Lenox Dale, MA Homes for Sale

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  /4

  $500,000

  • Land
  • 3.44 Acres
  • $145,349 per Acre

  117 Lime Kiln Rd, Lenox, MA 01240

  Ready to build! Build your own Berkshire Home on this beautiful 3.44 acre parcel in the heart of the Berkshires! The land is partially cleared and ready for construction, with septic design plans already with public water and power on the street. Set on a quiet road, this property offers privacy with a true Berkshire feel while being close to many cultural attractions including, Tanglewood, The

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  (413) 393-2997

  117 Lime Kiln Rd, Lenox, MA 01240
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  /46

  $1,280,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd, Lenox, MA 01240

  Set within a private enclave of luxury homes just moments from downtown Lenox, this exceptional Berkshires condominium offers a rare combination of refined design, extraordinary privacy, and protected long-range views.Positioned at the far end of the development, the home benefits from owned development rights that safeguard sweeping easterly views of October Mountain and preserve the surrounding

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 319-9976

  18 Highcrest Rd, Lenox, MA 01240
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  /42

  $2,649,000

  • 6 Beds
  • 6.5 Baths
  • 6,225 Sq Ft

  250 West St, Lenox, MA 01240

  Seconds—not minutes—from Tanglewood’s main gate, this reimagined contemporary estate in Lenox is tucked into a sunlit woodland setting offering rare privacy and unrivaled proximity. Originally built in 2017 and completely updated in 2020, the home features soaring ceilings, rich mahogany and cherry finishes, a chef’s kitchen, and multiple entertaining spaces. The ground-floor primary suite is

  

  Selina Lamb

  Birch Properties

  (413) 423-1264

  250 West St, Lenox, MA 01240
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  /42

  $1,280,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd Unit 20, Lenox, MA 01240

  

  Selina Lamb

  Birch Properties

  (413) 591-5654

  18 Highcrest Rd Unit 20, Lenox, MA 01240
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  /4

  $215,000

  • Land
  • 14.3 Acres
  • $15,035 per Acre

  L16 Reservoir Rd, Out-Of State, MA 99999

  Discover an unparalleled opportunity with this stunning 14.3-acre parcel, perfect for building your dream home or if needed, subdividing into its original three lots. Featuring a pre-installed driveway, electrical service with a transformer, and a large 36 x 50 foundation that was started for a garage/barn, this property is both convenient and versatile. Enjoy the natural beauty of streams,

  

  Gary Fuls Jr

  Gary L Fuls DBA Re/MAX Transit

  (866) 819-0148

  L16 Reservoir Rd, Out-Of State, MA 99999
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  /43

  $445,000

  • 2 Beds
  • 3 Baths
  • 1,814 Sq Ft

  35 Chapman Rd, Pittsfield, MA 01201

  Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  (413) 323-3512

  35 Chapman Rd, Pittsfield, MA 01201
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  /6

  $150,000

  • Land
  • 3.01 Acres
  • $49,834 per Acre

  230 Chanterwood Rd, Lee, MA 01238

  Priced below assessed value, this is the perfect canvas for your dream home! This 3-acre corner lot is tucked away on one of Lee's most desirable roads, offering a blend of privacy and accessibility. Enjoy the serenity of nature while still being just minutes from everything that makes the Berkshires special- 5 minutes to the Premium Outlets and Mass Pike, and a short drive to world-renowned

  Jessie Carlino MACCARO REAL ESTATE

  230 Chanterwood Rd, Lee, MA 01238
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  /46

  $749,000

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  360 Housatonic St, Lenox, MA 01240

  Lenox MA Colonial on 0.92 acres with 4 bedrooms, 2.5 baths, and 2,184 sq ft of well maintained living space. This move in ready Berkshire home features a spacious eat-in kitchen, formal dining room, bright living room with wood floors, and a screened porch overlooking the yard. Enjoy outdoor living with two decks, a paver patio with BBQ area, and beautiful perennial gardens. Upstairs offers four

  Samantha Homeyer BIRCH PROPERTIES

  360 Housatonic St, Lenox, MA 01240
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  /11

  $85,000

  • Land
  • 9.44 Acres
  • $9,004 per Acre

  800 Cape St, Lee, MA 01238

  Exceptional opportunity in East Lee! 9.44 acres located in the desirable RB zone offering a flexible mix of residential and business uses. This expansive parcel provides the ideal setting for a residence, live/work concept with plenty of room for creative possibilities. Enjoy a peaceful Berkshire setting while maintaining convenient access to Lee, Lenox, and the Mass Pike. Whether you are looking

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  800 Cape St, Lee, MA 01238
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  /41

  $4,850,000

  • 13 Beds
  • 13.5 Baths
  • 9,510 Sq Ft

  2 Kemble St, Lenox, MA 01240

  The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental.The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  2 Kemble St, Lenox, MA 01240
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  /6

  $34,900

  • 1 Bed
  • 780 Sq Ft

  155 Water St Unit 5, Lee, MA 01238

  Opportunity awaits in Lee! Located at 155 Water Street #5, this mobile home has been fully gutted and is ready for a complete renovation. A true blank slate, offering endless potential for investors, contractors, or buyers looking to customize from the ground up.Major improvements have already been started, including a brand-new roof and new doors. Custom-sized windows have been purchased and are

  Cheryl Ryan BISHOP WEST REAL ESTATE

  155 Water St Unit 5, Lee, MA 01238
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  /23

  $179,000

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft

  735 Cape St, Lee, MA 01238

  Great price for this charming three bedroom, one full bath single level home with detached garage and outbuilding. Many improvements made over the years, including vinyl windows, connection to town sewer, electrical service and breaker box, well, galvanized oil tank and furnace. Some TLC needed but a great starter home with amazing potential. Conveniently located just minutes to the center of

  Cortney Dupont COHEN & WHITE ASSOCIATES

  735 Cape St, Lee, MA 01238
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  /23

  $3,400,000

  • 14 Beds
  • 16.5 Baths
  • 11,945 Sq Ft

  615 Laurel St, Lee, MA 01238

  An exceptional opportunity awaits at 615 Laurel Street, Lee, MA, presenting a property of enduring character with 530 feet of lakefront. The expansive interior environment encompasses fourteen dedicated bedrooms, each offering an individual sanctuary for rest and rejuvenation. Complementing these private quarters are sixteen full bathrooms, providing unparalleled comfort and convenience

  Mitchell B Muroff Mitchell B. Muroff

  615 Laurel St, Lee, MA 01238
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  /49

  $625,000

  • 4 Beds
  • 2 Baths
  • 1,960 Sq Ft

  121 West Rd, Lee, MA 01238

  Set on a quiet road just minutes from downtown Lee and downtown Stockbridge, this renovated extended Cape offers space and privacy. Nearly the entire home has been thoughtfully updated while maintaining warmth and character throughout. Front blue stone patio, wonderful mudroom/breezeway that adds everyday convenience and connects the home to the garage. The main level offers a bright eat-in

  Lisa Kelley MACCARO REAL ESTATE

  121 West Rd, Lee, MA 01238
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  /86

  $1,590,000

  • 4 Beds
  • 3.5 Baths
  • 3,805 Sq Ft

  130 E Dugway Rd, Lenox, MA 01240

  Two beautifully landscaped acres with perennial gardens blooming throughout the season. An exceptional 10-room home offers privacy, views, and effortless Berkshire living just minutes from downtown Lenox and Tanglewood. The home features an open and inviting layout with a fireplaced living room and a chef's kitchen designed for gathering and entertaining. A stunning four-season sunroom

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  130 E Dugway Rd, Lenox, MA 01240
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  /80

  $1,400,000

  • 4 Beds
  • 4 Baths
  • 3,379 Sq Ft

  2 Saint Andrews Ct, Lenox, MA 01240

  Welcome to elegant single-level living in one of Lenox's most coveted locations. Ideally positioned on prestigious Saint Andrews Drive, this exceptional home offers privacy, comfort, and stunning views--just minutes from the heart of the Berkshires.This expansive 3,379-square-foot residence features four bedrooms and four full baths, thoughtfully designed for both everyday living and

  Jose Larios LAMACCHIA REALTY, INC

  2 Saint Andrews Ct, Lenox, MA 01240
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  /36

  $278,800

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

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

  Looking for one-level living in the heart of the Berkshires? Comfort, convenience and move-in-ready appeal is what you'll find at this Heron Pond condo! Well-maintained, 1 br/1ba unit filled with natural light includes living room, separate dining room, updated bath and galley kitchen. Outside, relax on your own stone patio. Enjoy peaceful surroundings, the pond, and beautifully kept grounds.

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
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  /53

  $449,000

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

  500 Walker St, Lenox, MA 01242

  Charming 3 bedroom, 2 bath spacious New England Farmhouse with wide board pine floors, updated kitchen & baths, natural gas heat & hot water, vinyl replacement windows, home office/den and first floor laundry room/mudroom. New beautiful 20x18 bluestone patio & retaining wall installed in 2022.

  Matt Carlino MACCARO REAL ESTATE

  500 Walker St, Lenox, MA 01242
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  /48

  $974,999

  • 6 Beds
  • 9 Baths
  • 4,652 Sq Ft

  560 Stockbridge Rd, Lee, MA 01238

  Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room,

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  560 Stockbridge Rd, Lee, MA 01238
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  /34

  $535,000

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

  31 Saint Ann's Ave, Lenox, MA 01240

  This charming bungalow offers the Lenox lifestyle you've been dreaming of ✨ Located on a quiet dead-end street just steps from downtown, enjoy morning coffee, local dining, or evenings at Tanglewood before strolling home under the stars 🌙Inside, approximately 1,700 square feet blends warmth and comfort--perfect as a second home, weekend escape, or full-time living. There is also

  Amy Shufelt BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
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  /47

  $337,500

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

  7 Rolling Hills Unit 7-1, Lenox, MA 01240

  Think spring in the Berkshires and enjoy condo living in Lenox at Rolling Hills. Spacious end unit brings in natural light and offers two bedrooms/two baths on upper level with an additional full bath and family room/office on the finished lower level. In this unit owners have replaced the custom-sized slider and the windows adding to energy efficiency. Central a/c, natural gas. The former golf

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  7 Rolling Hills Unit 7-1, Lenox, MA 01240
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  /49

  $859,900

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

  135 East St, Lee, MA 01238

  Custom built home! 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 doors lead

  Lisa Kelley MACCARO REAL ESTATE

  135 East St, Lee, MA 01238
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  /15

  $358,000

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  4 Morgan Manor Unit 4, Lenox, MA 01240

  Lenox in-town condo.....ready for a new owner, need a close location to Tanglewood, Shakespeare and Company, The Mount, Venfort Hall, Kennedy Park, Pleasant Valley Wildlife Sanctuary? Well this is the perfect location!2 bedrooms, 1 full bath, wood floors and carpeted bedrooms, great light ....fully applianced kitchen....Easy to show!

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  4 Morgan Manor Unit 4, Lenox, MA 01240
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  /30

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft

  200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262

  Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
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  /60

  $2,185,000

  • 3 Beds
  • 3.5 Baths
  • 4,752 Sq Ft

  14 Old Tree Farm Rd, Stockbridge, MA 01262

  A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking

  Claire Pollart WILLIAM RAVEIS - BERKSHIRE

  14 Old Tree Farm Rd, Stockbridge, MA 01262
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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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  /56

  $1,490,000

  • 4 Beds
  • 4.5 Baths
  • 3,991 Sq Ft

  9 October Hill Dr, Lenox, MA 01240

  Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a

  Paula McLean PAULA MCLEAN REALTORS INC.

  9 October Hill Dr, Lenox, MA 01240
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  /43

  $495,000

  • 3 Beds
  • 1.5 Baths
  • 1,686 Sq Ft

  155 Laurel St, Lee, MA 01238

  This thoughtfully updated home blends warmth, comfort, and history. An amazing front porch welcomes you before you even step inside, and the short walk to downtown or quick drive to the lake offers an easy, connected Berkshire lifestyle. Inside, bright and inviting rooms and beautiful wood floors create a natural sense of warmth, while the layout makes everyday living feel effortless. Flexible

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  155 Laurel St, Lee, MA 01238
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  /42

  $1,399,900

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

  45 Forest St, Lee, MA 01238

  This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. 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

  Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

  45 Forest St, Lee, MA 01238
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  /12

  $485,000

  • 1 Bed
  • 1 Bath
  • 1,344 Sq Ft

  2 Devon Rd, Lee, MA 01238

  Bring your contractors and your imagination to this unique fixer-upper, an old carriage barn with an attached apartment. The spacious barn features original beams with large open areas. The lush grounds are complemented by charming rock walls and rustic outbuildings. With a convenient location close to all the Berkshire attractions, this property is ideal for transformation into a one-of-a-kind

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  2 Devon Rd, Lee, MA 01238
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  /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
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  /28

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  46 Housatonic St Unit 2B, Lenox, MA 01240

  Beautiful two bedroom, two bath condo perfectly situated in the center of Lenox, Massachusetts-the cultural heart of the Berkshires. Enjoy high Ceilings, beautiful wood floors, large windows, and abundant natural light throughout. The spacious layout features a gas fireplace, granite countertops, and a gas stove in the modern kitchen. The inviting living room opens to a private balcony, perfect

  Patricia Andrew STONE HOUSE PROPERTIES, LLC

  46 Housatonic St Unit 2B, Lenox, MA 01240
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  /50

  $7,975,000

  • 8 Beds
  • 6.5 Baths
  • 9,364 Sq Ft

  399 Under Mountain Rd, Lenox, MA 01240

  Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  399 Under Mountain Rd, Lenox, MA 01240
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  /39

  $759,000

  • 3 Beds
  • 2.5 Baths
  • 2,381 Sq Ft

  103 Alpine Trail, Pittsfield, MA 01201

  Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open

  Cortney Dupont COHEN & WHITE ASSOCIATES

  103 Alpine Trail, Pittsfield, MA 01201
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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

  MOTIVATED SELLER! 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

  Cortney Dupont COHEN & WHITE ASSOCIATES

  19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
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  /8

  $449,000

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

  180 Center St, Lee, MA 01238

  Huge price adjustment! 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

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  180 Center St, Lee, MA 01238
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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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  /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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  /45

  $349,900

  • 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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