luxury houses with terrace for sale Lenox, United States

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.

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!

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.

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!

This light-filled 3 bedroom 1920's classic Colonial cottage home is located in a quiet dead end surrounded by 80 acres of protected state land. The large .75 acre property is level with perennial flower gardens, mature trees and a large backyard with access to the forest and river. This special home has many original details such as the pine and fir wood floors, handcrafted woodwork, beadboard, glass door knobs, and classic chandelier. The home features 3 bedrooms, 1 full bathroom, living room, dining area, a charming country kitchen with new unique brand retro fridge. A lovely large front 3-season porch with large picture windows. The partially finished basement serves as a wonderful family room/play space and laundry area with new washer and dryer. The oversized detached 2 car garage can also be used as a workshop, storage or garden shed. Recent updates include electrical, insulation, interior paint, and professional landscaping. Ideally located close to town, parks, local schools, Tanglewood and Pontoosuc Lake. A must see to appreciate this home's charm, special location and all the amenities this home has to offer.

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

Enjoy easy one level easy living in this sought after southeast tree-lined street with nhomes built of brick or stone creating a New England picture perfect neighborhood. See the updated kitchen, and bath, manageable two bedrooms with unfinished attic space for more in the future. Outfitted with central air conditioning for cooling comfort at your pleasure. A surprisingly large back yard all fenced in for privacy, shade trees, stone patio and firepit for fun fall nights with marshmallow roasting. Enter first onto the covered front porch where you sit and either enjoy a coffee or visit with passer bys hearing church bells in the distance. Enter an inviting dedicated entryway with a unique opening to peer into the fireplaced living room. The stone fireplace anchors the room with handsome handcrafted masonry to chase the chill and set the mood after dinner in the sun filled dining room. Sliders lead to the oversized bonus sun room grounded with flagstone flooring and with a mini-split for all season use. Cooking and socializing set up for you in a beautiful 15 year newer kitchen featuring stainless steel appliances, cherry cabinetry topped with quality quartize, finished with color coordinated tile backsplash and floor o expertly compliment and complete the look with a designers touch. Thoughtfully planned to chop and create delectable dinners with the ease of preparation on butcher block countertops surrounding the electric cooktop slide in oven. The charming round top hallway leads to two bedrooms and a remodeled full bath for another expensive feature finished for your enjoyment. Upstairs use your vision to complete the unfinished attic for overflow space in the future. The backyard playground is generously sized and fully fenced in. The raised bed vegetable garden ideally frames the vegetables and rear property line while keeping the bunnies out. Experience this magical setting with natural sunlight glistening through the willow tree leaves while a gentle breeze sways the branches in whimsy. Close to schools, park, Canoe Meadows Wildlife Sanctuary, coffee shops, ice creams and frozen yogurt parlors, cheesecake café' and specialty pizza place known for its homemade Berkshire Mountain Baked bread and pizza crust. In-town conveniences abound with dry cleaning, mailing center, pharmacy and bank choices. Welcome to quaint, cozy, wholesome living in this sweet and petite home with room to grow. Have it all and be home for the holidays.

Classic side hall colonial set on a premiere southeast parkway awaits you. Elegance, grace and space greet you with this soundly built beautifully styled traditional home. You're welcomed onto this covered front porch to join the neighborhood ''porching'' without envy. This home has been lovingly updated over the years with roof, windows, boiler, electrical, and lighting creating an incredible opportunity to just move in and love living in the southeast. Centrally located to all that is Berkshire - lakes, hiking, downtown art and theatre and Lenox music or Williamstown - The Clark. A sweeping staircase greets you in the grand entry filled with natural light. Open to the generously sized formal living room with a warm and charming gas fireplace for a peaceful evening by the fire. This living room fits the expansive sized sectional sofa for all to enjoy time snuggling together. This space is situated next to the sun filled family room outfitted with a wall of built-ins for the toys, games and plenty of floor space for the tiny tot playhouse, kitchen and gym set that are bigger than life. Convenient first floor full bath designed with an easy access shower and shared laundry making everyday chores lighter. An elegant and oversized dining room is holiday ready for friends, family members and new folks in the neighborhood to gather, dine and make new memories. More oversized windows compliment the dining experience with natural lighting and a stylish new fixture finish the room with class and style. The kitchen is outfitted with an abundance of cabinets, corner sink and window peering into the fenced back yard and a newer glass front refrigerator to add to its thoughtful styling and functionality. Don't miss the mudroom space with closets and cabinets for all coats, boots, seasonal outfittings and school backpacks. Head upstairs the quick way with the back staircase to bedrooms to grab and go on a busy morning or saunter up the front staircase for a beautiful more elevated experience as you retreat at the end of busy day to the graciously sized bedrooms, and gleaming wood floors. A shared full bath and abundance of closets give everyone the space and privacy they need. The third level attic room is heated and finished for overflow fun and enjoyment by teens or use it for creative crafting that need not be disturbed while in the process of creating lego building, painting, sewing, or anything your heart desires. The backyard features a rear deck and fenced in grassy play area adjacent to the two car detached garage perfect for the vehicles, off season snowblower and lawnmower, workbench and or storage. Ideally centrally located to all Berkshire attractions and closely situated with everyday conveniences for mailing, dry cleaning, banking and pharmacies. Close to the downtown cultural district for art galleries, museums, movies and dining. Minutes away to hiking, lakes, parks, and schools. So much to enjoy so get ready for Halloween - one of the most visited neighborhoods in town. See it to believe its simplistic beauty and make it your home for the upcoming holiday season!

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main floor for year round comfort. The first-floor primary suite offers a private retreat with a spacious spa-like bath, featuring a large shower, soaking tub, and generous walk-in closet. An impressive entry foyer sets the tone with a sleek architectural staircase, powder room, and coat closet. A two-car attached garage provides ease and convenience. Upstairs, a dramatic loft overlooks the great room and sits adjacent to a second bedroom suite, perfect for guests or family. Separate from the two main suites, a private guest wing includes two additional bedrooms, a large sitting room, and a shared full bath, offering a comfortable and flexible space for visitors. Despite its very quiet mountain-top privacy, the property is ideally situated just 10 minutes from Tanglewood and downtown Lenox. Enjoy effortless access to I-90, making trips to Boston or New York City remarkably convenient. Nearby West Stockbridge offers a charming village atmosphere with boutique shops, a local marketplace, wine store, café, inviting restaurants, and even an old-fashioned hardware store—everything you need within a short and scenic drive.

This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace. The adjoining kitchen and dining areas are designed for gathering, with cherry floors, custom pine cabinetry, a large island, and stainless appliances. A large screened porch and wraparound deck extend the living space outdoors and take in the wooded setting and ridge views. The luxurious first-floor primary suite offers private porch access and a spacious bath with soaking tub and separate shower. First-floor laundry completes the main-level living arrangement. Upstairs are three additional bedrooms and two full baths. The walk-out lower level includes a dedicated home gym and additional flexible space. Beyond the pool area are several other amenities, including a dramatic fire pit tucked into a natural rock outcropping, a children's playground, and open lawn for games and play. Private but not remote, the property is just minutes from downtown West Stockbridge, with Stockbridge, Lenox, Great Barrington, and Tanglewood all within easy reach.

Discover the warmth and possibilities of this cozy yet spacious two bedroom, one bath home in desirable Southeast Pittsfield. Offering a blend of vintage character and comfortable living space, this inviting residence is ready for its next owner to bring their own vision and make it their own. A sweet enclosed front porch welcomes you inside, where beautiful hardwood floors and warm wood paneling add character and appeal. The inviting living room offers plenty of space to relax, while a separate dining room provides room for holiday meals and entertaining. The large eat-in kitchen features an abundance of cabinetry and an opportunity to create a space tailored to your taste. Two spacious bedrooms, ample closet space, and large windows that invite in natural light add to the home's appea Replacement windows and a newer furnace are additional features to appreciate. Natural-gas forced-air heat serves the first floor, with electric heat on the second floor. Outside, enjoy a private backyard with room to garden, relax, or create your own outdoor retreat. With its desirable location, vintage charm, and comfortable room sizes, this home offers an appealing opportunity to build equity while bringing your own vision to life!

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.

Experience the perfect balance of grand-scale architecture and tranquil nature in this stunning 6,000+ sq. ft. modern Colonial. Nestled on 3.42 manageable acres within a private enclave near Onota Lake, this 5-bedroom, 5.5-bath estate offers sweeping meadow views just minutes from the world-class arts of Tanglewood and The Clark. The entry is marked by dramatic dry-laid stonework, leading into an interior defined by soaring heights. The heart of the home is a two-story living room featuring vaulted ceilings and a floor-to-ceiling stone fireplace. The expansive living space of the great room flows effortlessly into a gourmet chef's kitchen equipped for high-end entertaining with dual refrigerators, double wall ovens, and a center island cooktop with a built-in griddle. High-top island seating allows for social cooking and a sizable breakfast area flanked by a wall-to-wall credenza—ideal for buffet-style hosting. The home's floor plan thoughtfully blends communal areas with distinct privacy across three levels. The main level is designed for complete convenience and the primary suite is a true sanctuary. It features a private egress to the pool and a hidden back staircase leading to a secluded loft—perfect for a library or reading nook overlooking the suite. The upper level offers a sweeping gallery balcony overlooking the great room, leading to four spacious bedrooms. This includes two private ensuites and two additional bedrooms serviced by a full bath and a dedicated laundry room. The lower level is an entertainment hub featuring a home theater, gaming space, gym, full bath, and a secondary egress for easy garage access. The fully-fenced backyard makes for a resort-style oasis. Host movie nights on the expansive deck, or relax by the heated inground pool and custom-finished patio. The designer firepit is anchored by a unique stone compass inlay, and a poolside full bathroom ensures guests never need to track water through the main house. For the automotive hobbyist or enthusiast, a high-end, three-bay attached garage is professionally finished with epoxy floors, industrial-style metal cabinets, and an EV charger. You will also find a massive, 50x40 detached shop with four bays and oversized doors. Whether for housing a car collection, an RV, or a professional art studio, the possibilities of this space are endless. Embrace the Berkshire landscape in a home where every detail has been considered. Whether you are heading out for fine dining or staying in to enjoy your private oasis, Blythewood Estates offers a lifestyle of unparalleled peace and sophistication.

Welcome to Bons Reves House, a beautifully designed escape tucked away on nearly seven acres in the most desirable part of the Austerlitz hills. Built in 1985 and meticulously renovated and expanded by a top builder in 2012 and again in 2025, this 4-bedroom, 3.5-bath contemporary home feels like a luxury treehouse hidden among mature hardwoods and surrounded by large estates and high-end residences. Custom millwork, natural stone and wood surfaces, bespoke plaster treatments, and designer-chosen paint colors all speak to exceptional quality. The gracious, flowing layout offers plenty of room for gathering, and bedrooms tucked into separate wings create privacy and practicality. This is a home built as much for weekend entertaining as it is for quiet days spent resting and recharging.On the first floor, a renovated chef's kitchen with stone countertops, custom cabinetry, multiple prep areas, and an island breakfast bar make it a true country kitchen, with plenty of room for gatherings and holidays. It flows into a Thanksgiving-sized dining area and a large, inviting living room centered around a cozy wood burning fireplace. Just off the kitchen, a newly built four-season sunroom looks out through oversized windows onto treetops and the ridgeline beyond. A mudroom with laundry, a full bath, and a powder room round out this level.Up one set of stairs, the primary suite has vaulted ceiling, multiple closets, and a full bath with a dramatic architectural sensibility. A second staircase off the kitchen leads to two more bedrooms and a full bath. Down on the lower level, an additional bedroom joins a studio or work space, an exercise area, and a newly built window-lined sitting room, offering room to spread out or tuck away.Outside, the wraparound Trex deck, front porch, fenced garden, handbuilt stone walls, and professionally landscaped grounds create a storybook atmosphere for outdoor living. The wooded acreage surrounding the home creates a natural buffer for privacy and quiet. Recent upgrades reflect real investment in the property: new windows, six new heat pumps, a recently replaced roof, a generator, a new garage door, and a freshly painted interior and exterior.The location suits both a weekend retreat and a full-time home. Just 15 minutes from Chatham, 20 to Great Barrington, MA, 35 minutes to Hudson, 45 minutes to Albany, and two-and-a-half hours to New York City, Bons Reves House puts summer evenings at Tanglewood, a movie night in Chatham, dinner out, and gallery walks through Great Barrington and Hudson all within easy reach. Local golf courses and cycling routes round out the list of ways to spend a day here. Convenient to the region's best amenities and attractions, the home still feels hidden away from the world.

Charming 3-bed Cape in Pittsfield, this home perfectly blends classic warmth with versatile living spaces. Glowing hardwood floors throughout and an expansive primary bedroom that spans the second floor to serve as a private retreat. First floor features 2 bedrooms, full bath, cozy living room, and eat-in kitchen. The lower level features a spacious basement room perfect for a family room. Outdoor living is a highlight, starting with a brand-new front porch that offers fantastic curb appeal. The large back deck overlooks a beautifully maintained yard ideal for entertaining, gardening, or outdoor relaxation. Complete with a one-car garage and a handy 8x10 storage shed, this inviting Berkshires home delivers exceptional comfort, convenient storage, and great space both inside and out-- a must see!

Rare, renovated Berkshire investment compound on 0.59 acres in pedestrian-friendly Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Moments from Berkshire Mountain Bakery; minutes to downtown Great Barrington and Tanglewood. A rare, turnkey find!

Originally built in the year 1800 on one the areas most historically significant roads lies this delightful antique farmhouse brimming with original details and charm. Perched above the road with its wrap around porch you are immediately transported to a simpler time where quality and beauty mattered. Further selling the vision, the periphery of your view is flanked with mature trees and one of two large barns providing a nostalgic aesthetic and endless opportunities. The barn closer to the home contains a garage for sheltered parking and the ability to create a guest house, work studio, private gym or anything you can dream up. In fact, there's room for all of those options within the same structure. A serene hilltop view in the distance beckons you to walk through the more than five and half acres of lawn, meadow and fruit trees to the second barn structure to continue dreaming up the possibilities. Currently this space is absolutely perfect to host outdoor dinner parties and gatherings with a bucolic view. The interior experience begins in the entry parlor, anchored by a traditional wood-burning stove. Original wide plank painted floors flow seamlessly into a spacious dining area bathed in natural light. Adjacent to this space, the modernized kitchen offers optimized storage solutions and updated appliances. The main level extends toward the rear of the residence, where the family room features stunning beamed ceilings that evoke a historical atmosphere. Completing this floor is a versatile adjoining room, ideally suited for guest accommodations or a home office and also conveniently hosts the laundry room. Up the wooden stairwell from the entry parlor three bedrooms and a bathroom surround the landing which has enough room to be its own library/reading space. The bedrooms are quite large for the era continuing this property's themes of charm, beauty and modern comfort. Just minutes away from Queechy Lake, where residents can enjoy access via an annual pass, its prime location offers easy reach to Chatham, Ghent, and Hudson on the New York side, while Great Barrington, West Stockbridge, and the Berkshires are equally accessible. Whether you are looking for a full-time residence or a perfect weekend retreat from NYC or Boston, this home serves as an ideal destination.