Berkshire, MA Homes near St. Mary's School

• 

  

  

  /46

  $789,000

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

  19 Hawthorne Rd Unit GH 4, Stockbridge, MA 01262

  This White Pines Garden Unit is a must see if you are considering condominium living in this sought after community. Open living Great Room/kitchen/dining with double volume glass to take in the view, fireplace & guest bath on main level. The lower level greets you with a tiled floor sunroom w/direct access to the spacious decking w/private courtyard outdoor space. The primary ensuite, guest

  Mary Jane White COHEN & WHITE ASSOCIATES

  19 Hawthorne Rd Unit GH 4, Stockbridge, MA 01262
• 

  

  

  /14

  $396,200 Sold Jul 21, 2025

  • 938 Sq Ft
  • $422/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1968

  5 Morgan Manor Unit 9, Lenox, MA 01240

  This unit is the ''trifecta'' of Morgan Manor: first floor, 2 BR and with garage! Plus it's been fully renovated and has a gorgeous eat in cherry/granite/stainless kitchen, updated bath and beautiful hardwood floors throughout. Maintenance fees of $716/month include your heat, hot water, basic cable/internet and all exterior maintenance....furnishings available if you want to just bring your

  Mary Jo Piretti PIRETTI REAL ESTATE

  5 Morgan Manor Unit 9, Lenox, MA 01240
• 

  

  

  /34

  Est $587,299 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,978 Sq Ft

  70 Franklin St, Lee, MA 01238

  70 Franklin St, Lee, MA 01238
• 

  

  

  /43

  $725,000

  • 4 Beds
  • 3 Baths
  • 2,610 Sq Ft

  770 Summer St Unit 15A, Lee, MA 01238

  Enjoy unobstructed views of Laurel Lake from this first-floor unit at Lakeside at Foxhollow. This spacious 4-bedroom, 3-bath condo features two fully finished levels, two outdoor decks (including one waterfront), and two primary suites--one on each floor--plus resort-style amenities. The perfect opportunity to create your ideal lakeside retreat.The professionally managed community offers an

  Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

  770 Summer St Unit 15A, Lee, MA 01238
• 

  

  

  /37

  $400,000 Sold Jul 16, 2025

  • 1,152 Sq Ft
  • $347/SF
  • 431 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  15 Elk Dr, Lee, MA 01238

  Welcome to Leisure Lee -- where natural beauty meets modern comfort in the heart of the Berkshires.Nestled in a serene setting just moments from the crystal-clear waters of Goose Pond, this contemporary ranch-style home offers the perfect blend of relaxation, recreation, and year-round living. Leisure Lee is a private community treasured for its peaceful ambiance, exclusive lake access, and

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  15 Elk Dr, Lee, MA 01238
• 

  

  /41

  Est $595,110 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,861 Sq Ft

  92 Hubbard St, Lenox, MA 01240

  92 Hubbard St, Lenox, MA 01240
• 

  

  /45

  $1,499,000

  • 4 Beds
  • 4.5 Baths
  • 3,190 Sq Ft

  121 E Dugway Rd, Lenox, MA 01240

  Stunning Georgian Colonial style home on a lovely 4A private lot is ready for its new owners! In pristine condition, this 4 BR, 4.5 baths home offers hardwood floors throughout, first floor Primary Suite, open great room concept with cherry cabinetry in kitchen and granite counters, gas fireplace in the great room, formal dining or music room and first floor study with full bath. The second

  Mary Jo Piretti PIRETTI REAL ESTATE

  121 E Dugway Rd, Lenox, MA 01240
• 

  

  /49

  $487,500 Sold Jul 15, 2025

  • 3,210 Sq Ft
  • $152/SF
  • 17 Days On Market

  • 6 Beds
  • 2.5 Baths
  • Built 1901

  9 High St, Lenox, MA 01240

  Nestled in one of the most desirable towns in the Berkshires, this charming multi-family home presents a rare and exciting opportunity for investors, contractors, or visionary homeowners. Set on a spacious and desirable lot, this as-is property is ready to be reimagined--offering the perfect canvas for renovation, expansion, or transformation. The home features two side-by-side living units, each

  Diane Thorson WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  9 High St, Lenox, MA 01240
• 

  

  /22

  Est $341,993 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft

  395 Fairview St, Lee, MA 01238

  395 Fairview St, Lee, MA 01238
• 

  

  /16

  $939,000

  • 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
• 

  

  /11

  $1,370,000 Sold Jul 15, 2025

  • 1,109 Sq Ft
  • $1235/SF
  • 34 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 2017

  165 Kemble St Unit 2, Lenox, MA 01240

  Discover luxury living at Canyon Ranch with this 1-bedroom condo, boasting a chef's kitchen with marble countertops, and an expansive great room with a marble gas fireplace. Savor your morning coffee on the serene private balcony. The primary suite is a retreat with a spa-like marble bathroom, ample walk-in closet, and a cozy fireplace. Exclusive resort membership provides access to unparalleled

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  165 Kemble St Unit 2, Lenox, MA 01240
• 

  

  /30

  Est $402,034 Not Listed For Sale

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

  60 Margerie St, Lee, MA 01238

  60 Margerie St, Lee, MA 01238
• 

  

  /68

  $1,400,000

  • 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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  /28

  $498,500 Sold Jul 10, 2025

  • 1,470 Sq Ft
  • $339/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  120 Via Maria, Lee, MA 01238

  Perched high atop the desirable Via neighborhoods of Lee, this 1997 single-level home is simply waiting for you to arrive and make it your own. The house sits on a corner lot and expansive yard, situated at the end of a quiet loop road, with beautiful views of October Mountain in the distance. The interior space is open, airy, and bright, with a large kitchen and dining area opening to back deck,

  Stephen Daoust STONE HOUSE PROPERTIES, LLC

  120 Via Maria, Lee, MA 01238
• 

  

  /41

  Est $619,899 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,868 Sq Ft

  15 Via Maria, Lee, MA 01238

  15 Via Maria, Lee, MA 01238
• 

  

  /59

  $875,000

  • 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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  /40

  $660,000 Sold Jul 10, 2025

  • 1,853 Sq Ft
  • $356/SF
  • 133 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262

  Some of the best views the Berkshires have to offer. One of the ''Great Estates'' conversions, Winden Hill condos are in Stockbridge, but within 1.5 miles of downtown Lenox and a short drive to Tanglewood. Located in the Smith building - this unit features 2 bedrooms each with private bath. Easy entertaining in the great room with fireplace and vaulted ceiling. French door leads to the

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262
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  /33

  Est $711,308 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,804 Sq Ft

  770 Summer St Unit 2C, Lee, MA 01238

  770 Summer St Unit 2C, Lee, MA 01238
• 

  

  /48

  $640,000

  • 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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  /26

  $550,000 Sold Jul 09, 2025

  • 597 Sq Ft
  • $921/SF
  • 6 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1900

  170 Main St, Lenox, MA 01240

  The most charming ''tiny house''....the one you drive by all the time and it makes you smile! Open kitchen/dining/living with a separate bedroom and full bath. Beautiful hardwood floors, tongue & groove on the walls, charming windows and a snazzy blue door complete the picture. Full basement plus two outbuildings with lots of potential. Mini split for heat and A/C or supplement with the

  Mary Jo Piretti PIRETTI REAL ESTATE

  170 Main St, Lenox, MA 01240
• 

  

  /26

  Est $384,509 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  135 Church St, Lee, MA 01238

  135 Church St, Lee, MA 01238
• 

  

  /38

  $895,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,194 Sq Ft

  33 Interlaken Rd, Stockbridge, MA 01262

  Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

  Lori Rose STONE HOUSE PROPERTIES, LLC

  33 Interlaken Rd, Stockbridge, MA 01262
• 

  

  /13

  $105,000 Sold Jul 08, 2025

  • Land
  • 0.78 Acre
  • $134,615 per Acre

  • 210 Days On Market

  0 Plunkett St, Lenox, MA 01240

  Lenox - Partially wooded corner lot at the junction of Plunkett and Laurel Lake Road. Much of the lot has been mowed and maintained over the years with an established lawn. Town water and natural gas on the street. Close to Laurel Lake, Shakespeare, the Mount and High Lawn Farm and minutes to Lenox village.

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  0 Plunkett St, Lenox, MA 01240
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  /32

  Est $650,703 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  11 Stonebridge Way, Lee, MA 01238

  11 Stonebridge Way, Lee, MA 01238
• 

  

  /28

  $799,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,773 Sq Ft

  11 Prospect Hill Rd Unit 1, Stockbridge, MA 01262

  This 3 Bedroom, 2 Bath unit on the historic grounds of Oronoque Estate checks off all the boxes. Only 14 units in complex, this Villa offers one floor living, attached garage, high ceilings, recently renovated natural cherry custom cabinetry, walk in shower in primary bath, low Stockbridge taxes, propane heat, central air conditioning, wood burning fireplace. Two guest bedrooms, a screened in

  Susan Baum BERKSHIRE HOMES AND CONDOS

  11 Prospect Hill Rd Unit 1, Stockbridge, MA 01262
• 

  

  /34

  $885,000 Sold Jun 30, 2025

  • 2,189 Sq Ft
  • $404/SF
  • 17 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1996

  3 Willard Hill Rd, Stockbridge, MA 01262

  LIGHT-FILLED CONTEMPORARY CAPE on a premier road in the historic Interlaken section of Stockbridge. The open-concept first floor includes a living area with a wood-burning fireplace, dining area with a glass door leading to a large deck, and a recently remodeled kitchen. A half bath and a primary bedroom suite with a full bath complete the first floor. Upstairs, is a second primary suite with a

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  3 Willard Hill Rd, Stockbridge, MA 01262
• 

  

  /9

  Est $290,633 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  786 East St, Lee, MA 01238

  786 East St, Lee, MA 01238
• 

  

  /53

  $780,000 Pending

  • 4 Beds
  • 4 Baths
  • 2,688 Sq Ft

  85 E Main St, Stockbridge, MA 01262

  This meticulously renovated antique cottage is nestled in a picturesque, private setting along the banks of Kampoosa Brook in the sought-after area of Stockbridge. With thoughtful attention to detail throughout, this charming home beautifully blends historic character with modern conveniences, making it a delightful surprise for contemporary living.Inside, you'll find several cozy spots to relax

  Susan Laidlaw COMPASS MASSACHUSETTS , LLC GB

  85 E Main St, Stockbridge, MA 01262
• 

  

  /34

  $1,392,500 Sold Jun 25, 2025

  • 4,800 Sq Ft
  • $290/SF
  • 236 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 1989

  125 Old Stockbridge Rd, Lenox, MA 01240

  A grand two-story foyer with a beautifully crafted staircase welcomes your entrance to this stately home. The spacious rooms are bathed in natural light. Wonderful details include two fireplaces, French doors, butler's pantry, back staircase, beautiful wood floors. Large eat-in kitchen and formal dining room. Gracious back porch off the family room looks out to the lovely meadow and woods.

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  125 Old Stockbridge Rd, Lenox, MA 01240
• 

  

  /33

  Est $705,429 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,407 Sq Ft

  55 Sherwood Dr, Lenox, MA 01240

  55 Sherwood Dr, Lenox, MA 01240
• 

  

  /41

  $199,900

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

  12 Crystal St, Lenox Dale, MA 01242

  Great investment property! Opportunity to renovate this duplex and make it your own! This is a 5 bed, 2 bath duplex (3 bed, 1 bath one unit and 2 bed, 1 bath second unit). Being sold as is. This will sell fast. Buyer responsible to do your own due diligence.

  Derek Greene The Greene Realty Group

  12 Crystal St, Lenox Dale, MA 01242
• 

  

  /39

  $615,250 Sold Jun 25, 2025

  • 1,600 Sq Ft
  • $385/SF
  • 28 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1963

  9 Sullivan Ln, Lenox, MA 01240

  Charming move-in-ready 4-bedroom, 2-bath home, thoughtfully renovated in 2010. This home combines modern updates with comfort and convenience. The full renovation in 2010 included a new septic system, Buderus boiler, all new windows, roof & Hardie Plank siding and an upstairs expansion including a shed dormer, 3 bedrooms, and a full bath. This home has been continually updated and maintained over

  Erin Candee LANCE VERMEULEN RE, INC., LENOX

  9 Sullivan Ln, Lenox, MA 01240
• 

  

  /37

  Est $678,297 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  15 Sargent Brook Rd, Lenox, MA 01240

  15 Sargent Brook Rd, Lenox, MA 01240
• 

  

  /7

  $365,000

  • 5 Beds
  • 1 Bath
  • 2,490 Sq Ft

  15 Golden Hill Rd, Lee, MA 01238

  Spacious colonial home with tremendous potential for restoration or move-in / flip. Built in the early 1900s, this 5-bedroom gem stands proudly atop Golden Hill Rd. The home is ready for some TLC to bring it back to its full glory. A spacious five-bedroom house includes extra rooms for office or leisure, including a 3-season patio, private backyard and terrific two-level barn.

  John Segalla HOUSATONIC REAL ESTATE

  15 Golden Hill Rd, Lee, MA 01238
• 

  

  /11

  $126,000 Sold Jun 24, 2025

  • 741 Sq Ft
  • $170/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1923

  100 Canal St, Lee, MA 01238

  Discover comfort and convenience in this 3 bedroom, 1 & 1/2 bath home located just minutes from the heart of the town. Perfectly sized for anyone seeking a manageable space without sacrificing style or functionality!

  Janice Braim CARRIAGE HOUSE REAL ESTATE

  100 Canal St, Lee, MA 01238
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  /30

  Est $335,935 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  491 Chapel St, Lee, MA 01238

  491 Chapel St, Lee, MA 01238
• 

  

  /29

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 1,538 Sq Ft

  208 Main St, Lee, MA 01238

  Prime Downtown Lee Investment Opportunity Located on a highly visible corner lot in the heart of downtown Lee, this versatile three-unit building offers a blend of residential and commercial income potential. The property includes two residential units--currently operated as successful short-term rentals--and one commercial space currently leased to a massage therapist. The first-floor efficiency

  Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  208 Main St, Lee, MA 01238
• 

  

  /12

  $371,000 Sold Jun 18, 2025

  • 837 Sq Ft
  • $443/SF
  • 57 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1850

  57 Main St Unit 10, Stockbridge, MA 01262

  Beautiful first floor condo that has been rehabbed. This beautiful Knoll Condominium is walk to town in a beautiful lovely setting. Lots of natural light in this unit and it so charming , Laundry room and storage area in the building, Perfect location if you like to walk to the Red Lion Inn and downtown. Close to all the Berkshire attractions. No Pets

  Kathleen Hopkins CARRIAGE HOUSE REAL ESTATE

  57 Main St Unit 10, Stockbridge, MA 01262
• 

  

  /22

  Est $303,518 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,040 Sq Ft

  214 High St, Lee, MA 01238

  214 High St, Lee, MA 01238
• 

  

  /56

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  100 Church St, Lee, MA 01238

  Welcome to this warm and inviting ranch-style home nestled in the heart of the Berkshires! This inviting property features 3 bedrooms, 2 full bathrooms and a comfortable layout ideal for everyday living and entertaining. This unique property includes a separately deeded lot presenting endless possibilities that sets this property apart. Whether you value privacy and space or want room to grow and

  Lisa Kelley MACCARO REAL ESTATE

  100 Church St, Lee, MA 01238

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