Insights
Local Market & Lifestyle Insight
Town guides, market perspectives, and practical guidance for buyers and sellers across Northern Westchester County, NY.
Written from the towns themselves (the same walks, Main Streets, and train platforms you'll see in my videos), these articles cover what makes each town different and what buyers and sellers should know before they make a move.
Buyer Education
July 2026 · 7 min read
Moving from NYC to Northern Westchester: An Honest Starter Guide
What city buyers actually need to know before house-hunting up here: how the towns differ, why the Harlem Line shapes everything, and why renting first is a smart move, not a cop-out.
Community Guide
July 2026 · 6 min read
Bedford, Bedford Hills, or Katonah? One Town, Three Very Different Lifestyles
Bedford, Bedford Hills, and Katonah are three hamlets of a single town that feel nothing alike. Here's the historic village, the commuter hamlet, and the walkable Main Street explained, and who each one suits.
Seller Education
July 2026 · 5 min read
What Fashion Taught Me About Selling Your Home
Before real estate, Michael Winter ran brands at Ralph Lauren and Nautica. Here's how a career in fashion (merchandising, film, and story) shapes the way he markets a listing today.
Announcement
July 2026 · 2 min read
Welcome to the New Home of The Westchester Guy
Michael Winter's new digital home is live: the place for Northern Westchester town guides, market perspectives, and a direct line to the Westchester Guy. Here's what's coming.