Homes for Sale near Berkshire Waldorf High School

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  /20

  $3,995,000

  • 15 Beds
  • 15 Baths
  • 11,945 Sq Ft

  615 Laurel St, Lee, MA 01238

  The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

  Pamela J Long EAST COAST INN BROKERS

  615 Laurel St, Lee, MA 01238
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  /56

  $979,000

  • 5 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  850 Summer St Unit M14, Lee, MA 01238

  Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

  Katie Williams STONE HOUSE PROPERTIES, LLC

  850 Summer St Unit M14, Lee, MA 01238
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  /42

  $465,000

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  42 East St, Stockbridge, MA 01262

  Set on 6.4 scenic acres, this classic New England farmhouse captures the timeless spirit of Stockbridge, a town beloved for its rich history and cultural legacy. This 2-bed 2-bath home offers authentic charm, featuring beautiful hardwood floors, a spacious kitchen, family room + 1st floor full bath, and a welcoming front porch that evokes a slower, simpler time. Thoughtful updates include a newer

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  42 East St, Stockbridge, MA 01262
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  /68

  $1,299,000

  • 4 Beds
  • 5 Baths
  • 6,500 Sq Ft

  160 High St, Lee, MA 01238

  Once the First Methodist Episcopal Church, built in 1898, this incredible 6,500 sq ft property has been thoughtfully reimagined as a two-family residence and offers unparalleled potential for an artist's dream live/work space. Located just a short walk from downtown on a 3/4 lot abutting an 18 acre nature reserve, this building is ideally positioned to offer both the tranquility of the Berkshires

  Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

  160 High St, Lee, MA 01238
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  /49

  $635,000

  • 3 Beds
  • 3 Baths
  • 2,476 Sq Ft

  4 Main St, West Stockbridge, MA 01266

  Don't miss this one-of-a-kind opportunity to own a commercially zoned, mixed-use property offering exceptional live/work potential in a prime in-town location along the Williams River. This uniquely designed 3-bedroom, 3-bath home includes a versatile accessory apartment, making it ideal for those seeking a combination of residential comfort and business flexibility. Enjoy water views from two

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  4 Main St, West Stockbridge, MA 01266
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  /78

  $1,475,000

  • 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
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  /68

  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 3,354 Sq Ft

  176 W Center Rd, West Stockbridge, MA 01266

  The lovely approach to this gorgeous estate property ensures serenity, privacy, and the beauty of living in the country and includes a 3 bed 2 1/2 bath main house and a gorgeous architect designed guest house. Offering 2 ensuite bedrooms with balconies, dramatic exposed beams, vaulted ceilings, and gas fireplace the guest house is an extraordinary place to host family and friends both

  Lori Rose STONE HOUSE PROPERTIES, LLC

  176 W Center Rd, West Stockbridge, MA 01266
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  /19

  $775,000

  • 8 Beds
  • 4 Baths
  • 3,192 Sq Ft

  35 Main St, West Stockbridge, MA 01266

  Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

  Matt Carlino MACCARO REAL ESTATE

  35 Main St, West Stockbridge, MA 01266
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  /19

  $949,000

  • 11 Beds
  • 6 Baths
  • 4,863 Sq Ft

  Unlisted Address

  Fully Rented In Town 5-Family Investment Opportunity. Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures.

  Matt Carlino MACCARO REAL ESTATE

  Unlisted Address
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  /24

  $299,900

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

  2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

  Come experience this charming condo in the beautiful Heron Pond Community in Stockbridge. Thoughtful use of space with large, private front patio facing expansive manicured lawns and gardens. Enjoy 1-level living, (1-bed,1-bath with separate dining room) fully applianced kitchen with pantry and instant boiling water faucet. Washer and Dryer included. Zoned smart heating thermostats.

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
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  /43

  $699,000

  • 3 Beds
  • 2.5 Baths
  • 2,135 Sq Ft

  770 Summer St Unit 3A, Lee, MA 01238

  Welcome home to Lakeside condominiums at Foxhollow! An established condo community perfectly positioned between Lee/Lenox/Stockbridge close to all area attractions! Desirable ground level unit features easy living. Enjoy morning coffee on your spacious deck taking in open rolling lawns and mountain views. Open living/dining with fireplace, updated kitchen w quartz counters, stainless

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  770 Summer St Unit 3A, Lee, MA 01238
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  /46

  $649,900

  • 9 Beds
  • 4 Baths
  • 4,152 Sq Ft

  1057 Main St, Great Barrington, MA 01236

  Great investment opportunity! A very rare property offered for the first time outside the family in over 90 years! This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior and updated units are just a few of the benefits of this investment. In the bustling village of

  Ryan Lane GILCREST PROPERTIES

  1057 Main St, Great Barrington, MA 01236
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  /36

  $729,000

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft

  204 Cottage St, Great Barrington, MA 01236

  TWO HOMES FOR FAMILY LIVING OR INVESTMENT! So much to love about this property. The Main House exudes charm & warmth, and across the way a 2004 Cottage was added, creating the perfect income producer, family dwelling or Guest house. The Main house is tastefully updated preserving the cozy esthetic. 2 Bedroom, 2 Bath, Den, Great Room, and Country Kitchen. The Cottage, w/open plan living has

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  204 Cottage St, Great Barrington, MA 01236
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  /48

  $620,000

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  770 Summer St Unit 5D, Lee, MA 01238

  Welcome to 5D Lakeside at Foxhollow - a beautifully updated 3-bedroom, 3-full-bath condo offering the perfect blend of modern comfort and classic Berkshire charm.Enjoy seasonal views of sparkling Laurel Lake from your enclosed summer porch, the ideal spot for morning coffee or evening gatherings. Inside, you'll find a thoughtfully updated kitchen and baths, a cozy wood-burning fireplace, and

  Paula McLean PAULA MCLEAN REALTORS INC.

  770 Summer St Unit 5D, Lee, MA 01238
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  /43

  $595,000

  • 2 Beds
  • 1 Bath
  • 1,688 Sq Ft

  3 & 5 Swamp Rd, West Stockbridge, MA 01266

  Historic Greek Revival & Grange Hall, a unique residence for the next owner. In-town privacy overlooking stunning Shaker Mill Pond. Enjoy private backyard, patio with water views, glorious sunsets, canoeing & even ice skating in the winter. Within walking distance to restaurants & markets. The house, c1840, has two bedrooms, formal dining room, eat-in country kitchen, living room with fireplace &

  Scott Sawyer STONE HOUSE PROPERTIES, LLC

  3 & 5 Swamp Rd, West Stockbridge, MA 01266
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  /45

  $369,000

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

  205 High St, Lee, MA 01238

  Enjoy downtown living in this 4 Bedroom 2 Bath New England farmhouse. Built in the early20th century, this home has a diverse use of residential, commercial or mixed use on a residential street. The kitchen has been updated with plenty of cabinet space. A cozy living room fireplace and a enclosed porch with numerous windows that welcome fresh summertime breezes and a patio for summer leisure

  Anthony Caropreso MACCARO REAL ESTATE

  205 High St, Lee, MA 01238
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  /53

  $849,000

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

  328 Park St, Great Barrington, MA 01230

  Two beautifully renovated duplexes within walking distance to the charming village of Housatonic. Enjoy scenic views of the Housatonic River from each unit. All utilities are separate, making this an ideal investment. All units are fully rented.

  Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  328 Park St, Great Barrington, MA 01230
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  /51

  $2,250,000

  • 4 Beds
  • 4 Baths
  • 2,738 Sq Ft

  8 Yale Hill Rd, Stockbridge, MA 01262

  A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  8 Yale Hill Rd, Stockbridge, MA 01262
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  /56

  $1,395,000

  • 4 Beds
  • 2 Baths
  • 2,058 Sq Ft

  45 Swamp, West Stockbridge, MA 01266

  1950s retro home, rich with family history, situated on 30+ acres of land & offering expansive westerly views & gentle sloping fields. Pathways lead to Shaker Mill Pond & Cone Brook which run the entire length of the property. Interior features include 2 BRs, office & full bath on the main level, 2 BRs & full bath on the second floor, a quaint kitchen, & living room. Additionally, a fully heated

  Paige Paluch LANCE VERMEULEN RE, INC

  45 Swamp, West Stockbridge, MA 01266
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  /24

  $339,900

  • 3 Beds
  • 1.5 Baths
  • 1,140 Sq Ft

  90 Maple St, Lee, MA 01238

  Come and see this quaint, cape style home situated close to downtown Lee. This home has been completely renovated. A spacious kitchen includes new cabinets, stone countertops and appliances. The living room and dining room are flooded with natural light and are the perfect space for entertaining. Also located on the first floor are a bedroom and a half bath. The primary bedroom and full

  Melinda Boos KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  90 Maple St, Lee, MA 01238
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  /3

  $975,000

  • Land
  • 132 Acres
  • $7,404 per Acre

  0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

  This is a generous hillside parcel with a perc and potential views to the west. It is just over the hill from Stockbridge Bowl and Tanglewood, in an area of fine homes.

  Jim Stark L. J. STARK AND CO.

  0 Lenox Rd Unit 246122, West Stockbridge, MA 01266
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  /17

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  lot 1 N Beckett, Lee, MA 01238

  Single Family modular home on 3 Acres of land, in a serene and beautiful setting. There are two Modular homes to pick from, the New Haven and the Rolling Brook. Nestled in a peaceful, wooded landscape, this lot offers a perfect blend of privacy and natural beauty while being conveniently located. Minutes to walking trails, Basin Pond, and Finery Pond are at your back yard. Lenox and Stockbridge's

  The Mary Scimemi Team Leading Edge Real Estate

  lot 1 N Beckett, Lee, MA 01238
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  /30

  $655,000

  • 5 Beds
  • 3 Baths
  • 3,035 Sq Ft

  133 Front St, Great Barrington, MA 01236

  Unique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has its own kitchen and bath ideal

  Judi Panzano HOUSATONIC REAL ESTATE

  133 Front St, Great Barrington, MA 01236
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  /13

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  528 Walker St, Lenox Dale, MA 01242

  Large well maintained Colonial on a half acre lot. Large open kitchen with lots of cabinet space. Sliders off kitchen leading to back deck. Bright and sunny living space with a bonus den or office. 3 full sized bedrooms. 2 full baths. Laundry hookups on 2nd floor for convenience. Seller willing to buy down the mortgage rate on this home. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

  Tyler Scaglione Cameron Real Estate Group

  528 Walker St, Lenox Dale, MA 01242
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  /51

  $549,000

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft

  190 Willow St, Lee, MA 01238

  Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare

  Kim Bergland RED HORSE REAL ESTATE, LLC

  190 Willow St, Lee, MA 01238
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  /35

  $520,000

  • 3 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  220 N Plain Rd, Great Barrington, MA 01230

  An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could

  Martin Albert COMPASS MASSACHUSETTS , LLC GB

  220 N Plain Rd, Great Barrington, MA 01230
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  /45

  $1,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,395 Sq Ft

  62 Stockbridge Terrace, Lee, MA 01238

  Updated and spacious condo just a short distance from Main Street Stockbridge, and all Berkshire attractions! Premier Unit at Stockbridge Terrace! Enjoy peaceful living on a quiet cul-de-sac with limited number ofunits. The main level living setup is perfect, featuring a large primary bedroom with an en-suite bath and walk-in closet, an open-concept kitchen that has been recently updated complete

  Lauren Molk ELYSE HARNEY REAL ESTATE

  62 Stockbridge Terrace, Lee, MA 01238
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  /37

  $729,000

  • 5 Beds
  • 5 Baths
  • 2,698 Sq Ft

  395 Laurel St, Lee, MA 01238

  Incredible location, close to everything Berkshires. One of the most iconic properties in South County located just north of the new housing development in downtown Lee. This property has a total of 3 residential units and 2 commercial units. Unit A ($1,600/mo.) is a two bedroom townhouse style apartment. Unit B ($1,300/mo.) is a two bedroom apartment. Unit C ($950/mo) is a one bedroom apartment.

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  395 Laurel St, Lee, MA 01238
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  /10

  $199,000

  • Land
  • 1.31 Acres
  • $151,907 per Acre

  245 Spring St, Lee, MA 01238

  One of two beautiful building lots available on Spring Street, Lee. Lee has been voted one of the top 10 northeastern small towns in New England. Idyllic setting on quiet country road yet 2 miles from Stockbridge, 3 miles to Tanglewood, and 5 minutes to Laurel Lake! Build your dream home and enjoy all the Berkshires has to offer! Beautiful place to live, ample outdoor recreation, farm to table

  Lisa Kelley MACCARO REAL ESTATE

  245 Spring St, Lee, MA 01238
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  /40

  $1,995,000

  • 6 Beds
  • 8 Baths
  • 10,507 Sq Ft

  14 Pine St, Stockbridge, MA 01262

  Prime Owner-User/Investment Property in the heart of historic Stockbridge. Currently an Educational Facility with Retail, Office and Residential Units. Can be combined for Offices, Medical, Educational, Gallery, Apartments/Condos, or any use that demands a location in one of the most well known and loved towns in America. Fully upgraded mechanicals, large Parking facilities and Handicapped

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  14 Pine St, Stockbridge, MA 01262
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  /8

  $199,000

  • Land
  • 1.31 Acres
  • $152,025 per Acre

  235 Spring St, Lee, MA 01238

  Beautiful building lot available on Spring Street, Lee. Voted one of the top 10 small northeastern towns in New England! Idyllic setting on quiet country road yet 2 miles from Stockbridge, 3 miles to Tanglewood, and 5 minutes to Laurel Lake! Build your dream home and enjoy all the Berkshires has to offer! Beautiful place to live, ample outdoor recreation, farm to table food and world class

  Lisa Kelley MACCARO REAL ESTATE

  235 Spring St, Lee, MA 01238
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  /27

  $359,900

  • 3 Beds
  • 1 Bath
  • 1,428 Sq Ft

  6 Margerie St, Lee, MA 01238

  Welcome to this inviting and well-built 3-bedroom Brick Cape nestled in the heart of the picturesque town of Lee, MA. Located on a convenient desirable street, this home offers a perfect blend of classic charm and modern convenience. Step inside to discover a spacious living room with fireplace, potential expansion of living area in the lower level full basement with laundry and a formal dining

  Paula McLean PAULA MCLEAN REALTORS INC.

  6 Margerie St, Lee, MA 01238
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  /50

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,647 Sq Ft

  2 Wallace Rd Unit 2E, Stockbridge, MA 01262

  Welcome to Heron Pond Condominiums in charming Stockbridge, where comfort meets convenience in a tranquil setting. This beautiful condominium offers an ideal combination of spacious living and cozy charm, featuring 2 or 3 bedrooms and 2 full baths. The screened porch is ideal to relax and enjoy nature without the bugs, a serene space to unwind, whether you're enjoying morning coffee or evening

  Paula McLean PAULA MCLEAN REALTORS INC.

  2 Wallace Rd Unit 2E, Stockbridge, MA 01262
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  /25

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  54 Division St, Great Barrington, MA 01230

  This beautifully renovated 1,792 sq. ft. home offers a unique opportunity for buyers seeking modern updates with the chance to add personal finishing touches. Major renovations including:*New Electrical and plumbing*New Windows*Fresh interior paint*kitchen with new cabinets*Fully renovated first-floor bathroom*New 3-bedroom septic system*Primary bathroom with new toilet and sink* 3 Mini splits

  John Segalla HOUSATONIC REAL ESTATE

  54 Division St, Great Barrington, MA 01230
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  /51

  $1,125,000

  • 9 Beds
  • 9 Baths
  • 5,690 Sq Ft

  465 Chapel St, Lee, MA 01238

  Prime Investment Opportunity - Fully Occupied 9-Unit Victorian on 2.5 Acres!This exceptional income-producing property features a beautifully maintained Victorian-style building with nine rental units--a mix of studios, four 1-bedroom units, and one spacious 2-bedroom apartment with open-concept kitchens. Situated on 2.5 acres, the property offers ample off-street parking for 15 cars, a

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  465 Chapel St, Lee, MA 01238
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  /26

  $239,000

  • Land
  • 8 Acres
  • $30,508 per Acre

  13 Rattlesnake Mountain Rd, Stockbridge, MA 01262

  PRIME BERKSHIRE LAND - FEEL 'AWAY FROM IT ALL' YET YOU ARE MOMENTS FROM THE BEST OF THE BERKSHIRES. $158,000+ UNDER ASSESSED VALUESet on a serene & forested country road, this location makes the perfect retreat - yet you are in the heart of the Berkshires just minutes to Stockbridge & Lenox, Tanglewood, The Bowl, The Mount, Kripalu, Great Barrington, the Pike, shopping & more. The single home

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
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  /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
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  /16

  $295,000

  • Land
  • 25 Acres
  • $11,697 per Acre

  0 Glendale Rd Unit 245211, Stockbridge, MA 01262

  Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. Many possibilities - build on the north lot and keep the south lot for extra

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  0 Glendale Rd Unit 245211, Stockbridge, MA 01262
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  /52

  $1,675,000

  • 12 Beds
  • 7 Baths
  • 8,881 Sq Ft

  29 Main St, West Stockbridge, MA 01266

  Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

  Suzann Ward HOUSATONIC REAL ESTATE

  29 Main St, West Stockbridge, MA 01266
• 

  

  /60

  $1,350,000

  • 4 Beds
  • 4.5 Baths
  • 3,395 Sq Ft

  82 Stockbridge Terrace, Lee, MA 01238

  Prepare to be wowed when you visit this luxury condo at Stockbridge Terrace! The details, custom features and craftmanship are second-to-none! Seeking one-level living? Literally just bring your suitcase as furnishings can be available in this well-appointed one-owner home. Entertain in style with open floor plan. The living/great room's centerpiece is the stone fireplace, oversized windows

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  82 Stockbridge Terrace, Lee, MA 01238

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