Beautifully updated and lovingly maintained Colonial in the heart of Great Barrington. Bright, sunny, and truly move-in ready, this inviting home offers a combination of classic charm and comfortable modern living. The first floor features a welcoming mudroom, updated kitchen, heated sunroom, dining room, living room, family room, laundry, and full bath, providing plenty of space for both everyday living and entertaining. Upstairs are three comfortable bedrooms and a second full bath. Outside, enjoy a lovely yard and charming covered porch--perfect for relaxing and enjoying the neighborhood. Ideally located with easy access to Great Barrington's vibrant town center, library, restaurants, shops, and churches. A warm and beautifully cared-for home in a wonderful convenient location.

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals--just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train.

Make this fabulous White Pines Garden Unit your next home in the Berkshires in this sought after community. Cathedral ceiling Great Room open to dining and updated kitchen w/beautiful natural light and two story wall of glass with primary en suite & guest bedroom w/full bath, bonus room on lower level all leading to your private deck with amazing privacy. Amenities include one of the parking spaces for this unit is out the front door, assoc. clubhouse w/indoor pool & exercise room, HarTru tennis courts, walking trails and deeded rights to the private beach frontage on Stockbridge Bowl for swimming, kayaking or moor your boat...all within minutes from Tanglewood and the Village of Lenox.

Upper Rhoda Pond waterfront in Copake, New York (southern Columbia County) is a very special place. About 2 hours from NYC, it is a private 78 acre body of water with no public access and no gasoline engines. The waterfront includes new docks and kayak to row out to your exclusive floating raft. This 3 BR + office has 3 BA and is approximately 1944 sf with a full basement. The open floorplan lends itself to family, friends and entertaining. Wood burning fireplace to warm up on those chilly summer nights. Fiber optic is on the premises. The screened porch has panels, so that you can take in the country location and water views all year round. There is even a heater out there. The lower level works as a family room. The sale includes a pool table and ping pong table. Storage galore.

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.

Over 4500 square foot commercial space set on over 3 acres in New Marlborough. 10 Minutes to Main Street Great Barrington. The possibilities are endless with this property.

This is a rare opportunity to own the breathtaking Berkshire views you've always dreamed of. Tucked into a neighborhood of distinguished homes just minutes from Lake Garfield, this 4-acre lot overlooks spectacular panoramic views with dazzling sunsets. Abutted by protected conservation land to the northeast, this is a site truly worthy of your dream home!

Located on a quiet country road, this 18.5-acre parcel offers beautiful mountain views, privacy, and a peaceful setting. Just minutes from Williams College, the Clark Art Institute, and town amenities, it's the perfect place to create your ideal retreat in the heart of the Berkshires. The property is under Chapter 61A.

Wake up to breathtaking panoramic waterfront views & end every day with spectacular sunsets from this exceptional ranch offering approx. 170' of waterfront frontage.This well-maintained home features 3 bedrooms, 2 full baths & an inviting open layout designed to showcase the stunning scenery.The sunroom, with walls of glass sliders, opens to an expansive deck-perfect for entertaining, relaxing or simply enjoying the peaceful waterfront setting.Inside, a beautiful stone gas fireplace creates a warm focal point, while radiant heat in the upper level & basement floors provides year-round comfort.Additional features include central a/c, new windows throughout & a walkout basement offering easy access to the outdoors & possibility of an ADU. The business zoning provides added flexibility for

Barns, Brook & Beautiful Living Uniquely spanning the Williamstown, MA and Pownal, VT state line, this inviting property combines New England charm with exceptional flexibility. The expanded 3,500 sq ft home offers 4 bedrooms and 2 full baths, including an option for a first-floor bedroom. Warm, connected living spaces include a stone-fireplaced family room, open kitchen and dining area, a cozy tavern room with wet bar, and a shaded patio for summer enjoyment. The 3.4-acre Vermont parcel features Broad Brook along its boundary plus two outstanding outbuildings: a 30'×40' insulated and finished barn with office and 12' ceilings, and a 30'×50' three-bay garage with 12' rafter clearance--ideal for vehicles, equipment, hobbies, or future conversion. With the house on 0.6 acres in MA and the

Otis Wood Lands lakefront Contemporary on OWL Lake with four bedrooms and three full bathrooms. Open kitchen/dining/living area with views of the lake. Spacious, two-level screened-in porch with deck access. First-floor primary suite with private deck access, and two additional bedrooms and full bathroom on the main level. Large lower level with walk-out access and fourth bedroom. Community amenities include pool, tennis/pickleball courts, lodge, playground, beach and community lake for non-motorized boats. Reserve fund fee of $4,000 due from buyer at closing. Woodstove disconnected prior to closing.

Set on four private acres along a quiet stretch of road near the Housatonic, this is a property that keeps to itself. No sightlines from the neighbors, no road noise to speak of, just the sound of the brook that runs through the back of the yard. This is a place built for quiet enjoyment, and the land delivers it in full. The gardens are the kind that take decades to get right, and someone got them right. The driveway is lined with rhododendrons that light up every spring, and from there the whole landscape is paced to bloom straight through summer. Fruit trees, azaleas, perennials, blueberries, raspberries. Walk it in July and you understand: this wasn't landscaping, it was devotion. And for all that's established, there's still room to put your own touch.

Stockbridge Investment Opportunity Fully Rented In Town 5-Family Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures. Can also be purchased as part of a investment portfolio 35 Main Street West Stockbridge ,Ma MLS# 249539

Drive in beneath the trees and the house appears in a pool of sunlight, set well back from a quiet road with gardens, lawn and woods gathered around it. There is an immediate sense of having arrived somewhere apart. Private and peaceful, yet not isolated, this one-owner West Stockbridge home has the easy spirit of a modern farmhouse and a distinctly relaxed way of living--a place to slow down and settle in. An inviting front porch, screened by the surrounding landscape, is private enough to become a place of its own--for morning coffee, reading or the pleasure of doing very little.

Some Berkshire homes are simply places to live. Others become part of the way you want to live. The Oronoque Villas are among those rare places. Built in the mid-1990s on the historic grounds of Oronoque--one of Stockbridge's great Berkshire cottages--just eight freestanding villas were thoughtfully sited within the estate landscape, complementing the original mansion, now home to distinctive condominium residences. Surrounded by mature trees, sweeping lawns, and established gardens, this villa offers the warmth and privacy of a house, the simplicity of one-level living, and the freedom to lock the door and leave whenever adventure calls. Whether as a year-round home or a favorite Berkshire retreat, life here has a wonderful way of slowing you down.

Welcome to life on beautiful Pontoosuc Lake, where breathtaking sunrise views and year-round waterfront living await. This charming, move-in-ready home offers the perfect combination of comfort, thoughtful updates, and low-maintenance living in a truly special lakefront setting. The open and airy living room features soaring vaulted ceilings, expansive windows that capture stunning lake views, abundant natural light, and a cozy gas fireplace, creating a warm and inviting space to relax or entertain. The well-designed floor plan includes spacious first-floor bedrooms with generous walk-in closets, updated bathrooms, newer flooring, Anderson windows, skylights, and multiple heating zones for added comfort.

First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first level, is a charming screened porch for dining or just taking in the sounds of nature. An open deck on the backside of the main level awaits your enjoyment. The 2nd level contains two VERY large bedrooms Ensuite; both with walk-in closets along with more locations for maximizing the distant views. The finished lower/walkout level has a full bath for a possible 4th Ensuite and living space

Sometimes fairy tales do come true... Tucked away on five private acres in Monterey, this singular handcrafted Berkshire cottage feels as though it emerged from a storybook. Natural-edge wood siding, steep rooflines, a massive fieldstone chimney and a tower-like upper level rise from a landscape of hydrangeas, woodland and a grape-covered arbor. Inside, the house is an irresistible mix of rustic character and thoughtful updates. Original wood floors, reclaimed hand-hewn beams, paneled walls, arched doors and unexpected architectural details give each room its own identity. The dramatic great room is the heart of the house, where soaring volume, exposed beams, richly paneled walls and an immense fieldstone fireplace create a space that feels far removed from everyday life.

Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat along with 2.5 updated bathrooms.

These are the Berkshire views you've been dreaming of. Meadow, mountains and enormous sky surround you in nearly every direction, with stunning westerly views across preserved fields to the lower Taconic Mountains. Morning light moves across the meadow; evenings end with the sun dropping behind the ridgeline. Spring brings wildflowers and returning birds, summer fills the fields with native plants and pollinators, autumn moves across the mountains in color, and winter transforms it all to snow-covered meadow and white-capped peaks. Perhaps your greatest pleasure will be getting out into it--walking the fields, cross-country skiing after fresh snow, watching the birds and wildlife, or discovering what has changed in the meadow from one day to the next.