Most people think real estate investing means buying a rental property and watching the money roll in. The reality is more complex — and more rewarding. Daniel Berger, broker-owner of RE/MAX Prestige Properties in Westchester County, New York, has spent the last decade selling investment properties and buying them himself. That hands-on experience informs advice that goes beyond what a generic investing guide offers.
With tight inventory, multifamily demand outpacing supply, and commuter-driven rental markets holding steady, Westchester County offers specific opportunities for investors willing to put in the work. Here is what Berger has learned — and what everyday investors should know before putting their money into real estate right now.
High-Demand Westchester Properties
Not all investment properties perform equally in today’s market. In Westchester County, multifamily homes — where owners live in one unit and rent out the others — rank among the most in-demand property types with the least available supply.
“Multifamilies are probably the most in demand with the least supply,” Berger says. For a first-time investor, a two- or three-family home offers a practical entry point. Owners can offset their mortgage with rental income, manage the property on-site, and build equity in a market that has been consistently strong for a decade.
Properties within walking distance of commuter train stations are another reliable category. Proximity to Metro-North lines matters to renters, and that demand stays stable even when the broader market slows.
Calculate Costs Realistically
This is where many first-time investors go wrong. They fall in love with a property, stretch their budget, and are then surprised by the true cost of ownership.
Berger is direct: the purchase price is just the beginning. Investors must account for renovation costs, ongoing maintenance, future capital expenses such as a new roof or HVAC system, and realistic rental income.
“A property doesn’t just cost what you buy it at on closing,” he says. “It’s how much work does it need, how much money does it need to be able to get it to be the asset that you want it to be.”
Investors should build a simple profit-and-loss projection before making an offer. Key questions to address: What is the realistic monthly rent? What are the mortgage, tax, insurance, and maintenance costs? What happens if the unit sits vacant for 60 days? If the numbers only work under perfect conditions, that is a warning sign.
Investors have different goals. Some want a 10% return. Others are satisfied with 3% to 5% if it means holding a tangible asset rather than a stock market position. Defining those goals before shopping is essential, because a good deal means something different to everyone.
Current Investment Picks
What distinguishes Berger’s perspective is that he invests alongside his clients. In the past year, he purchased a townhouse in his own town, gut-renovated it, and added it to his rental portfolio, projecting a 10% return on investment. He also co-invested in a former firehouse on Main Street in Beacon, New York, roughly an hour north of Westchester County. The project includes commercial retail space on the ground floor and four apartments on the upper floors.
Both investments reflect the same criteria Berger applies when advising clients: strong rental demand, a clear income-and-expense projection, and a realistic renovation budget factored in before the purchase. Neither was a quick acquisition. Each required evaluating the full cost of getting the property to perform as intended — not just the purchase price, but the capital needed to make it the asset it was meant to become.
Risks to Anticipate
Investors often focus on upside and underestimate friction. Berger has seen deals fall apart for reasons unrelated to the property itself: a lender who did not complete due diligence, open permits surfacing during the review process, or a buyer stalling to delay closing. In one recent case, a buyer deliberately slow-rolled a closing, seeking pre-approvals for planned work before taking ownership and incurring costs. Recognizing that pattern early, Berger says, is part of protecting a deal.
His approach is to get ahead of potential problems before listing or making an offer. On the seller side, that means identifying open permits, code violations, and needed repairs before they surface in due diligence. On the buyer side, it means assembling professionals who are proactive — inspectors, attorneys, and lenders who anticipate issues rather than react to them. The deals that fall apart, in his experience, are rarely the result of market conditions. They are the result of people and process failures that disciplined preparation can often prevent.
Long-Term Investment Outlook
Real estate investing in Westchester County is not a get-rich-quick strategy. It rewards investors who research thoroughly, run the numbers honestly, and remain patient. Inventory remains tight, multifamily supply continues to lag behind demand, and suburban migration from New York City shows no signs of slowing.
For investors entering now, the advantage lies in discipline rather than timing. Those who underwrite conservatively, plan for vacancies, and treat properties as businesses are positioned to build durable returns over the next decade.
About the Expert: Daniel Berger is broker-owner of RE/MAX Prestige Properties in Westchester County, New York, with a decade of experience running his own brokerage.
This article is intended for informational purposes only and does not constitute legal, financial, or investment advice. The views and opinions expressed herein reflect those of the individuals quoted and do not represent an endorsement of any company, product, or service mentioned. Readers should conduct their own due diligence and consult qualified professionals before making any investment decisions.