Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views.Step inside to discover an extra-large chef's kitchen seamlessly connected to a delightful breakfast room, sunroom, and screened porch, each offering tranquil views of the pool and raised garden beds. The inviting living room, complete with a cozy fireplace, flows effortlessly into the dining area, creating an ideal space for entertaining. Adjacent, find a sunlit den and office area, bathed in natural light.

Nestled in the lovely gated community of Woodmont Estates, this magnificent Georgian Schultz-designed home offers five bedrooms and five baths, with effortless access to all the Berkshires have to offer. Step through the elegant front entrance into a grand foyer featuring an open stairway, flanked by a formal dining room and spacious living room. Continue on to the expansive chef's kitchen, complete with a large center island and sun-filled breakfast area.Upstairs, the second floor showcases generously sized bedrooms, including a luxurious primary suite with its own private office area.Outdoors, enjoy a stunning wraparound deck overlooking the in-ground pool--perfect for entertainment and relaxation. The beautifully landscaped grounds feature an open outdoor fireplace surrounded by

Custom modern home with open plan living area, high ceilings and oversized windows everywhere bringing in tremendous natural light. One level living with large gorgeous marble kitchen, great working island and wall pantry. Guest wing off entry with two bedrooms and a hall bath. Entry hall has a powder room, hooks for coats and closet. The primary suite, on the south side, has french doors to private backyard with saltwater pool, walk-in closet, soaking tub and separate shower. Sited at the back of the 1.5 acres the house sits nicely above the front yard and allows for a more private backyard area to enjoy the pool, patio and fire pit. Large full basement and custom shed are just a few more of the perks of this thoughtful home.

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5 private acres along prestigious Crofut Street, the estate offers 5 bedrooms and 5 baths, including twin primary suites ideal for hosting friends and family year-round. Gracious living and dining rooms, a peaceful sunroom, a cozy study, and a large eat-in kitchen with Viking range and butler's pantry combine period elegance with modern comfort. This turn-key estate is offered fully furnished and

MOTIVATED SELLER; WILLING TO NEGOTIATE ON UPGRADES AND IMPROVEMENTS. Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 4,200 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a covered portico into a soaring cathedral-ceiling great room filled with natural light and serene woodland views. A wonderful screened porch expands the living space for peaceful mornings or easy entertaining. The open layout seamlessly connects the living, dining, and chef's kitchen, featuring premium appliances, quartz countertops, and a spacious island. A sophisticated split-bedroom design.

Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor pools. Outdoor highlights include a hot tub, pool house with bathroom, pavilion, garden, and a fully enclosed treehouse for summer overnights, along with deeded Queechy Lake rights for swimming and kayaking.The main wing of the home features a dramatic triple-height great room with a fieldstone fireplace, flanked by a wraparound deck.

Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of meadows, a sparkling pool, and the stately barn. The barn itself is a wonder, waiting to be reimagined--perhaps as a guest house, an artist's studio, or a setting for unforgettable gatherings.Surrounded by farms and opening to distant hills, the landscape feels both boundless and intimate. The pool, perfectly placed, invites leisurely afternoons and is graced with its own elegant pool house.

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side brings in the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screened porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked by 3,000-sq ft of stunning living spaces that seamlessly blend design, sophistication, comfort. From the glass walls that open to sweeping views, to its bespoke kitchen or design forward guest suite, every inch has been crafted to inspire. Host gatherings on the spacious screened deck, unwind by the 360 glass fireplace, find solitude in the ''Tower'' - and redefine living, creating, & thriving.

BREATHTAKING 360 DEGREE VIEWS Rarely does such a magical property come along with so much to offer. A well built and spacious home with Pickle Ball, Tennis, Swimming Pool, Gazebo, Lake frontage, Lush Green Lawn, Pastures, A Three Car Garage, Outbuildings, VIEWS FROM EVERY ROOM. Kitchen has Sub-Zero refrigerator, Wolf cooktop, large center island and a wall of windows overlook the gorgeous gardens and view. Formal dining room with wet bar and 500 bottle temperature controlled wine storage. A formal living room w/ a fireplace, a spacious family room for watching movies, a gym with a wall of windows looking to Mt Greylock, It is one of the most beautiful properties in the Berkshires. Equidistant to north & south Berkshire County. Close to all the Berkshires has to offer. IT WON'T DISAPPOINT

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for four-season enjoyment of the Berkshires lifestyle--Tanglewood, Lenox village, farm-to-table dining, ski slopes, hiking-this custom-built 2017 home was fully reimagined and entirely updated in 2020 by master craftsmen. Every detail has been elevated to support both elegant entertaining and relaxed daily living.Dramatic ceiling heights and a sun-drenched upper gallery define ... see more

The Quarry - A One-of-a-Kind Berkshire Estate on 60 Private Acres!Singular, stunning, and secluded--the quarry pool at the heart of this 60-acre Berkshire estate is truly one of its kind: the culmination of geology, industry, and artistry. Carved into a reclaimed limestone quarry and framed by towering stone walls and a 16-foot waterfall, the quarry pool is a marvel in and of itself--equal parts art installation, private resort, and natural wonder.Measuring approximately 20 by 40 feet, the quarry pool sits within a landscape of curated gardens, open lawn, and forested acreage--entirely private and protected. The property offers the potential for additional dwellings, making it as versatile as it is visually striking.

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a - see more

Set on 11 enchanting acres in the pastoral town of New Marlborough, Massachusetts, this exceptional Berkshires estate offers a rare convergence of architectural refinement, natural splendor, and modern luxury. Designed by an architect and originally built in 1984, the main house, guest house, and pool house were all fully renovated in early 2025 to create a cohesive, contemporary compound with timeless style and enduring grace.A long, private drive leads through an arboretum-like collection of mature trees to a secluded setting that feels both cultivated and wild. Here, heirloom stone walls, glacial rock formations, and a shimmering pond define the landscape. Master-crafted stone paths and terraces by local masons integrate the home with its natural surroundings, while new

Hawks Nest Ridge. Quiet privacy on 8.6 acres. Decks, patio, screened porch and pool all enjoy the view and the natural setting. Dramatic open floor plan with walls of windows to the views, soaring stone fireplace spanning three stories. Cook's kitchen with walk-in pantry. First floor primary suite with gas fireplace and dressing room all abutting library and office. 5 private bedroom suites in total each with their own sitting areas. Family room with wet bar and gas fireplace. Exercise room with steam shower. 3-bay garage. A very special retreat with plenty of room for guests and entertaining. Just a short jaunt to dining, shopping, recreational and cultural venues in West Stockbridge, Lenox, Stockbridge and Great Barrington. (No showings 12/24 until after 1:00 on 12/27)

April Hill, an exquisite 1850 Greek Revival masterpiece. 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.

Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a two-bedroom guest wing. An oversized two-car garage, generous boot room, and laundry complete this level. Upstairs, a spacious flex loft with full bath and custom sauna provides an inviting retreat. Remarkably comfortable for such soaring volumes, the home offers spaces equally suited for reflection or relaxation. Welcome to Long House. This luxury offering will be unveiled over the next two weeks.

The interiors at Riversmeet complement the exceptional landscape surrounding it and were carefully envisioned by the brilliant designer Louise Copeland. The first floor contains the main living space is lined with windows to Hudson River views. Mudroom with laundry, powder room, and a finished garage/gym/studio complete the first floor. The second floor homes two large bedroom suites, each with unique views of the twelve-acre property. The grounds at Riversmeet are exceptionally well cultivated, with gunite pool with a stone patio, and bluestone dining terrace. Through the woods is a series of trails leading to a lookout deck, a striking ridge, and the banks of the Roeliff Jansen Kill, offering easy access to the Hudson for kayaking and boating.

Introducing 
FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy5BR/5BA timeless home built for this wildly beautiful placeStand between your home, overlooking your private lake, and your barns, Turn 360 degrees--everything you see you could own. Pure sanctuary in the highest possible sense.Nearly 1,500 acres where Thorp Brook winds through marshlands, Seymour Mountain rises to 1,682 feet, and miles of trails beckon for every outdoor pursuit. The kind of American dream that exists now only because someone saved it.SHOWINGS BEGIN TUESDAY, AUGUST 26