Lenox Real Estate

Welcome to Lenox, Massachusetts – a charming gem nestled in the heart of the picturesque Berkshire County. This quaint town is renowned for its stunning natural beauty, vibrant cultural scene, and rich history, making it a perfect destination for both residents and visitors alike.

Lenox is surrounded by the breathtaking landscapes of the Berkshire Mountains, offering an array of outdoor activities year-round. Whether you enjoy hiking along scenic trails, skiing down powdery slopes in winter, or simply soaking in the serene views, Lenox provides a perfect backdrop for nature enthusiasts. The town is also home to the iconic Tanglewood Music Center, the summer home of the Boston Symphony Orchestra, where the magic of music fills the air during the warmer months.

In addition to its cultural offerings, Lenox boasts a charming downtown area filled with boutique shops, art galleries, and delightful restaurants that cater to every palate. Stroll along the tree-lined streets and discover local artisans and unique finds, or indulge in a farm-to-table dining experience that showcases the best of the region’s culinary delights.

Rich in history, Lenox features beautifully preserved architecture, including the historic Ventfort Hall Mansion and Gilded Age Museum, which offers a glimpse into the opulent lifestyles of the past. The town’s warm and welcoming community fosters a sense of belonging, making it an ideal place to call home.

With its captivating blend of nature, culture, and history, Lenox, MA, invites you to explore its charm and discover the perfect place to create lasting memories. Come experience the magic of Lenox – where every day feels like a getaway!

Newest Listings in Lenox

$2,295,000

31 Baths ⋅ 73567766 MLS

A rare opportunity to acquire an established 11.90± acre campus in Lenox, Massachusetts, with substantial institutional infrastructure and educational use permitted by right within the property's R1A residential zoning district.At its center is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The historic mansion has served as the academic and administrative center of Hillcrest Educational Center, with classrooms, offices, and gathering spaces throughout. Original details remain, including handsome woodwork, fireplaces, and a striking ballroom; the house also historically included bedrooms on its upper floors.The campus includes two dormitory buildings with approximately 24 bedrooms and shared common spaces, plus a separate multi-level academic/support building with commercial kitchen and dining facilities, classrooms, offices, library, conference, and medical/infirmary spaces. A substantial gymnasium offers potential for athletics, fitness, indoor tennis, pickleball, squash, wellness programming, or other recreational uses. Additional support buildings, parking, internal circulation, public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, and commercial sprinklering in select buildings support continued campus operation.The property is zoned R1A residential, with educational use permitted by right. Any alternative use, subdivision, or redevelopment is subject to Town of Lenox zoning and applicable approvals.Hillcrest currently operates on the property under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518283.Offered at $2,295,000.

349 Old Stockbridge Rd, Lenox

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.

$2,295,000

31 Beds ⋅ 29 Baths ⋅ 73567764 MLS

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 mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate—historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.

349 Old Stockbridge Rd, Lenox

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.

$879,000

3 Beds ⋅ 3 Baths ⋅ 73563529 MLS

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 retreat—along with 2.5 updated bathrooms. Downstairs, a vast, full open basement provides endless possibilities for exceptional storage, a home gym, or a recreation room. Beyond the interior, your ultimate outdoor sanctuary awaits in a professionally landscaped, fully fenced-in yard lined with a lush hemlock hedge for total privacy. Spend sunny summer days lounging by the sparkling in-ground saltwater pool, while the built-in swing set adds ready-to-use fun for family and guests. Complete with major exterior upgrades including an updated roof, newer siding, a spacious 2-car garage, and a shed, this exceptional property delivers total peace of mind and the best of Berkshire living right at your doorstep.

22 Post Rd, Lenox

Listing courtesy of Listing Agent: The Allain Group from Listing Office: Compass.

$279,900

3 Beds ⋅ 2 Baths ⋅ 73559755 MLS

Large well maintained Colonial on a half acre lot. Large open kitchen with lots of cabinet space. Sliders off kitchen leading to back deck. Bright and sunny living space with a bonus den or office. 3 full sized bedrooms. 2 full baths. Laundry hookups on 2nd floor for convenience. Seller willing to buy down the mortgage rate on this home. One year American Home Shield Warranty included. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

528 Walker St, Lenox

Listing courtesy of Listing Agent: Bob DeVito from Listing Office: Cameron Real Estate Group.

$3,195,000

34 Beds ⋅ 31 Baths ⋅ 73518284 MLS

Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways, parking, public water, sprinkler systems, mixed heating, and up to 600 amp electrical service. Also included is a 1,826 SF residence on 4.74± acres across three contiguous parcels offering additional flexibility. Currently operated as an educational campus, the property offers compelling long-term potential for institutional, residential, wellness, medical, hospitality, or mixed-use concepts. Buyers to conduct due diligence.

349 Old Stockbridge Rd, Lenox

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.

$3,195,000

31 Baths ⋅ 73518283 MLS

349 Old Stockbridge Rd, Lenox

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.

$4,850,000

13 Beds ⋅ 14 Baths ⋅ 73496031 MLS

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 strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

2 Kemble, Lenox

Listing courtesy of Listing Agent: Cameron Volastro from Listing Office: William Pitt Sotheby's International Realty.

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