Step into this beautifully renovated home, where natural sunlight fills spacious, oversized rooms, creating a warm and inviting atmosphere. Every detail has been thoughtfully updated, showcasing a fresh, modern aesthetic complemented by brand-new appliances. The expansive primary bedroom features two closets, with one large enough to serve as a nursery or home office, complete with two windows for abundant light. Perfectly positioned in a prime location--just minutes from Jiminy Peak Mountain Resort, tranquil lakes, and convenient shopping--this home seamlessly blends comfort, style, and accessibility.

Lovely, meticulously maintained home in southeast Pittsfield offers spacious living. Attractive kitchen with large dining area leading to deck. Generous yard with fenced area for pets or kids, a garden area, large shed. There is an ''in-law'' arrangement in the lower level that has living room, bedroom or dining room, a den or dining or bedroom, kitchenette, full bath and door to the garage.Three bedrooms on first floor with nice closets, and there is a full bath. 2 car garage with work area. Come and see this home! Open house 10/25 10:30-12:30

Enjoy one-level living in downtown Great Barrington! This charming 3-bed, 1-bath mid-century ranch is your perfect Berkshire retreat. Nestled on a quiet cul-de-sac, the home sits on a spacious 0.41-acre lot with mature trees. Features include an attached 2-car garage/workshop, large private yard, original wood floors and an updated heating system. The real gem? Unique B2 zoning allows for a home business, studio, or office! Enjoy an unbeatable location--walk to shops & dining, with downtown and attractions like Tanglewood and Butternut just minutes away. This versatile property is a rare find offering both a peaceful home and a prime business opportunity.

Welcome to this beautifully maintained 4-bedroom, 2-bath home that is truly move-in ready! The primary bedroom includes a sitting room with cherry cabinetry, a full bath and a large walk-in closet for added privacy and convenience. With its maintenance free vinyl siding, spacious 3.5-car garages, and inviting large porch, this property offers curb appeal and practicality in equal measure. You'll also find a bright and airy sun room, ideal for relaxing, entertaining, or enjoying your morning coffee in any weather. Step inside to find freshly painted rooms and stunning red oak floors throughout, complemented by abundant natural woodwork that adds warmth and timeless character. One-bedroom features brand-new Pergo flooring, while the kitchen boasts new luxury vinyl and updated appliances.

The charm of yesteryear meets the comfort and convenience of today in this beautifully maintained 3 Bedroom, 2 Full Bath Lenox Colonial, set high on a picturesque village knoll. Enjoy wood floors, an open-concept kitchen and dining area with exposed brick, and a central yet wonderfully private location.All the major updates have been thoughtfully completed, including a newer roof (2021), updated furnace and hot water heater, replacement windows, and fresh interior and exterior paint. Efficient natural gas heat and hot water keep living comfortable year-round.

Step into history with this captivating 4-bedroom, 3-bathroom single-family home, offering 2,288 sq. ft. of living space. Built in the 1860s, this residence exudes charm while incorporating numerous modern updates for contemporary comfort. Nestled on a quarter-acre lot in a quiet town, this home boasts a lush yard and a fully screened-in porch, perfect for enjoying serene mornings and tranquil evenings. The spacious rooms provide versatility and ample living space, while abundant storage. A standout feature is the standalone two-car garage. Experience a unique blend of historic elegance and modern luxury in this remarkable property--an ideal sanctuary for those seeking a peaceful, yet connected lifestyle

Two homes on almost 5 acres! Have you always dreamed of living a sustainable, homesteading life with your family and extended family? This property makes generational living possible! The ''cabin'' is 2,106 sq ft with updated bathrooms, mainfloor laundry, 2 fireplaces with wood and pellet stove inserts, primary bedroom with large cedar lined walk in closet. Impressive P&B exposed wood throughout the home adds character and a rustic feel. Second home is 1728 sq ft has updated bathrooms, 2 fireplaces, updated kitchen and large bedrooms. Both homes are surrounded by gardens, fruit trees and some open pasture. A barn on the property can be converted for livestock or can be used as a workshop and potting shed. 6.51 acres across the street may also be available.

Don't miss this unique historic property -- truly a GEM! Ready for quick rental income and perfect to enjoy as spring arrives. A wonderful second home to share with family! Imagine a short stroll to downtown Lenox for coffee, a quiet dinner, and a beautiful night at Tanglewood under the stars. Just one street from downtown and steps from St. Ann's Church, this 1,700 sq. ft. bungalow blends charm with comfort inside and out. With a strong rental history (up to $16,000 in summer income), could be a ideal turnkey furnished investment or personal retreat. Enjoy 2025 tax breaks, settle in for the 2026 Tanglewood season, and explore Lee, Stockbridge, or Great Barrington. Embrace the arts this summer!

Spacious split foyer with addition of a year-round heated Florida room featuring inground, heated, fiberglass pool, hot tub, its own granite kitchen, full bath, & Tiki bar, making it ideal for hosting gatherings; or cover the pool and the entire floor with an already existing truss floor system when not using the pool..has 2 egresses, for a great guest/in-law space that can be closed off to the main home. Enlarged, Primary bedroom includes a full bath, walk-in closet and sliders to sneak out to the pool area. Glass room has gas, ceramic tiled fireplace and the main dining room has a field stone fireplace (for cozy New England days). All 3 bedrooms are very large with closet space. There are many extra storage closets throughout the home, as well as an oversized 2 car garage.

The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect you to the landscape. Your backyard is a protected nature preserve, guaranteeing permanent privacy. The property features a handsome 24x30 horse barn with 2+ acres of paddocks, plus a separate lower-level guest apartment--perfect for weekend visitors or a private home office. A complete package blending modern convenience with pastoral beauty and cultural access.

Charm. You'll find it in this 3BR, 2.5BA West Stockbridge home. The charm of a farmhouse fence, lush with white hydrangeas, roses, and day lilies, set along a peaceful street where neighbors jog, push strollers, or walk their dogs. The charm of luminous freshly painted interiors and windows framing views of greenery on all sides--mists atop Lenox Mountain, vivid sunsets, and star-spangled night skies. The charm of a spacious enclosed porch for relaxing and entertaining, a 400sf insulated, 'do-with-it-what-you-will' barn with French doors and patio, perennial gardens, overarching maples. Practical charms, too: new roof, new primary bath, updated systems, 2-car garage, 2 minutes to Six Depot, 10 to Tanglewood, 16 to Guidos. Charm and privacy, with room to dream, create. Make it your own.

Beautiful riverside home offering comfort, flexibility, and in-town convenience. The front 2BR/2BA residence features soaring ceilings, skylights, an open kitchen, private riverfront deck, and an oversized ensuite bedroom. A spacious lower level provides room for guests, hobbies, or work. A charming garden area overlooking the Williams River adds outdoor enjoyment. The attached 1BR/1BA apartment has its own entrance, deck, and shared laundry access. Sale subject to owner leasing back the apartment for $2,000/mo. Custom built-ins, Rais wood stove, mini-split heat/AC, ceiling fans and generous storage. Just 3.9 miles to Tanglewood and steps from shops, dining, and recreation. Your Berkshire pied a terre awaits!

A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to grocery stores and the hospital, while ample on-site parking provides a crucial amenity for all residents. Adding to its value, a detached garage/workshop offers the flexibility to be rented separately for additional income or used as a storage amenity for tenants.

Check out this unique opportunity to own an historical gem in the heart of Colebrook. This beautiful antique colonial sits on five fairly level acres which encompasses a pond, many fruit trees and berry bushes. Perfect for a growing family or someone looking for a country retreat with Norman Rockwell views. The ''Cooper House'' is an historical icon in this town; a perfectly located corner lot that is equal distance to Great Barrington, MA and Torrington, CT, and only minutes to Winsted, CT and Norfolk ,CT. Allows you to be close to Skiing, Shopping, restaurants, town Community center, Post office, town pond and newly renovated Colebrook Store. This charming town has a close community feel. Don't miss your chance to own a piece of history. Make sure to set up your showing today!

Welcome to this exceptional 3-bedroom, 2-bathroom lakefront retreat w/an in-ground pool,located in the highly sought-after Otis Woodlands community. Perfectly situated on OWL Lake, this home offers a rare combination of natural beauty, modern upgrades, and an array of resort-style amenities, making it the ideal country escape or full-time residence.Step inside to an open-concept living area with soaring vaulted ceilings and abundant natural light streaming through large windows. The spacious kitchen boasts gleaming granite countertops, newer appliances, and custom cabinetry, creating the perfect space for entertaining or quiet meals. The living room, with its inviting warmth and charm, seamlessly flows into the dining area, making this home perfect for gatherings with family and friends.

Welcome home! This magnificent 23-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. Enjoy walks, rides and cross-country skiing through woods and meadows on the maintained trails that meander through the 23 acres. A low-maintenance wild garden of perennial flowers and shrubs produces a kaleidoscope of colors during the spring and summer seasons. A large, private office area with high-speed internet provides a productive ''work from home'' environment. The first floor features an eat-in country kitchen with an antique Glenwood stove. The formal living room, with its wood-burning fireplace, is ideal for cozy evenings.

This historic 4-bedroom 3.5-bath home sits on a beautifully landscaped 1-acre lot surrounded by ornamental trees, vibrant flower gardens and mature plantings. Originally built around 1800, this comfortable well-maintained house features high ceilings, warm wood flooring, and plenty of period charm. The main level welcomes you with a spacious living room accented with Greek Revival moldings, an expansive bay window with built-in window seats, and an inviting wood-burning fireplace. Nearby, a charming den offers another wood burning fireplace and quiet spot to relax with a book. Off the living room, the formal dining room can comfortably accommodate a large crowd at holiday gatherings...

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion--with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision--be it modern apartments, stylish offices, retail space, or a dynamic studio. Spacious and bright with 5,180 sq ft across two levels Excellent bones

GORGEOUS LOW MAINTENANCE HOME IN LOW TAX EGREMONT. A move-in ready opportunity, just minutes to the NY & CT borders AND Great Barrington. This home is ready for occupancy just in time for Ski Season. Wonderful chef's kitchen with open plan Living/Dining. The upper level hosts a grand primary en- suite, with a dedicated office space and seating area, AND its own screened porch. Two additional Bedrooms and full Bath provide total comfort for family and guests. The expanded deck, fire pit and level yard great for family & friends. Two car attached garage, Generator, and meticulously maintained grounds. Custom shed, has studio or play house potential. Dog fenced area. Hy's Fried, Egremont Barn & Catamount Ski area minutes away. Trains 20 minutes away.

Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond, just minutes away, this home is a haven for those who crave both serenity and adventure.Where Modern Elegance Meets Natural Beauty A Grand Welcome - A wraparound deck, inground pool, and upper balcony invite you to take in the forested surroundings, framed by black aluminum railings and Trex boards built for beauty and longevity.