Welcome to this spacious 4-bedroom, 2-bathroom home offering 1,865 sq ft. of comfortable living space on a generous 1.42 acre lot in the beautiful town of Cheshire. This property features a bright and inviting layout, well-sized bedrooms, and ample room for everyday living or entertaining. New vinyl siding, gutters & awnings added in the most recent years. Enjoy the privacy and outdoor possibilities that come with an expansive lot & beautiful Trex deck leading to the above ground pool. Perfect for gardening, recreation or simply taking in the peaceful surroundings. A wonderful opportunity to own a versatile home in a serene Berkshire County location. Schedule your showing today!

Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The setting is exceptional, stroll just minutes to the Red Lion Inn, cafes, shops, and the library; at the end of the street, pick up beloved local trails toward Laura's Tower for quick nature escapes. A manageable 6,970 sq ft lot keeps weekends free for play, gardening, or launching out to the Berkshires' cultural highlights: Tanglewood, Norman Rockwell Museum, Naumkeag, and more.

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.

Classic country charm awaits you in the foothills of Cheshire Massachusetts and escape home to privacy and serenity in Central Berkshire to live and play in the great outdoors. Enjoy hiking out your door and follow the Appalachian Trail even reach Mount Greylock, bike ride north and south on the Ashuwillticook Trail exercising and exploring the beautiful farmlands and countryside as you immerse yourself in nature for miles and miles. Stay home and escape on your very own 4.5 wood acres for foraging mushrooms and enjoying your fairytale woodland animals with a trail cam in the comfort and warmth of this Berkshire traditional country colonial. Experience quality craftsmanship with wood paneled walls and ceilings blended beautifully with a country pallet of colors on sheet rocked walls.

The dream of your Berkshire country getaway can become a reality and enhanced by the amenities of the Otis Woodlands. Whether it's just enjoying this country home by sitting around the fire pit or use of the tennis courts,pool,lake, or exercise room. A simple hike in the nature of the Berkshires is also right out your door.

Two multi-family homes on one lot, a two family and a four family. An apartment in each in needs updating. A short distance to downtown. All separate utilities

Berkshire County log home on 10 acres affording big sky views. Gaze at Mt Greylock State Reservation from one of your four outdoor gathering spaces including the hot tub or rustic fire pit steps from the 760+ ft of unfinished space in the walkout lower level. Multiple heat pumps for your heating and cooling needs with a back up propane fired hot water boiler heating system offering radiant heat. Plenty of solar on the oversized 4 bay detached garage to keep your utility bill low flanked by an oversized firewood shed. This custom 3 bedrooms, 2 full bath log paradise offers an open floor plan for entertaining or just easy living. The perfect mountainside retreat moments from North Adams and Williamstown or short drive to all things outdoors from white water rafting, fishing or hiking

Welcome to this spacious and light-filled home just moments from scenic Pontoosuc Lake! Enjoy breathtaking sunrises and sunsets from your open-concept upper level, featuring soaring ceilings and expansive windows that fill the space with natural light. The beautifully updated kitchen offers ample room for dining and entertaining, complete with a breakfast bar and generous seating options--all perfectly positioned to enjoy the peaceful surroundings. The oversized primary bedroom boasts a flowing layout and a large walk-in closet, creating a serene retreat. Downstairs, the expansive lower level offers endless potential--ready to be finished to suit your style and needs.

Country Farm: Sixty Acre cattle Farm. Remodeled country Home with beautiful open fields and Yokum Brook running through the back lot were the cows use to sip cool water and graze. The farm consists of 5 different parcels of land with the barn across from the main house. You'll find a modern Kitchen and bath. The main Bedroom has a low deck and full-length windows looking out to the pastures and Apple trees were deer frolic and feed. A rock count yard with a fireplace and trellises holding grapevines makes a lovely entertainment area Most of the land is open fields.The barn has two garages, and the lower level has a feeding station. A shop and 2 hay lofts Although the cows are gone the farmer remains in the home, please respect his privacy. Showing by request only.

Introducing the Beautiful Spacious Ranch in a Great Neighborhood! Easy Living at Its Finest! Key Features:- Prime Location: Close to Main St.- Impeccably Maintained & Beautifully Updated- Stylish Granite Countertops for a Touch of Elegance- Lower Level Living Area/In-Law Unit, Extra Space for Guests or Rental Income Opportunity, Second Kitchen with Cozy Eat-In Area, Spacious Living Room for Entertaining, Large Bedroom & Full Updated Bathroom with Walkout Access.

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.

Loft 208 at Greylock WORKS is a beautifully proportioned 1BR | 1.5BA + Study Berkshires residence set within the region's most celebrated mill conversion, offering 1,150 SF of refined, light-filled living. With 12.5-foot ceilings, expansive volume, and an elegant L-shaped living and dining area, the home blends the character of the original mill with elevated contemporary detailing to create a warm and versatile modern loft.The open kitchen and main living space feature restored hardwood floors, hand-burnished structural elements, and regionally sourced schist countertops selected to heighten the building's material richness.

Stunning contemporary high-tech home. Custom built. Ideal for entertaining and large gathering. The spacious living room flows into an open dining and large kitchen with stainless & granite. Primary bedroom and full bath along with a 2nd bedroom and full bath plus laundry are all on the first floor. 3rd bedroom and full bath are in the loft and 2 extra rooms; full bath and a huge family room are downstairs. This also would be a perfect Air B & B. Charging station, fiber optics. Beautiful creamy wood floors and vaulted high ceilings, custom shaped windows throughout the house bring in beautiful day light. Two Ponds for kayaking & swimming are walking distance. Central A/C, propane heat. Circular driveway, Southern exposure. Roof solar system owned. MUST SEE.

Fantastic 4 BR Otis Wood Lands Contemporary situated at the end of a cul-de-sac close to all community amenities! This spacious home has great spaces for family and friends. Price includes furniture. Community amenities include pool, tennis/pickleball courts, fitness room, playground, lodge, lake and beach. New septic in 2023, new hot water heater 06/2025, new roof 2003. $4,000 reserve fund fee due from buyer at closing.

Exceptional Multi-Use Property. Spacious commercial space complemented by a fully renovated two-bedroom apt. Strategically positioned in a high-traffic location - minutes to bustling Great Barrington - this 4,892 SF property has outstanding potential. Versatile main floor ideal for various commercial ventures, while the residential units provide excellent live/work opportunities. In addition, the property features a separate 1 BR apt. & 2 oversized detached garages, all of which have generated steady rental income. Recent upgrades (electrical, plumbing, HVAC, septic system, and most windows) ensuring modern efficiency. With a proven history of strong income across all units this property presents a great opportunity to run a business while leveraging rental revenue to support your vision.

Check out this unique opportunity to own a 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 a 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 and Norfolk, CT. 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!

Set within the region's most celebrated mill conversion, Loft 207 at Greylock WORKS is a beautifully scaled 1BR | 1.5BA + Study Berkshires residence offering 1,250 SF of luminous, corner-exposure living. With 12.5-foot ceilings, expansive proportions, and oversized windows drawing natural light from two sides, this refined home blends industrial authenticity with contemporary design, creating a generous and distinctly modern loft environment.The open kitchen and the generous living and dining area showcase the architectural character of the original mill: gorgeously restored hardwood floors, hand-burnished structural elements, and regionally sourced schist countertops selected by the project's architects to elevate the building's historic textures.

A Berkshire dream home! Nestled in a quiet private setting to enjoy the outdoors. This 3 bedroom 3 full bath home is empty and ready to go. Great lighting nice open kitchen dining/living area. Additional room can be used as a den or 1st floor bedroom. Wood stove insert for chilly fall nights while enjoying your 3 seasoned screened porch. Oversized 2 car garage. Full basement could be completed as extra space. Handicap accessibility

Discover your dream retreat in this stunning log home, nestled on 37 acres of breathtaking land that adjoins over 1,000 acres of serene state forest. This oasis offers an unmatched blend of tranquility and natural beauty, allowing you to escape from the hustle and bustle of everyday life. Imagine sipping your morning coffee on the wrap-around deck, soaking in the picturesque mountain views. Indulge in the ultimate relaxation experience with a soak in your wood-fired hot tub or a rejuvenating session in your outdoor sauna. Step inside and be captivated by the charming open floor plan. The chef's kitchen is a culinary enthusiast's dream, featuring a large island, elegant granite countertops, and a high-end Viking stove, perfect for entertaining guests or creating culinary masterpieces.

Welcome to this stunning one level living, 3 bedroom, 3 bathroom home on a serene 4 acre lot. Designed for comfort and style, it features a bright first floor living area with large picture windows and a charming fireplace. The spacious kitchen offers a skylight, breakfast nook, and access to a screened porch perfect for relaxing. Cherry Floors flow throughout (except the kitchen and baths), and the large dining room is ideal for entertaining. Enjoy a generous deck, two car garage, brand new Buderus Boiler, and new air conditioning system.This Berkshire escape could be yours to enjoy and is minutes from Tanglewood, Norman Rockwell, Chesterwood, Berkshire Theatre, and minutes to the charming towns of Stockbridge, Great Barrington, Lee, Lenox, West Stockbridge!