105 houses for sale in Leisure Lee

A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are spaced apart for maximum privacy; the open living area takes center stage for entertaining. Post-and-beam great-room/atrium w stone floor. Open kitchen w custom cherry cabinetry. First floor primary suite. Outside, enjoy over 4 acres of privacy: lawn, gardens and your own nature trails! Deeded rights to the White Pines beach on Stockbridge Bowl. Walking distance to Tanglewood! Must see!

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space. With its distinctive contemporary design and solid architecture, this property presents an exciting opportunity for thoughtful updates that can enhance both style and value. A rare chance to create something truly special in one of Lenox's most desirable settings. View in person and experience the warmth, character, and connection to nature that make this home so unique

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

Well-maintained 3-bedroom, 2.5-bath ranch offering over 1,800 sq ft of comfortable living space. This home features a spacious upper-level bonus room with a fireplace, perfect for a family room, office, or entertaining space. The main level offers a functional layout with bright living areas and three bedrooms, providing flexibility for a variety of uses. A finished basement adds even more living space, ideal for a rec room, gym, or additional lounge area. Additional highlights include a one-car garage, convenient mudroom/laundry area, and a beautifully maintained interior throughout. Situated on just over a half-acre, the property offers a generous yard with room to enjoy the outdoors. A versatile home with space across multiple levels, offering flexibility and functionality

This thoughtfully updated home blends warmth, comfort, and history. An amazing front porch welcomes you before you even step inside, and the short walk to downtown or quick drive to the lake offers an easy, connected Berkshire lifestyle. Inside, bright and inviting rooms and beautiful wood floors create a natural sense of warmth, while the layout makes everyday living feel effortless. Flexible spaces adapt to your needs whether that's a home office, playroom, studio, or additional lounge area. With many updates throughout, the home feels modern and refreshed while still honoring its original character. A property that balances charm with convenience!

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 downtown living in this 4 Bedroom 2 Bath New England farmhouse. 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 for summer leisure living. Convenient to all Berkshire cultural and recreational attractions

Ideally located in desirable street in Lee, this well-maintained Cape blends classic charm with thoughtful modern updates. Surrounded by beautiful landscaping, the home features 4 bedrooms and 2 full baths, including 2 bedrooms and a full bath on the first floor for convenient one-level living. The updated 2022 kitchen offers granite countertops, modern appliances, and stylish finishes. Recent improvements include new windows, doors, and boiler. Enjoy warm wood floors throughout, a gorgeous wood-burning fireplace, and a generously sized partially finished basement for added living or recreational space. Relax on the spacious backyard deck overlooking the landscaped yard. An oversized 2-car garage provides ample storage and workspace

Charming three-bedroom, one full bath ranch offering the ease and convenience of one level living in a highly desirable neighborhood. Situated on a spacious lot, just shy of a half-acre, this home features a large, fenced backyard perfect for entertaining, gardening or simply enjoying the outdoors. Wrap around deck overlooking above ground pool, creating the ideal summer setting. Inside you will find a comfortable eat-in kitchen, front living room, updated bathroom and 3 bedrooms. Partially finished basement that provides additional room for a family room, home office, gym and laundry. Conveniently located close to schools and downtown Lee, 'Gateway to the Berkshires'

Beautifully renovated ranch in a quiet neighborhood in Lee, offering comfort, style, and lots of natural light. This move-in-ready home features all the brand-new updates, new roof, new gas heating system, new kitchen, new bathroom, new everything. The bright and flexible bonus room could be perfect as a third bedroom, home office, or guest space. Enjoy peaceful surroundings while being just minutes from Lee shopping and dining, and the Berkshires' most sought-after summer attractions, Tanglewood and Jacob's Pillow. Whether you're looking for a full-time residence or weekend retreat, this thoughtfully updated home combines modern living with a prime location close to everything the area has to offer

Set along a country road in Lee, this historic farmhouse dating to 1824 features many details associated with antique Berkshire homes. Wide plank floors, exposed beams, fireplaces, original wood details, and sun-filled rooms can be found throughout the property.Rolling fields, mature trees, and distant hill views are visible from many rooms and living spaces. Updates over time blend with the home's antique character. With more than 2,500 square feet and a flexible layout, the property offers potential for single-family living, multi-generational use, or other possibilities.Set on a one-acre corner lot near Golden Hill Forest and the historic Golden Hill Bridge, this property offers historic character and Berkshire scenery

Ranch-style home located on a quiet street in Lee with a huge backyard offering plenty of space for gardening and recreation. Based on feedback 3 rooms now have brand new carpet ! This 3-bedroom, 1-bath home features central air conditioning, solid mechanical systems, and a functional layout. While some cosmetic updates would help bring out its full potential, the home offers a great opportunity to build equity and make it your own

Set on just under an acre along one of Lee's most desirable roads, this beautifully maintained home combines timeless design, quality craftsmanship, and exceptional outdoor living. Overlooking peaceful meadows with stunning sunset views, the setting offers the perfect balance of privacy and natural beauty. Designed for both entertaining and everyday living, the backyard is truly the centerpiece of the property. A tiered bluestone patio creates multiple spaces to gather and relax, featuring a built-in outdoor kitchen, gas fire pit, and a heated saltwater plunge pool by Soake Pools. Mature landscaping, professionally designed landscape lighting, and a charming storage building complete the outdoor space, creating a backyard that feels like your own private retreat. Inside, the home is warm, inviting, and thoughtfully designed. The eat-in kitchen is the heart of the home with a large center island, custom cabinetry, premium JennAir appliances, and direct access to the patio for seamless i

Welcome home to this sweet and petite one level easy living ranch style home. Sun filled bright spaces invite you to relax and enjoy the end of each day in this thoughtfully planned layout. Boasting a king size bedroom, two other bedrooms, and an updated full bath. The galley style kitchen is comfortable for baking and creating all the dinner gatherings you wish. Comfortable everyday dining is open to living and a lovely added sunroom for extra living space and enjoyment. French doors lead to a generously sized back yard with perrenial plantings and a shade tree for an outdoor cool evening escape and playtime. Central to all that is Berkshire and Lee with a quaint downtown, shopping, schools, dining, and antiques. Close to parks, playgrounds and October Mountain State Forest for fun!

Located on desirable Golden Hill Rd a true ' FIXER UPPER ' that sits on 8 acres with mountain views giving you the opportunity for expansion and the possibility to build your dream home, or ADU. The house has 3 Bedrooms,1 Bath, Living room and an eat-in Kitchen. The Garage is in very poor condition and may need to be taken down. House is being sold AS-IS, no negotiation or concession for any inspection issues. Accepted offer is subject to approval by the Massachusetts Estate Recovery Unit/ Commonwealth of Massachusetts (MassHealth). Just minutes from downtown Lee, the entrance to the Mass Pike, Rt 102 to Stockbridge and Great Barrington Rt 20 north brings you to Laurel Lake, Lenox, Tanglewood and more of the Berkshires

Stunning architect designed space with soaring ceilings, floating staircases and numerous high-end features. Ideally situated on nearly 3/4 acre abutting an 18-acre nature reserve. Just a short walk to downtown Lee shops and restaurants. Lots of room for a pool, tennis court, and/or pickleball court. Minutes from the best places in the Berkshires. Great investment opportunity with the nearby $100 million Eagle Mill development. Lots of room with 4,000 square feet of living space plus a separate 2,500 square foot area with large stained glass windows to create a second dwelling unit, studio, chapel, gym, office, or entertainment extravaganza. Combining the best of new construction with old charm, you need to view this amazing space to experience its magnificence!

Huge price adjustment! Discover an exceptional investment opportunity to own two duplex homes on a single parcel, perfect for investors looking for a practical investment in the town of Lee. Four units total, these properties are ideal for generating consistent rental income. Close to downtown, shopping, major employers as well as banking and all popular Berkshire attractions. Tenants enjoy attached, private garaged parking

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

A rare beauty on historic yale hill! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants. Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3 Bedrooms, 3 Baths, has a lovely brookside courtyard wu002FPergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A must see!

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance

Nestled in a quiet, private neighborhood, this beautifully maintained ranch offers easy single-level living with minimal steps for entry and a seamless flow throughout. Ideally situated in the heart of the Berkshires, you'll be minutes from Tanglewood, Jacob's Pillow, Shakespeare & Company, the Norman Rockwell Museum, and Berkshire Botanical Garden. The updated kitchen features quartz countertops, white cabinetry with brass hardware, tile flooring, and a striking fireplace crafted from local quarried marble with a bluestone hearth. A second fireplace enhances the inviting living room. The home offers three spacious bedrooms, including a primary suite with a private bath, first-floor laundry, and a large basement providing exceptional storage. Outside, enjoy a spectacular 30' mid-century-inspired deck with Trex railings and wire accents overlooking a private yard perfect for relaxing and taking in breathtaking Berkshire sunsets. Comfort, convenience, & the best of Berkshire living

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

Pre-Construction: Step into a brand-new construction home designed to bring together modern comfort, generous space, and the natural beauty of the Berkshires. The heart of the home is an expansive open kitchen, dining, and family room area made for entertaining, slow mornings, and everyday living, complete with a walk-in pantry and seamless access to the rear deck. A separate study and additional living room offer flexibility for working from home, guests, or quiet retreat space. Upstairs, the vaulted primary suite features oversized walk-in closets and a spacious bath, joined by 3 additional bedrooms, multiple full baths, and second-floor laundry. A full unfinished basement offers future expansion potential, solar-ready design, and an attached 2-car garage add modern convenience. Ideally situated in Becket, moments from hiking, lakes, skiing, local trails, and the renowned Jacob’s Pillow arts destination, with year-round access to everything the Berkshires is known for

The Possibilities are endless! Family Compound & 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 73240- in Commercial

Escape to your own mountaintop retreat at Homestead in the Sky. This rare offering includes two parcels totaling 56 private acres with breathtaking views, perfect for a family compound, homestead, horse property, or peaceful mountain getaway. The 10-year-young home captures stunning views from nearly every room. The custom kitchen features granite countertops, handcrafted tile, gas range, double ovens, and opens to a sun-filled living room with soaring ceilings, a wall of windows, and slider to deck overlooking Goose Pond, Mount Greylock, and the Berkshires. The primary suite offers a custom bath and walk-in closet. Outside, enjoy a greenhouse with lower-level goat barn, raised gardens, open pasture potential, miles of trails for horses, hiking or ATVs, plus a heated 28'x48' workshop with 14' ceilings. A truly exceptional mountain estate with endless possibilities