Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail--from the textured walls to the light pouring in at all hours--creates a sense of romance and possibility.The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest.

Charming home in a private setting, close to all area attractions. The oversized front porch leads you inside to a light filled first floor, with newly finished hardwood floors and high ceilings. The living and dining rooms offer flexible space for relaxing or entertaining. The kitchen has lovely southern light, as well as access to the back deck for summer dining. Upstairs are two generously sized bedrooms, and a full bathroom w/ laundry. The third floor has a finished bonus space as well as an unfinished storage area. Outdoor amenities include a nice size yard, storage shed, and an in-ground pool.The property has a new 3 bedroom septic system, and a full de-leading compliance certificate. Minutes to downtown W. Stockbridge, 10 minutes to Tanglewood, and 35 minutes to Albany.

NORTH EGREMONT - Almost 18 elevated acres with sweeping views of the Berkshire Hills that has been surveyed, flagged with enough road frontage to subdivide once. An open meadow with woodlands as a backdrop make this parcel most desirable....a must see!

Charming Light-Filled Farmhouse with Additional AcreageThis beautiful 4-bedroom, 2.5-bath farmhouse is rich with character and filled with natural light throughout. Timeless wide-plank wooden floors add warmth and charm, perfectly complementing the home's classic farmhouse style.Set in a picturesque country setting, the property sits on a one-acre lot with an additional acre included, offering space, privacy, and endless possibilities. Two outbuildings provide flexible use for storage, workshops, hobbies, or future projects.Peaceful, bright, and full of charm, this property offers the perfect balance of updated, comfortable living and open land--an ideal retreat for those seeking the beauty of country life with room to grow.

*NEW PRICE* HISTORIC RAILROAD STATION WITH CABOOSE. Built in 1893. Renovated in 2018, 2,134 sf. Unique opportunity to own a piece of Lee History. Restored and converted for Bar/Restaurant use. Centrally located in downtown. Seating for 65 plus Outdoor Deck. Parking for 30 cars. Property also available for Lease (MLS# 243435).

Nestled in Sheffield Village on 8+ acres, this charming New England farmhouse blends rustic character with modern comfort. Featuring 3 bedrooms, 2 baths, wood floors, beams, Great Room with a gas stove offers a warm inviting space Enjoy a country kitchen with a pantry. Screened in porch with outdoor patio, gardens, and two sheds for storage or hobbies. Perfect as a private sanctuary or Airbnb, this property combines timeless charm, tranquil surroundings, and great potential.

Welcome to 13149 NY 22, Canaan, NY 12029 a beautifully updated 3 bedroom, 1.5 bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient single level layout provides comfortable flow between the bright living spaces and the three well sized bedrooms. Recent improvements include a brand new roof, ensuring years of worry free ownership. An attached heated two car garage adds convenience and storage, while the expansive yard gives you plenty of room to garden, relax, or simply enjoy the quiet surroundings.

Situated on an elevated lot in desirable Walden Village, this meticulously maintained home offers a private backyard perfect for outdoor entertaining. The main level features a convenient primary suite with a full ensuite bath, a guest powder room, and the convenience of first-floor laundry. An elegant, open floor plan provides excellent flow for both entertaining and everyday living, and a bonus family room adds flexible living space. Upstairs are two additional bedrooms and a full bath. All bathrooms have been updated, and the home has been carefully maintained, making it move-in ready. Enjoy close proximity to community amenities, including the tennis courts and pool.

Welcome to 42 Lexington Parkway, a beautifully maintained Colonial tucked into one of Southeast Pittsfield's most desirable neighborhoods. Offering over 1,800 square feet of living space, this home is larger than it appears and filled with thoughtful updates throughout. A freshly painted exterior and exceptional curb appeal make this a home you'll love coming back to.A beautiful, wide, and gracious foyer sets the tone as you enter. Inside, the main living area is spacious and inviting, centered around a classic wood-burning fireplace, perfect for cozy evenings. Sun-filled rooms, a flexible den/sunroom, and a generous layout create an ideal setting for both everyday living and memorable gatherings.

Located in the desirable Clayton section of New Marlborough, this 3-bedroom, 2-bath home offers a rare opportunity to own 7.2 acres with 383 feet of frontage on the Konkapot River. The property features a natural setting with direct river access and plenty of room to make it your own.The home has a functional layout with three bedrooms and two full baths. While move-in ready, it would benefit from updating and general maintenance. Being sold as-is.Conveniently located near the Connecticut border--just minutes to Canaan, CT, and a short drive to downtown Sheffield and other Southern Berkshire attractions.Enjoy the natural beauty and quiet charm of the Berkshires with the potential to customize and enhance this well-located property.

Imagine starting your mornings with coffee on the deck and ending your evenings under the open sky. This charming 2 bedroom, 1 bathroom home offers the perfect balance of comfort and simplicity, with inviting indoor spaces and Excalibur Lake front views. Whether you're looking for a peaceful retreat or a place to gather with loved ones, this home is designed for entertaining and making memories. With a history of short-term rental use, this home presents a unique opportunity for those seeking both a personal retreat and income potential. 10 minutes from Jacobs Pillow Dance Festival. Boat, Swim, Relax-Repeat! Everyday feels like a vacation in this ranch home.

Step inside to find an inviting ranch-style home set on 15 acres of peaceful, private land, offering the perfect blend of comfort and tranquility. This home offers an EXCEPTIONAL layout, centered around a well appointed kitchen with stone countertops, ample cabinetry, stainless appliances & a kitchen island-blending seamlessly into an oversized family room showcasing a beautiful gas fireplace. Complemented by a formal dinning room and family friendly living room with sliders leading to the new composite deck over looking a fully fenced area for kids and pets to play and enjoy! Featuring three bedrooms, including a lovely primary en-suite complete with a custom shower, jetted tub & walk-in-closet. First floor laundry room, half bath with entry/mudroom area complete the main level

Welcome to 184 Washington Mountain Rd -- an inviting three-bedroom, one-and-a-half bath raised ranch ideally situated in a quiet, highly desirable location. This thoughtfully updated home features a stylish eat-in kitchen that flows seamlessly into a bright, open living area with direct access to a sunroom, creating the perfect space for relaxing or entertaining year-round. Beautiful hardwood floors add warmth & timeless appeal throughout the main level. The primary suite offers the convenience of a private ensuite half bath, while the finished lower level provides versatility with a spacious family room & dedicated office area. Outside, a generously sized backyard offers ample space for outdoor enjoyment. A rare opportunity to enjoy comfort, space, and location in one exceptional home.

This condo is beautifully renovated with high end finishes. Styled right out of a design magazine, this 2 bedroom and 2 bath condo comes fully furnished. Excellent rental history. Located at the base of the mountain right next to the express lift, this is the perfect place for your winter ski retreat. Parking spot included and ski locker. The property has access to an indoor hot tub and fitness center. Outdoor heated pool. HOA covers internet, cable, road maintenance, landscaping,,snow removal, trash removal and water.

BRIDGERTOWN CXV A great opportunity to own or invest in a 2-unit In-town property. 3 bedroom first floor with 1 bath, 2nd Floor is a spacious and light 1 bedroom, 1 bath. Hardwood floors, Updated boiler system. Just a quick stroll across the bridge and your in town for all your shopping and entertainment. This is a great chance to own and live while bringing some income in to offset expenses. Make this your next choice to enjoy life in the Berkshires, where everyone wants to be.

Indian Lakes property with gorgeous lakes two beaches for swimming or kayaking &clay tennis courts. This log sided 3 bedrooms 2bath cabin sits in the Hill towns of Becket, Middle of the Berkshires easy to get to Stockbridge, Gt Barrington 3 ski areas 7 lakes and October State forest.2 new baths and new kitchen with stainless appliances and granite counter tops is ready to show. Cozy up to the wood burning fireplace. Two bedrooms and full bath on the main level, Kitchen living room and dining are all open under a vaulted wood ceiling.The downstairs has a full bath & Bedroom with a wood stove and large den. I love the little screened in Porch off the kitchenand a large Barbecue deck off to the side all facing the woods about 8 mins' from I-90 Lee, Stockbridge /Lenox exit.

Experience the perfect blend of historic character and peaceful riverside living in this four-bedroom, 1.5-bath Colonial farmhouse. Nestled on 1.8 sprawling acres in the heart of Clarksburg, this property offers a rare opportunity to own a piece of New England heritage with a front-row seat to nature. This home features spacious rooms with ease and flow throughout the floorplan. 1.8 acres of versatile land, providing plenty of space for gardening, recreation, or simply enjoying the privacy of the countryside with river views. This property includes garage/barn, perfect for a workshop, studio, or preserving the rustic aesthetic of the homestead. Offering a tranquil backdrop that is increasingly hard to find, a balcony and deck thoughtfully situated to maximize its most stunning river views.

AMAZING 3 Bedroom, 2.5 Bath Contemporary in a Wonderful South Pittsfield Neighborhood! Immaculate inside and out, this home offers an open, bright floor plan perfect for everyday living or a second home retreat. Enjoy beautiful wooded views from the rear Trex deck, fireplaced family room, and kitchen. The new granite kitchen features wood floors and flows seamlessly into the main living spaces.The spacious primary suite includes a beautifully updated bath with a large walk-in shower. Additional highlights include a gas fireplace, oversized 2-car garage, fenced yard with wooded land abutting the property for added privacy, and a quiet dead-end street location. A truly move-in ready home in a desirable setting!

Enjoy one-level living in downtown Great Barrington! This charming 3-bed, 1-bath mid-century ranch is your perfect Berkshire retreat, featuring a cozy wood stove in the living room for those crisp mountain evenings. 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 and 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.

Spacious and filled with natural light, this four bedroom, two bath home offers incredible potential and timeless charm. Featuring large windows throughout the home makes it bright and inviting, with a comfortable layout with a full kitchen, formal dining room, cozy sitting room, and a charming fireplace in the living room which is perfect for relaxing evenings. Generously sized rooms provide plenty of space to make your own. Ideally located within walking distance to town, this property is a wonderful opportunity for a first-time homebuyer or investor to bring fresh vision and updates to an already solid home. Enjoy just minutes away from the best of all the Berkshires cultural attractions, Berkshire Theatre Norman Rockwell Museum, Tanglewood, Historic Red Lion Inn and more!