Homes for Sale near Hillcrest Educational Centers

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  /20

  $3,799,000

  • 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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  /14

  $199,500

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

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

  Light, updated, and move in ready this 1BR/1BA, 800 sq ft condo at Lenox Heights offers easy Berkshire living minutes to downtown Lenox and Tanglewood. The renovated kitchen features crisp cabinetry and stainless appliances, opening to a sunny living/dining area with sliders to a private rear balcony, perfect for morning coffee or unwinding after a show. Plush wall-to-wall carpeting creates a

  Samantha Homeyer BIRCH PROPERTIES

  260 Pittsfield Rd Unit B-5, Lenox, MA 01240
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  /18

  $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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  /49

  $949,000

  • 1 Bed
  • 1.5 Baths
  • 3,810 Sq Ft

  30 Great Barrington Rd, West Stockbridge, MA 01266

  The renovation of this 1930's Cape Cod by a master craftsman and his designer wife into the stunning modern day Contemporary it is today, while preserving some of the original highlights,is nothing short of a design miracle. The immense Great Room with the 60 foot wall of glass overlooking the terraced stone wall that leads to a stream and pine forest is the focal point of this special home. The

  Cortney Dupont COHEN & WHITE ASSOCIATES

  30 Great Barrington Rd, West Stockbridge, MA 01266
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  /41

  $635,000

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

  4 Main St, West Stockbridge, MA 01266

  Don't miss this one-of-a-kind opportunity to own a commercially zoned, mixed-use property offering exceptional live/work potential in a prime in-town location along the Williams River. Whether you're a small business owner, creative entrepreneur, or someone creating a unique lifestyle setup - this is your opportunity to own a space that works as hard as you do. This efficiently designed

  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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  /27

  $935,000

  • 4 Beds
  • 4 Baths
  • 2,280 Sq Ft

  21 East St, Stockbridge, MA 01262

  Nestled in the heart of the Berkshires, this spacious Colonial on 14+ acres offers privacy, potential, and long-term value. With only two owners, it's been well cared for and currently functions as a private residence and doggy daycare. Updates include the kitchen, baths, carpets, back deck, and landscaping--while still leaving room for added equity. Features include solar panels, well water, a

  Brianna Boffoli NON-MEMBER / RECIPROCAL

  21 East St, Stockbridge, MA 01262
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  /59

  $859,900

  • 4 Beds
  • 3 Baths
  • 2,732 Sq Ft

  135 East St, Lee, MA 01238

  Rustic Style Expansive Cape. Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French

  Lisa Kelley MACCARO REAL ESTATE

  135 East St, Lee, MA 01238
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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

  $949,000

  • 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

  $1,950,000

  • 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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  /24

  $285,000

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

  2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

  Come experience this charming condo in the beautiful Heron Pond Community in Stockbridge. Thoughtful use of space with large, private front patio facing expansive manicured lawns and gardens. Enjoy 1-level living, (1-bed,1-bath with separate dining room) fully applianced kitchen with pantry and instant boiling water faucet. Washer and Dryer included. Zoned smart heating thermostats.

  Patricia Andrew STONE HOUSE PROPERTIES, LLC

  2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
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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

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

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

  $620,000

  • 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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  /45

  $549,000

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

  31 Saint Ann's Ave, Lenox, MA 01240

  OPEN HOUSE Sunday Sept. 21, 2025 from12-2pm!Beautifully located near downtown Lenox!The Claude and Louise Delahaye House is tucked away on peaceful St. Ann's Ave, just steps from the iconic St. Ann's Church!Lenox's shops, dining, and cultural attractions are just a stroll away!Inside, 1,700 sq ft of tastefully updated living space blends preserved period details with modern touches. OWN - Instead

  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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  /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
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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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  /17

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  lot 1 N Beckett, Lee, MA 01238

  Single Family modular home on 3 Acres of land, in a serene and beautiful setting. There are two Modular homes to pick from, the New Haven and the Rolling Brook. Nestled in a peaceful, wooded landscape, this lot offers a perfect blend of privacy and natural beauty while being conveniently located. Minutes to walking trails, Basin Pond, and Finery Pond are at your back yard. Lenox and Stockbridge's

  The Mary Scimemi Team Leading Edge Real Estate

  lot 1 N Beckett, Lee, MA 01238
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  /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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  /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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  /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
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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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  /45

  $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, and all Berkshire attractions! Premier Unit at Stockbridge Terrace! Enjoy peaceful living on a quiet cul-de-sac with limited number ofunits. The main level living setup is perfect, featuring a large primary bedroom with an en-suite bath and walk-in closet, an open-concept kitchen that has been recently updated complete

  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 - PITTSFIELD

  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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  /26

  $239,000

  • Land
  • 7.83 Acres
  • $30,508 per Acre

  13 Rattlesnake Mountain Rd, Stockbridge, MA 01262

  PRIME BERKSHIRE LAND - FEEL 'AWAY FROM IT ALL' YET YOU ARE MOMENTS FROM THE BEST OF THE BERKSHIRES. $158,000+ UNDER ASSESSED VALUESet on a serene & forested country road, this location makes the perfect retreat - yet you are in the heart of the Berkshires just minutes to Stockbridge & Lenox, Tanglewood, The Bowl, The Mount, Kripalu, Great Barrington, the Pike, shopping & more. The single home

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
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  /41

  $1,499,900

  • 12 Beds
  • 7 Baths
  • 7,956 Sq Ft

  45 Forest St, Lee, MA 01238

  This stunning 6-family home sits on 1.5 acres, just a couple minutes away from the Lee Outlets, a convenient location with easy access to the Mass Pike. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and primary bedroom on the the 1st floor, and 3 bedrooms

  Maria Liccardi Lamacchia Realty, Inc.

  45 Forest St, Lee, MA 01238
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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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  /60

  $1,350,000

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

  82 Stockbridge Terrace, Lee, MA 01238

  Prepare to be wowed when you visit this fully furnished luxury condo at Stockbridge Terrace! Move-in ready and lightly lived in, this one-owner home features many custom finishes. Seeking one-level living? This condo delivers. Entertain in style with open floor plan. The living/great room's centerpiece is the stone fireplace, oversized windows and cherry floors. Enjoy the formal dining room or

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  82 Stockbridge Terrace, Lee, MA 01238
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  /4

  $549,000

  • 5 Beds
  • 3 Baths
  • 2,899 Sq Ft

  5, 15, 17 Fuller St, Lee, MA 01238

  Prime Commercial / Residential / Mixed-Use Development Parcel on Route 20. Corner Parcel. Almost a full Acre. Comprised of 2 Lots. High traffic count,. Zoning allows for several uses. **Includes 2 Residential Buildings that can be delivered tenanted, vacant or can be raised by Seller for an additional fee.(note: Property delineation lines on photographs are approximations only.)

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  5, 15, 17 Fuller St, Lee, MA 01238
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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

  $230,000 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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