combines character and stability with modern updates, including hardwood floors, spacious layouts, and separate hot water and electric meters for each

  Christian Garner NOCHER REALTY

  55 Crystal St, Lenox, MA 01240
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  /42

  $1,399,900

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

  45 Forest St, Lee, MA 01238

  This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. 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

  Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

  45 Forest St, Lee, MA 01238
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  /42

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  16 Swamp Rd, West Stockbridge, MA 01266

  The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original detail. The wood-paneled living room features a handsome brick hearth with beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large window overlooks the

  Vashti Poor LANCE VERMEULEN RE, INC

  16 Swamp Rd, West Stockbridge, MA 01266
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  /13

  $197,950

  • Land
  • 3.6 Acres
  • $54,986 per Acre

  46 Pease Terrace, Lee, MA 01238

  Nestled in a quiet and private Lee neighborhood, at the end of a dead end street,this 3.6 (+-) parcel offers a perfect blend of seclusion and convenience. Thisserene setting is minutes to downtown Lee, local shops, restaurants, and all the cultural offerings of Berkshire County. Approximately half level and cleared, with unique rock formations and a woodedridge on the west side, this parcel is

  Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  46 Pease Terrace, Lee, MA 01238
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  /30

  $680,000

  • 3 Beds
  • 1.5 Baths
  • 1,562 Sq Ft

  18 Willow Ln, Lenox, MA 01240

  Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra

  Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  18 Willow Ln, Lenox, MA 01240
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  /4

  $50,000

  • Land
  • 18 Acres
  • $2,778 per Acre

  20 Forest St, Lee, MA 01238

  An incredible opportunity awaits with this 18-acre property, formerly known as the Westfield River Paper Mill. Featuring three existing buildings and a private driveway, this property offers endless potential for the right buyer. Whether you envision developing a new business venture, utilizing the land for recreation or hunting, or exploring its unique industrial history, the possibilities are

  TRU2YOU Realty Group The Neighborhood Realty Group

  20 Forest St, Lee, MA 01238
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  /51

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,706 Sq Ft

  30 Pease Terrace, Lee, MA 01238

  Introducing the Beautiful Spacious Ranch in a Great Neighborhood! Easy Living at Its Finest! Key Features:- Prime Location: Close to Main St.- Impeccably Maintained & Beautifully Updated- Stylish Granite Countertops for a Touch of Elegance- Lower Level Living Area/In-Law Unit, Extra Space for Guests or Rental Income Opportunity, Second Kitchen with Cozy Eat-In Area, Spacious Living Room for

  Matt Carlino MACCARO REAL ESTATE

  30 Pease Terrace, Lee, MA 01238
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  /53

  $3,750,000

  • 5 Beds
  • 7.5 Baths
  • 6,022 Sq Ft

  2650 Swamp Rd, Richmond, MA 01254

  April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  2650 Swamp Rd, Richmond, MA 01254
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  /12

  $485,000

  • 1 Bed
  • 1 Bath
  • 1,344 Sq Ft

  2 Devon Rd, Lee, MA 01238

  Bring your contractors and your imagination to this unique fixer-upper, an old carriage barn with an attached apartment. The spacious barn features original beams with large open areas. The lush grounds are complemented by charming rock walls and rustic outbuildings. With a convenient location close to all the Berkshire attractions, this property is ideal for transformation into a one-of-a-kind

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  2 Devon Rd, Lee, MA 01238
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  /59

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,706 Sq Ft

  1772 Swamp Rd, Richmond, MA 01254

  Set on 3 private, beautifully landscaped acres in the heart of Richmond, Massachusetts, 1772 Swamp Road offers the perfect blend of space, comfort, and potential. This 4-bedroom, 2.5-bath home provides a solid foundation, flexible floor plan, and updates in all the right places including a newer furnace, metal roof, and whole-house generator giving you peace of mind and room to make it your

  Heather Gallagher JAN PERRY REALTY & ASSOCIATES, LLC

  1772 Swamp Rd, Richmond, MA 01254
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  /9

  $475,000

  • Land
  • 20.87 Acres
  • $22,760 per Acre

  0 East St, Lenox, MA 01240

  This stunning 20+ acre building lot in Lenox, with frontage on East and Housatonic St. is the perfect place to build your dream home. The gently sloping land leads up towards westerly sunsets, while offering distant views of October Mountain to the east. With its peaceful and private setting, imagine waking up every day to the stunning views from your new home, surrounded by the serene natural

  Gary Johnston STONE HOUSE PROPERTIES, LLC

  0 East St, Lenox, MA 01240
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  /28

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  46 Housatonic St Unit 2B, Lenox, MA 01240

  Beautiful two bedroom, two bath condo perfectly situated in the center of Lenox, Massachusetts-the cultural heart of the Berkshires. Enjoy high Ceilings, beautiful wood floors, large windows, and abundant natural light throughout. The spacious layout features a gas fireplace, granite countertops, and a gas stove in the modern kitchen. The inviting living room opens to a private balcony, perfect

  Patricia Andrew STONE HOUSE PROPERTIES, LLC

  46 Housatonic St Unit 2B, Lenox, MA 01240
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  /32

  $549,000

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft

  7 Park St, Stockbridge, MA 01262

  Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The

  Samantha Homeyer BIRCH PROPERTIES

  7 Park St, Stockbridge, MA 01262
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  /17

  $499,000

  • 2 Beds
  • 1 Bath
  • 1,015 Sq Ft

  18 Hill Rd, Stockbridge, MA 01262

  Log Cabin in Stockbridge! Tucked away at the end of a country road, this charming log home offers warmth, privacy, and convenience - and it's close to Tanglewood. Beautifully maintained inside and out, it sits on two wooded acres with a welcoming front porch. Inside you will find a cozy retreat - a living room with cathedral ceilings, pine floors, and a working fireplace. The updated kitchen

  Marie Bourassa SIGNATURE ASSOCIATES

  18 Hill Rd, Stockbridge, MA 01262
• 

  

  /3

  $1,300,000

  • Land
  • 118 Acres
  • $11,017 per Acre

  0 Furnace Rd, Richmond, MA 01254

  Rarely will you see a beautiful, undisturbed major land parcel totaling 118 acres anywhere in Berkshire County. This parcel has 91 acres in Richmond and the remaining 27 acres in West Stockbridge. The land is bisected by Furnace brook. There are wetlands in one section. Property is currently in Chapter 61A Forest Management.

  Suzanne Crerar STONE HOUSE PROPERTIES, LLC

  0 Furnace Rd, Richmond, MA 01254
• 

  

  /35

  $699,000

  • 3 Beds
  • 3 Baths
  • 1,829 Sq Ft

  36 Glendale Rd, Stockbridge, MA 01262

  Welcome to this stunning one level living, 3 bedroom, 3 bathroom home on a serene 4 acre lot. Designed for comfort and style, it features a bright first floor living area with large picture windows and a charming fireplace. The spacious kitchen offers a skylight, breakfast nook, and access to a screened porch perfect for relaxing. Cherry Floors flow throughout (except the kitchen and baths), and

  Patricia Andrew STONE HOUSE PROPERTIES, LLC

  36 Glendale Rd, Stockbridge, MA 01262
• 

  

  /11

  $62,000

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  130 #4 Water St, Lee, MA 01238

  Conveniently located in South Lee. The friendly Allen Mobil Park is located just off the Mass Pike in the heart of the business district of Lee. No Car? No problem here, public transportation access at your front door. 2 Bedrooms, vaulted ceilings, huge kitchen, washer and dryer in bathroom. $350 monthly lot rent

  Melissa Zoe Hirsch ZOE MELISSA HIRSCH REAL ESTATE

  130 #4 Water St, Lee, MA 01238

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