Pittsfield, MA homes for sale & real estate

Pittsfield, MA Homes for Sale

Welcome to 221 Bailey Road in Lanesboro, MA, an exquisite ranch-style home offering approximately 4,200 sqft of luxurious living space. Nestled on 87 acres atop a mountain, this property provides unparalleled privacy and breathtaking views that enhance its serene atmosphere. The open-concept living area is perfect for entertaining, featuring abundant natural light and seamless flow between spaces. Energy efficiency is a hallmark of this home, ensuring comfort year-round while minimizing utility costs. Ample room for family and guests, this stunning residence combines modern amenities with the tranquility of nature. Some of the amenities this home offers a three car garage, heated in ground

Pittsfield, MA Homes for Sale

Recently renovated two-family home offering true turnkey convenience! Both units feature brand-new kitchens and bathrooms, updated heating systems, and stylish laminated flooring throughout. With all utilities fully separated, this low-maintenance property is ideal for investors seeking a hassle-free addition to their portfolio. Whether you're expanding your investments or starting fresh, this well-updated, income-ready property is the perfect fit.

Pittsfield, MA Homes for Sale

Investor Opportunity with Strong Upside! This 1.5-story New England–style bungalow offers an excellent value-add opportunity for investors and renovators seeking equity growth. Featuring a large enclosed front porch, the home currently includes 3 bedrooms and 2 bathrooms, with a flexible floor plan that may allow for the addition of a 4th bedroom and/or home office, enhancing future rental or resale potential. The main level offers a functional layout with a living room, dining room, and kitchen—providing a solid footprint for renovation and modernization. Located just a short walk to Pontoosuc Lake, a highly desirable Pittsfield amenity with park access, boating, walking paths,

Pittsfield, MA Homes for Sale

Located in the desirable, gated community of Woodmont Estates, this thoughtfully updated home offers a timeless layout, flexible living spaces, and easy access to the best of the Berkshires. Inside, vaulted ceilings, expansive windows, and hardwood oak floors create a light-filled and inviting atmosphere, anchored by a gas fireplace and elegant details. The custom kitchen serves as the heart of the home, featuring maple cabinetry, granite countertops, updated finishes, and a layout that flows effortlessly into both formal and casual living spaces—ideal for everyday living and entertaining alike. The primary suite is a true retreat, complete with his and hers walk-in closets and a well