Homes for Sale near Lenox Memorial High School

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.

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial

Paula McLean PAULA MCLEAN REALTORS INC.

AVAILABLE TO RENT FROM 10/1/2026 TO MAY 30, 2027. Perfectly located within 10 minutes to Tanglewood, this all one floor Ranch home is fully furnished and nicely appointed. The Galway Court neighborhood experiences limited traffic situations while making the trip to the center of Lenox and its shops and restaurants an easy bike ride for anyone so inclined. Like to golf? The Miraval Country Club is

George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout

Molly Gillon COMPASS MASSACHUSETTS , LLC GB

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

Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

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,

Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

Iconic Lenox home: very rarely does a home with this historic integrity come on the market...now is your time to continue its legacy . Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining

Mary Jo Piretti PIRETTI REAL ESTATE

Totally renovated and move-in ready mobile home in Lenox! This 2-bedroom home is located on a quiet dead-end street in the Berkshire Mobile Park and offers a nice deck along with an ample side yard to enjoy. Shed in the back needs some repairs to the roof.

Tanya Shepardson Lamacchia Realty, Inc. - Dalton

Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Fantastic Offer! Custom-designed & beautifully maintained one-owner residence offering 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm & Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community & the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens & music. A beautiful open floor plan features a

Heather Gallagher STONE HOUSE PROPERTIES, LLC

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

Tyler Scaglione Cameron Real Estate Group

Enjoy easy Berkshire living in this recently updated, bright and inviting 2-bedroom, 950 sq. ft. top-floor condo. An oversized slider brings in an abundance of natural light and creates a more open, spacious feel. Set within a pet-friendly community, residents enjoy a gas BBQ/picnic area, children's playground, tennis and pickleball courts, heated pool & walking trails. Comfortable and

Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

Lovely Lenox Condo in the Beautiful Berkshires. Welcome home to this exceptional end-unit condominium at Rolling Hills in Lenox, offering a wonderful combination of comfort, privacy, scenic surroundings, and Berkshire lifestyle. This beautifully updated 3-bedroom, 3-full-bath residence offers approximately 1,552 square feet of living space with thoughtful improvements throughout. The inviting

Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly

Suzann Ward HOUSATONIC REAL ESTATE

Don't miss this Lenox beauty tucked away on a quiet side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

Enjoy effortless living in this beautifully renovated, move-in ready condo, perfectly situated between the vibrant energy of Pittsfield and the charm of Lenox center.This one-bedroom condo features brand new carpeting, generous closet space, and a modern kitchen with newer cabinetry and an updated bathroom. Natural light fills the living space, where sliding glass doors lead you to a private

Molly Gillon COMPASS MASSACHUSETTS , LLC GB

Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with

Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

Spacious first-floor one-bedroom, one-bath apartment at 55 Crystal St in Lenoxdale. This unit features a large open-concept living, dining, and kitchen area with plenty of natural light and stainless steel appliances. The generously sized bedroom offers ample closet space, and the full bathroom includes a tub/shower. Heat is included in the rent, helping keep monthly expenses predictable. The

Christian Garner NOCHER REALTY

STUNNING VIEWS for as far as you can see from this modern unit located in Winden Hills Vanna building. Open common spaces washed in natural light; Great room with scenic views, fireplace and built ins, kitchen with charm and character open to dining. Primary w/en suite full bath, two guest bedrooms and additional one and half baths. This unit comes with access to the elevator for convenience, a

Cortney Dupont COHEN & WHITE ASSOCIATES

Enchanting Lenox Cottage minutes to Tanglewood- 2 Bedroom / 2 Full Bath RetreatThe bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch & 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand-new back deck, an ideal setting for summer evenings. 2 Bedrooms on second floor, with

Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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

India Ward NON-MEMBER / RECIPROCAL

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

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living

Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

Envision waking up in this beautifully renovated New England farmhouse in quaint Lenoxdale Village. Enjoy morning sunrises on the front patio and quiet evening dinners on the terrace, all just minutes from the world-class culture of Tanglewood and the iconic downtowns of Lenox and Stockbridge. Inside, original hardwood floors flow throughout a versatile layout featuring 3-4 bedrooms, a cozy

Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON