This meticulously maintained 1900 farmhouse seamlessly blends timeless historic character with refined modern updates, creating a move-in ready retreat just minutes from the vibrant energy of downtown Great Barrington. Every corner of this classic three-bedroom, two-bathroom home reflects thoughtful care and craftsmanship, offering an ideal balance of warmth, functionality, and quintessential Berkshire charm. At the heart of the residence is a stunning cook's kitchen, thoughtfully renovated and fully outfitted with updated appliances, expansive counter space, and storage. Sunlit living spaces flow naturally throughout the main floor, showcased by rich, beautifully preserved wood floors that anchor the

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot w/ almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen,bathrooms as well as furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for the next owners to create their own Berkshire journey and memories.

Spacious single-level living in Woodmont Estates! Set on 3.04 acres across two lots, this 3,400 sq. ft. home offers 4 bedrooms, 2.5 baths, an updated kitchen, renovated primary bath, custom library, private office, four-season sunroom with newer Andersen windows, and a large bonus room with endless possibilities. Recent improvements include a repaired retaining wall and tree removal that opened up the front entry, bringing in more natural light and enhancing curb appeal. Enjoy mature landscaping, seasonal water views, a brook, sunrise views, protected land beyond, central air, natural gas heat, and a full walkout lower level with abundant storage and future potential.

Styled, spacious, and serene, this exceptional French Country-inspired contemporary residence offers a rare balance of peaceful seclusion and remarkable accessibility. Perfectly positioned just moments from the cultural richness of the Berkshires, idyllic New England country living, and convenient routes to both Boston and New York, it is a home that effortlessly connects tranquility with convenience. Bordering the pristine 115-year-old grounds of the historic Blandford Golf Club, the property enjoys an extraordinary setting where protected fairways create an ever-changing natural canvas and uninterrupted views stretching for miles. The approach is equally captivating, with thoughtful landscaping featuring a striking Rising Sun Redbud and elegant Yellow Magnolia.

Set in a peaceful West Pittsfield neighborhood, 35 Meadow Ridge is a sophisticated contemporary home with spacious thoughtfully designed living. Soaring 12 foot ceilings and cherry hardwood floors welcome you inside. The main level features a family room with built-ins, living room with gas fireplace, dining room, eat-in kitchen and access to the outdoor deck. The second floor offers an expansive primary suite, 2 additional bedrooms, 2 full baths, and flexible fourth room for use as bedroom, den or gym.A finished walk-out basement includes a family room and ensuite bedroom adding valuable space. This versatile home offers exceptional comfort and flexibility.Moments from Pittsfield State Forest, Onota Lake, downtown dining and short drive to Tanglewood. This is Berkshire living at its best!

Light, airy & effortlessly inviting this 4 bedroom & 3 full bath home is made for Berkshire Living. Walls of windows & a sun filled sunroom bring the surrounding woodlands into nearly every room, while a brand new oversized deck sets the stage for long summer dinners & relaxing afternoons. A separate grilling deck offers the perfect spot for outdoor cooking & easy entertaining. Spacious interior rooms, abundance of natural light & multiple gathering spaces make this an exceptional year round retreat. Then there's the Otis Wood Lands lifestyle w/ an incredible array of amenities including a private lake, clubhouse, swimming pool, tennis/pickleball & playground. It's the perfect pairing of a beautiful home & a welcoming community offering everything you need to relax, play and entertain.

To Be Built - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 2.14-acre lot (MLS # 248343), featuring a private well, 3-bed septic design, and underground electric. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.

This well-loved antique home offers a rare combination of history, thoughtful updates, and natural beauty. Set on 14+ acres with sweeping westerly mountain views, Carefully maintained over the years, the property has benefited from significant improvements, including an updated foundation, electrical and plumbing systems, heating system, windows, and roof. The home offers four bedrooms, two full baths, and a full basement, providing comfortable living space with the character and charm of an earlier era. Outside, the property unfolds across fields, gardens, mature fruit trees, and open land, with direct abutting state land and access to the Appalachian Trail nearby. An oversized detached garage with a second floor offers ample room for vehicles, equipment, storage, or a workshop.

''ON THE HILL'' Condo at The Oakwoood! Town-House style unit in a prime location. Located in a highly desirable setting, this property offers easy access to town, putting Shops, Dining, and local amenities just minutes away. 3-Bedrooms, 2-Baths,a large Living Room with vaulted ceiling & fireplace, Enjoy the community pool and beautifully landscaped property. Have coffee on the deck and take in the Eastern Mountain View! Great in all seasons with Ski areas, hiking and cultural attractions nearby.

Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone patio with firepit, and beautifully landscaped grounds. Spacious living and family rooms with woodburning fireplace and generous mudroom/office. Offering three bedrooms, three baths, plus a versatile creative space, studio/sitting room, endless possibilities. Minutes to downtown Lee, Stockbridge, Lenox, Tanglewood, shopping, dining and all that the Berkshires has to offer for year-round living.

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 3.59-acre lot (MLS # 248344), installed private well, perc test/soil evaluation complete, and underground electric in place. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.

Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and entertaining. Outside, you'll find a large barn, a greenhouse and impeccable gardens ideal for gardening enthusiasts or creative projects. This property is not just a home; it's an opportunity to enjoy the tranquil beauty of West Stockbridge, with its vibrant community and picturesque surroundings. Located minutes from many local attractions including Tanglewood and minutes from the highway.

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.

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

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.

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

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.

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.

Striking and sophisticated riverfront condominium in superb location, with close proximity to restaurants, shops and theater on Spring and Water Streets, the Taconic Golf Club, Williams College, and the Clark Art Institute. One of only 6 recently built town house units on the river in the handsome Cable Mills complex, number 8 has benefitted beautifully from the discerning taste and style of its owner, with elegant yet understated lighting fixtures, and enchanting touches of color and texture throughout. Light-filled with an abundance of large windows, it offers as well two terraces and two upper decks providing opportunities for al fresco dining and fresh air relaxation. A sleek suite of Thermador appliances graces the kitchen/dining area which includes both a breakfast nook with