Windsor Homes for Sale

Welcome to Windsor, Massachusetts – a hidden gem nestled in the picturesque Berkshire County! With its breathtaking landscapes and serene atmosphere, Windsor is the perfect blend of rustic charm and modern convenience. This quaint town, known for its stunning natural beauty, is surrounded by lush forests, rolling hills, and pristine lakes, making it an ideal destination for nature lovers and outdoor enthusiasts alike.

Windsor offers a tight-knit community where neighbors become friends, and local events bring everyone together. The town's rich history is reflected in its well-preserved architecture and charming small-town vibe, while its proximity to larger cities like Pittsfield and Lenox ensures you have access to all the amenities you need. Whether you’re looking for a peaceful retreat or a place to raise a family, Windsor provides a welcoming environment that feels like home.

Currently, there are beautiful homes for sale in this enchanting area, perfect for those looking to embrace the Berkshire lifestyle. From cozy cottages to spacious family homes, the real estate market in Windsor boasts a variety of options to suit every taste and budget. Imagine waking up to stunning views, enjoying outdoor activities right at your doorstep, and being part of a community that values connection and camaraderie.

Don’t miss your chance to own a piece of this idyllic town! Explore the homes for sale in Windsor, MA, and discover the perfect property to call your own. Your dream home awaits in this charming Berkshire haven!

Newest Windsor Homes for Sale

$749,900

5 Beds ⋅ 4 Baths ⋅ 73564933 MLS

Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

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.

$425,000

4 Beds ⋅ 3 Baths ⋅ 73547523 MLS

This is a ''niche home'' in a ''niche location'' so the seller's have lowered their price to bring in more buyers! Come check out this spacious home on 1 acre in Windsor MA! A welcoming formal living room and separate formal dining room set the tone for refined entertaining, while a huge party room featuring a full bar and cozy fireplace is perfect for gatherings, game nights, or hosting large events. Bright, open kitchen has pasture views, a gas stove and white cabinets! Heated enclosed front porch is perfect for the entry catch all space! The house is set nicely back from the road with a 3 car detached garage and a circular driveway. Central Berkshire Schools. Windsor residents receive Notchview passes for cross country skiing - and it's right out your back door!

2241 Route 9, Windsor

Listing courtesy of Listing Agent: Kolleen E. Schmitt from Listing Office: Keller Williams Realty.

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