140 properties for sale in Leisure Lee

Turnkey Berkshire cottage on Shales Brook, completely reimagined from top to bottom. This stylish two-bedroom, two-bath retreat pairs thoughtful design with an idyllic waterside setting, just around the corner from Jacob's Pillow and approximately 10 minutes from downtown Lee. Nearly every element of the home has been renewed, including the kitchen, bathrooms, plumbing, electrical, septic system, heating system and hot water system. The bright, open living space features wood floors, a beautifully renovated kitchen with custom cabinetry finished in a rich Farrow and Ball green, and a striking vintage copper Malm wood-burning stove that adds warmth and character. Two king-size bedrooms and two beautifully updated baths create a comfortable and functional layout. A screened-in porch and spacious deck extend the living space outdoors, surrounded by mature trees and the peaceful sounds of nature. One of the property's most special features is its frontage on Shales Brook. Relax on the scre

'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

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

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 and Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with appro

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 and Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with appro

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 a requisite annual resort membership with full access to Canyon Ranch's world-renowned wellness amenities. Just minutes from the Berkshires' acclaimed cultural attractions, fine dining and outdoor recreation, this is a rare opportunity to enjoy luxury, wellness and timeless design in one extraordinary home

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 rare offering of 118 acres in the highly sought-after Tyringham Valley. Sage Hill Farm encompasses an exceptional landscape of rolling meadows and woodlands, mature landscaping, exquisite gardens, beautifully crafted hardscape and handsome barns. Dating to 1817, the main house retains many of its original architectural details and is complemented by a partially renovated 1970s addition and separate 1941 guest house. The grounds are impressive, with a beautiful setting for the heated in-ground pool and ample areas to enjoy the property's extraordinary acreage. The original house and addition offer generous accommodations for family and guests, including six bedrooms and four bathrooms, two of which are roughed for plumbing. The inviting and comfortable guest house with 3 bedrooms and 3.5 baths, accessed by its own driveway, includes a garage/barn and is reached by a charming walking bridge over Hop Brook (see Documents for further details about the guest house). An exceptional opportu

A rare offering of 118 acres in the highly sought-after Tyringham Valley. Sage Hill Farm encompasses an exceptional landscape of rolling meadows and woodlands, mature landscaping, exquisite gardens, beautifully crafted hardscape and handsome barns. Dating to 1817, the main house retains many of its original architectural details and is complemented by a partially renovated 1970s addition and separate 1941 guest house. The grounds are impressive, with a beautiful setting for the heated in-ground pool and ample areas to enjoy the property's extraordinary acreage. The original house and addition offer generous accommodations for family and guests, including six bedrooms and four bathrooms, two of which are roughed for plumbing. The inviting and comfortable guest house with 3 bedrooms and 3.5 baths, accessed by its own driveway, includes a garage/barn and is reached by a charming walking bridge over Hop Brook (see Documents for further details about the guest house). An exceptional opportu

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

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!

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

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!

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

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

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!

Rare opportunity to own an original Becket Woods home! This beautiful contemporary home nestled on 4+ acres offers privacy, seasonal water views, year-round mountain views, and sunsets you won't want to miss! Open concept, floor to ceiling windows, 2 fireplaces, unique floating floor, large exposed wood beams, newly refinished pine floors, new carpeting in 2 bedrooms, newly renovated 1st floor bath. Finished basement with bedroom, full bath and walkout slider. Enclosed screened porch, open deck off main living area, additional deck off the primary bedroom. 26x40ft garage with 12ft doors built in 2019 can be used for a variety of purposes. LP Smartside siding, 50yr asphalt shingles and Anderson A-Series windows installed in 2016. Jacob's Pillow is 2 miles away. Other points of interest such as: Tanglewood, Norman Rockwell Museum, Chesterwood, Red Lion Inn, and Kripalu are within 30 minutes. Otis Ridge Ski Area is 15 minutes away, Bousquet Ski Area is 30 minutes away, Jiminy Peak and Cat

The Possibilities are endless! Family Compound and Retreat ! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl capacity, and the Post and Beam Utility Barn two levels. Photos are from the past when it was running as a venue. It has frontage on Washington Mt Rd, Frost Rd and Lovers Lane Rd. Come view this unique property you won't be disappointed. All Information to be confirmed by Buyer. See Also MLS Listing 73240084 in Commercial

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

Contemporary home built in 2012 on over 11 acres walking distance to Stockbridge center. Original house was taken down and this sun-drenched home was built on the saved footprint. Main floor has a small living area off the entry open to large kitchen and dining with sliders to the deck, primary suite with walk-in closet and deck access, 1/2 bath and access to the oversized garage. Second floor has vaulted ceilings, a large landing, second living area, 2 guest rooms with a hall bath and another primary suite. There are two porches off the second floor, one small off the primary and the other flanking the East side - covered for protected enjoyment. The Konakpot Brook winds through the back of the 11+ acres giving access to fishing and just relaxing by the water

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

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!

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

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!

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

Charming 1930 Stockbridge home perfectly located just minutes from the iconic Red Lion Inn, dining, and shopping in town. This spacious 4-bedroom, 2.5-bath residence features a large enclosed front sun porch, offering a bright and inviting space to relax. The home retains original character and details throughout with gorgeous hardwood floors throughout and generous living and dining rooms ideal for gatherings. The large kitchen and barn garage add to the property's potential. Enjoy the spacious rear deck and backyard, perfect for outdoor activities and entertaining. This sunlit home is ready for its next chapter and your vision, offering plenty of opportunity for a full renovation to create your dream residence in a coveted location