luxury houses for sale Lenox, United States

Embrace effortless seasonal living in this beautifully maintained, vintage three-season cottage. Nestled on a quiet, unpaved lane in the desirable Mahkeenac Heights community, this two-bedroom home offers the quintessential Berkshires getaway. Recent thoughtful updates include fresh flooring and an opened-up floor plan that maximizes natural light and flow. Step outside onto expansive decking designed for alfresco dining. Whether you are spending your mornings at the local lake beach or your evenings taking in world-class music at nearby Tanglewood, this private haven offers prime proximity to the best of Lenox and Stockbridge.

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location-- where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room-- perfect for gathering with friends and family. A large pantry provides exceptional storage and functionality. For more formal occasions, enjoy a separate dining room, elegant sitting room, and formal living room. A heated sunroom offers year-round enjoyment, while a dedicated first-floor office/library provides ideal work-from-home flexibility. Upstairs, you'll find four spacious bedrooms and two full bathrooms, offering ample room for family and guests alike. Practicality meets versatility on the main level with a convenient laundry/mudroom and half bath located just off the garage. Above the garage, a finished bonus space with its own full bathroom presents endless possibilities-- whether as a private studio, guest suite, bedroom, or additional family room. In a highly desirable Richmond location near Lenox and all that the Berkshires have to offer, this property combines space, light, and flexibility with an unbeatable address close to Tanglewood. A rare opportunity to enjoy quintessential Berkshires living.

Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-study home features triple-glazed windows, super-insulated envelopes, and geothermal climate control.

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 perennial 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!

Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An oversized three-car garage and finished lower level provide ample storage, while expansive windows showcase the surrounding landscape. Available furnished. This exceptional property is move-in ready and an ideal Berkshire retreat.

Located in Stockbridge, this 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. 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. Who could ask for anything more?

This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

Quitessential 1831 side hall Colonial. Charming home located in the village of Interlaken in the town of Stockbridge, MA. Just minutes to Lenox, downtown Stockbridge, and the Berkshire Botanical Center. Listen to the babbling water from the Larrywaug Brook and visit the nearby town park. Sit on the deck or around the firepit to soak in the atmosphere of privacy and peace. This 3 bedroom, 1.5 bath house has been meticulously updated. These updates include: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer. Garage is partitioned for a workshop but can easily be converted to a one-car garage again.

Gracefully situated on a gentle sloping hillside street this distinctively designed multi-level home offers distant and seasonal Berkshire mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home and grounds, you can embrace the vast privacy, open land and 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 peacefulness. 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 sized formal living and dining rooms ideal for entertainment, memories and laughs to be shared. Relax in comfort and warmth of the brick fireplace fully framed with wall to wall windows balancing light while inviting the outdoors in. Adjoined to the expansive cooks kitchen topped with granite countertops, triple windows for full backyard viewing, and spacious everyday dining which leads to a private and expansive rear deck and screened sunroom. Step inside and ascend a half flight of stairs to the bedroom level, where four generously sized bedrooms offer both comfort and ample space. These rooms share a spacious full hall bath. The private, king-sized primary suite welcomes you each morning with cheerful and soothing sunrise views over the October Mountain ridgeline. Descend to the walk-out entry level, which features a versatile home office or guest suite, a third full bath, and a convenient shared laundry area all situated on the lower entry level close to the oversized two-car garage. The next lowest level remains unfinished, providing an excellent opportunity for large-scale storage, a workshop, or additional creative uses. This is a unique opportunity in this glorious Berkshire Summer market, situated close to Lenox for enriched entertainment, Pittsfield's Guido's Fresh Marketplace for gourmet, farm-fresh foods. Enjoy lake activities at Pontoosuc or Onota Lake within 20 minutes or indulge in hiking and mountain biking at October Mountain and kayaking or hunting at Canoe Meadows Wildlife Sanctuary. With incredible views at home and endless outdoor adventures nearby, this residence offers the best of Berkshire living.

Welcome to this wonderful Colonial in a quiet, sought after neighborhood in Lee, MA. 3 bedrooms, 2.5 baths, and a finished lower level. Enjoy an expansive deck overlooking the rear yard; providing plenty of outdoor living space. Amenities include vinyl siding, gas heat, hardwood floors, eat-in kitchen, dog fence, and a two car attached garage.

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that caters to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 square foot heated indoor arena, which includes an owner's apartment and viewing area--and a professional-grade outdoor ring.

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.

Embrace classic New England living in this 3-bedroom, 2-bathroom home boasting 1,664 square feet of old-world charm, warmth, and character. Ideally located along East Main Street, this residence offers an unbeatable, close-to-everything village lifestyle while maintaining a remarkably quiet, private sanctuary indoors and out. Inside, a bright and open floor plan is filled with natural light, highlighted by rich hardwood floors, exposed timber beams, and thoughtful architectural details. The inviting main level features a cozy living room, a dedicated library nook with built-in shelving, and a sunlit dining area wrapped in oversized glass panels. The well-appointed kitchen includes a stylish SMEG refrigerator, a Bosch dishwasher, and gas cooking. The home's two full bathrooms blend distinct charm and functionality, featuring an updated downstairs bath alongside an upstairs bath complete with a classic clawfoot tub. Outside, the fully fenced backyard serves as a serene retreat complete with peaceful mountain views--the perfect backdrop for morning coffee or casual entertaining. Quintessential Berkshires living is right at your doorstep, with iconic village favorites like the Red Lion Inn, The Lost Lamb, Stockbridge Coffee, the local library, tennis courts, scenic hiking trails, and the Berkshire Theatre Festival all within easy reach. Futhermore, this property has a successful short-term rental history. All-around, a must see!

Introducing 444 Pomeroy Ave, a true neighborhood icon! This one ticks all the boxes: Curb appeal to the max with mature perennial plantings, gracious front yard, private side yard with hot tub, and the true star of the show--the screened porch, which you won't want to leave in the summer. The home is spacious with a cook's kitchen and dining room, plus an ample, fire-placed living room with built-ins galore. First floor 1/2 bath and period details and charm that cannot be replicated today. Upstairs, 3 sizable bedrooms, and a fully renovated bathroom with Italian marble counters, tiled walk-in shower, and radiant heat. The partially finished lower level features another bedroom for guests. A large two car garage was added, with exceptional loft storage space above. Be ready to fall in love!

Welcome to 100 Boyston Street Ext, an extensively updated Pittsfield home with every major element renewed for a warm, modern, turnkey feel. The first floor features a bright open layout, a brand new contemporary kitchen, and connected living and dining spaces. Two first floor bedrooms and a full bath add flexibility for single level living or guests. Upstairs primary suite with refinished hardwood floors and a renovated bath. The layout is functional and offers more space than expected. Major updates include a new roof, new heating and cooling with a heat pump, all new bathrooms, a new kitchen, new main level flooring, and refinished floors upstairs. Fully move in ready in a convenient Pittsfield location.

Gracious colonial style home in the heart of the southeast historic neighborhood minutes to upstreet cultural art and theatre district with museums, galleries, theatres, eclectic dining, and more. This home awaits your finishing touches is search of a new homeowner with a sense of style and interior design to make this beauty the show piece it deserves to be. Abundance of living spaces on multi levels, finished attic for six bedrooms boasting three full baths and one half bath. Modern kitchen and primary bath give you the start you need. New hot water baseboard heating system and incredible front yard that is edged in custom cut marble for easy care maintenance. Lower level walk-out offers more space for exercise, crafting and workshop space. Incredible oversized yard for fun and enjoyment

Welcome to this immaculately maintained two-family home--a turnkey property that meets today's timeless standards! This choice 2-family home beautifully balances sophisticated living with incredible versatility, making it an ideal match for owner-occupants, multigenerational families, or savvy investors alike. Including features you are sure to love: Modern Living: Bright, open floor plan living areas featuring fresh paint and updated appliances. Comfort and Convenience: Both units boast primary bedrooms with ensuite baths, large dedicated laundry areas, updated windows, and pristine ceramic-tile bathrooms. Flex Space: A partially finished basement offers the perfect canvas for storage, workshop, craft area, home gym, etc. Outdoor Oasis: Enjoy your morning coffee or warm evenings from the screened-in porch or private second-floor deck, all overlooking a backyard ideal for gardening and relaxing by the charming water fountain. Whether you are looking for rental income or a spacious multifamily retreat, this property offers an extraordinary lifestyle opportunity!

Enjoy easy, turn key living in this spotless, beautifully maintained 3 bedroom, 1 bath ranch style home! Ideally situated in one of Southeast Pittsfield's most desirable neighborhoods, this classic residence combines quality construction, timeless appeal, and exceptional value. Beautiful hardwood floors extend throughout the thoughtfully designed main level floor plan. The warm and inviting living room features custom built in cabinetry, a cozy fireplace, and a picture window offering seasonal mountain views. The dining room features built ins and is complemented by a well appointed kitchen with stainless appliances. Three bedrooms include a generously sized primary bedroom with a walk-in closet. The living space extends naturally into the scenic three season sunroom, which offers direct access to the deck and overlooks the lovely, level backyard. The lower level provides abundant storage and includes a spacious area with excellent potential to create additional finished living space, a playroom, home office, or recreation area. Outside, enjoy the level backyard and outdoor deck, perfect for relaxing or entertaining. Central air conditioning, replacement windows and a convenient one car attached garage add to the comfort and practicality of this well maintained home. A wonderful opportunity to own a quality built property in a highly desirable Pittsfield location! Note: Total square footage excludes the three-season sunroom.

Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the formal dining room and a tastefully remodeled kitchen. Enjoy year-round tranquility in the heated four-season sunroom or relax in the separate main-floor den featuring a cozy gas fireplace and sliders leading out to the rear deck. A generous first-floor bedroom, full bath, and dedicated laundry room offer effortless single-level living convenience. Upstairs, find a sprawling primary suite with a walk-in closet, a second sizable bedroom, and a fully renovated full bath. The lower level expands your entertaining footprint with a heated family/recreation room and workout space, alongside a large unfinished workshop and mechanical storage area. Out back, the private half-acre lot creates a peaceful retreat complete with a custom storage shed, mature landscaping, and the gentle backdrop of Sackett Brook. Featuring an attached two-car garage, natural gas heat, and public utilities, this turnkey home offers suburban tranquility just minutes from downtown Pittsfield, Lenox, and all Berkshire cultural attractions.