Rare offering of over six acres ''On the Hill'', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace.. porch-privacy-garage..open acreage bordered by woods.. walking distance to Main Street, Skiing and Lake Mansfield nearby...Five bedrooms, three baths. Formal living room.Plenty of room for expansion.

Your waterfront lifestyle begins at this Hayes Pond sanctuary. From sunrise paddles to sunsets savored from the deck, this home is your private four-season escape in the Berkshires. The modern, open interior is designed to celebrate the water, with soaring cathedral ceilings and a wall of windows that frames the stunning lake view. A cozy wood stove, bright sunroom, and a large deck provide perfect spaces for relaxing or entertaining. This 4-bedroom retreat includes a primary suite featuring a calming soaking tub. Your private, grassy shoreline is your personal gateway to the lake--perfect for launching kayaks, fishing, swimming, or the occasional bonfire. This is the ultimate waterfront escape, where every detail is focused on a life lived by the water.

Discover a stunning oasis in this custom-built contemporary home, ideally situated in a picturesque and private setting. Enjoy tranquil views of a serene pond, beautiful gardens, and flourishing fruit trees, all while basking in an abundance of natural light. This home is a dream for those who love to entertain. The spacious dining room and inviting living room, complete with a cozy fireplace, provide the ideal backdrop for gatherings, complemented by three spacious decks that extend your living space outdoors. Culinary enthusiasts will delight in the oversized cook's kitchen, featuring charming terra cotta floors, premium appliances, a generous center island, and ample dining space. Retreat to the luxurious first-floor primary bedroom suite, which offers a large walk-in closet,

Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires.Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind.

Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide flexibility for guests or additional family members. The open kitchen/dining area is perfectly positioned to capture southeast-facing views. The primary suite includes a luxurious bath and expansive walk-in closets. On the lower level there is a private walkout suite, full bath, gym, and kitchenette. 3 car oversized garage/shop and generator.

Nestled in picturesque Alford, this inviting four-bedroom, 4.5-bath home blends comfort and flexibility in a serene Berkshire setting. The first-floor primary suite features a private ensuite bath, ideal for easy living. Thoughtfully designed spaces offer room for guests, work, or hobbies, while seasonal views bring natural beauty indoors throughout the year. With low Alford taxes and a peaceful location close to all the Berkshires have to offer, this home is a rare and appealing find.

Two beautifully landscaped acres with perennial gardens blooming throughout the season. An exceptional 10-room home offers privacy, views, and effortless Berkshire living just minutes from downtown Lenox and Tanglewood. The home features an open and inviting layout with a fireplaced living room and a chef's kitchen designed for gathering and entertaining. A stunning four-season sunroom transitions to a screened porch in the warmer months, allowing you to enjoy the surrounding landscape year-round. Four bds, + office/den, & 3.5 bths, allows ample space for family/guests. Primary suite offers a peaceful retreat w/ modern bth & private deck w/ hot tub. Outdoor is a spacious deck, built in kitchen & in-ground pool, + a 2 car garage w/elec charger. Beauty, privacy and convenience.

The equestrian elegance of this 55 acre property starts at the gated driveway. Perched on the hilltop is a fully equipped custom build multi use barn entirely heated by radiant floor heat and includes 8 14x14 stalls w/ autowaterers perfect for the breeder or veterinarian. Includes kitchenette, office, laundry and bathroom. Also included is a heated equipment shed and workshop, a heated drive through aisle for large trucks, washstalls and more! The grounds include 8 paddocks with waterers, an exercise track, 3 large pastures. A second barn offers 12 additional stalls. The meticulously kept grounds is professionally landscaped and a covered wrap around porch greets guests into the home. Kitchen has quartz counters, GE profile appliances and a slider out to a large patio

Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make every season a revelation. Custom-built in 2000 from timber milled directly on the property, this 4,842 sq ft home carries an irreplaceable provenance that announces itself at every turn. A native stone fireplace anchors the soaring vaulted great room. An ash sapling banister curves to the interior balcony above. Antique leaded glass casts dappled light across wide-plank floors.

Nestled beside 900 acres of Alford Springs Nature Preserve, this contemporary colonial is sited on 5.8 acres. Built in 2005 and fully renovated in 2021, it boasts high-efficiency HVAC and hot water, 14GW of seller-owned solar, an open main floor plan, gorgeous kitchen with top-of-the-line appliances, front porch, screened porch, large 2-car garage, and generously-sized rooms throughout. Two spacious additional rooms adjacent to the primary and a guest suite are currently used as a gym and office/studio. Move-in ready with incredible privacy yet 15min to the center of Great Barrington.

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling.

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

A rare opportunity to own a masterfully reimagined circa-1861 post-and-beam barn, transformedinto a one-of-a-kind luxury estate set on 89 pristine acres in the heart of Columbia County.Surrounded by sweeping pastoral views, open fields, and tranquil natural beauty, thisexceptional property offers privacy, scale, and timeless craftsmanship.The residence spans approximately 6,000 square feet across two levels, seamlessly blendinghistoric character with modern sophistication. Soaring ceilings, exposed beams, and wide-plankwood floors milled from trees harvested directly from the property*create an authenticconnection to the land and the home's heritage.At the heart of the home is a dramatic great room, ideal for entertaining or quiet evenings

Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views to the northern Connecticut hills. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County.

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 wood burning 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. 4 private bedroom suites in total each with their own sitting areas and additional sleeping options. 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.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury.

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and suites all with stunning, private bathrooms. The Lakehouse is exquisitely appointed and furnished with an eye toward showcasing the clean, graceful architectural details of the original lake cottage while adding modern ''creature comforts'' and ''cutting edge'' bathroom design. The Lakehouse is perfect for large families to gather for long weekends or extended vacations year 'round.

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.

Blue Hill Farm: an 1820 Center Hall Colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land surrounded by the Umpachene River on three sides. There are long views to the west of the Taconic Range from inside and outside of the home, and a grouping of supportive barns to the south across a very rarely traveled, narrow dirt road. Offered for the first time since 1967, this is truly an unusual and rare offering with development possibilities featuring extraordinary views.

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.