186 properties for sale in Lenox Dale

Pristine, Move-In Ready End-Unit with Unobstructed Meadow Views and Paid-in-Full Assessment Skip the stress, delays, and skyrocketing costs of renovating a fixer-upper. This exceptional, updated end-unit in the highly sought-after Rolling Hills community offers the ultimate move-in-ready Berkshires retreat, combining premium privacy with unmatched financial value. While other units in the area may require immediate, out-of-pocket improvements, this home is completely updated and waiting for you. The Premium Location Advantage Positioned as a rare end-unit, this property offers a level of privacy most units simply cannot match. Your living spaces look out onto gorgeous, unobstructed views of protected meadows and woodlands. Watch deer, foxes, turkeys, and vibrant birdlife change with the seasons directly from your private deck and sliding glass windows. Resort-Style Amenities Just 4 Minutes from Historic Lenox Center Leave the lawn care and snow removal behind. Your monthly fees grant y

Rare opportunity to own a beautifully restored Berkshire cottage at 17 Main Street, perfectly situated in the vibrant heart of downtown Lenox. This remarkable property, originally built in 1883 and once the residence of Gilded Age shipping magnate John Schermerhorn, combines historic elegance with modern comfort. The home underwent a comprehensive renovation between 2021 and 2025, including 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-ideal for private entertaining or everyday living. All systems are new, including a four-zone HVAC and seven mini-splits for year-round comfort. With eight bedrooms (plus potential for a ninth), five fireplaces with new gas log sets, and inviting communal spaces, this home offers in-town living at its best. Enjoy the ultimate walk-to-everything life

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The secon

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 warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite-pool, fitness center, clubhouse, and tennis-all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see

Luxury Living at Twelve Oaks Village - Privacy, Elegance and Mountain Views Discover an exceptional blend of luxury, comfort, and privacy in this beautifully situated end-unit condominium at Twelve Oaks Village. Nestled at the end of a peaceful cul-de-sac, this spacious residence offers stunning easterly views of October Mountain and three full levels of thoughtfully designed living space. Built in 2004, this elegant 4-bedroom, 5-bath residence features a gracious open floor plan, ideal for both intimate gatherings and effortless entertaining. The desirable first-floor primary suite, complete with a walk-in closet, offers the convenience of main-level living. A screened porch and private deck invite you to relax, dine, and take in the tranquil natural surroundings. With generous accommodations for family and guests, this home offers the perfect balance of private retreats and inviting gathering spaces. Enjoy the exceptional amenities of Twelve Oaks Village, including tennis courts, a s

Exceptional investment opportunity in the heart of the Berkshires! Mixed use building featuring six residential apartments and one street level commercial storefront in a high visibility Main Street location. Minutes from the Massachusetts Turnpike, this property offers easy access as a gateway to the Berkshires. Diversified income potential from residential and commercial tenants. This property is in a highly desirable location

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 featuring high-end Bosch appliances, hardwood floors, tiled baths, in-unit laundry, central air, natural gas heat, and an abundance of windows. All major systems have been updated, providing modern comfort and efficiency while complementing the property's historic character. Both primary bedrooms featu

Terrific opportunity to own a piece of Historic Lenox. Set back from the road, secluded by deciduous shade tree. Spacious front lawn and close to village This is a diamond in the rough and with some sweat equity could be a shining star. Original wood floors throughout. One car garage and garden shed in backyard which is very private. HW heater 1 yr old. Enclosed Porch has new footings and roof is about 8 years old. Call today for your private viewing. Won't last long

This charming and move-in ready home invites you to settle into an easy Berkshire lifestyle. The first floor offers the comfort of one-level living, with a bedroom, full bath, laundry, and welcoming living spaces, while the second floor provides additional bedrooms and room for guests. Recent updates include an updated electrical service, refreshed interiors, and a beautiful enclosed porch made for slow mornings and quiet evenings. Just moments from shopping and dining, with downtown Lenox minutes away, Bousquet Mountain Ski Resort and Sports Center 4 minutes away, and Tanglewood about 10 minutes away. Spend your days exploring scenic trails, discovering local favorites, or enjoying the beauty of the Berkshires in every season

Welcome to 34 School Street in Lee, the Gateway to the Berkshires! Walk to downtown shops, restaurants, and local attractions from this spacious 8-room, 4-bedroom, 2-full-bath home. Freshly painted throughout, this inviting home features beautiful hardwood floors, first-floor laundry, and a versatile floor plan offering the possibility of a first-floor bedroom. Enjoy two enclosed porches, one in front and one in back, providing additional space to relax. An oversized two-car garage offers plenty of room for vehicles, storage, or hobbies. A separate fenced yard is ideal for pets, young children, or outdoor enjoyment. Convenient to interstate highways, cultural attractions, and all the Berkshires have to offer. A wonderful combination of location, charm, and flexibility!

Enjoy easy one level living in this open floor plan all one level home with detached 2 car garage. Natural gas heat, public water and sewer, newer roof with solar panels on a lease -(see document tab) Nice deck with mountain views. Tons of potential, all on a flat 2 acre lot. This is a fixer upper, priced below assessemnt and is being sold as is. Subject to probate license to sell

Full of character and opportunity, this well-maintained brick Dutch Gambrel offers a versatile two-family layout in a convenient location close to downtown Lee. The first-floor unit features 1 bedroom and 1 bathroom, while the second-floor apartment offers 2 bedrooms and 1 bathroom. Both units provide warm, inviting living spaces with hardwood floors and separate heating systems for added comfort and convenience. Whether you're looking to expand your investment portfolio or seeking an owner-occupied property with rental income potential, this home offers plenty of possibilities. Enjoy easy access to downtown Lee, scenic hiking and biking trails, October Mountain, Tanglewood, local theaters, restaurants, shopping, and all the amenities that make South Berkshire County such a desirable plac to live. A wonderful opportunity to own a distinctive property in a prime location!

Opportunity to complete this renovation. Extensive site work has already been completed. $25,000 of Tree removal in 2022, kerosene tank removal in 2022, New Septic system designed and installed in 2023, Asbestos Remediation in 2025, New roof with new 3/4 plywood board in 2025, Installed 3 new remote controlled skylights in 2025, 3 more trees removed in 2025, U-driveway installed in 2025. Deeded Lake Rights and private beach for Owners Only. House is directly across from the path to the beach. Goose Pond is noted to be one of the cleanest lakes in Massachusetts. Finish this renovation or add a foundation of build your dream home in this highly sought after Lake Community

Bring your vision to this true fixer-upper offering plenty of potential for the right buyer! This 3-bedroom, 1.5-bath home features beautiful hardwood floors in portions of the home, along with an oversized garage offering ample space for parking, storage, or a workshop. The property is in need of updating and renovation, providing an opportunity to restore, reimagine, and make it your own. Conveniently located just minutes from downtown Lee and I-90, with easy access to many of the Berkshires' popular attractions, shopping, dining, and outdoor recreation. A great opportunity for a buyer ready to roll up their sleeves and bring new life to this property!

Turn-key Berkshire retreat! Beautifully renovated throughout, this contemporary chalet feels like a brand-new home. Cathedral ceiling, abundant windows, and an open concept living, dining and kitchen area create a bright, inviting atmosphere. The main level features a primary bedroom with an en-suite bathroom, plus a convenient half bath with laundry hook-ups. The second level offers an open loft, overlooking the main living area, complemented by an additional bedroom and full bathroom. A finished walk-out lower level provides wonderful space for recreation, family room or guests. Enjoy the spacious deck in this natural setting with intermittent stream and no HOA! Convenient to Jacobs's Pillow, Tanglewood and the Berkshires cultural and recreational venues, with easy access to I-90

Beautiful 3-bedroom, 2-bath ranch home offering an inviting layout, excellent flow, and plenty of room to spread out across 2,448 square feet. You'll never feel cramped in this spacious and comfortable home. The location is hard to beat-just minutes from downtown Lee and a short drive to downtown Lenox, yet tucked away on a peaceful country road. Enjoy scenic pastoral and mountain views while walking through the neighborhood, or step onto The Pinnacle, a town-owned hiking trail located just steps from your door. After a day of exploring, relax on the back deck and take in the tranquil country setting

Enjoy light filled living in this prime end unit at beautiful October Mountain. 'Gateway to the Berkshires', Lee, Ma. Open concept living and dining area features a two-sided wood burning fireplace shared with a vaulted family room, where skylights add to the abundant natural light throughout the home. Mini splits provide heating and cooling for year-round comfort. First floor bedroom and full bath and walk in shower. Second floor offers two additional spacious bedrooms and full bath. Primary bedroom offers two generous closets and newer carpeting. A full, unfinished basement offers ample storage and potential for future use. Great location across from the community pool and tennis courts. Easy access to I-90 and cultural venues, dining and attractions that make the Berkshires so special!

Immaculate unit in move-in condition. 1st floor bedroom and a 1st floor stall shower with glass door. Hugh 3 season room with glass and screens to enjoy the Berkshire air. Hardwood floors in living and dining area. Upscale stainless steel refrigerator and Bosch Dishwasher. Two bedrooms and full bath with tub/shower upstairs. Unfinished lower level with work bench, brand new washer and (older) dryer. Village at Oct Mtn offers heated pool, har-tru tennix courts, EV charging, canoe/kayak racks. Central location to all the cultural activities and restaurants. The condo fee of $702.97 (actually paid quarterly) is broken down into two portions. 1.)contribution to capital reserves $212.50 plus 2.) $490.48 towards operating expenses

Charming home brimming with character and far more space than meets the eye! A lovely front porch with mahogany floors welcomes you to gracious living and dining spaces, wood floors throughout, and a stately fireplaced living room. The updated kitchen features an abundance of cherry cabinetry, plus a first-floor laundry, half-bath, den, and a useful office addition. Upstairs offers three ample bedrooms-including a primary with his/hers closets-and an updated bathroom with a walk-in shower. The walk-up attic provides additional storage or could easily be finished. Outside, find a detached one-car garage, large back deck and a great fenced-in back yard perfect for pets and fun. Sidewalks to town; minutes to Laurel Lake and Lenox. A well loved and cared for home, ready for its next chapter!

Living history awaits your vision! Own a piece of history dating back to the 1700's -one of the oldest homes in Lee. A captivating antique home that began its story over two centuries ago, with a significant brick addition in the 1800's. The results are layers of character rarely found today. Living and dining rooms with fireplaces, Four bedrooms and two baths offer solid bones for a savvy renovator, and the bonus walk-in attic is a hidden gem - vaulted ceiling, back staircase ready to add creative space. This is a true marathon investment for someone who sees beyond the to-do list to the incredible potential underneath. Storied charm, endless possibility, bring your vision and make history your own. Two car garage, set on almost an acre of open sunny land on a quiet country road

Sweet, well-maintained Cape-style home just up the hill from downtown Lee, offering 3 bedrooms on nearly half an acre. The home features a recently remodeled kitchen with maple cabinets and granite countertops, newly remodeled bathroom, enclosed front porch, and insulated second-floor bonus room with flexible living space. Recent improvements include newer electrical wiring, a roof approximately seven years old, and a furnace approximately twelve years old. The fenced backyard is an exceptional retreat with a new in-ground pool and retractable cover, hot tub, separate 10' x 16' heated studio/pool house, and garden shed. Walk to downtown Lee and the golf course, with easy access to the Mass Pike. Enjoy the Berkshires from this convenient Lee location, approximately 7 miles from Tanglewood and 10 miles from Jacob's Pillow. Nearby Goose Pond and Laurel Lake offer opportunities for swimming, boating, fishing, hiking, and enjoying the outdoors. The separate 10' x 16' studio/pool house has e

Experience upscale, maintenance-free living in desirable Devon Meadows, where the beauty and tranquility of the Berkshires meet exceptional comfort and convenience. Ideally located near Lenox and Stockbridge and just 5 minutes from Tanglewood, this impressive luxury condominium places you close to the heart of the region's renowned cultural, dining, shopping, and outdoor attractions while offering the peaceful surroundings of a country setting. Designed with both everyday living and entertaining in mind, the home features a spacious, open floor plan with an easy flow between living areas. The first floor provides the convenience of one-level living with a generous primary bedroom suite and first-floor laundry. A versatile fifth bedroom on this level offers flexibility and could easily serve as a private home office, den, library, or comfortable guest room. The second floor provides additional space for family and guests with three generously sized bedrooms and two full baths. A spaciou

Enjoy downtown living in this 4 Bedroom 2 Bath New England farmhouse. Zoning is Residential and Business. Built in the early20th century, this home has a diverse use of residential, commercial or mixed use on a residential street. The kitchen has been updated with plenty of cabinet space. A cozy living room fireplace and a enclosed porch with numerous windows that welcome fresh summertime breezes and a patio with fenced private yard for summer leisure living. Convenient to all Berkshire cultural and recreational attractions

This charming and historic sweet country home is located walking distance to the quintessential New England town of Lee situated in the majestic Berkshires. This home has been used as a short term rental with outstanding rental history. This would be a dream primary home or vacation home. Lots of flexibility if you are looking for a 2nd home get away that produces income when you are not there. Large center island butcher block country kitchen. Beamed ceilings in kitchen, dining room and living room. Three full, absolutely spectacular upgraded luxury bathrooms. walk up finished attic and a welcoming front porch. The yard is just perfectly magical offering privacy for entertaining with a large fire-pit and outdoor dining area. So many updates perfectly mingled with old world charm and character. Fall in love with this charmer !

EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for entertaining. A stunning wrought iron detail by Ivan Bailey enhances the staircase. A media room with glass-paned sliders and built-in bookcases completes the exceptional living space. The first floor primary ensuite is a true retreat, boasting a soaring vaulted ceiling and two large walk-in closets. The second floor offers three additional bed rooms, and two full baths. A large screen porch and patio takes in the lovely landscape. A three-car garage completes this magnificent property located in centrally located Stockbridge. Central to all Berkshire County and cultural venues!

A UNIQUE OPPORTUNITY TO OWN A SPACIOUS LENOX HOME IN A PRIVATE, COUNTRY SETTING AT A REASONABLE PRICE. 4BR, 2.5 BATHS, WITH HARDWOOD FLOORS, OPEN KITCHEN/DINING AREA, LARGE OPEN DECK, PELLET STOVE AND AN IN-GROUND POOL. LOVELY LANDSCAPING WITH STONE WALLS, GARDENS AND OPEN LAWN AREA FOR ATHLETICS OR JUST RELAXING. GREAT CENTRAL LOCATION, A SHORT DISTANCE TO TANGLEWOOD, TOWN AND YOUR FAVORITE BERKSHIRE ATTRACTIONS AND CULTURAL EVENTS

Enjoy easy one level living in this open floor plan all one level home with detached 2 car garage. Natural gas heat, public water and sewer, newer roof with solar panels on a lease -(see document tab) Nice deck with mountain views. Tons of potential, all on a flat 2 acre lot. This is a fixer upper, priced below assessemnt and is being sold as is. Subject to probate license to sell

HOME BEING SOLD AS IS NO NEGOTIATION ON INSPECTION ISSUES. THE PRICE IS NOT NEGOTIABLE. Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom, 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer

'A Perfect Place Farm' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for. a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley

Dramatic Price Reduction creates opportunity for updates and remodel. Gracefully situated on a gentle sloping hillside street this distinctively designed, quality built, multi-level home offers distant neighborhood mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home to embrace privacy, natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined residence is a private enclave offering 4-5 bedrooms, 3 full bath, masterfully landscaped set on 1.5 acres with unique tree selection, blooming shrubs and pollinator flowering perrenials. Just 10 minutes to the culture, cuisine and art offerings of Lenox especially the sounds of Tanglewood. Minutes to all that is Berkshire while being immersed in renowned peaceful Follow the gently curved stone stairway to the covered front porch and enter into an open and spacious entry with an intriguing glimpse of flowers exquisitely private. Be welcomed into a graciously siz