Luxury homes for sale & real estate in 01240, MA

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ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the

$2,295,000

31 beds21.5 baths38,415 sq ft

Original mansion • Handsome woodwork • 11.90 acres

349 Old Stockbridge Rd, Lenox, MA 01240

NEW 30 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Move-in ready and beautifully upgraded, freestanding home offers the ease of one-level living paired with over 4,600 sf over three finished levels. Four br, 4.5 bat and a walkout lower level. Live at the desirable Miraval golf/resort campus. Hardwood floors flow throughout the main living area, anchored by a striking double-sided fireplace wi stone hearth connecting the living and family rooms. Custom shades throughout add a polished, designer touch. Rear deck offers magnificent views of October Mountain. Upper level includes open loft, private office, 2 br with en-suite baths. Lower level extends the living space significantly, ideal for guests with bedroom, bath, media/exercise room, glas

$1,950,000

4 beds4.5 baths4,612 sq ft

Freestanding home • Private office • Open loft

9 Fairwynds Dr, Lenox, MA 01240

FLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Crosby House, a property with a storied Lenox history and a location second to none, presents a rare opportunity to own a residence of remarkable character, scale, and flexibility in the heart of the village. Currently configured as two spacious residences, this distinctive multifamily property offers an exceptional array of possibilities. Subject to applicable zoning, permitting, and approvals, the existing configuration may offer the potential to be thoughtfully combined into one extraordinary single-family residence or could provide the foundation for two highly distinctive condominium residences. Each residence offers two plus bedrooms and two full baths, along with generous kitchens fe

$1,685,000

4 beds4 baths3,282 sq ft

Private deck • Flexible spaces • Historic character

30 Cliffwood St, Lenox, MA 01240

FLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet

$879,000

3 beds2.5 baths2,262 sq ft

Cozy gas fireplace • Updated windows • 0.99 acre lot

22 Post Rd, Lenox, MA 01240

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Extraordinary opportunity to own a showcase of New England history and hospitality--17 Main Street, a masterfully restored Berkshire cottage in the vibrant heart of downtown Lenox. Originally built in 1883 and once owned by Gilded Age shipping magnate John Schermerhorn, this landmark property blends historic grandeur with modern comfort. Between 2021 and 2025, the residence underwent a comprehensive top-to-bottom renovation: a new 30-year roof, upgraded electrical and plumbing, 8.5 renovated bathrooms, custom millwork, and restored original hardwood floors. The gourmet kitchen features a Viking 8-burner oven, KitchenAid designer dishwasher, and commercial-grade refrigeration--perfect for bo

$3,925,000

8 beds8.5 baths6,000 sq ft

New 30-year roof • Renovated bathrooms • Gourmet kitchen

17 Main St, Lenox, MA 01240

Property at 41 Tucker St, Lenox, MA 01240, 3 beds, 4 baths

$1,400,000

3 beds4 baths3,740 sq ft

41 Tucker St, Lenox, MA 01240

Property at 165 Kemble St #18, Lenox, MA 01240, 3 beds, 3.5 baths

$4,150,000

3 beds3.5 baths3,348 sq ft

165 Kemble St #18, Lenox, MA 01240

Property at 7 Wheatley Dr, Stockbridge, MA 01262, 4 beds, 4 baths

$2,950,000

4 beds4 baths5,696 sq ft

7 Wheatley Dr, Stockbridge, MA 01262

Property at 11 Hawthorne, Stockbridge, MA 01262, 19 beds, 23 baths

$14,500,000

19 beds23 baths19,364 sq ft

11 Hawthorne, Stockbridge, MA 01262

Property at 14 Fairway Dr, Lenox, MA 01240, 6 beds, 5.5 baths

$1,595,000

6 beds5.5 baths4,099 sq ft

14 Fairway Dr, Lenox, MA 01240

Property at 11 Hawthorne Rd, West Stockbridge, MA 01266, 19 beds, 23 baths

$14,500,000

19 beds23 baths19,364 sq ft

11 Hawthorne Rd, West Stockbridge, MA 01266

Property at 20 E Dugway Rd, Lenox, MA 01240, 7 beds, 6.5 baths

$1,650,000

7 beds6.5 baths5,693 sq ft

20 E Dugway Rd, Lenox, MA 01240

Property at 2 Kemble, Lenox, MA 01240, 13 beds, 13.5 baths

$4,850,000

13 beds13.5 baths9,510 sq ft

2 Kemble, Lenox, MA 01240

Property at 3 A Coldbrooke Dr, Lenox, MA 01240, 4 beds, 3.5 baths

$1,399,000

4 beds3.5 baths2,968 sq ft

3 A Coldbrooke Dr, Lenox, MA 01240

Property at 18 Highcrest Rd, Lenox, MA 01240, 4 beds, 4.5 baths

$1,039,000

4 beds4.5 baths3,691 sq ft

18 Highcrest Rd, Lenox, MA 01240

Property at 399 Under Mountain Rd, Lenox, MA 01240, 8 beds, 6.5 baths

$7,975,000

8 beds6.5 baths9,364 sq ft

399 Under Mountain Rd, Lenox, MA 01240

Property at 9 October Hill Dr, Lenox, MA 01240, 4 beds, 4.5 baths

$1,190,000

4 beds4.5 baths3,991 sq ft

9 October Hill Dr, Lenox, MA 01240

$1,400,000

Land14.60 acres (lot)

286 Lee Rd, Lenox, MA 01240

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ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Nestled on 7.79 private mountaintop acres, this distinguished 1916 Italianate Berkshire Cottage sparkles with original architectural details, beautiful fireplaces throughout, and a stunning reflection pool surrounded by mature gardens. Four spacious bedrooms include a luxurious primary suite with sitting room, while the grand great hall creates perfect spaces for both intimate gatherings and gracious entertaining. The lower level features an elegant one-bedroom guest apartment plus a separate catering kitchen, utility rooms and two one car garages, while the main house enjoys lovely terraces facing south, east and west. Surrounded by 200 protected acres near world-class Tanglewood - your ow

$1,525,000

5 beds4.5 baths8,866 sq ft

Mature gardens • Grand great hall • 7.79 acre lot

720 South St, Pittsfield, MA 01201

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Fabulous historic church. Located in the Stockbridge hamlet of Interlaken. Quiet and exclusive neighborhood just off Rt. 183. Stylishly decorated by a renowned architect and designer. High ceilings, huge windows, and mahogany fittings. Beautifully restored kitchen with many original details. Marble topped sink/counter. Walk through to the magnificent living area to step back in time to an earlier era. Then on to the nave to enjoy soaring ceilings, oversized windows and room for entertaining. Enjoy this 'party space. ' Or use for an artist studio, recording studio or any pastime that needs space. Minutes to Berkshire Botanical Garden, Tanglewood and the center of Historic Stockbridge.

$1,200,000

1 bed1 bath3,556 sq ft

Restored kitchen • Soaring ceilings • Renowned architect

6 Willard Hill Rd, Stockbridge, MA 01262

FLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Some homes offer extraordinary settings. Others offer exceptional living. Rarely does one offer both. Embracing its extraordinary setting, this classic center hall Colonial is all about the way it lives. The heart of the home is an inviting open kitchen with a breakfast nook and a beautiful sitting area where walls of glass and French doors open to a stunning stone patio, tranquil waterfall, and exquisitely landscaped gardens. The adjoining dining room and front-to-back living room with a soaring cathedral ceiling and charming fireplace create warm, inviting spaces for family gatherings and entertaining. A magnificent 1800 sf post & beam barn with cathedral ceilings offers endless pos

$1,999,999

3 beds3.5 baths3,000 sq ft

Breakfast nook • Landscaped gardens • Tranquil waterfall

14 Old Tree Farm Rd, Stockbridge, MA 01262

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Bring your BOAT and enjoy all that the Stockbridge Bowl has to offer. This charming home has deeded rights to the lake, as well as its own dock space! The house was recently renovated with all top of the line mechanicals and appliances. Bosch, Miele, & Fisher Paykel. Central AC. One level living with two bedrooms and two full baths. Open concept living with a large front deck and yard for entertaining. Inside is an original log fireplace for those chilly winter nights. All new cedar lined closets and freshly painted throughout. A three-minute walk to your boatslip and private neighborhood dock, you can sit and watch the sunset from the best spot on the bowl. Make an appointment to vie

$949,000

2 beds2 baths1,125 sq ft

Own dock space • Cedar lined closets • 0.44 acre lot

10 Mahkeenac Ter, Stockbridge, MA 01262

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-s

$4,975,000

3 beds3.5 baths4,359 sq ft

Vermont slate • 10.73 acre lot • 2 garage spots

5 Deer Hill Rd, West Stockbridge, MA 01266

ABOUT THIS HOME
Luxury Home for sale in 01240, MA:
A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is

$2,800,000

8 beds5.5 baths6,761 sq ft

Wine cellar • Billiards room • Intricate millwork

497 Holmes Rd, Pittsfield, MA 01201

Property at 161 Turkey Trot Rd, Richmond, MA 01254, 5 beds, 4.5 baths

$1,560,000

5 beds4.5 baths3,409 sq ft

161 Turkey Trot Rd, Richmond, MA 01254

Property at 236 Main St, Lee, MA 01238, 10 beds, 6.5 baths

$975,000

10 beds6.5 baths9,024 sq ft

236 Main St, Lee, MA 01238

Property at 16 Old Tree Farm Rd, Stockbridge, MA 01262, 5 beds, 4.5 baths

$2,995,000

5 beds4.5 baths3,862 sq ft

16 Old Tree Farm Rd, Stockbridge, MA 01262

Property at 851 Lenox Rd, Richmond, MA 01254, 4 beds, 3.5 baths

$1,050,000

4 beds3.5 baths3,984 sq ft

851 Lenox Rd, Richmond, MA 01254

Property at 2650 Swamp Rd, Richmond, MA 01254, 5 beds, 7 baths

$3,495,000

5 beds7 baths6,022 sq ft

2650 Swamp Rd, Richmond, MA 01254

Property at 10 Mahkeenac Shores Rd, Stockbridge, MA 01262, 4 beds, 3 baths

$1,999,000

4 beds3 baths1,932 sq ft

10 Mahkeenac Shores Rd, Stockbridge, MA 01262

Property at 802 State Rd, Richmond, MA 01254, 7 beds, 7.5 baths

$2,950,000

7 beds7.5 baths4,000 sq ft

802 State Rd, Richmond, MA 01254

Property at 160 High St, Lee, MA 01238, 4 beds, 5 baths

$995,000

4 beds5 baths6,300 sq ft

160 High St, Lee, MA 01238

Property at 752 State Rd, Richmond, MA 01254, 4 beds, 5 baths

$2,200,000

4 beds5 baths5,821 sq ft

752 State Rd, Richmond, MA 01254

Property at 21 Dan Fox Dr, Pittsfield, MA 01201

$898,000

Land12.84 acres (lot)

21 Dan Fox Dr, Pittsfield, MA 01201

Luxury Homes for Sale in 01240

There are currently 18 luxury homes for sale in 01240 at a median listing price of $914K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 01240 stay on the market for 60 days. This map is refreshed with the newest listings in 01240 every 15 minutes.

In the past month, 9 homes have been sold in 01240. In addition to houses in 01240, there were also 12 condos, 1 townhouse, and 2 multi-family units for sale in 01240 last month. Find your dream home in 01240 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 01240 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 01240. If you're looking to sell your home in the 01240 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 01240 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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