Berkshire, MA Homes

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  /40

  $1,795,000

  • 4 Beds
  • 3 Baths
  • 5,469 Sq Ft

  17 East St, Lenox, MA 01240

  Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 300-6860

  17 East St, Lenox, MA 01240
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  /4

  $1,305 - $3,447 per month

  Forge

  1 - 3 Beds

  66 Brushwood Way, Lenox, MA 01240

  Forge is a brand new mixed-income housing community currently under construction in Lenox, MA. The development will include 65 apartments within 13 townhome-style buildings, and a community clubhouse. Each building at Forge will contain 5-6 apartments, with a mix of one-, two-, and three-bedroom apartments available at various income tiers (30, 60, 120% AMI). Apartments will have their own

  66 Brushwood Way, Lenox, MA 01240
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  /45

  $1,150,000 Sold Jul 31, 2025

  • 2,995 Sq Ft
  • $384/SF
  • 29 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2006

  4 Stoneledge Rd, Lenox, MA 01240

  Charming Lenox contemporary cape on 1 acre. Located in an area of fine homes, this 4 bedroom 4.5 bath home has the following amenities: Screen porch, eat in kitchen with island, family room with fireplace, primary bedroom suite on the main floor, dining room, den, attached two car garage, finished lower level ...great space office or exercise area... natural gas heat, central air, town water

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  4 Stoneledge Rd, Lenox, MA 01240
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  /36

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /30

  $2,450,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  165 Kemble St Unit 17, Lenox, MA 01240

  Nestled within the serene, world-renowned Canyon Ranch Lenox campus, this bespoke two-bedroom, two-and-a-half-bath home is among the most private and luxuriously appointed in the Berkshires. A rare opportunity to own a residence where every detail--from architecture to finishes--echoes sophisticated European elegance while embracing the wellness-centered ethos of Canyon Ranch living.Inside,

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 547-4966

  165 Kemble St Unit 17, Lenox, MA 01240
• 

  

  /20

  $1,082 per month

  Lenox Schoolhouse Apartments

  Studio

  109 Housatonic St, Lenox, MA 01240

  The Berkshires' newest community is NOW OPEN!!! Newly renovated studios and one bedrooms with ALL UTILITIES INCLUDED* - Spacious open layouts, brand new interiors, plush carpet, sunlit windows, abundant closet space. Lenox Schoolhouse Apartments is within walking distance to the center of town. Enjoy the local shops, art galleries, restaurants and entertainment. You'll be sure to experience

  109 Housatonic St, Lenox, MA 01240
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  /27

  $265,000 Sold Jul 23, 2025

  • 800 Sq Ft
  • $331/SF
  • 89 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1860

  34 Church St Unit 2, Lenox, MA 01240

  Discover the perfect opportunity in the heart of downtown Lenox with a Church Street view! This charming condo is an ideal choice for investors, second homeowners, or those seeking a convenient lifestyle. This unit boasts two bedrooms, two full baths, beautiful wood floors, and a cozy gas fireplace. You will immediately have access to various shops, restaurants, and Tanglewood just minutes away!

  Jessica Rizzo Lamacchia Realty, Inc.

  34 Church St Unit 2, Lenox, MA 01240
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  /26

  Est $446,289 Not Listed For Sale

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

  26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

  26 Old Stockbridge Rd Unit 4, Lenox, MA 01240
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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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  /25

  $610,000 Sold Jul 22, 2025

  • 1,720 Sq Ft
  • $355/SF
  • 11 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2011

  2 Evergreen Trail, Lenox, MA 01240

  Enjoy the peaceful life at Lenox Woods...look out your back windows or screened porch at conservation land and the occasional deer. And inside, you'll enjoy the open living with great room and gas fireplace, kitchen with granite, first floor Primary Suite with vaulted ceiling, plus the finished 2nd floor with family room, 2 large bedrooms with full bath in between and a sweet, newly finished 4th

  Mary Jo Piretti PIRETTI REAL ESTATE

  2 Evergreen Trail, Lenox, MA 01240
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  /41

  Est $609,449 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
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  /60

  $5,150,000

  • 7 Beds
  • 8.5 Baths
  • 7,073 Sq Ft

  1 Pinecroft Dr, Lenox, MA 01240

  Gated Berkshire Stone Estate in exclusive Pinecroft compound with Canyon Ranch Living and its 125 maintenance-free acres. Optional membership. Turnkey home features elevator, 300-year-old reclaimed timber floors and large gourmet kitchen. Great room boasts floor-to-ceiling stone fireplace, wet bar, Nano doors to screened lanai. Two primary en suite bedrooms with cedar closets. Lower level: gym,

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1 Pinecroft Dr, Lenox, MA 01240
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  /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
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  /42

  Est $2,262,662 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,625 Sq Ft

  809 East St, Lenox, MA 01240

  809 East St, Lenox, MA 01240
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  /82

  $2,550,000 Pending

  • 6 Beds
  • 6.5 Baths
  • 7,143 Sq Ft

  13 Taconic Ave, Lenox, MA 01240

  An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  13 Taconic Ave, Lenox, MA 01240
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  /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
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  /52

  Est $2,173,679 Not Listed For Sale

  • 6 Beds
  • 8 Baths
  • 7,155 Sq Ft

  801 East St, Lenox, MA 01240

  801 East St, Lenox, MA 01240
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  /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
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  /23

  $355,000 Sold Jul 15, 2025

  • 1,552 Sq Ft
  • $229/SF
  • 3 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1976

  9 Rolling Hills Unit 5, Lenox, MA 01240

  This immaculate 2Bd, 3 Ba Move In condition unit is being offered Turn Key - fully furnished and fully stocked! But what really makes this unit special are the gorgeous Berkshire views from your private deck!The unit is completely updated & painted. Just bring your clothes and enjoy the pool, tennis & pickle ball courts, kayak racks, community victory garden, book club, mah jong, Bridge.

  Susan Baum BERKSHIRE HOMES AND CONDOS

  9 Rolling Hills Unit 5, Lenox, MA 01240
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  /51

  Est $551,015 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,929 Sq Ft

  142 New Lenox Rd, Lenox, MA 01240

  142 New Lenox Rd, Lenox, MA 01240
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  /70

  $1,290,000

  • 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

  Nicole Moore KELLER WILLIAMS REALTY

  257 W Mountain Rd, Lenox, MA 01240
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  /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
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  /33

  Est $780,905 Not Listed For Sale

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

  55 Sherwood Dr, Lenox, MA 01240

  55 Sherwood Dr, Lenox, MA 01240
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  /38

  $710,000

  • 3 Beds
  • 2 Baths
  • 2,081 Sq Ft

  51 New Lenox Rd, Lenox, MA 01240

  Meticulous craftsmanship and timber frame construction define this charming Colonial Dutch gambrel residence, combining comfort and practicality for everyday living. High-grade timber framing and solid construction give this home character and a warm, inviting atmosphere with its wood accents.Gather around the stone fireplace in the inviting living room, or whip up meals in the kitchen equipped

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  51 New Lenox Rd, Lenox, MA 01240
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  /28

  $253,207 Sold Jul 14, 2025

  • 1,552 Sq Ft
  • $163/SF
  • 47 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1976

  8 Rolling Hills Unit 9, Lenox, MA 01240

  Welcome to The Rolling Hills Townhouse Community in the glorious town of Lenox, Mass. The facility boasts the finest of amenities including a fully equipped clubhouse, fitness center, pool, tennis, community gardens and walking trails for you and your furry friends. Only minutes from downtown fine restaurants, shopping , Shakespeare&Company and Tanglewood. The school system is one of the most

  Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  8 Rolling Hills Unit 9, Lenox, MA 01240
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  /37

  Est $689,105 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
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  /61

  $1,650,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 4,049 Sq Ft

  38 Taconic Ave, Lenox, MA 01240

  Here is your VERY rare opportunity to own a truly gracious in-town Lenox Victorian. With every inch of this lovely residence meticulously updated, the attention to detail and quality craftsmanship evident throughout ensures the ideal blend of aesthetics and modern day convenience.From the stunning entry foyer, to two front parlors, to the grand dining room and expansive wet bar, you will find

  Anne Meczywor ROBERTS & ASSOC. REALTY, INC

  38 Taconic Ave, Lenox, MA 01240
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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
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  /13

  Est $566,434 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  234 Lee Rd, Lenox, MA 01240

  234 Lee Rd, Lenox, MA 01240
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  /114

  $929,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,608 Sq Ft

  67 Dunmore Ct, Lenox, MA 01240

  This gorgeous 4-bedroom, 3-bathroom home sits on a spacious corner lot surrounded by beautiful native landscaping, offering both privacy and curb appeal. Step inside to find a bright and inviting layout with ample space for entertaining and everyday living. The kitchen features newly redone floors (2025), and the large back deck provides the perfect space for outdoor gatherings or quiet

  Sara Bresett NOCHER REALTY

  67 Dunmore Ct, Lenox, MA 01240
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  /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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  /39

  Est $975,534 Not Listed For Sale

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

  4 October Hill Rd, Lenox, MA 01240

  4 October Hill Rd, Lenox, MA 01240
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  /24

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  130 West St, Lenox, MA 01240

  LOCATION, LOCATION, LOCATION....Steps to Morris School....minutes to Tanglewood or Main Street for shopping, the library, groceries or dinner! This 3 bedroom 2 bath 1890's home sits on a half acre lot with large fenced area for pets....this home is waiting for your decorating and updating ideas. First floor bedroom, full bath, living room, dining, kitchen and great enclosed rear porch....steps

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  130 West St, Lenox, MA 01240
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  /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
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  /54

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,883 Sq Ft

  215 Kemble St, Lenox, MA 01240

  215 Kemble St, Lenox, MA 01240
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  /14

  $219,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  260 Pittsfield Rd Unit B-5, Lenox, MA 01240

  Freshly updated 1 BR/1 BA condo at Lenox Heights. This light‑filled, 800 sq ft condo boasts athoughtfully renovated kitchen with new cabinetry and stainless‑steel appliances, plus plushwall‑to‑wall carpeting for a fresh, clean aesthetic. Step outside onto your private balcony toenjoy your morning coffee. On‑site amenities include an outdoor pool, tennis courts, and

  Samantha Homeyer BIRCH PROPERTIES

  260 Pittsfield Rd Unit B-5, Lenox, MA 01240
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  /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
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  /29

  Est $292,061 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft

  6 Morgan Manor Unit 11, Lenox, MA 01240

  6 Morgan Manor Unit 11, Lenox, MA 01240
• 

  

  /13

  $290,000

  • 1 Bed
  • 1 Bath
  • 709 Sq Ft

  3 Morgan Manor Unit 3 - 8, Lenox, MA 01240

  Welcome to 3‑8 Morgan Manor, a charming one-bedroom condo nestled in the heart of Lenox Village. This move-in-ready unit offers a sunlit layout with cozy carpeting, and efficient space. The condo fee includes heat, hot water, gas, water, and sewer, making for truly hassle-free living. Located in a well-maintained building just steps from downtown Lenox, you'll enjoy easy access to

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  3 Morgan Manor Unit 3 - 8, Lenox, MA 01240
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  /35

  $345,000 Sold Jun 20, 2025

  • 1,552 Sq Ft
  • $222/SF
  • 1 Day On Market

  • 2 Beds
  • 3 Baths
  • Built 1976

  4 Rolling Hills Unit 4-9, Lenox, MA 01240

  Move right into this beautifully updated two-bedroom, three full bath condo located in the highly sought-after Rolling Hills Condo Association in picturesque Lenox, Massachusetts. The brand-new kitchen is a standout feature, boasting all-new cabinetry, stylish butcher block countertops, updated flooring, and a complete suite of modern appliances. Throughout the main living areas, quality laminate

  Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  4 Rolling Hills Unit 4-9, Lenox, MA 01240

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