Berkshire, MA Homes

/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

Selina Lamb

BIRCH PROPERTIES

(413) 300-6860

17 East St, Lenox, MA 01240
/17
$12,500 per month
- 3 Beds
- 2 Baths
- 1,861 Sq Ft
- House for Rent
5 Beachwood Dr, Stockbridge, MA 01262

Delightful, classic Berkshires summer cottage in the Beachwood enclave. Shares in gorgeous community beach at south end of the Stockbridge Bowl (Lake Mahkeenac.) Enjoy swimming, kayaking, etc. Minutes to Tanglewood and all the cultural delights of the Berkshires. 3BR including primary suite with bath. 1 Queen BR, 1 Br with double bunk beds. Fantastic large screened porch with dining. LR with

Selina Lamb

Birch Properties

(413) 610-3637

5 Beachwood Dr, Stockbridge, MA 01262
/34
$290,000 Sold Aug 04, 2025
- 1,584 Sq Ft
- $183/SF
- 6 Days On Market
- 3 Beds
- 1 Bath
- Built 1948
350 Laurel St, Lee, MA 01238

There is a charm of yesteryear with this three bedroom one bath cape. The first floor has a formal dining room with hardwood floors. A living room with a wood burning fireplace along with hardwood flooring under the carpet. The kitchen has retro metal cabinets with Formica counter tops. The second floor has the three bedrooms all with hardwood floors. The one bedroom above the garage has knotty

Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

350 Laurel St, Lee, MA 01238

/36
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,269 Sq Ft
4 Lee Rd, Lee, MA 01238

4 Lee Rd, Lee, MA 01238

/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.

Selina Lamb

Birch Properties

(413) 343-5283

9 Wheatleigh Dr, Stockbridge, MA 01262
/4

$1,305 - $3,447 per month

Forge

1 - 3 Beds

66 Brushwood Way, Lenox, MA 01240

Forge is a brand new mixed-income housing community currently under construction in Lenox, MA. The development will include 65 apartments within 13 townhome-style buildings, and a community clubhouse. Each building at Forge will contain 5-6 apartments, with a mix of one-, two-, and three-bedroom apartments available at various income tiers (30, 60, 120% AMI). Apartments will have their own

66 Brushwood Way, Lenox, MA 01240
/43
$450,000 Sold Aug 01, 2025
- 1,940 Sq Ft
- $232/SF
- 9 Days On Market
- 3 Beds
- 3 Baths
- Built 1968
60 Paul Dr, Lee, MA 01238

Expanded three- or four-bedroom ranch-style home offering the convenience of one-level living. The spacious living room is highlighted by a striking picture window with operable transom vents above, providing panoramic sunset views and refreshing cross-breezes. This classic mid-century design floods the space with natural light and is complemented by hardwood floors and a cozy wood-burning

Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

60 Paul Dr, Lee, MA 01238

/36
Not Listed For Sale
Unlisted Address

Unlisted Address

/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.

Selina Lamb

BIRCH PROPERTIES

(413) 722-5098

9 Wheatleigh Dr, Stockbridge, MA 01262
/11
$2,600 per month
- 3 Beds
- 1.5 Baths
- 1,165 Sq Ft
- Apartment for Rent
125 Center St Unit 2, Lee, MA 01238

Available Immediately! Second floor apartment. Three bedroom with a full bathroom and a half bathroom. In unit washer and dryer. The house is equipped with generator so you never have to worry about power outages again. Pets negotiable. First, last and security due at signing. Employment verification, background check, credit check and references required.

Timothy Dunn Venture

125 Center St Unit 2, Lee, MA 01238
/45
$1,150,000 Sold Jul 31, 2025
- 2,995 Sq Ft
- $384/SF
- 29 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2006
4 Stoneledge Rd, Lenox, MA 01240

Charming Lenox contemporary cape on 1 acre. Located in an area of fine homes, this 4 bedroom 4.5 bath home has the following amenities: Screen porch, eat in kitchen with island, family room with fireplace, primary bedroom suite on the main floor, dining room, den, attached two car garage, finished lower level ...great space office or exercise area... natural gas heat, central air, town water

Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

4 Stoneledge Rd, Lenox, MA 01240

/5
Est $29,006 Not Listed For Sale
Unlisted Address

Unlisted Address

/30
$2,450,000 Under Contract
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
165 Kemble St Unit 17, Lenox, MA 01240

Nestled within the serene, world-renowned Canyon Ranch Lenox campus, this bespoke two-bedroom, two-and-a-half-bath home is among the most private and luxuriously appointed in the Berkshires. A rare opportunity to own a residence where every detail--from architecture to finishes--echoes sophisticated European elegance while embracing the wellness-centered ethos of Canyon Ranch living.Inside,

Selina Lamb

BIRCH PROPERTIES

(413) 547-4966

165 Kemble St Unit 17, Lenox, MA 01240
/20

$1,082 per month

Lenox Schoolhouse Apartments

Studio

109 Housatonic St, Lenox, MA 01240

The Berkshires' newest community is NOW OPEN!!! Newly renovated studios and one bedrooms with ALL UTILITIES INCLUDED* - Spacious open layouts, brand new interiors, plush carpet, sunlit windows, abundant closet space. Lenox Schoolhouse Apartments is within walking distance to the center of town. Enjoy the local shops, art galleries, restaurants and entertainment. You'll be sure to experience

109 Housatonic St, Lenox, MA 01240
/52
$975,000 Sold Jul 25, 2025
- 2,010 Sq Ft
- $485/SF
- 10 Days On Market
- 4 Beds
- 3 Baths
- Built 1948
66 Interlaken Rd, Stockbridge, MA 01262

Handsome redesign and total renovation in 2017. Living space all on one convenient level. Light bright interior. Well-designed kitchen opens to the great room with cathedral ceiling, fireplace and access to the three-season porch. Primary suite privately set at one end of the house and additional 3 bedrooms and 2 baths (1 ensuite) at the other end of the house. Den. Beautiful wood floors.

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

66 Interlaken Rd, Stockbridge, MA 01262

/26
Est $446,289 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,538 Sq Ft
26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

/53
$2,649,000
- 6 Beds
- 6.5 Baths
- 4,289 Sq Ft
250 West St, Lenox, MA 01240

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

Selina Lamb

BIRCH PROPERTIES

(413) 423-1264

250 West St, Lenox, MA 01240
/20
$1,800 per month
- 1.5 Baths
- 1,920 Sq Ft
- Property for Rent
236 Main St, Lee, MA 01238

Prime location located on Main St. in Downtown Lee within a short walking distance to new EAGLE MILL development project with a total of 135 new housing units. This turnkey unit has been designed and used as a restaurant, deli and sandwich shop and has seating for 12 with parking in front and behind the building. Highly visible centrally located to serve the business and residential community.

Tim Gallagher STONE HOUSE PROPERTIES, LLC

236 Main St, Lee, MA 01238
/27
$265,000 Sold Jul 23, 2025
- 800 Sq Ft
- $331/SF
- 89 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1860
34 Church St Unit 2, Lenox, MA 01240

Discover the perfect opportunity in the heart of downtown Lenox with a Church Street view! This charming condo is an ideal choice for investors, second homeowners, or those seeking a convenient lifestyle. This unit boasts two bedrooms, two full baths, beautiful wood floors, and a cozy gas fireplace. You will immediately have access to various shops, restaurants, and Tanglewood just minutes away!

Jessica Rizzo Lamacchia Realty, Inc.

34 Church St Unit 2, Lenox, MA 01240

/22
Est $400,840 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,257 Sq Ft
410 Greylock St, Lee, MA 01238

410 Greylock St, Lee, MA 01238

/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

Selina Lamb

BIRCH PROPERTIES

(413) 343-4919

19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
/48
$2,900 per month
- 1 - 3 Beds
- 2 Baths
- 1,000 Sq Ft
- House for Rent
1579 Pleasant St, South Lee, MA 01260

Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.

1579 Pleasant St, South Lee, MA 01260
/25
$610,000 Sold Jul 22, 2025
- 1,720 Sq Ft
- $355/SF
- 11 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2011
2 Evergreen Trail, Lenox, MA 01240

Enjoy the peaceful life at Lenox Woods...look out your back windows or screened porch at conservation land and the occasional deer. And inside, you'll enjoy the open living with great room and gas fireplace, kitchen with granite, first floor Primary Suite with vaulted ceiling, plus the finished 2nd floor with family room, 2 large bedrooms with full bath in between and a sweet, newly finished 4th

Mary Jo Piretti PIRETTI REAL ESTATE

2 Evergreen Trail, Lenox, MA 01240

/25
Est $529,400 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,872 Sq Ft
280 Mandalay Rd, Lee, MA 01238

280 Mandalay Rd, Lee, MA 01238

/60
$5,150,000
- 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
/5
$12 per month
- 0.5 Baths
- 2,106 Sq Ft
- Property for Rent
10 Valley St, Lee, MA 01238

2106 SF OFFICE SPACE. Building B available for immediate occupancy. New bathroom. Ample power. LED lighting. Central Air. In addition to base rent of $12.00/sf/yr tenant pays for heat, electricity, security, trash removal, telecommunications renter's/liability insurance and taxes. Tenant, at tenants expense, may make alterations. Landlord pays for insurance, water & sewer, snow removal and

Rich Aldrich WILLIAM PITT SOTHEBY'S - LENOX

10 Valley St, Lee, MA 01238
/14
$396,200 Sold Jul 21, 2025
- 938 Sq Ft
- $422/SF
- 5 Days On Market
- 2 Beds
- 1 Bath
- Built 1968
5 Morgan Manor Unit 9, Lenox, MA 01240

This unit is the ''trifecta'' of Morgan Manor: first floor, 2 BR and with garage! Plus it's been fully renovated and has a gorgeous eat in cherry/granite/stainless kitchen, updated bath and beautiful hardwood floors throughout. Maintenance fees of $716/month include your heat, hot water, basic cable/internet and all exterior maintenance....furnishings available if you want to just bring your

Mary Jo Piretti PIRETTI REAL ESTATE

5 Morgan Manor Unit 9, Lenox, MA 01240

/34
Est $567,304 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,761 Sq Ft
15 Greylock St, Lee, MA 01238

15 Greylock St, Lee, MA 01238

/82
$2,550,000 Pending
- 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
/48
$3,600 per month
- 1 - 3 Beds
- 2 Baths
- 1,000 Sq Ft
- House for Rent
1579 Pleasant St, South Lee, MA 01260

Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.

1579 Pleasant St, South Lee, MA 01260
/37
$350,000 Sold Jul 18, 2025
- 1,919 Sq Ft
- $182/SF
- 37 Days On Market
- 4 Beds
- 2 Baths
- Built 1979
881 Holmes Rd, Pittsfield, MA 01201

Enjoy beautiful mountain views from this spacious 4-bedroom, 2-bath Pittsfield split-level on Holmes Road. Featuring a bright open layout, large picture windows, and fresh interior updates, this home offers a flexible floor plan with generous living space. The lower level includes space ideal for a home office or family room. Enjoy outdoor living on the rear deck and a large private yard. With a

Ed Rich BISHOP WEST REAL ESTATE

881 Holmes Rd, Pittsfield, MA 01201

/38
Est $413,270 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,569 Sq Ft
180 Forest St, Lee, MA 01238

180 Forest St, Lee, MA 01238

/29
$995,000
- 4 Beds
- 2.5 Baths
- 2,008 Sq Ft
9 Yale Hill Rd, Stockbridge, MA 01262

9 Yale Hill was built c1880 by prominent Berkshire architect Joseph McArthur Vance as a summer cottage for La Chaumiere in the village of Stockbridge, the estate up the hill. Artfully put together, the cottage is incredibly charming in its original details and lovely elements that have been added over the years. The house is tucked in amongst perennial gardens and beautiful neighboring homes. The

Annabel Taylor Four Seasons Sotheby's International Realty

9 Yale Hill Rd, Stockbridge, MA 01262
/48
$3,800 per month
- 1 - 3 Beds
- 2 Baths
- 1,000 Sq Ft
- House for Rent
1579 Pleasant St, South Lee, MA 01260

Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.

1579 Pleasant St, South Lee, MA 01260
/37
$400,000 Sold Jul 16, 2025
- 1,152 Sq Ft
- $347/SF
- 431 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
15 Elk Dr, Lee, MA 01238

Welcome to Leisure Lee -- where natural beauty meets modern comfort in the heart of the Berkshires.Nestled in a serene setting just moments from the crystal-clear waters of Goose Pond, this contemporary ranch-style home offers the perfect blend of relaxation, recreation, and year-round living. Leisure Lee is a private community treasured for its peaceful ambiance, exclusive lake access, and

Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

15 Elk Dr, Lee, MA 01238

/34
Est $307,199 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,360 Sq Ft
208 High St, Lee, MA 01238

208 High St, Lee, MA 01238

/46
$789,000
- 2 Beds
- 2.5 Baths
- 1,922 Sq Ft
19 Hawthorne Rd Unit GH 4, Stockbridge, MA 01262

This White Pines Garden Unit is a must see if you are considering condominium living in this sought after community. Open living Great Room/kitchen/dining with double volume glass to take in the view, fireplace & guest bath on main level. The lower level greets you with a tiled floor sunroom w/direct access to the spacious decking w/private courtyard outdoor space. The primary ensuite, guest

Mary Jane White COHEN & WHITE ASSOCIATES

19 Hawthorne Rd Unit GH 4, Stockbridge, MA 01262
/4
$2,400 per month
- 2 Beds
- 1 Bath
- 130 Sq Ft
- House for Rent
177 Laurel St, Lee, MA 01238

Located in Lee, is this 2BR, 1 Bath, duplex home, with updated bathroom tile floor, hardwood and laminated flooring throughout, freshly painted. No smoking 1st and last references and credit check

177 Laurel St, Lee, MA 01238
/49
$487,500 Sold Jul 15, 2025
- 3,210 Sq Ft
- $152/SF
- 17 Days On Market
- 6 Beds
- 2.5 Baths
- Built 1901
9 High St, Lenox, MA 01240

Nestled in one of the most desirable towns in the Berkshires, this charming multi-family home presents a rare and exciting opportunity for investors, contractors, or visionary homeowners. Set on a spacious and desirable lot, this as-is property is ready to be reimagined--offering the perfect canvas for renovation, expansion, or transformation. The home features two side-by-side living units, each

Diane Thorson WILLIAM PITT SOTHEBY'S - GT BARRINGTON

9 High St, Lenox, MA 01240

/49
Est $505,092 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,352 Sq Ft
85 Highfield Dr, Lee, MA 01238

85 Highfield Dr, Lee, MA 01238

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