Tucked away on a quiet country road just minutes from downtown Great Barrington, this charming single-level ranch offers the perfect Berkshire retreat. Set on two private acres, the home is surrounded by mature trees and natural beauty- with nearby access to trails. Step inside to a bright interior featuring a spacious living room anchored by a beautiful stone fireplace. The kitchen offers crisp white cabinetry, and modern countertops. Two bedrooms and a full bath complete the main level. Whether you're seeking a full-time residence or a peaceful getaway, 245 Long Pond offers all the charm and abuts preservation land conveniently located near Tanglewood, theaters, and more.

Amazing opportunity to own a ski vacation home right in the heart of Village Center is this totally turnkey 2 bedrooms 2 full baths unit with an outside balcony. Private parking spot. Private ski locker. No stairs. 10 foot ceilings throughout. Crown molding. Easy access to the slopes.

Nestled on a quiet country road, this well-kept ranch offers the ease of single-level living with ample space to relax, entertain, and make your own. The home features an inviting floor plan with plenty of natural light and room for upgrades, allowing you to personalize each space to your taste.Enjoy seamless indoor-outdoor living with a large back deck--perfect for gatherings or quiet mornings surrounded by nature. Features include: Generous sized living spaces, gas fireplace, spacious primary bedroom with en suite bathroom, three additional bedrooms offering flexibility for guests or home office(s), full-size basement provides generous storage or the potential to create even more living space & oversized two-car garage for additional

Settle into the quiet charm of the Windemere Lake community with this 8.592-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake--a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.

Settle into the quiet charm of the Windemere Lake community with this 7.166-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake--a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.

Prime Downtown Lee Investment Opportunity Located on a highly visible corner lot in the heart of downtown Lee. Currently be run as a successful short to extended stay business. The studio unit renting for $125 to $175 per day depending on the season and the two bedrooms unit renting for $125 to $175 a day depending on the season. There is a third unit office space that is being rented for $300 a month which is well below market. The property is well-maintained, with a newer furnace and a single water heater serving the building. Ample off-street parking is available at the rear of the lot--a rare find in a downtown setting. Whether you're seeking an investment with immediate income or a property with the flexibility for mixed-use possibilities, this Main Street location delivers both

This well-cared-for colonial home has been cherished by the same owners for over seven decades and is ready to welcome its next chapter. The first floor offers a spacious layout with a large kitchen, dining room with access to a seasonal porch, a living room featuring a wood-burning fireplace, a family room with half bath, and a four-season sunroom surrounded by windows overlooking the backyard. Upstairs, the primary bedroom impresses with double closets and a vaulted ceiling, complemented by three additional bedrooms and a full bathroom. The fully finished basement provides valuable extra living space with a laundry room, 3/4 bath, and game room. Recent updates include a new roof (2021), heating system (2023), and refinished floors with fresh paint (2025).

Live in the center of Great Barrington with a private backyard of almost 3 acres on the river! This renovated farmhouse has an inviting kitchen with cozy wood stove, first floor primary suite and 2 spacious bedrooms with a shared bath on second floor. Beautiful wide-plank floors and built-ins preserve this home's history. A solar rooftop system, fully owned, brings energy efficiency and electricity credits. Front porch, back deck and two car garage with second story and an EV charger complete this in-town gem!

Yes, the Jim's House of Shoes building is for sale! Great location in the heart of North St, downtown Pittsfield. 4 large front display windows, 3 entrances and exits, full, usable 5,500 sq. ft. basement with inside access. Start a business here; move a business here; be part of Pittsfield's rejuvenation!

To be built-Single level townhouse in a well established neighborhood. This home will offer 3 bedrooms, 2 full bathrooms, Living room, Kitchen/Dining room, Laundry room, Utility room, attached garage and front and back porches. Home will be built with the new SIP (Structural Insulated Panel) construction. This system is highly energy-efficient and has better performance against wind and seismic forces, making it ideal for high-performance, sustainable, and resilient homes. The asking price includes stock amenities and fixtures, upgrades and or changes may be subject to price adjustments. Specifics of interior finishes are availible upon request. Now is your chance to own this brand new home!

To be built-Single level townhouse in a well established neighborhood. This home will offer 3 bedrooms, 2 full bathrooms, Living room, Kitchen/Dining room, Laundry room, Utility room, attached garage and front and back porches. Home will be built with the new SIP (Structural Insulated Panel) construction. This system is highly energy-efficient and has better performance against wind and seismic forces, making it ideal for high-performance, sustainable, and resilient homes. The asking price includes stock amenities and fixtures, upgrades and or changes may be subject to price adjustments. Specifics of interior finishes are availible upon request. Now is your chance to own this brand new home!

This stunning 39-acre property offers the perfect setting for your dream home. Ideally situated just 5 minutes from Millerton, 20 minutes from Hillsdale, and 20 minutes from the Wassaic Train Station, it provides both tranquility and convenience. Choose from multiple potential homesites, each featuring an elevated position with seasonal views of the Taconic Range and a beautiful mix of open meadows and wooded areas- including a stream. With buried electric and a shared driveway already in place, much of the groundwork has been done for you. An exceptional opportunity to create a peaceful country retreat with easy access to both Columbia and Dutchess Counties.

Multi-family in a convenient location, walking distance to town and shopping, bus line nearby.Well maintained. The perfect location, walking distance to restaurants and shopping, public transportation nearby.

Tucked away in the desirable, low-tax community of Richmond, Massachusetts, this 3-bedroom, 2-bathroom ranch, surrounded by higher-priced properties, offers comfortable single-floor living. The open-concept living area, filled with natural light, includes a recently updated kitchen and features quartz countertops, quality stainless appliances, and ample counter space. The master suite includes a newly updated bathroom. Two additional spacious bedrooms offer flexibility for guests or a home office. A privately owned solar array provides net-zero energy, combining eco-conscious living with cost savings. Located just 4 miles from Tanglewood, the Berkshires' premier cultural attraction, 5 miles from Lenox, the region's culinary hub, 4 miles from West Stockbridge, and 5 miles from Balderdash C

Located in the Historic District of the picturesque town of Heath, this former Artist loft has been thoughtfully maintained and expanded over the years. Large, expansive spaces greet you as you walk into the 3304 sqft. home with three bedrooms and three bathrooms. There is a separate sizeable bright kitchen wing with a great view of the large private yard, or you can enjoy the yard on the 2nd-floor deck. The home also has a 2-plus acre meadow with a small barn perfect for a hobby farmer or a horse enthusiast. This unique, comfortable house is set in a very private, peaceful setting, offering a tranquil escape from the hustle and bustle of everyday life.

Welcome home to this warm and inviting property set in a quiet and desirable Pittsfield neighborhood. With a comfortable flow and plenty of space for gathering, this home is ideal for entertaining and spending time with loved ones, especially as we head into the winter months. Inside, you'll find 3 bedrooms, 2 full baths, and 1,890 sq. ft. of well-designed living space. The cozy downstairs living room features a gas fireplace insert, perfect for chilly evenings, while the open kitchen/dining area, as well as a wet bar make this home an entertainers dream. The heated sun porch off the kitchen offers a bright, relaxing spot to enjoy year-round!

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.

A charming 1900's farmhouse, thoughtfully renovated for modern living, just over the Lenox line in Pittsfield. Set on 1 acre with sweeping views of the Berkshire Hills, the property also includes a two-car garage, workshop, and small horse barn. Relax in the shaded garden nook beneath the pergola, or enjoy the eat-in kitchen at the back of the home with views of fields and hills. Includes a full bath on first floor. Upstairs, you'll find two spacious bedrooms, each with its own bathroom. All this just minutes from Lenox Center and Tanglewood. Truly a quiet country retreat with easy access to all the Berkshires has to offer.