Lenox Dale, MA Homes for Sale

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  /4

  $600,000

  • Land
  • 3.44 Acres
  • $174,419 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

  $1,420,000

  • 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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  /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.

  

  Selina Lamb

  Birch Properties

  (413) 343-5283

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /8

  $998,000

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

  19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

  Exceptional ready-to-build opportunity in the heart of the Berkshires. This rare 9.1-acre estate parcel offers direct frontage on tranquil Lily Pond, a private, non-motorized body of water known for its serenity, protected natural setting, and long, unobstructed views. A winding driveway follows a charming brook and leads across a brand-new bridge to an incredibly private pond-front building

  

  Selina Lamb

  Birch Properties

  (413) 343-4919

  19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
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  /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.

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 722-5098

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /42

  $1,650,000

  • 4 Beds
  • 3 Baths
  • 7,027 Sq Ft

  17 East St, Stockbridge, MA 01262

  Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with an addition that respects the original proportions while opening new possibilities for contemporary living. Set along the Stockbridge–Lenox corridor on 13+/- acres (9

  

  Selina Lamb

  Birch Properties

  (413) 300-6860

  17 East St, Stockbridge, MA 01262
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  /42

  $1,420,000

  • 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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  /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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  /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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  /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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  /42

  $435,000

  • 3 Beds
  • 1.5 Baths
  • 1,293 Sq Ft

  184 Washington Mountain Rd, Lee, MA 01238

  Welcome to 184 Washington Mountain Rd -- an inviting three-bedroom, one-and-a-half bath raised ranch ideally situated in a quiet, highly desirable location. This thoughtfully updated home features a stylish eat-in kitchen that flows seamlessly into a bright, open living area with direct access to a sunroom, creating the perfect space for relaxing or entertaining year-round. Beautiful hardwood

  The Mazzeo Duo BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  184 Washington Mountain Rd, Lee, MA 01238
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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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  /37

  $329,900

  • 3 Beds
  • 1.5 Baths
  • 1,563 Sq Ft

  1070 Holmes Rd, Pittsfield, MA 01201

  Wonderful home located at the southern end of Holmes Rd. Moments away from Tanglewood and other cultural attractions of the Berkshires. Close to skiing at Bousquet, shopping and restaurants. This ranch style home features a large living room with a fireplace. Formal dining room leads into the kitchen. Three good sized bedrooms, a full bath and half bath all on one level. The kitchen opens out to

  Derek Strzepa NOCHER REALTY

  1070 Holmes Rd, Pittsfield, MA 01201
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  /15

  $368,000

  • 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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  /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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  /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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  /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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  /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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  /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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  /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

  $499,000

  • 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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  /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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  /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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  /35

  $535,000

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

  31 Saint Ann's Ave, Lenox, MA 01240

  This charming bungalow offers the kind of lifestyle people come to the Berkshires dreaming about.! Tucked away on a quiet dead-end street just steps from the heart of Lenox, From here, you can walk into town for morning coffee, linger over dinner at your favorite local spot, or head to Tanglewood on a summer evening and travel back home under the stars. It's peaceful and private, yet perfectly

  Amy Shufelt BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
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  /58

  $469,900

  • 6 Beds
  • 3 Baths
  • 2,346 Sq Ft

  131 Center St, Lee, MA 01238

  *OPEN HOUSE Sat Feb 14th 10:30 am - 12 pmThis beautiful multifamily home consists of 3 two-bedroom apartments. One unit is currently rented while the other two units are vacant and have been recently renovated with new kitchens with quartz countertops, updated bathrooms, new lifeproof flooring, new carpeting and painting. These two apartments come with Lead Paint compliance certificates! Each one

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  131 Center 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.

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  0 East St Unit 235893, Lee, MA 01238
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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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  /7

  $150,000

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

  230 Chanterwood Rd, Lee, MA 01238

  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 rare blend of privacy and accessibility. Enjoy the serenity of nature while still being just minutes from everything that makes the Berkshires special--only 5 minutes to the Premium Outlets and Mass Pike, and a short drive to world-renowned cultural destinations like

  Jessie Carlino MACCARO REAL ESTATE

  230 Chanterwood Rd, Lee, MA 01238
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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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  /8

  $1,269,000

  • 6 Beds
  • 4 Baths
  • 3,334 Sq Ft

  1574 Pleasant St, Lee, MA 01260

  Ashley Rose NON-MEMBER / RECIPROCAL

  1574 Pleasant St, Lee, MA 01260
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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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  /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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  /40

  $499,500

  • 2 Beds
  • 1.5 Baths
  • 1,520 Sq Ft

  30 Clifden Ct Unit 2, Lenox, MA 01240

  Birchwood Village in Lenox! Conveniently located near the center of Lenox, Tanglewood and Miraval. This home offers two upstairs bedrooms, a great room with vaulted ceilings and a fireplace, a large kitchen/dining space, walk out flex space downstairs, deck and an attached garage.

  Marie Bourassa SIGNATURE ASSOCIATES

  30 Clifden Ct Unit 2, Lenox, MA 01240
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  /42

  $489,000

  • 4 Beds
  • 2 Baths
  • 2,234 Sq Ft

  140 Theresa Terrace, Lee, MA 01238

  Welcome to this solid, well-built four-bedroom, two-bath raised ranch, built in 1969 and nestled in a wonderful neighborhood just minutes from beautiful Laurel Lake. The main living area features a beautiful brick fireplace anchored in the center of the room, hardwood floors throughout the first floor, offering warmth and timeless appeal. This home provides a functional and flexible layout with a

  Lisa Kelley MACCARO REAL ESTATE

  140 Theresa Terrace, Lee, MA 01238
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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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  /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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  /23

  $215,000

  • 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 personal or business use. Featuring a brand new roof, the property is ideal for a variety of purposes, including retail, restaurant, residential, professional offices, or even a bed and

  Laiken Rapisarda Lamacchia Realty, Inc.

  1 Pittsfield Rd, Lenox, MA 01240
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  /14

  $172,950

  • Land
  • 3.6 Acres
  • $48,042 per Acre

  46 Pease Terrace, Lee, MA 01238

  Nestled in a quiet and private Lee neighborhood, at the end of a dead end street,this 3.6 (+-) parcel offers a perfect blend of seclusion and convenience. Thisserene setting is minutes to downtown Lee, local shops, restaurants, and all the cultural offerings of Berkshire County. Approximately half level and cleared, with unique rock formations and a woodedridge on the west side, this parcel is

  Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  46 Pease 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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  /51

  $599,900

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft

  40 Prospect Hill Rd, Stockbridge, MA 01262

  Location is everything with this light-filled contemporary ranch on Prospect Hill. Ready for quick occupancy! Five minutes from downtown Stockbridge or to Tanglewood and so close to the town beach on Stockbridge Bowl. This three bedroom, two bath home has been lovingly cared for. Living room and dining with hardwood floors, built-in shelving and built-in storage. Quality updates in the primary

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  40 Prospect Hill Rd, Stockbridge, MA 01262

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