Lenox, MA Homes

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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

  $1,082 total monthly price

  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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  /49

  $627,500 Sold Sep 12, 2025

  • 2,265 Sq Ft
  • $277/SF
  • 94 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1989

  7 Cedar Ln, Lenox, MA 01240

  Improved Price! Four bedroom, 2.5 bath, 2265 sq. ft., move in ready home awaits you! 2018 renovated kitchen with granite counters opens to a natural light filled breakfast nook from sliders that open to an expansive Trex deck (2018). A double sided wood burning brick fireplace finishes off this handsome layout. The other side of the fire place opens to a den with sliders. Living room, dining

  Margaret Apkin WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  7 Cedar Ln, Lenox, MA 01240
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  /36

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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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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  /28

  $1,700 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Townhouse for Rent

  18 Elm St, Lenox Dale, MA 01242

  Amazing bright 3 bedroom with great southern exposure, 1 bathroom nice quiet townhouse in Lenox Dale, 5 min by car to historical downtown Lenox, 15 min to Pittsfield. Amenities included are: dishwasher, hardwood floors, updated kitchen, washer and dryer, small rear yard, front porch , and enclosed rear porch. Off street parking for two vehicles. Absolutely no smoking in or on

  18 Elm St, Lenox Dale, MA 01242
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  /48

  $594,000 Sold Sep 05, 2025

  • 1,919 Sq Ft
  • $310/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1960

  296 Housatonic St, Lenox, MA 01240

  Move right into this beautifully updated Lenox ranch--just a stroll to downtown on sidewalks through lit intersection, Woods Pond, and October Mountain! Filled with charm and thoughtful updates, this 3-bedroom, 2.5-bath home features hardwood floors, a spacious bonus room with convenient half bath, and a finished lower level with full bath--perfect for guests, work, or recreation. Step outside to

  Victoria Standring LAMACCHIA REALTY, INC

  296 Housatonic St, Lenox, MA 01240
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  /26

  Est $412,526 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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  /30

  $2,450,000 Pending

  • 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
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  /4

  $1,305 - $3,447 total monthly price

  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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  /38

  $555,000 Sold Aug 28, 2025

  • 1,965 Sq Ft
  • $282/SF
  • 52 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  76 New Lenox Rd, Lenox, MA 01240

  Welcome to your charming colonial retreat in Lenox! This inviting 4-bedroom, 2-bath home offers a perfect blend of space, comfort and convenience, ideally located near a variety of Berkshire attractions.As you step inside, you'll be greeted by a bright and airy family room, complete with built-in shelves and sliding doors that lead to a brand-new deck, perfect for overlooking your fenced

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  76 New Lenox Rd, Lenox, MA 01240
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  /41

  Est $607,171 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

  $4,950,000

  • 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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  /24

  $2,500 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  71 Housatonic St Unit Upper Level, Lenox, MA 01240

  Welcome to this charming downtown apartment in the heart of Berkshire County! Nestled in a vibrant and picturesque area, this beautifully appointed, fully furnished space offers the perfect blend of modern amenities and classic New England character.For your ultimate comfort, most utilities are included with the exception of cable/internet, allowing you to move in without a worry.

  71 Housatonic St Unit Upper Level, Lenox, MA 01240
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  /47

  $660,000 Sold Aug 22, 2025

  • 2,242 Sq Ft
  • $294/SF
  • 2 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  36 Tucker St, Lenox, MA 01240

  Charming and versatile, this home is a well-maintained two-family home just steps from downtown Lenox. With two separate units offering 2 bedrooms and 1 full bath each, this property is perfect for investors, multi-generational living, or owner-occupied. Each unit features hardwood floors, full kitchens, separate utilities, and bright, comfortable living spaces. Enjoy the spacious backyard and

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  36 Tucker St, Lenox, MA 01240
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  /42

  Est $2,357,637 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

  • 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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  /25

  $261,500 Sold Aug 18, 2025

  • 1,296 Sq Ft
  • $202/SF
  • 184 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  874 East St, Lenox, MA 01240

  If you are looking for a Lenox home, don't miss this one! Three bedroom, two bath expanded cape with walk-out basement. First floor includes two bedrooms and a full bath. Hardwood throughout much of the house. Kitchen opens to a year-round heated sunroom that opens to a deck and overlooks the spacious back yard. Traditional cape with a bedroom with hardwood, bonus room and full bath on the

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  874 East St, Lenox, MA 01240
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  /52

  Est $2,152,982 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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  /51

  $1,998,000

  • 12 Beds
  • 10.5 Baths
  • 7,979 Sq Ft

  7 Hubbard St, Lenox, MA 01240

  Welcome to The Dewey, a rare opportunity to own one of Lenox's most iconic residences. Built in 1767, this remarkable property--known as the Israel Dewey House--stands as a testament to early American architecture and timeless elegance. Set in the heart of the Berkshires, It beautifully bridges centuries of history with the comforts of today.The Main HouseSpanning 6,839 square feet across three

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  7 Hubbard St, Lenox, MA 01240
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  /53

  $625,000 Sold Aug 12, 2025

  • 1,687 Sq Ft
  • $370/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  73 Birchwood Ln, Lenox, MA 01240

  Neat as a pin and a gardener's delight! Sited near the end of a cul-de-sac this Lenox neighborhood home offers so much to come home to! First floor features fireplaced front-to-back living room that opens to an updated three-season sunroom. Formal dining with built-in storage, open kitchen with access to rear deck. Recently remodeled 1st floor full bath with walk-in shower. Second level

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  73 Birchwood Ln, Lenox, MA 01240
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  /51

  Est $547,218 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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  /43

  $1,085,000

  • 3 Beds
  • 2.5 Baths
  • 2,084 Sq Ft

  220 Kemble St, Lenox, MA 01240

  A Former Gardener's Cottage ReimaginedOnce the Gardener's Cottage for the historic Bishop Estate, this enchanting Lenox property blends storybook charm, thoughtful updates, and timeless craftsmanship. Mature Ginkgo and Beech trees, wildflowers, and perennials frame the approach, while a gazebo and saltwater pool anchor the garden landscape, creating a private retreat within walking distance of

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  220 Kemble St, Lenox, MA 01240
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  /28

  $475,000 Sold Aug 12, 2025

  • 1,380 Sq Ft
  • $344/SF
  • 35 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1860

  127 Housatonic St, Lenox, MA 01240

  LOCATION- DOWNTOWN LENOX! Upstairs has 3 bedroom, 1 bath. Main level has nice flow. Kitchen and dining has direct access to back patio and attached garage. Large living room flows out to front covered sitting porch. New decking and steps go down to the walk out full basement with workshop. Walk to public tennis /pickle ball courts, ball fields, food / cafes, Kennedy Park & Lenox Community

  Donna DiGrigoli DIGRIGOLI REAL ESTATE

  127 Housatonic St, Lenox, MA 01240
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  /33

  Est $755,033 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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  /70

  $1,100,000 Open Sat 11:30AM - 1:30PM

  • 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

  $265,000 Sold Aug 12, 2025

  • Land
  • 2 Acres
  • $132,500 per Acre

  • 53 Days On Market

  0 Old Stockbridge Rd, Lenox, MA 01240

  This 2-acre property just .4 mi. from the center of Lenox is an opportunity of a lifetime to build your Berkshire dream luxury/lifestyle home. This historical property was the site for the home of Jonathan Hinsdale-first European inhabitant in the town of Lenox (1750). Adjacent to Shakespeare & Company Campus and just minutes from Tanglewood and all the local attractions. Town

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  0 Old Stockbridge Rd, Lenox, MA 01240
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  /37

  Est $680,697 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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  /50

  $1,950,000

  • 5 Beds
  • 4.5 Baths
  • 4,301 Sq Ft

  20 E Dugway Rd, Lenox, MA 01240

  Lenox Estate on 36 Acres - Two HomesJust one mile from the center of Lenox, this unique estate offers exceptional space and versatility with two separate residences. The main home boasts 4,100 square feet with five bedrooms and three and a half bathrooms--perfect for spacious living or entertaining. The second home is a charming 1,200-square-foot residence with two bedrooms and two full baths,

  Tanya Shepardson LAMACCHIA REALTY, INC

  20 E Dugway Rd, Lenox, MA 01240
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  /22

  $110,000 Sold Aug 08, 2025

  • 1,152 Sq Ft
  • $95/SF
  • 18 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1993

  i-6 Robert Ave, Lenox, MA 01240

  This charming 2 bedroom, 1.5 bathroom manufactured home is located in the Berkshire Mobile Home Park community. With a little tender loving care, this unit could serve as a wonderful vacation home or a cozy full time dwelling. Just minutes from downtown Lenox, and Pittsfield; this unit enjoys easy access to many of the cultural and recreational activities that make the Berkshires a special place

  Cristian Sanchez COHEN & WHITE ASSOCIATES

  i-6 Robert Ave, Lenox, MA 01240
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  /13

  Est $581,256 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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  /63

  $749,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,630 Sq Ft

  33 Brunell Ave, Lenox, MA 01240

  Enjoy modern country living in this beautifully renovated walk-to-town Lenox home. With exceptional curb appeal and an open concept, well-designed layout, this stylish property features a living room with a gas fireplace and built-in shelving, a well-equipped kitchen (with large pantry), which opens to the dining area w/ a slider to the sunny deck. Entering with groceries, the side entry has an

  Lori Rose STONE HOUSE PROPERTIES, LLC

  33 Brunell Ave, Lenox, MA 01240
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  /39

  $502,500 Sold Aug 08, 2025

  • 1,798 Sq Ft
  • $279/SF
  • 19 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1953

  80 Plunkett St, Lenox, MA 01240

  Lenox ranch in pristine condition! Freshly painted exterior, gleaming hardwood floors; wide hallway and generously proportioned rooms. Vintage kitchen opens to rear deck. The large unfinished basement/workshop has potential for additional finished space with some full-sized windows and walk-out. Custom built for the owner's family, this home has never been on the market before! The

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  80 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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  /45

  $1,499,000 Pending

  • 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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  /61

  $1,550,000 Sold Aug 06, 2025

  • 4,049 Sq Ft
  • $383/SF
  • 13 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1880

  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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  /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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  /114

  $929,900 Pending

  • 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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  /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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  /29

  Est $297,806 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

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