186 properties for sale in Lenox Dale

Offered for the first time in 40 years, this White Pines condo is a rare opportunity to own a residence within one of Stockbridge's most storied properties. Rich with musical history, both White Pines and this particular residence have fascinating ties to local and international music scenes. Filled with natural light, this gracious two-bedroom, two-bath condominium offers generous living spaces and an inviting, easy flow. The beautiful great room is the heart of the home, with two distinct sitting areas and a dedicated dining space-ideal for both relaxed everyday living and entertaining. A large primary suite provides a private retreat, while the second bedroom and full bath offer flexible space for guests or creative pursuits. Set moments from Tanglewood and with exceptional access to Stockbridge Bowl, White Pines captures so much of what makes life in the Berkshires special. Residents enjoy a private beach on the Bowl with dedicated kayak storage, along with an indoor swimming pool

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 area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

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 area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

10 BEAUTIFUL PRIVATE ACRES. MOVE-IN READY HOME. ENDLESS POSSIBILITIES! The opportunity you've been waiting for! Set on 10 breathtaking private acres in beautiful Becket, this spacious 4-bedroom, 2-bath home, built in 2005, offers an exceptional combination of privacy, comfort, and untapped potential. The interior is move-in ready, allowing you to settle in immediately while making the property your own. A walkout lower level with impressive ceiling height offers exciting possibilities for additional finished living space. A Generac generator adds peace of mind. While the exterior could benefit from some TLC, the opportunity to make improvements, build equity, and create something truly special is undeniable. Whether you're seeking a peaceful country retreat, a year-round residence, or a property with room to grow, 10 private acres and a move-in ready home are a combination that's hard to beat. Bring your vision, embrace the possibilities, and make this incredible property your own!

This 2 Bedroom 3 full Bath townhouse has been tastefully renovated with granite counters, Stainless appliances and thought given to the smallest of details throughout. The multi levels give you a large open floor plan leading out to your deck where in the mornings you can enjoy the sunrise and relax in the evenings. On the lower level you have a family room, Studio or whatever fits your lifestyle, with unique closets and plenty of storage, Laundry and utility room with more storage space. This community has so much to offer, you'll have access to the Clubhouse, sauna, outdoor pool, tennis, walking trails, Community garden, storage for your Kayak and fenced dog park. Just in time to enjoy the Fall and Holiday season in the Berkshires. Restaurants and Shopping are just around the corner!

Beautiful ranch with attached garage and inground pool with new fence! Upon entering the home you will be welcomed by a cozy living room with wood burning fireplace. The kitchen is open to the dining area, which has sliders to the newer Trex deck with electric awning, backyard and pool. The primary bedroom offers two closets and private primary bathroom with walk-in shower. There are 2 additional bedrooms and full bathroom, for a total of 3 bedrooms and 2 baths. Vinyl siding, vinyl replacement windows, city water/sewer and a new high efficiency heat and hot water system complete this home! Plus there are two sheds! This home sits on 0.71 acres, and the adjacent 0.53 lot is also being included, for a total of 1.24 acres in the beautiful town of Lenox, just minutes from Tanglewood and town!

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 soaking tub and separate shower. Two additional bedrooms and full bath; all w hardwood flooring. Central a/c; natural gas heat/hot water; attached two-car garage. Easy maintenance perennial gardens with a focus on native and specimen plantings -over 100 species carefully planned to bloom continuously wowing sight and scent! Abutting preserved land with year-round brook-your own magical retreat!

Spacious 5-bedroom Colonial on a quiet dead end street in Lee, MA. Walk to downtown shops, restaurants and schools. The home features an open kitchen that flows into the dining area, great for entertaining. Also on the first level is a half bath, a den or office, and a spacious living room. A bonus front room/breezeway could be used for a home gym, mud room or hobby room. An attached 1 car garage, car port and large driveway for parking. Five upstairs bedrooms offer room for family, guests, or a home office. Enjoy the private backyard and distant mountain views. Minutes to the Mass Pike, Tanglewood, Kripalu, and Berkshire ski areas

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

Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra convenience. Enjoy morning coffee on the front porch or unwind in the private backyard-ideal for relaxing or entertaining. With sidewalks leading straight to town, you'll love being just a short stroll from shops and restaurants, all while enjoying the tranquility of a quiet neighborhood setting. Move-in ready and full of charm, this home offers small-town living at its best

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

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office, or creative studio. The expansive, level lawn presents a rare opportunity to create a private estate setting with ample room for a pool, tennis court, or beautifully landscaped gardens. Completing the p

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

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

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

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect David Rothstein, the house is ideally positioned to engage its landscape. Large bay windows invite natural light and frame views of water, trees, and gardens. Custom cherry woodwork adds warmth and craftsmanship. The layout is both flexible and refined. First floor primary suite supports single level living, while 3 additional bedrooms and a library occupy the upper level. Lofts, towers and quiet alcoves create varied, unexpected spaces without sacrificing function. Post-and-beam great-room/atrium w stone floor takes center stage for entertaining. A former indoor pool has been transformed into a st

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect David Rothstein, the house is ideally positioned to engage its landscape. Large bay windows invite natural light and frame views of water, trees, and gardens. Custom cherry woodwork adds warmth and craftsmanship. The layout is both flexible and refined. First floor primary suite supports single level living, while 3 additional bedrooms and a library occupy the upper level. Lofts, towers and quiet alcoves create varied, unexpected spaces without sacrificing function. Post-and-beam great-room/atrium w stone floor takes center stage for entertaining. A former indoor pool has been transformed into a st

Looking for one level living' Must see ranch in the southeast. This Polo Acres updated home is just over the Lenox line and close to all the Berkshires have to offer. Enter from the covered porch into a spacious welcoming entry. The light-filled living room with fireplace and gleaming wood floors flows into the dining area and three-season sunroom with awning. The large kitchen opens to a flagstone patio for outdoor dining and BBQs. First-floor laundry adds convenience. Primary suite with full bath/walk-in shower plus two additional bedrooms and a second full bath. Enjoy the partially fenced yard, oversized two-car garage, and full basement with a 2nd fireplace and large windows offering the potential for future living or recreation space

A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The 'Ice House' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Rental income' This property has a very nice history of rental income! Who could ask for anything more' Call for a showing today

Beach days, porch evenings and Tanglewood concerts make this the perfect three-season Berkshire cottage. Vaulted ceilings and a fieldstone fireplace anchor the living room, while two bedrooms and a versatile loft provide comfortable space for family and friends. The screened in-porch extends the living space for long summer afternoons and evenings, while the dining room is filled with windows that bring nature inside. Set in the welcoming community of Mahkeenac Heights, this cottage is just a short walk to the town beach at Stockbridge Bowl and close to the Berkshires' many cultural attractions. A wonderful retreat for enjoying all the Berkshires have to offer!

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

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

Fantastic Offer! Custom-designed and beautifully maintained one-owner residence offering 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm and Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community and the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens and music. A beautiful open floor plan features a totally upgraded kitchen with gas stone fireplace overlooking the woods. Adjacent screened porch opens to a private paver patio surrounded by native gardens. 1st floor en-suite bedroom provides an ideal 1-level living. Upstairs the spacious primary suite offers double closets, a beautifully appointed bath with quartz countertops, double sinks, generous linen closet, tile tub and shower. A 3rd en-suite bedroom plus another bedroom/office complete the upper level. Additional features include central A/C and Vac, coat closet, pantry, hardwood floor, custom glass shower doors, new HVAC and a 220-

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

Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and entertaining. Outside, you'll find a large barn, a greenhouse and impeccable gardens ideal for gardening enthusiasts or creative projects. This property is not just a home; it's an opportunity to enjoy the tranquil beauty of West Stockbridge, with its vibrant community and picturesque surroundings. Located minutes from many local attractions including Tanglewood and minutes from the highway

Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 and3 all in 2023.Can also be purchased as part of a investment portfolio 13 Park Street Stockbridge, MA MLS#249532

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office, or creative studio. The expansive, level lawn presents a rare opportunity to create a private estate setting with ample room for a pool, tennis court, or beautifully landscaped gardens. Completing the p

A UNIQUE NEW HOME UNDER CONSTRUCTION IN THE HEART OF STOCKBRIDGE, MASSACHUSETTS Historic Living: In an era of increasingly homogenized architecture, this extraordinary timber frame Dutch house replica offers something rare: a true sense of place. Rooted in the early traditions of the surrounding Housatonic Valley, the home is a thoughtful homage to the region's European heritage-crafted with authenticity, integrity, and many locally sourced materials designed to age gracefully. Inspired by early 18th-century Dutch design, the residence features massive anchor beam construction, a steeply pitched roof, thick plank floors and richly textured materials that develop warmth and patina over time. Traditional casement windows with deep sills, exposed timber framing, and masonry fireplaces evoke a timeless aesthetic while integrating seamlessly with the surrounding Berkshire landscape. Behind its historic character lie modern mechanical systems-where exceptional craftsmanship meets innovative