Windsor Real Estate

Welcome to Windsor, Massachusetts—a hidden gem nestled in the picturesque Berkshire County. This charming town, with its idyllic landscapes and rich history, offers a perfect blend of rural tranquility and vibrant community spirit. Known for its stunning natural beauty, Windsor is surrounded by rolling hills, lush forests, and serene lakes, making it an ideal destination for outdoor enthusiasts and nature lovers alike.

Windsor boasts a tight-knit community where neighbors become friends, and local events foster a strong sense of belonging. The town’s quaint charm is evident in its historic buildings and the friendly faces you encounter in local shops and eateries. Whether you’re savoring a homemade meal at a local diner or exploring one of the many seasonal fairs, you’ll find that Windsor is a place where tradition and warmth thrive.

Outdoor activities abound in Windsor, with countless opportunities for hiking, fishing, and camping in the nearby state parks. The area is also known for its scenic beauty during the fall, when vibrant foliage paints the landscape in hues of red, orange, and gold. For those who appreciate the arts, the Berkshires are home to a flourishing cultural scene, with galleries, theaters, and music festivals just a short drive away.

As you consider making Windsor your home, you’ll discover a community that values both nature and neighborliness. With its charming atmosphere, beautiful surroundings, and a welcoming spirit, Windsor, MA, offers an unparalleled quality of life for families, retirees, and everyone in between. Come see what makes this quaint town so special!

Newest Listings in Windsor

$35,000

73569612 MLS

Lot 134 Shaw Rd, Windsor

Listing courtesy of Listing Agent: Evamarie Best from Listing Office: Wolcott Realty.

$724,900

5 Beds ⋅ 4 Baths ⋅ 73564933 MLS

Tucked away on 3.24 wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across multiple finished levels. The main home features four bedrooms, 2.5 baths, spacious living, family and dining rooms, plus a third-floor great room and additional flex space. A separate in-law suite adds exceptional versatility with its own kitchen, living room, bedroom, full bath, deck and upper-level flex room—ideal for extended living, guests or a variety of household needs. Soaring ceilings, exposed timber beams, hardwood floors and a dramatic center chimney add character throughout, complemented by multiple wood-burning fireplaces, a pellet stove and abundant natural light. Additional highlights include an owned 9.52 kW solar system, oversized attached garage, spacious decks and generous parking, all within a short drive of Berkshire attractions and Northampton.

255 High St Hill Rd, Windsor

Listing courtesy of Listing Agent: Reciprocal Reciprocal from Listing Office: Berkshire Reciprocal.

$699,900

4 Beds ⋅ 3 Baths ⋅ 73553438 MLS

Enjoy comfort, space, and privacy in this custom 8-room post and beam home set on 25.3 scenic acres. The property features 2½ bathrooms, Bruce hardwood floors, first-floor laundry, and a spacious living room with high ceilings and a pellet fireplace. The partially finished basement adds living space with a family room, wood-burning fireplace, and bar area. An oversized two-car garage provides added convenience and storage above. Outside, you’ll find a15x26 in-ground pool with pavilion, 3 storage sheds, a 24’ x 20’ barn, a large rear wooden deck, and a front Trex deck. The acreage offers excellent privacy and plenty of room for recreation, gardening, animals, equipment storage, or hobby farming. Whether you’re looking for a peaceful country retreat or a property with room to grow, this estate offers a rare opportunity to own acreage, outbuildings, a pool, and generous living space.

200 Peru Rd, Windsor

Listing courtesy of Listing Agent: Zahi Haddad from Listing Office: Zee Haddad Realty.

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