Thinking about buying a two-, three-, or four-family in Boston? Smart move. Multifamily assets can combine steady cash flow, long-term appreciation, and tax advantages—plus optional “house hacking” if you live in one unit. This guide walks you through the Boston-specific lens: the property types you’ll see, how to underwrite them, what to watch out for, and tactical playbooks that actually move the needle.

Boston is one of the most dynamic and resilient real estate markets in the country. Whether you’re a first-time investor or an experienced landlord looking to expand your portfolio, understanding the nuances of this market can help you build lasting wealth. In this post, I’ll walk you through what makes Greater Boston such a strong investment opportunity, where to look, and how to approach your first or next deal.

They say real estate tells the story of a place — and nowhere is that more true than Massachusetts. From windswept island estates and presidential retreats to historic Gilded Age mansions and gleaming modern penthouses, the Bay State is home to some of the most extraordinary properties in the world.

I’m Chris, Managing Broker at Remmes & Co., and today I’m taking you inside the ten most expensive homes ever sold in Massachusetts — counting down from #10 to #1. These aren’t just houses. They’re architectural masterpieces and cultural landmarks that capture the essence of New England luxury.