Homes for Sale near Hillcrest Educational Centers

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  /10

  $225,000

  • Land
  • 3.26 Acres
  • $69,018 per Acre

  88 Great Barrington Rd, West Stockbridge, MA 01266

  Cleared 3+ acre lot ready to be built in a desirable West Stockbridge location. Wonderful south facing site, set off the road with distant uninterrupted views. Existing driveway presents easy access. Previous owner had percolation tests done which allows for a below grade septic system. Plans for the septic system are included. The site has already be approved by the DEP. Architectural plans for

  Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

  88 Great Barrington Rd, West Stockbridge, MA 01266
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  /26

  $349,900

  • 2 Beds
  • 1 Bath
  • 1,570 Sq Ft

  1600 Pleasant St, Lee, MA 01238

  Nestled in the scenic Berkshires just two minutes from Stockbridge, this charming two-bedroom, one-bath home perfectly balances comfort, creativity, and convenience. Inside, a cozy living room invites relaxation, while the modern kitchen--with ample counter space--sets the stage for culinary inspiration. Both bedrooms offer peaceful retreats, filled with natural light and warmth.A standout

  Ryan Lane GILCREST PROPERTIES

  1600 Pleasant St, Lee, MA 01238
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  /48

  $499,000

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft

  190 Willow St, Lee, MA 01238

  : Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare

  Kim Bergland RED HORSE REAL ESTATE, LLC

  190 Willow St, Lee, MA 01238
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  /49

  $780,000

  • 3 Beds
  • 2 Baths
  • 2,046 Sq Ft

  17 Iron Mine Rd, West Stockbridge, MA 01266

  Designed for country living and entertaining, the heart of the home centers around a sun-filled great room with vaulted ceilings, wood beams, and French doors leading to a private deck. The chic kitchen has marble counters, subway tile, stainless steel appliances, gas stove and a peninsula for prep and dining. The 1st-floor primary suite offers a walk-in closet, updated full bath and deck access.

  Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

  17 Iron Mine Rd, West Stockbridge, MA 01266
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  /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
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  /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
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  /15

  $649,000

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  17 Beachwood Dr, Stockbridge, MA 01262

  Discover a truly exceptional opportunity to own a spacious 3-bedroom seasonal cottage on 1.3 acres of uniquely private land in one of the Berkshires' most desirable lakeside enclaves.Nestled in the serene and exclusive Beachwood community on Stockbridge Bowl, this property offers the perfect balance of natural beauty, privacy, and cultural access. Residents enjoy steps to a private beach,

  Franz Forster FRANZ J. FORSTER R. E.

  17 Beachwood Dr, Stockbridge, MA 01262
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  /19

  $550,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  15 W Stockbridge, Stockbridge, MA 01262

  The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect

  C. Ethan Watt WILLIAM PITT SOTHEBY'S - SALISBURY

  15 W Stockbridge, Stockbridge, MA 01262
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  /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
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  /18

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,480 Sq Ft

  2200 Swamp Rd, Richmond, MA 01254

  Enjoy easy one-level living in this well-kept ranch home, lovingly owned and updated by a single family since it was built. A welcoming porched entry opens to a bright living room featuring a large picture window and a beautiful stone-faced wood-burning fireplace.This 3-bedroom, 1-bath home features hardwood floors throughout and a functional layout. The family room off the garage leads into a

  Sherrie Cardillo BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  2200 Swamp Rd, Richmond, MA 01254
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  /8

  $535,000

  • 8 Beds
  • 8 Baths
  • 2,657 Sq Ft

  180 Center St, Lee, MA 01238

  Discover an exceptional investment opportunity to own two duplex homes on a single parcel, perfect for investors looking for a practical investment in the town of Lee. Four units total, these properties are ideal for generating consistent rental income. Close to downtown, shopping, major employers as well as banking and all popular Berkshire attractions. Tenants enjoy attached, private garaged

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  180 Center St, Lee, MA 01238
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  /54

  $2,500,000

  • 5 Beds
  • 4.5 Baths
  • 5,233 Sq Ft

  55 Main St, Stockbridge, MA 01262

  Historic Elegance Reimagined!Wellness-forward design. Artisan craftsmanship. In-town privacy.A Kitchen Rebuilt from the Ground Up: At the heart of the home, a brand-new chef's kitchen makes a bold, refined statement with honed dark gray granite countertops, crisp white shaker cabinetry, and minimalist matte black fixtures. Oversized divided-light windows flood the space with natural light, while

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  55 Main St, Stockbridge, MA 01262
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  /20

  $3,599,000

  • 15 Beds
  • 15 Baths
  • 11,945 Sq Ft

  615 Laurel St, Lee, MA 01238

  The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

  Pamela J Long EAST COAST INN BROKERS

  615 Laurel St, Lee, MA 01238
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  /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
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  /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
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  /36

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,476 Sq Ft

  4 Main St, West Stockbridge, MA 01266

  Beautiful riverside home offering comfort, flexibility, and in-town convenience. The front 2BR/2BA residence features soaring ceilings, skylights, an open kitchen, private riverfront deck, and an oversized ensuite bedroom. A spacious lower level provides room for guests, hobbies, or work. A charming garden area overlooking the Williams River adds outdoor enjoyment. The attached 1BR/1BA apartment

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  4 Main St, West Stockbridge, MA 01266
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  /23

  $523,995

  • Land
  • 10.02 Acres
  • $52,279 per Acre

  0 Swamp Rd, Richmond, MA 01254

  This 10-acre parcel in scenic Richmond, available for the first time in generations, offers a rare chance to build your dream home in the heart of the Berkshires. Surrounded by open farmland and natural beauty, this property provides a peaceful and inspiring setting for a country retreat or a year-round residence. The land features gently rolling meadows filled with wildflowers and native

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  0 Swamp Rd, Richmond, MA 01254
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  /19

  $775,000

  • 8 Beds
  • 4 Baths
  • 3,192 Sq Ft

  35 Main St, West Stockbridge, MA 01266

  Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

  Matt Carlino MACCARO REAL ESTATE

  35 Main St, West Stockbridge, MA 01266
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  /19

  $929,000

  • 11 Beds
  • 6 Baths
  • 4,863 Sq Ft

  Unlisted Address

  Fully Rented In Town 5-Family Investment Opportunity. Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures.

  Matt Carlino MACCARO REAL ESTATE

  Unlisted Address
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  /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
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  /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 appliances

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  770 Summer St Unit 3A, Lee, MA 01238
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  /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
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  /47

  $549,000

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

  31 Saint Ann's Ave, Lenox, MA 01240

  Don't miss this unique historic property -- truly a GEM! Ready for quick rental income and perfect to enjoy as spring arrives. A wonderful second home to share with family! Imagine a short stroll to downtown Lenox for coffee, a quiet dinner, and a beautiful night at Tanglewood under the stars. Just one street from downtown and steps from St. Ann's Church, this 1,700 sq. ft. bungalow blends charm

  Audrey Matys BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
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  /45

  $369,000

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  205 High St, Lee, MA 01238

  Enjoy downtown living in this 4 Bedroom 2 Bath New England farmhouse. Built in the early20th century, this home has a diverse use of residential, commercial or mixed use on a residential street. The kitchen has been updated with plenty of cabinet space. A cozy living room fireplace and a enclosed porch with numerous windows that welcome fresh summertime breezes and a patio for summer leisure

  Anthony Caropreso MACCARO REAL ESTATE

  205 High St, Lee, MA 01238
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  /51

  $2,100,000

  • 4 Beds
  • 4 Baths
  • 2,738 Sq Ft

  8 Yale Hill Rd, Stockbridge, MA 01262

  A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  8 Yale Hill Rd, Stockbridge, MA 01262
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  /56

  $1,395,000

  • 4 Beds
  • 2 Baths
  • 2,058 Sq Ft

  45 Swamp, West Stockbridge, MA 01266

  1950s retro home, rich with family history, situated on 30+ acres of land & offering expansive westerly views & gentle sloping fields. Pathways lead to Shaker Mill Pond & Cone Brook which run the entire length of the property. Interior features include 2 BRs, office & full bath on the main level, 2 BRs & full bath on the second floor, a quaint kitchen, & living room. Additionally, a fully heated

  Paige Paluch LANCE VERMEULEN RE, INC

  45 Swamp, West Stockbridge, MA 01266
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  /3

  $975,000

  • Land
  • 131.69 Acres
  • $7,404 per Acre

  0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

  This is a generous hillside parcel with a perc and potential views to the west. It is just over the hill from Stockbridge Bowl and Tanglewood, in an area of fine homes.

  Jim Stark L. J. STARK AND CO.

  0 Lenox Rd Unit 246122, West Stockbridge, MA 01266
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  /13

  $324,900

  • 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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  /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

  Lori Rose STONE HOUSE PROPERTIES, LLC

  2 Kemble St, Lenox, MA 01240
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  /16

  $1,800,000

  • 40 Beds
  • 20 Baths
  • 30,000 Sq Ft

  15 East St, Stockbridge, MA 01262

  Located in a Sngle Family zoned area on a desirablle, private parcel consisting of nine total buildings with an in-ground pool amongst other amenities. Property is available for sale, lease or equity investment by new partners. This is an amazing property on the border of Stockbridge and Lenox with close proximity to Albany / Hartford / I-91. Many opportunities for possible hotel, B&B, family

  Tim Damon Mercury Real Estate

  15 East St, Stockbridge, MA 01262
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  /50

  $1,295,000

  • 4 Beds
  • 4.5 Baths
  • 3,395 Sq Ft

  62 Stockbridge Terrace, Lee, MA 01238

  Updated and spacious condo just a short distance from Main Street Stockbridge, downtown Lenox, and all the Berkshires has to offer! Premier Unit at Stockbridge Terrace: Enjoy peaceful living on a private cul-de-sac with a limited number of units. The main level living setup is perfect for the primary resident, featuring a large primary bedroom with an en-suite bath and walk-in closet, an

  Lauren Molk ELYSE HARNEY REAL ESTATE

  62 Stockbridge Terrace, Lee, MA 01238
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  /11

  $39,900

  • Land
  • 1.9 Acres
  • $21,000 per Acre

  289 Antelope Dr, Lee, MA 01238

  Welcome to the private Leisure Lee community. Tucked away awaits the sandy beach of Goose Pond, a dock with boat moorings and two tennis courts. Create your own dream home with this elevated wooded lot. A short drive to the Lee outlets and close proximity to Tanglewood and all cultural events the Berkshires have to offer.

  Tanya LeRose THE KINDERHOOK GROUP

  289 Antelope Dr, Lee, MA 01238
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  /49

  $650,000

  • Land
  • 52.35 Acres
  • $12,416 per Acre

  206 Stevens Glen Rd, Richmond, MA 01254

  In the heart of the Berkshires, this exceptional 50+ acre parcel presents a rare opportunity steeped in natural beauty and historical significance. With three approved building lots already in place, the property offers incredible potential--for development, investment, or the creation of a private multi-residence retreat. Bordering the picturesque Stevens Glen and abutting conserved lands, the

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  206 Stevens Glen Rd, Richmond, MA 01254
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  /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
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  /16

  $295,000

  • Land
  • 25.22 Acres
  • $11,697 per Acre

  0 Glendale Rd Unit 245211, Stockbridge, MA 01262

  Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. Many possibilities - build on the north lot and keep the south lot for extra

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  0 Glendale Rd Unit 245211, Stockbridge, MA 01262
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  /52

  $1,675,000

  • 12 Beds
  • 7 Baths
  • 8,881 Sq Ft

  29 Main St, West Stockbridge, MA 01266

  Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

  Suzann Ward HOUSATONIC REAL ESTATE

  29 Main St, West Stockbridge, MA 01266
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  /7

  $88,000

  • Land
  • 1.42 Acres
  • $61,972 per Acre

  0 East St Unit 235893, Lee, MA 01238

  Two building lots being sold together with 324 feet of road frontage with an estimated 1.42 total acres. So, there are possibilities to build one or two house on the property. Site has access to electric water, sewer, and natural gas. There is one temporary approved curb cut.

  Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  0 East St Unit 235893, Lee, MA 01238
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  /2

  $289,000

  • Land
  • 3.69 Acres
  • $78,320 per Acre

  0 Interlaken Cross Rd, Stockbridge, MA 01262

  A pristine building lot in the heart of the Berkshires! Parcel B at Echo Valley is a 3.69-acre wooded, buildable lot offering a beautiful blank canvas for your dream home. Located off Interlaken Cross Road in Stockbridge, MA, this level parcel is easy to work with and provides excellent flexibility for siting your house, garage, and outdoor living spaces. Just minutes from Tanglewood, Stockbridge

  Lisa Berry Simply Sell Realty

  0 Interlaken Cross Rd, Stockbridge, MA 01262
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  /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

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