Lenox, MA Homes

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  /26

  Est $681,784 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft

  143 W Mountain Rd, Lenox, MA 01240

  143 W Mountain Rd, Lenox, MA 01240
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• 

  

  

  /26

  $425,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  153 E Dugway Rd, Lenox, MA 01240

  **Opportunity Awaits!**Great Lenox location. Three bedroom, one bath Ranch style home is nestled on 1.14 acres of land on a picturesque street, this gem offers 1344 sq ft on the main floor, with a full walkout lower level to a beautiful large yard. Minutes to downtown, Tanglewood and the best of the Berkshires.

  Matt Carlino MACCARO REAL ESTATE

  153 E Dugway Rd, Lenox, MA 01240
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  /16

  $297,375 Sold May 29, 2025

  • 709 Sq Ft
  • $419/SF
  • 2 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1968

  2 Morgan Manor Unit Bldg 2 - Unit 3, Lenox, MA 01240

  Immaculate and move-in ready! Looking for a walk-to-town setting? Morgan Manor is close to the village; close to Shakespeare, The Mount, and a short 2 mile drive to Tanglewood. Gleaming hardwood floors, open and updated kitchen. fully applianced including an in-unit stack washer/dryer. Updated lighting, freshly painted, newly replaced windows, custom window treatments. Additional dedicated

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  2 Morgan Manor Unit Bldg 2 - Unit 3, Lenox, MA 01240
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  /58

  Est $1,319,601 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,199 Sq Ft

  100 Old Stockbridge Rd, Lenox, MA 01240

  100 Old Stockbridge Rd, Lenox, MA 01240
• 

  

  

  /57

  $635,000

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  4 Evergreen Trail, Lenox, MA 01240

  Heirloom peonies and fragrant David Austin rose varieties adorn the walkway of this Berkshire hidden gem inviting you into tranquillity, peace and calm. Once indoors, you'll find easy living. The first level has an open kitchen and living area with a gas fireplace, large primary bedroom with a full bath and walk-in closet along with a screened in patio which overlooks a well established low

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  4 Evergreen Trail, Lenox, MA 01240
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  /30

  $315,000 Sold May 28, 2025

  • 1,493 Sq Ft
  • $211/SF
  • 52 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1870

  26 Old Stockbridge Rd Unit 2, Lenox, MA 01240

  Welcome to the Symphony Condominiums just footsteps from downtown Lenox and a short drive to Tanglewood. Enter in to a chef's dream kitchen featuring ample cabinetry for all your storage needs, expansive countertops for effortless meal prep, and a spacious design that invites both cooking and gathering. Off of the kitchen is a formal dining area that leads to a large private balcony with the

  Cory Evangelisto NOCHER REALTY

  26 Old Stockbridge Rd Unit 2, Lenox, MA 01240
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  /43

  Est $930,211 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  49 Sargent Brook Rd, Lenox, MA 01240

  49 Sargent Brook Rd, Lenox, MA 01240
• 

  

  /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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  /32

  $975,000 Sold May 28, 2025

  • 2,264 Sq Ft
  • $431/SF
  • 2 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  7-B Coldbrooke South -- Unit 7B, Lenox, MA 01240

  Abutting Wyndhurst's Historic Golf Club and Miraval Berkshire Resort - a luxurious wellness destination, this desirable Coldbrooke condo has been beautifully maintained and updated and allows living in Lenox to be easy and convenient. Well laid out floor plan to include a renovated cook's kitchen, large light filled living room with gas fireplace, dining area, and cheerful four season sun

  Lori Rose STONE HOUSE PROPERTIES, LLC

  7-B Coldbrooke South -- Unit 7B, Lenox, MA 01240
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  /32

  Est $504,384 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  870 East St, Lenox, MA 01240

  870 East St, Lenox, MA 01240
• 

  

  /45

  $599,900

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  31 Saint Ann's Ave, Lenox, MA 01240

  OWN - Instead of Renting - this Tanglewood Season! A unique opportunity with past rental income up to $16,000 for the summer months--ideal for music lovers and art-minded Berkshires visitors. This 1915 gem--the Claude and Louise Delahaye House--is tucked away on peaceful St. Ann's Ave, just steps from the iconic St. Ann's Church. Enjoy an easy stroll to downtown Lenox's shops, dining, and

  Audrey Matys BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
• 

  

  /23

  $317,000 Sold May 20, 2025

  • 952 Sq Ft
  • $333/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  38 Hillside Dr, Lenox, MA 01240

  Nestled at the end of a quiet dead-end street, this cozy two-bedroom, one-bath ranch offers a fantastic opportunity in a sought-after location. Just a short walk to downtown Lenox, you'll enjoy easy access to shops, dining, and cultural attractions. Inside, the home features hardwood floors and a practical layout, ready for your personal touch. The full basement provides ample storage or

  Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  38 Hillside Dr, Lenox, MA 01240
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  /30

  Est $998,902 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,851 Sq Ft

  49 Reservoir Rd, Lenox, MA 01240

  49 Reservoir Rd, Lenox, MA 01240
• 

  

  /25

  $374,900

  • 3 Beds
  • 1 Bath
  • 1,986 Sq Ft

  349 New Lenox Rd, Lenox, MA 01240

  Spacious 3 Bed/1 Bath Colonial located in a quiet Lenox neighborhood. This charming home offers: gleaming hardwood floors, an oversized family room which could be used as a 1st floor primary, a new Refrigerator & Stove, Washer & Dryer hook ups on the 1st floor, attached garage, steam heat and plenty of light throughout! Savor the beautiful Berkshires, while you lounge in your expansive flat

  Timothy Johnson NOCHER REALTY

  349 New Lenox Rd, Lenox, MA 01240
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  /2

  $1,350,000 Sold May 15, 2025

  • 1,109 Sq Ft
  • $1217/SF
  • 0 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 2017

  165 Kemble St Unit 3, Lenox, MA 01240

  Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation''s premier spas. One of only 19 units, it features a spacious great room, primary suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  165 Kemble St Unit 3, Lenox, MA 01240
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  /26

  Est $735,992 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  109 West St, Lenox, MA 01240

  109 West St, Lenox, MA 01240
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  /6

  $290,000

  • 4 Beds
  • 2 Baths
  • 1,986 Sq Ft

  249 Pittsfield Rd, Lenox, MA 01240

  Opportunity knocks in the Berkshires! This 3-acre gem on scenic Route 7 in Lenox offers a rare blend of space, potential, and prime location. Nestled among mature trees and open land, the property features a 1,986 sq ft farmhouse-style home waiting to be restored to its former glory.With residential and commercial zoning, two curb cuts, and access to natural gas, public water, and public sewer,

  Jessie Downer LAMACCHIA REALTY, INC

  249 Pittsfield Rd, Lenox, MA 01240
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  /27

  $3,850,000 Sold May 15, 2025

  • 3,348 Sq Ft
  • $1150/SF
  • 39 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2017

  165 Kemble St Unit 18, Lenox, MA 01240

  Experience the pinnacle of wellness living in this exquisite Canyon Ranch penthouse in Lenox, a beacon of luxury in one of the nation's most revered destinations. Crafted with meticulous attention to detail by William Caligari, this 3,300+ square foot sanctuary is a testament to high-end design and serene living. The residence boasts three generously sized bedrooms, each with its own ensuite

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  165 Kemble St Unit 18, Lenox, MA 01240
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  /30

  Est $620,354 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,114 Sq Ft

  57 Housatonic St, Lenox, MA 01240

  57 Housatonic St, Lenox, MA 01240
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  /49

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 2,265 Sq Ft

  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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  /24

  $356,000 Sold May 09, 2025

  • 1,456 Sq Ft
  • $245/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1976

  5-1 Rolling Unit 5-1, Lenox, MA 01240

  This charming 2-bedroom, 2-bath corner condo features central A/C and an open, airy layout. The stylish living area is perfect for both relaxation and entertaining, while the well-equipped kitchen offers a convenient breakfast bar. The living and dining spaces flow effortlessly, leading to a private balcony with stunning Berkshire Mountain views. Rolling Hills offers exceptional amenities,

  Elisha Poirier STONE HOUSE PROPERTIES, LLC

  5-1 Rolling Unit 5-1, Lenox, MA 01240
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  /36

  Est $584,255 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  150 West St, Lenox, MA 01240

  150 West St, Lenox, MA 01240
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  /13

  $414,900

  • 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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  /33

  $1,111,111 Sold Apr 30, 2025

  • 1,248 Sq Ft
  • $890/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1957

  80 Under Mountain Rd, Lenox, MA 01240

  9+ Acres on Under Mountain Rd in Lenox!Very rare opportunity to purchase a home with 9.4 acres of cleared, level land on coveted Under Mountain Road in Lenox. This cherished property has been held in the same family for 70 years. Neighboring protected land, this unique parcel boasts distant views of the Berkshire hills.With 650+ feet of frontage, this parcel offers multiple building lot

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  80 Under Mountain Rd, 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
• 

  

  /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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  /42

  $975,000 Sold Apr 30, 2025

  • 3,017 Sq Ft
  • $323/SF
  • 25 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2002

  4 Woods Ln, Lenox, MA 01240

  Nestled within the breathtaking grounds of the former Cranwell Resort, now the renowned Miraval Resort, 4 Woods Lane offers the perfect blend of luxury, tranquility, and modern comfort. This exceptional 3-bedroom, 3.5-bath home boasts stunning distant views, bringing the beauty of nature right to your doorstep.The spacious first-floor primary suite ensures effortless living, with no stair entry

  Paula McLean PAULA MCLEAN REALTORS INC.

  4 Woods Ln, Lenox, MA 01240
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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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  /39

  $569,000

  • 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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  /37

  $875,000 Sold Apr 18, 2025

  • 2,691 Sq Ft
  • $325/SF
  • 6 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2004

  6 October Hill Dr Unit 6, Lenox, MA 01240

  LENOX CONDOMINIUM AT TWELVE OAKS VILLAGE This luxury residence offers an openfloor plan with soaring Great Room, gas fireplace, kitchen with stainless appliances and granite counters, open dining and direct access to a lovely screened porch and patio for summerenjoyment. This appealing floor plan features a main floor primary bedroom en suite, den/office, attached garage, half bath and hardwood

  Cortney Dupont COHEN & WHITE ASSOCIATES

  6 October Hill Dr Unit 6, Lenox, MA 01240
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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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  /5

  $385,900

  • Land
  • 16 Acres
  • $24,255 per Acre

  2 New Lenox Rd, Lenox, MA 01240

  Opportunity Knocks! Expansive Lenox parcel - currently 2 approved building lots (1.0 acre and 14.91 acres) w/ frontage on East Street and New Lenox Road. Seller has a proposed subdivision that would make it 4 lots (1.0 acre, 3.5 acres, 7.59 acres & 2.98 acres). Build your dream home or take advantage of this unbeatable development opportunity in highly sought after location! Water, sewer & gas on

  Sean Taylor MORESI REAL ESTATE PARTNERS

  2 New Lenox Rd, Lenox, MA 01240
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  /26

  $920,000 Sold Apr 18, 2025

  • 3,017 Sq Ft
  • $305/SF
  • 132 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2002

  22 Woods Ln, Lenox, MA 01240

  First time on the market this impeccably maintained townhome at Fairwynds II, is set on the grounds of Miraval, a luxury wellness resort and spa. It is just off the golf course at the end of a cul-de-soc. Open living plan on the first floor is great for gathering with others or just having a nice airy feel. This home is thoughtfully designed with 3 en suite bedrooms and each guest room having

  Suzanne Crerar STONE HOUSE PROPERTIES, LLC

  22 Woods Ln, Lenox, MA 01240
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  /28

  Est $710,061 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,140 Sq Ft

  461 Under Mountain Rd, Lenox, MA 01240

  461 Under Mountain Rd, Lenox, MA 01240
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  /26

  $574,900

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  178 New Lenox Rd, Lenox, MA 01240

  Summer Special - $5,000 seller contribution to buyer (for closing costs, decorating, furnishings - your choice!) for closing on or before 8/29/25. Move-in ready Lenox 3 bed 2 full bath with mountain views on 1 acre. Large screened back porch and front 3- season room. Town water and sewer, natural gas heat and see-through wild-life fence protects huge backyard. Recent updates - new roof, gutters,

  Sean Taylor MORESI REAL ESTATE PARTNERS

  178 New Lenox Rd, Lenox, MA 01240
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  /38

  $560,000 Sold Apr 11, 2025

  • 2,432 Sq Ft
  • $230/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1984

  30 Galway Ct, Lenox, MA 01240

  You can't beat the location of this Garrison Colonial, set on a rare 3.7-acre lot in desirable Lenox! Tucked back from the road for added privacy, this home offers hardwood floors, a spacious family room with a wood-burning fireplace and cathedral ceilings, a large country eat-in kitchen, and first-floor laundry. With four generously sized bedrooms, 2.5 bathrooms, and town services, it's designed

  Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

  30 Galway Ct, Lenox, MA 01240
• 

  

  /29

  Est $738,149 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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  /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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  /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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  /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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