Step into a world where historic charm meets contemporary living in this unique 4-bedroom, 4-bath Arts & Crafts home located in the heart of Southeast Pittsfield. This one-of-a-kind residence is brimming with character and has been lovingly maintained to showcase its original features while providing all the comforts of Berkshire living. This majestic home has a fascinating origin story. Built in the late 1800s, it was once the east wing of the summer residence of the Pillsbury family. Originally adjoined with the house behind it on Wendell Avenue and situated a half block away, the sprawling grand estate was divided into two separate homes, and carefully moved by horse in the early 1900s, establishing the neighborhood that would grow around them.

Welcome to 93 Roselyn Drive, a beautifully maintained, move-in-ready, light-filled mid-century gem with style, function, and effortless upkeep, ideally situated in Pittsfield's desirable west-side neighborhood.This home offers big-sky views and a private 0.75-acre yard - perfect for morning coffee, stargazing, or weekend gatherings on the expansive two-level deck overlooking mature, easy-to-care-for gardens.Inside are sun-filled rooms, a classic stone gas fireplace with remote control, a fabulous bonus room with large windows facing the backyard - ideal for a home office, family room, or yoga studio - plus a newly finished lower level adding more versatility with a full bath, cedar closet, laundry area, and plenty of room for a guest suite, media room, or private gym.

Welcome to 59 Joan Drive, a well appointed 4-bedroom, 2.5-bath raised ranch located in one of Pittsfield's premier neighborhoods. The main level boasts a bright living room, a modern kitchen with ample storage, and a dining area that opens to a spacious wrap around deck, ideal for outdoor gatherings. The master suite offers a private full bath, while three additional bedrooms provide plenty of space for family or guests. The finished lower level includes a versatile family room, 1/2 bath, laundry room and access to the 2 car garage. Perfectly set on approx .42 acres of land this property offers mountain views, yet in a neighborhood setting. This home comes with a one year transferable home warranty, whole house water filter and additional insulation was just added to increase efficiency.

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.

Prime Downtown Lee Investment Opportunity Located on a highly visible corner lot in the heart of downtown Lee, this versatile three-unit building offers a blend of residential and commercial income potential. The property includes two residential units--currently operated as successful short-term rentals--and one commercial space currently leased to a massage therapist. The first-floor efficiency unit features a compact, well-equipped kitchen with a stove, refrigerator, dishwasher, and microwave hood, plus a Murphy bed for space-saving convenience, and a full bath with a shower stall. The second-floor residential unit offers two bedrooms and a full bath with a tub shower combination. While this unit does not have a full kitchen, it presents opportunities for customization to suit future

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

This 1800's farmhouse was once home to The Ideal Shoe Company (Danvers, MA). It's a property rich with history, charm, and situated in the middle of 13+ gorgeous acres fit to explore, or simply revel in their beauty. Surrounded by hundreds of acres of conservation land, your adventures could be endless. Take in the tranquil sounds of the Westfield River while roaming the tree-lined paths or relaxing in the Gazebo. Once inside, hardwood floors and beautiful wood beams decorate nearly every room. Fire up the wood stove, grab a book from the library, and unwind in the spacious living room, the 3-season porch, or have a swim in the pool room. The impressive kitchen is ideal for entertaining, with easy access to an office/studio space and a newly renovated bath with laundry.

This updated ranch offers single-level living on a spacious, level yard framed by mature deciduous trees, providing natural privacy in one of Williamstown's most peaceful and desirable neighborhoods. Oak hardwood floors lead you into an inviting open living/dining area, complete with a bay window that frames serene views of the backyard. The renovated cherry kitchen boasts quartz countertops, stainless appliances, and a tile backsplash. The spacious primary suite includes a fireplace and renovated en suite bath, with flexibility for a third bedroom or office. Efficient comfort comes courtesy of leased solar panels, four Daikin mini-splits, and two fireplaces. A sunny deck and patio extend your living outdoors. Just minutes to Williams College...

Charming Renovated Cottage on The Hill - Great Barrington, MADiscover this beautifully renovated Four Square-style cottage in the heart of Great Barrington's coveted ''The Hill'' neighborhood--a rare pied-a-terre offering classic charm with modern upgrades. This delightful 2-bedroom home is nestled in the Southern Berkshires, just moments from downtown, Lake Mansfield, and preserved natural areas.Step inside to a brand-new kitchen, freshly painted interior, and hardwood floors throughout. All windows have been upgraded to energy-efficient Anderson, enhancing comfort and style. The exterior has been professionally repaired and painted. A newly fenced garden provides a private oasis, while dedicated off-street parking ensures convenience.

Open House 10-11-25, 11:00-1:00. Inside pictures to follow soon. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanicals. Freshly painted inside and out, this home is truly move-in ready. The stonework patio provides a picturesque setting with a fabulous screened porch. There is a convenient shed and generous oversized garage space. Ample storage throughout ensures all your needs are met. Discover the perfect balance of history and modernity in this delightful property.

Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including the Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, fitness center, interior bike storage, package delivery room, dog wash and on-site professional management.

WATERFRONT ON ASHMERE LAKE! You can relish the lake, right in your own backyard, and bask in the tranquil atmosphere while sitting on the deck overlooking the water, or from the enclosed porch or from the indoor spa tub. This home has an open kitchen - living room, with fireplace. Also has central air. The LL level has potential for finishing and also veiws the lake. A fantastic opportunity to own on the lake!Pellet stove included, windows are newer, propane heating a plus and central air conditioning. There is a minio garage door under, to bring your water toys in and out.

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility.

A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and laundry room. A separate 25' x 50' building, originally built in 1990 as an antique shop, now features a recently updated spacious 2 bedroom bungalow apartment currently rented for $2,200/mo. Additional space includes a large 3 bay workshop / garage for projects or other income uses. Close to Sheffield Green, Library, Dewey Hall, 10 min to GB or CT. House needs updating, but well worth the effort!

Looking for a corner unit at JJ's lodge? This 3 bedroom 2 full bath unit is literally steps away from the private locker room and walk out to the Berkshire Express. Beautiful distant Mountain vistas and views of the bunny hill where you can watch your kids learn how to ski and snowboard all from your private balcony! Multiple beds for family and friends. The unit has central AC and Heating with an electric fireplace for ambiance and looks. This unit is close to all the amenities like the summer pool, winter slopes, hiking trails, bars and restaurants. This one will not last long...

Welcome to this beautifully appointed & pristinely maintained residence that combines timeless character with modern upgrades. Situated on a desirable corner lot, offering a fully fenced-in yard. This spacious home features generously sized rooms throughout, offering comfort & elegance at every turn. The stunning kitchen is equipped with stainless steel appliances, soapstone countertop, quartz island and classic backsplash. A formal dining room flows seamlessly into the side porch, overlooking the serene side yard, perfect for entertaining. The expansive living room boasts a stacked stone wood-burning fireplace and built-ins. Just off the living room, a cozy sitting area with an electric fireplace provides a perfect spot for an office or a reading nook.

Step inside and be greeted by an inviting and light-filled interior. Offering 4 bedrooms and 3 baths, the thoughtful, open-flow floor plan is an entertainer's delight, ensuring guests are always part of the conversation, whether gathered around the large kitchen island or relaxing in the main living space.The versatility of two separate living rooms is a rare find, offering endless possibilities for a growing family, multi-generational living. Perfect entertaining space offered in the rear yard with patio fire pit and custom he/she shed. Amazing greylock views year round! Close to downtown and the local rail trail, just tucked away on a double lot nearing a full acre.

OPEN HOUSE Sat 7/5/25 11a-12:30p Welcome to your private escape in the heart of the Berkshires on a quiet country road. This expansive ranch-style home offers ample space for large family gatherings, house guests or entertaining. Enjoy the ease of one-level living with a bright, open floor plan and a grand brick fireplace anchoring the spacious main living area. The home features four spacious bedrooms and two updated full bathrooms along with a back deck and screened-in back porch overlooking the woodlands. The lower level offers even more flexibility with a private entrance, an additional bedroom, full bath and convenient kitchenette - perfect for guests, in-laws or potential rental income. There is also a large unfinished room with a second fireplace and walk-out access to

This beautiful three-bedroom two-bathroom condo is located in JJs Lodge in middle of it all. Spacious, immaculately clean and appointed with all the comforts of home - gaming, games, Ski locker, plus more! Walk out the lodge door to high-speed quad lift - you can't get any closer at Jiminy Peak to the mountain! This place offers all season fun in the Berkshires. Jiminy Peak has family fun and summertime pools and hot tubs. Master bedroom En Suite with Queen size bed. Deep jetted tub and shower. Second bedroom with Queen size bed. Third guestroom with two twin over full size bunk beds. Plentiful closet space and dresser space for settling in during your stay. Second bathroom has deep jetted tub and shower. This is your opportunity to own your own ski lodge condo.