33

Lenox Dale, MA Homes for Sale with Acreage

Section Image Section Image
  • /6

    $425,000

    • Land
    • 3.30 Acres
    • $128,788 per Acre

    9 Wheatleigh Dr, Stockbridge, MA 01262

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

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 722-5098

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • /5

    $998,000

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

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

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

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 343-4919

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
  • /40

    $1,795,000

    • 4 Beds
    • 3 Baths
    • 5,469 Sq Ft

    17 East St, Lenox, MA 01240

    Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 300-6860

    17 East St, Lenox, MA 01240
  • /6

    $425,000

    • Land
    • 3.30 Acres
    • $128,788 per Acre

    9 Wheatleigh Dr, Stockbridge, MA 01262

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

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 343-5283

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • /82

    $2,550,000

    • 6 Beds
    • 6.5 Baths
    • 7,143 Sq Ft

    13 Taconic Ave, Lenox, MA 01240

    An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every

    Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

    13 Taconic Ave, Lenox, MA 01240
  • /45

    $1,499,000

    • 4 Beds
    • 4.5 Baths
    • 3,190 Sq Ft

    121 E Dugway Rd, Lenox, MA 01240

    Stunning Georgian Colonial style home on a lovely 4A private lot is ready for its new owners! In pristine condition, this 4 BR, 4.5 baths home offers hardwood floors throughout, first floor Primary Suite, open great room concept with cherry cabinetry in kitchen and granite counters, gas fireplace in the great room, formal dining or music room and first floor study with full bath. The second

    Mary Jo Piretti PIRETTI REAL ESTATE

    121 E Dugway Rd, Lenox, MA 01240
  • /70

    $1,290,000 Open Sun 1:30PM - 3:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,844 Sq Ft

    257 W Mountain Rd, Lenox, MA 01240

    Nestled in the heart of the Berkshires, 257 W Mountain Road offers a rare blend of luxury and tranquility. This exquisite property is set on a serene, tree-lined road just minutes from downtown Lenox and Tanglewood. With refined finishes, spacious living areas, and walls of windows framing the lush landscape, every detail reflects elegance and comfort. The landscaped grounds feature stone

    Nicole Moore KELLER WILLIAMS REALTY

    257 W Mountain Rd, Lenox, MA 01240
  • /50

    $1,950,000

    • 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
  • /50

    $2,250,000

    • 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
  • /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
  • /25

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,325 Sq Ft

    18 East St, Stockbridge, MA 01262

    Set back on 2 private acres yet just 0.7 miles from Stockbridge's Norman Rockwell charm, this 1958 Cape offers the rare combination of village walkability and true privacy. Thoughtfully updated with lovely proportions throughout, it flows from kitchen to living room with wood-burning fireplace. The 1st-floor bedroom with full bath offers flexibility, while upstairs are two more bedrooms and a

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    18 East St, Stockbridge, MA 01262
  • /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
  • /26

    $425,000

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    153 E Dugway Rd, Lenox, MA 01240

    **Opportunity Awaits!**Great Lenox location. Three bedroom, one bath Ranch style home is nestled on 1.14 acres of land on a picturesque street, this gem offers 1344 sq ft on the main floor, with a full walkout lower level to a beautiful large yard. Minutes to downtown, Tanglewood and the best of the Berkshires.

    Matt Carlino MACCARO REAL ESTATE

    153 E Dugway Rd, Lenox, MA 01240
  • /29

    $912,000

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

    21 East St, Stockbridge, MA 01262

    **Price Improvement** Nestled in the heart of the Berkshires, this spacious Colonial sits on over 14 acres, offering privacy, potential, and long-term value. Currently operating as a doggy day care, but you wouldn't know it when you walk inside! Well-maintained & cared for. Recent updates include the kitchen, bathrooms, carpets, back deck, and front landscaping, while still leaving room for

    Brianna Boffoli Cameron Prestige, LLC

    21 East St, Stockbridge, MA 01262
  • /6

    $290,000

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

    249 Pittsfield Rd, Lenox, MA 01240

    Opportunity knocks in the Berkshires! 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 gas, public water, and public sewer,

    Jessie Downer LAMACCHIA REALTY, INC

    249 Pittsfield Rd, Lenox, MA 01240
  • /29

    $698,200

    • 4 Beds
    • 2 Baths
    • 1,850 Sq Ft

    170 Stockbridge Rd, Lee, MA 01238

    Charming 1930s Retreat with Water Views and Historic Charm - 170 Stockbridge Road, Lee MANestled just five minutes from both Stockbridge and the village of Lee, this beautifully restored 1930s gem offers the best of Berkshire living. Located near world-class cultural destinations--including Tanglewood, The Norman Rockwell Museum, and Jacob's Pillow--this home sits on a desirable lot overlooking

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    170 Stockbridge Rd, Lee, MA 01238
  • /49

    $650,000

    • 4 Beds
    • 2.5 Baths
    • 2,265 Sq Ft

    7 Cedar Ln, Lenox, MA 01240

    Improved Price! Four bedroom, 2.5 bath, 2265 sq. ft., move in ready home awaits you! 2018 renovated kitchen with granite counters opens to a natural light filled breakfast nook from sliders that open to an expansive Trex deck (2018). A double sided wood burning brick fireplace finishes off this handsome layout. The other side of the fire place opens to a den with sliders. Living room, dining

    Margaret Apkin WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    7 Cedar Ln, Lenox, MA 01240
  • /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
  • /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
  • /11

    $39,900

    • Land
    • 1.90 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
  • /10

    $199,000

    • Land
    • 1.31 Acres
    • $151,907 per Acre

    245 Spring St, Lee, MA 01238

    One of two beautiful building lots available on Spring Street, Lee. Lee has been voted one of the top 10 northeastern small towns in New England. Idyllic setting on quiet country road yet 2 miles from Stockbridge, 3 miles to Tanglewood, and 5 minutes to Laurel Lake! Build your dream home and enjoy all the Berkshires has to offer! Beautiful place to live, ample outdoor recreation, farm to table

    Lisa Kelley MACCARO REAL ESTATE

    245 Spring St, Lee, MA 01238
  • /82

    $595,000

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

    35 Chapman Rd, Pittsfield, MA 01201

    Country living at its best, with mountain views and plenty of land! This property features a renovated farmhouse, 2 car garage, 1 outbuilding and Barn all sitting on 9+ acres. It's only a few hundred feet from the Lenox townline, where Chapman Rd turns into East St. Pittsfield-Lenox Rd (Rt 20) is just around the corner. To be honest, I'm not going to overwhelm you with a lot of descriptions of

    Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    35 Chapman Rd, Pittsfield, MA 01201
  • /8

    $199,000

    • Land
    • 1.31 Acres
    • $152,025 per Acre

    235 Spring St, Lee, MA 01238

    Beautiful building lot available on Spring Street, Lee. Voted one of the top 10 small northeastern towns in New England! Idyllic setting on quiet country road yet 2 miles from Stockbridge, 3 miles to Tanglewood, and 5 minutes to Laurel Lake! Build your dream home and enjoy all the Berkshires has to offer! Beautiful place to live, ample outdoor recreation, farm to table food and world class

    Lisa Kelley MACCARO REAL ESTATE

    235 Spring St, Lee, MA 01238
  • /5

    $385,900

    • Land
    • 16 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
  • /26

    $574,900

    • 3 Beds
    • 2 Baths
    • 1,858 Sq Ft

    178 New Lenox Rd, Lenox, MA 01240

    Summer Special - $5,000 seller contribution to buyer (for closing costs, decorating, furnishings - your choice!) for closing on or before 8/29/25. Move-in ready Lenox 3 bed 2 full bath with mountain views on 1 acre. Large screened back porch and front 3- season room. Town water and sewer, natural gas heat and see-through wild-life fence protects huge backyard. Recent updates - new roof, gutters,

    Sean Taylor MORESI REAL ESTATE PARTNERS

    178 New Lenox Rd, Lenox, MA 01240
  • /9

    $589,000

    • Land
    • 21 Acres
    • $28,222 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
  • /50

    $1,125,000

    • 9 Beds
    • 9 Baths
    • 5,690 Sq Ft

    465 Chapel St, Lee, MA 01238

    Prime Investment Opportunity - Fully Occupied 9-Unit Victorian on 2.5 Acres!This exceptional income-producing property features a beautifully maintained Victorian-style building with nine rental units--a mix of studios, four 1-bedroom units, and one spacious 2-bedroom apartment with open-concept kitchens. Situated on 2.5 acres, the property offers ample off-street parking for 15 cars, a

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    465 Chapel St, Lee, MA 01238
  • /26

    $239,000

    • Land
    • 8 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
  • /75

    $2,895,000

    • 7 Beds
    • 9 Baths
    • 6,578 Sq Ft

    813 East St, Lenox, MA 01240

    Don't miss seeing the beautiful renovation just completed on this lovely Lenox Contemporary on almost 5A of privacy...enjoy incredible outdoor living spaces including an in-ground Gunite pool, Pavilion with outdoor kitchen and pool house with living space, kitchen, outdoor and indoor showers and even an outdoor TV! A real STAYCATION! The main house boasts lovely common spaces in the open floor

    Mary Jo Piretti PIRETTI REAL ESTATE

    813 East St, Lenox, MA 01240
  • /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
  • /7

    $89,500

    • Land
    • 1.42 Acres
    • $63,028 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
  • /2

    $39,900

    • Land
    • 2.40 Acres
    • $16,625 per Acre

    294 Antelope Dr, Lee, MA 01238

    Welcome to Leisure Lee! Nestled on the banks of Goose Pond, one of the most desirable lakes in Berkshire County, this community has so much going for it. Access to a sandy beach, boating, kayaking, and tennis courts, this friendly neighborhood is fun and relaxing. Enjoy nature and make lasting friendships, while exploring all that the area has to offer.Come and see this 2.4 acre, wooded parcel

    Lauren Rosen LANCE VERMEULEN RE, INC

    294 Antelope Dr, Lee, MA 01238
  • /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 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
How to Buy a Home How to Finance a Home How to Sell a Home