Berkshire, MA Homes near St. Mary's School

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  /50

  $4,985,000

  • 13 Beds
  • 13.5 Baths
  • 9,556 Sq Ft

  2 Kemble St, Lenox, MA 01240

  The Kemble, a registered ''Great Estate'' built in 1881 is located in the heart of the thriving downtown Lenox business district. This classic Colonial Revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  2 Kemble St, Lenox, MA 01240
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  /47

  $1,600,000 Sold Mar 31, 2025

  • 3,044 Sq Ft
  • $526/SF
  • 3 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2011

  37 Fairwynds Dr, Lenox, MA 01240

  This exceptional home, nestled in a world-class resort, is truly a rare gem that you don't want to miss! Imagine entering this spectacular 3-bedroom, 4-bath retreat drenched in natural light with living spaces designed to flow effortlessly, creating a welcoming and tranquil atmosphere. The open-concept living area transitions beautifully into a gourmet kitchen, ideal for entertaining loved ones

  Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

  37 Fairwynds Dr, Lenox, MA 01240
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  /75

  Est $1,766,525 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,064 Sq Ft

  47 Fairwynds Dr, Lenox, MA 01240

  47 Fairwynds Dr, Lenox, MA 01240
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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

  $375,000 Sold Mar 27, 2025

  • 2,016 Sq Ft
  • $186/SF
  • 47 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1975

  236 Washington Mountain Rd, Lee, MA 01238

  Lindal Cedar Home, sustainable and eco-friendly home on 1.20 acres of land. Chalet style home on private setting yet conveniently located to all the Berkshires has to offer! Large Great Room with field stone fireplace, tons of natural light with back wall of glass overlooking private yard.Cozy loft overlooking open concept Great Room, eat-in kitchen. lst floor bedroom and full cedar bathroom.

  Lisa Kelley MACCARO REAL ESTATE

  236 Washington Mountain Rd, Lee, MA 01238
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  /69

  Est $704,056 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,072 Sq Ft

  93 Hubbard St, Lenox, MA 01240

  93 Hubbard St, Lenox, MA 01240
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  /36

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  20 Summer St, Lee, MA 01238

  Antique Greek Revival style home overlooking downtown Lee! Beautiful view with splendid sunrises over October Mountain. Wise investment, located within the up-and-coming downtown redevelopment district in historic Lee, Ma. ''Gateway to the Berkshires'', voted one of the top ten small towns, known for the scenery, the arts and activities. This lovely home offers wood flooring throughout, light &

  Lisa Kelley MACCARO REAL ESTATE

  20 Summer St, Lee, MA 01238
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  /17

  $225,000 Sold Mar 24, 2025

  • Land
  • 10 Acres
  • $21,635 per Acre

  • 661 Days On Market

  Unlisted Address

  Prime Stockbridge land, prime Stockbridge location, and low Stockbridge taxes. A couple of short miles to Tanglewood in Lenox and a few minute drive to the Red Lion Inn in Stockbridge. Under a mile to Stockbridge public sandy beach on the Bowl. Includes drilled well already installed, septic design and roughed-in driveway. Excellent investment location for full or part-time

  Gary Johnston STONE HOUSE PROPERTIES, LLC

  Unlisted Address
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  /37

  Est $287,782 Not Listed For Sale

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

  325 Laurel St, Lee, MA 01238

  325 Laurel St, Lee, MA 01238
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  /39

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,764 Sq Ft

  9 Bolton Dr, Lenox, MA 01240

  If you're looking for a walk-to-town location, be sure to check out this colonial nestled on a quiet dead-end street! The main level features an open kitchen/dining, living room with gas fireplace and half bath. On the upper level - three spacious bedrooms, two full baths and laundry. Bonus space is a partially finished walk-out lower level/den or family room. Two car attached oversized

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  9 Bolton Dr, Lenox, MA 01240
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  /36

  $1,550,000 Sold Mar 14, 2025

  • 2,498 Sq Ft
  • $620/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2008

  8 Bean Hill Rd, Stockbridge, MA 01262

  Constructed in 2008, this contemporary New England classic offers a perfect balance of timeless charm and modern design. With high ceilings and abundant natural light, the home features an open, gracious floor plan that flows seamlessly, creating an inviting and airy ambiance throughout.The first-floor primary suite is a private retreat, thoughtfully designed for comfort and convenience. The

  Selina Lamb BIRCH PROPERTIES

  8 Bean Hill Rd, Stockbridge, MA 01262
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  /33

  Est $843,828 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,600 Sq Ft

  75 East St, Lee, MA 01238

  75 East St, Lee, MA 01238
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  /16

  $1,800,000

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

  15 East St, Stockbridge, MA 01262

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

  Tim Damon Mercury Real Estate

  15 East St, Stockbridge, MA 01262
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  /7

  $304,000 Sold Mar 14, 2025

  • Land
  • 51 Acres
  • $5,934 per Acre

  • 539 Days On Market

  Unlisted Address

  Building parcels for sale above the charming bucolic village of Tyringham near the pinnacle of Dorman Mountain. Ten parcels comprising 51 acres are ready for development or for your own Berkshires estate bordering the state forest and hundreds of acres of Trust land. A remote-feeling location, yet nearby the Mass Pike and approximately a two-hour drive from Boston. Low taxes and fiber internet

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  Unlisted Address
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  /28

  Est $2,138,197 Not Listed For Sale

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

  15 Blossom Hill, Lenox, MA 01240

  15 Blossom Hill, Lenox, MA 01240
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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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  /7

  $346,000 Sold Mar 14, 2025

  • Land
  • 58 Acres
  • $5,966 per Acre

  • 546 Days On Market

  Unlisted Address

  Building parcels for sale above the charming bucolic village of Tyringham near the pinnacle of Dorman Mountain. Nine parcels comprising 58 acres are ready for development or for your own Berkshires estate, bordering the state forest and hundreds of acres of Trust land. A remote-feeling location, yet nearby the Mass Pike and approximately a two-hour drive from Boston. Low taxes and fiber internet

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  Unlisted Address
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  /12

  Est $430,932 Not Listed For Sale

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

  880 East St Unit 19D, Lee, MA 01238

  880 East St Unit 19D, Lee, MA 01238
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  /11

  $39,900

  • Land
  • 1.90 Acres
  • $21,000 per Acre

  289 Antelope Dr, Lee, MA 01238

  Welcome to the private Leisure Lee community. Tucked away awaits the sandy beach of Goose Pond, a dock with boat moorings and two tennis courts. Create your own dream home with this elevated wooded lot. A short drive to the Lee outlets and close proximity to Tanglewood and all cultural events the Berkshires have to offer.

  Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

  289 Antelope Dr, Lee, MA 01238
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  /34

  $360,000 Sold Mar 03, 2025

  • 1,918 Sq Ft
  • $188/SF
  • 32 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  7 Crystal St, Lenox, MA 01240

  This charming, recently renovated two-family home offers modern updates and a convenient location in the heart of Lenox Dale, situated directly on the public bus line. Each unit features two bedrooms, updated kitchens, refreshed bathrooms, and new flooring throughout, complemented by stylish new siding. The front unit boasts a well-thought-out layout with a first-floor bedroom, a full

  Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  7 Crystal St, Lenox, MA 01240
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  /40

  Est $441,942 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,806 Sq Ft

  55 Mountain View Terrace, Lee, MA 01238

  55 Mountain View 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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  /12

  $350,000 Sold Mar 03, 2025

  • 872 Sq Ft
  • $401/SF
  • 25 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1850

  57 Main St Unit 4, Stockbridge, MA 01262

  Wonderful SECOND-FLOOR unit at The Knoll! Located on Main Street, Stockbridge. The Knoll Condominiums have always been desired for the convenient walk to town location and lovely park-like setting. Light and bright with lots of windows. Comfortable living/dining area, charming galley kitchen and spacious bedrooms. Convenient laundry room and private storage area in the building. Tennis courts

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  57 Main St Unit 4, Stockbridge, MA 01262
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  /21

  Est $354,466 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,460 Sq Ft

  96 Columbia St, Lee, MA 01238

  96 Columbia St, Lee, MA 01238
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  /3

  $180,000

  • Land
  • 11 Acres
  • $17,127 per Acre

  0 Goose Pond Rd, Tyringham, MA 01264

  Nestled in the picturesque Berkshires, this stunning 10-acre parcel in Tyringham, MA, offers an unparalleled opportunity to create your dream retreat. Located just moments from Goose Pond, this property boasts a perfect blend of privacy, natural beauty, and convenience to nearby cultural and outdoor attractions.

  Samantha Homeyer BIRCH PROPERTIES

  0 Goose Pond Rd, Tyringham, MA 01264
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  /29

  $285,000 Sold Feb 28, 2025

  • 1,665 Sq Ft
  • $171/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1885

  46 Fuller St, Lee, MA 01238

  Small town charm New England Farmhouse with modern amenities! Located in the town of Lee, ''Gateway to the Berkshires''. Walk down to the hometown parades and enjoy the fireworks from your front porch or stroll the downtown to your favorite shops and restaurants! Within walking distance to schools and playgrounds. This antique farmhouse offers a large front parlor w/bay window, formal dining room

  Lisa Kelley MACCARO REAL ESTATE

  46 Fuller St, Lee, MA 01238
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  /28

  Est $370,955 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  70 Summer St, Lee, MA 01238

  70 Summer 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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  /23

  $175,000 Sold Feb 28, 2025

  • 749 Sq Ft
  • $234/SF
  • 79 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1800

  40 Interlaken Rd, Stockbridge, MA 01262

  Welcome to this cozy bungalow, ideally located just minutes from Tanglewood. This property has endless potential to create a delightful Airbnb or the perfect starter home. Featuring 2 bedrooms, 1 bathroom, and a three- season sunporch to enjoy your morning coffee or a good book. Don't miss out on this great opportunity to put your finishing touches on this adorable home- schedule your viewing

  Shelley Cozzaglio LAMACCHIA REALTY, INC

  40 Interlaken Rd, Stockbridge, MA 01262
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  /29

  Est $754,143 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  82 Old Stockbridge Rd, Lenox, MA 01240

  82 Old Stockbridge Rd, Lenox, MA 01240
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  /7

  $125,000

  • Land
  • 4.70 Acres
  • $26,596 per Acre

  Lot # 1 Webster Rd, Tyringham, MA 01264

  Peace and tranquility reign on this beautiful country road. Two wooded, flat lots have been combined into one. See brand new survey with wetland delineation. 2022 perc tests in hand. Electric runs to #49, the abutter. Additional acreage available.

  Tony Segalla LANCE VERMEULEN RE, INC

  Lot # 1 Webster Rd, Tyringham, MA 01264
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  /37

  $600,000 Sold Feb 21, 2025

  • 1,528 Sq Ft
  • $393/SF
  • 42 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1910

  501 Walker St, Lenox, MA 01242

  Welcome to this stunning New England farmhouse, where classic charm meets modern convenience. Set on a beautifully landscaped property, this home boasts stonewalls, cobblestone-edged walk & driveways, and mature gardens filled with vibrant flowers and shrubs. Every detail of the exterior invites you to enjoy the serene surroundings.Step inside to discover a thoughtfully designed layout perfect

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  501 Walker St, Lenox, MA 01242
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  /15

  Est $453,717 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 2,743 Sq Ft

  10 Crystal St, Lenox Dale, MA 01242

  10 Crystal St, Lenox Dale, MA 01242
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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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  /33

  $557,500 Sold Feb 21, 2025

  • 3,340 Sq Ft
  • $167/SF
  • 122 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1920

  55 Cliffwood St, Lee, MA 01238

  Quiet dead end street a convenient short walk to the center of Lee as well as Ferncliff park with walking trails at the end of Cliffwood. House has been lovingly cared for with numerous upgrades. Successful B&B run by the owners in residence. Large fenced yard. Owned solar panels on roof. Wainscoting and many original period details. Generous sized rooms with lots of light.

  Carrie Swift Heck COMPASS MASSACHUSETTS , LLC GB

  55 Cliffwood St, Lee, MA 01238
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  /31

  Est $363,255 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,674 Sq Ft

  189 Housatonic St, Lee, MA 01238

  189 Housatonic St, Lee, MA 01238
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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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  /39

  $540,000 Sold Feb 21, 2025

  • 2,208 Sq Ft
  • $245/SF
  • 198 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1965

  180 Beaver Dam Rd, Lee, MA 01238

  The Gortamullen House-One of a kind, California Redwood home, built for Ambassador Walter Anneberg's family. Set at 1,700 ft. elevation, it provides peace and tranquility among 16,500-acre State Forest, the largest in Massachusetts Wildlife and pond life abound. Restore your soul in this calm, isolated nature haven on one and a half acres of beautiful preserve with a wildlife viewing deck in the

  Lisa Kelley MACCARO REAL ESTATE

  180 Beaver Dam Rd, Lee, MA 01238
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  /39

  Est $705,716 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,255 Sq Ft

  190 Hubbard St, Lenox, MA 01240

  190 Hubbard St, Lenox, MA 01240
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  /9

  $589,000

  • Land
  • 21 Acres
  • $28,222 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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