Berkshire County · Massachusetts
Windsor, MA Homes for Sale & Real Estate
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Windsor is a high, open hilltown on the eastern edge of Berkshire County, where the headwaters of the Westfield River begin. Route 9 climbs through the town between Dalton and Cummington, passing old farms, stone walls and long views west toward the Taconic Range. The settled areas are scattered along a few roads, with large tracts of conserved forest and fields in between.
Expect a rural mix of homes: antique farmhouses and capes, cabins and small seasonal places, and newer homes set on several acres with mountain views. Snow comes early and stays late at this elevation. Before you buy or list in Windsor, Dolan O’Rourke can help you look closely at wells, septic systems and road frontage.
Living in Windsor
Notchview Reservation
Notchview, a large Trustees property along Route 9, is known for its groomed cross-country ski trails in winter and woodland hiking in warmer months.
Windsor Jambs
In Windsor State Forest, Windsor Jambs is a narrow gorge where a brook drops through steep granite walls, viewed from a fenced overlook trail.
Westfield River headwaters
Branches of the Westfield River rise in Windsor, part of a river system recognized for its wild and scenic character.
Route 9 scenic drive
Route 9 crosses some of the highest ground in the Berkshires here, with open farmland and sweeping views on clear days.
Berkshire County · Massachusetts
Homes for sale in Windsor, MA
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Getting around and the outdoors
Getting around
Route 9 is the main road, running west to Dalton and Pittsfield and east through Cummington toward Northampton. Route 8A heads north toward Savoy and the Mohawk Trail. Pittsfield offers Amtrak and bus connections, and the Pioneer Valley is within driving range for larger shopping trips.
Parks and recreation
Notchview Reservation offers cross-country skiing and hiking, and Windsor State Forest adds Windsor Jambs, a picnic area and the river for swimming and fishing. Nearby Savoy Mountain State Forest and the Mohawk Trail extend options for camping, paddling and fall foliage drives.
Nearby communities
Buying or selling in Windsor?
Whether you are buying your first home, moving up, downsizing or investing, our agents will guide you from the first conversation to the closing table.
- Buyers: Learn about our Buyer Representation Services.
- Sellers: Explore our Seller Representation Services and flexible listing tiers.
- Home value: Find out what your Windsor home is worth.
Client reviews
What our clients say
I had the absolute pleasure of working with John Dolan and Dolan O’Rourke Real Estate Services while selling my mother’s home. We were going through an extremely difficult transition. We were both unfamiliar with the process of selling a home. From day one, John made himself readily available and kindly explained every part of the process to my mother, always making sure she understood each detail. His knowledge and expertise goes far and above what we expected. His constant communication never left us guessing – we felt very involved in every part of the process. I was caring for my mother on my own and he did everything in his power to ease the burden of selling her property. John knew I had great anxiety over our difficult situation and would always tell me not to worry. He always found a resolution to every bump in the road- and now I am finally worry free! John made us feel cared for and safe. We cannot thank him enough for his hard work. He helped us find a deal that we never could’ve imagined and changed our life for the better!
John was amazing with helping us in our home buying journey! His knowledge and patience made things very easy for us as first time home buyers. I highly recommend John to anyone who wants professionalism and someone who’s gonna get the job done! Thanks John!
We worked with John of Dolan O’Rourke Real Estate Services to purchase our first home in the Greater Boston area. As first time home buyers, John invested a lot of time early on to educate us about what to expect and strategies to consider. Throughout the process John had great communication, listening and advice as we navigated a challenging market. John was approachable, knowledgeable and always fun to be around as we looked at numerous houses, and helped us shape our conversations to really dial in to what we were looking for. We would love to recommend John for future real estate services and are so appreciative of his hard work.
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