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Homes for Sale in 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

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 423-1264

    250 West St, Lenox, MA 01240
  • /5

    $998,000

    • Land
    • 9.1 Acres
    • $109,670 per Acre

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

    RARE LUXURY: READY-to-BUILD MODERNIST RETREAT on EXCLUSIVE PRIVATE POND minutes to TANGLEWOODWelcome to a once-in-a-lifetime opportunity in the heart of the Berkshires. Set on 9.1 acres approximately acres of pristine land, this exceptional estate parcel offers frontage on tranquil Lily Pond, a private, non-motorized body of water that ensures peace, privacy, nature and views. Comprising the

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 343-4919

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
  • /6

    $395,000

    • Land
    • 3.3 Acres
    • $119,697 per Acre

    9 Wheatleigh Dr, Stockbridge, MA 01262

    RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 343-5283

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • /6

    $395,000

    • Land
    • 3.3 Acres
    • $119,697 per Acre

    9 Wheatleigh Dr, Stockbridge, MA 01262

    RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 722-5098

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • /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
  • /33

    $799,000

    • 4 Beds
    • 3 Baths
    • 2,123 Sq Ft

    70 Galway Ct, Lenox, MA 01240

    Beautifully maintained and updated, this charming Cape offers 2 first floor bedrooms and baths, 2 second floor bedrooms with full bath in between, cherry kitchen with granite counters, formal dining and living and a family room with fireplace, vaulted ceiling and sliders to the large deck. Enjoy this wonderful ''walking neighborhood'', close to Miraval Resort for pool, golf & fitness membership

    Mary Jo Piretti PIRETTI REAL ESTATE

    70 Galway Ct, Lenox, MA 01240
  • /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
  • /54

    $979,000

    • 5 Beds
    • 4.5 Baths
    • 2,800 Sq Ft

    850 Summer St, Lee, MA 01238

    Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

    Katie Williams STONE HOUSE PROPERTIES, LLC

    850 Summer St, Lee, MA 01238
  • /70

    $1,035,000

    • 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
  • /50

    $1,750,000

    • 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
  • /42

    $1,825,000

    • 4 Beds
    • 3.5 Baths
    • 3,452 Sq Ft

    16 Sedgwick Ln Unit 40, Lenox, MA 01240

    Luxury in Lenox......If you are looking for carefree living with fabulous amenities at a world class resort, this Fairwynds single family residence at Miraval/Wyndhurst may be the perfect spot for you. Beautifully renovated with sleek, clean lines, generous two volume great room with wood burning fireplace, direct access to screened porch and open decking; all open to the gourmet kitchen with

    Mary Jane White COHEN & WHITE ASSOCIATES

    16 Sedgwick Ln Unit 40, Lenox, MA 01240
  • /9

    $475,000

    • Land
    • 20.87 Acres
    • $22,760 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
  • /27

    $370,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    16 E New Lenox Rd, Lenox, MA 01240

    Welcome to this classic 1950s ranch on East New Lenox Road — full of character and comfort. Featuring three bedrooms and one full bath, this home showcases beautiful wood floors, freshly painted interiors, and that timeless New England charm that never goes out of style.Enjoy the added versatility of a three-season porch connecting to the attached two-car garage, perfect for morning coffee or an

    Bresdin Mihlek Coldwell Banker Realty - Western MA

    16 E New Lenox Rd, Lenox, MA 01240
  • /12

    $599,000

    • 4 Beds
    • 2 Baths
    • 2,170 Sq Ft

    30 Walker St, Lenox, MA 01240

    Discover the perfect blend of location and opportunity with this well-maintained two-family home in the heart of Lenox, Just steps from the Main Street of downtown, this property features a spacious three bedroom unit and a charming one bedroom unit- ideal for rental income, extended family, or guests, Enjoy privacy and outdoor relaxation in the lovely backyard, all while being close to shops,

    Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    30 Walker St, Lenox, MA 01240
  • /21

    $425,000

    • 3 Beds
    • 2 Baths
    • 3,038 Sq Ft

    137 Housatonic St, Lenox, MA 01240

    Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer.

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    137 Housatonic St, Lenox, MA 01240
  • /25

    $3,200,000

    • 2 Beds
    • 2.5 Baths
    • 1,956 Sq Ft

    165 Kemble St Unit 5, Lenox, MA 01240

    A Rare South-Facing Retreat at The Residences at Canyon RanchNestled within the serene, world-renowned Canyon Ranch Lenox campus, this two-bedroom, two-and-a-half-bath end unit is a rare offering--south-facing, luminous, and among the most private of its kind. More than a residence, it is an invitation to a life of balance, wellness, and quiet sophistication in the cultural heart of the

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    165 Kemble St Unit 5, Lenox, MA 01240
  • /21

    $1,400,000

    • Land
    • 14.6 Acres
    • $95,890 per Acre

    286 Lee Rd, Lenox, MA 01240

    A ONCE IN A LIFETIME OPPORTUNITY TO BUILD YOUR DREAM HOME ON A SPECTACULAR, 14 ACRE, WATERFRONT PROPERTY IN THE HEART OF THE BERKSHIRES. PRIVATE, QUIET, BUT NOT ISOLATED. FROM YOUR NEW RESIDENCE, BEAUTIFUL LAUREL LAKE IS AN EASY STROLL DOWN THE BOARDWALK TO YOUR PRIVATE DOCK AND SITTING AREA. FIVE MINUTES TO DOWNTOWN LENOX, TEN MINUTES TO TANGLEWOOD AND CONVENIENT TO ALL THE BERKSHIRES HAS TO

    Allen Bassen BERKSHIRE HOMES AND CONDOS

    286 Lee Rd, Lenox, MA 01240
  • /38

    $600,000

    • 2 Beds
    • 4 Baths
    • 1,870 Sq Ft

    19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262

    WHITE PINES IN STOCKBRIDGE Tasteful 2 bed 2 full and 2 half bath home offers generous great room with windows showcasing beautiful views. Wood burning fireplace graces open living/dining room with beautiful hardwood floors. Large en-suite primary has spa-like bath. Community amenities include private beach at Stockbridge Bowl, indoor pool, HarTru tennis courts and fitness center. Covered parking.

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262
  • /47

    $585,000

    • 2 Beds
    • 2.5 Baths
    • 1,935 Sq Ft

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262

    Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry closet. The second

    Cortney Dupont COHEN & WHITE ASSOCIATES

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
  • /39

    $238,500

    • 2 Beds
    • 2 Baths
    • 1,552 Sq Ft

    2 Rolling Hills Unit bldg2-4, Lenox, MA 01240

    As summer winds down... if you are looking for your fall/winter project - take a look at this value-priced Rolling Hills condo! Priced below assessed value to offer immediate equity, this two-bedroom/two bath unit has much to offer. Original parquet flooring now revealed under the former wall-to-wall carpet. Private rear deck looks toward Yokun Brook. Partially finished lower level with

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    2 Rolling Hills Unit bldg2-4, Lenox, MA 01240
  • /56

    $979,000

    • 5 Beds
    • 4.5 Baths
    • 2,800 Sq Ft

    850 Summer St Unit M14, Lee, MA 01238

    Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

    Katie Williams STONE HOUSE PROPERTIES, LLC

    850 Summer St Unit M14, Lee, MA 01238
  • /27

    $285,000

    • 2 Beds
    • 3 Baths
    • 1,770 Sq Ft

    2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240

    If you are looking for location, Rolling Hills is the place to be. Just minutes from Tanglewood, Shakespeare & Company, skiing, arts, and all of the Culture the Berkshires has to offer. This unit is right across from the Clubhouse/Pool/fitness room. This unit has 2 bedrooms, 3 baths, additional family room on the lower level and newer appliances. Enjoy the Tennis/pickle ball courts or take swim

    Toni Marie Gage SIGNATURE ASSOCIATES

    2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
  • /58

    $4,995,000

    • 7 Beds
    • 8 Baths
    • 13,261 Sq Ft

    319 Under Mountain Rd, Lenox, MA 01240

    Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

    Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    319 Under Mountain Rd, Lenox, MA 01240
  • /43

    $699,000

    • 3 Beds
    • 2.5 Baths
    • 2,135 Sq Ft

    770 Summer St Unit 3A, Lee, MA 01238

    Welcome home to Lakeside condominiums at Foxhollow! An established condo community perfectly positioned between Lee/Lenox/Stockbridge close to all area attractions! Desirable ground level unit features easy living. Enjoy morning coffee on your spacious deck taking in open rolling lawns and mountain views. Open living/dining with fireplace, updated kitchen w quartz counters, stainless

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    770 Summer St Unit 3A, Lee, MA 01238
  • /48

    $600,000

    • 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
  • /45

    $549,000

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

    31 Saint Ann's Ave, Lenox, MA 01240

    The Claude and Louise Delahaye House -- A Lenox Treasure Steps from St. Ann's ChurchTucked away on peaceful St. Ann's Avenue, this charming Lenox bungalow blends timeless character with modern comfort -- and it's just a short stroll to the village's boutique shops, cafes, and cultural landmarks.Inside, you'll find 1,700 sq. ft. of tastefully updated living space, where preserved period details

    Audrey Matys BERKSHIRE LISTINGS

    31 Saint Ann's Ave, Lenox, MA 01240
  • /6

    $250,000

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

    249 Pittsfield Rd, Lenox, MA 01240

    Opportunity knocks in the Berkshires! COMMERCIALLY & RESIDENTIALLY ZONED. 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

    Reciprocal Reciprocal Berkshire Reciprocal

    249 Pittsfield Rd, 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
  • /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
  • /5

    $385,900

    • Land
    • 15.91 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
  • /23

    $215,000 New Construction

    • 3 Beds
    • 1 Bath
    • 2,552 Sq Ft

    1 Pittsfield Rd, Lenox, MA 01240

    Don't miss this rare chance to acquire and revitalize a property brimming with original character. Located on a well-traveled road with excellent visibility, this 1.25-acre lot offers endless possibilities for commercial use.Featuring a brand new roof, the property is ideal for a variety of purposes, including retail, restaurant, professional offices, etc. Inside, you'll find an abundance of

    Laiken Rapisarda LAMACCHIA REALTY, INC

    1 Pittsfield Rd, Lenox, MA 01240
  • /10

    $365,000

    • 5 Beds
    • 1.5 Baths
    • 2,490 Sq Ft

    15 Golden Hill Rd, Lee, MA 01238

    This incredibly spacious home built in the early 1900s features 5 bedrooms, an eat-in kitchen, a formal dining room, an office, a family room, a library with built-ins, and a backyard of more than a half acre with distant views and space for a good size garden as well as room for a pool. A fabulous 2-story barn offers extended space awaiting your vision. Mature plantings offer a feeling of

    John Segalla HOUSATONIC REAL ESTATE

    15 Golden Hill Rd, Lee, MA 01238
  • /13

    $349,900

    • 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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