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| Sold by David Mayhew - 15 acre estate and horse property, walk to the beach - $1,950,000 |
Why Urban Apartment Renters Should Consider a
Weekend Home as Their First Property Purchase
For many urban renters, the traditional path to homeownership — buying a condo or starter home in the city — has become increasingly out of reach. Skyrocketing prices, fierce competition, and limited inventory make the idea of owning in your current zip code feel more like a fantasy than a financial goal. But what if the smartest first step on the property ladder isn’t in your city at all?
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| Sold by David Mayhew - waterfront property with magnificent western views overlooking cove with beach and dock - $1,750,000 |
More and more city dwellers are flipping the script and making their weekend home their first home. Here’s why it might make sense for you to buy your second home first in the towns east and west of New Haven, Connecticut and along the Connecticut River.
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| Sold by David Mayhew - beachfront/waterfront property with western views over Long Island Sound - $900,000 (fixer upper) |
Affordability
Real estate prices are far lower than in New York City. For the cost of a city down payment, you might be able to buy a modest home outright. Monthly mortgage payments may be lower than your current rent, and you’ll start building equity while still enjoying your urban lifestyle during the week.
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| Sold by David Mayhew - water views over Long Island Sound, bike to beach - $760,000 |
Rental Income Potential
Your second home can double as a short-term rental when you’re not using it. Platforms like Airbnb and VRBO make it easier than ever to offset costs by hosting travelers. In some cases, weekend or seasonal rentals can bring in enough income to cover most or all of your monthly expenses.
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| Sold by David Mayhew - beachfront condo with 180 degree views over Long Island Sound - $950,000 |
Lifestyle Balance and Mental Health
Urban life can be exciting — but also exhausting. A weekend home gives you a place to unplug, unwind, and reset. Whether you prefer hiking trails and quiet lakes or farmer’s markets and small-town charm, having a place that offers contrast to your weekday routine can be a major boost to your well-being.
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| Sold by David Mayhew - antique home on its own peninsula on Long Island Sound with two sandy beaches - $1,500,000 |
A Head Start on Real Estate Wealth
Waiting to afford your dream city apartment may mean years of continued renting — and missing out on the wealth-building benefits of ownership. A weekend home can serve as a strategic financial stepping stone. Over time, you’ll gain equity, benefit from any appreciation, and potentially build up your savings with rental income.
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| Sold by David Mayhew - one-of-a-kind contemporary with Long Island Sound views and walk to the beach - $607,837 (fixer upper) |
Later, when you're ready to buy in the city or upgrade to a larger property, you may be able to tap into your vacation home’s equity or sell it for a profit.
Future Flexibility
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| Sold by David Mayhew - cozy riverfront with dock in serene location - $903,000 |
Your weekend home could eventually become more than a getaway. As remote work becomes more common and hybrid schedules become the norm, some owners shift from visiting part-time to living there full-time. What starts as a weekend escape could one day be your retirement home, your remote work base, or your family's main residence.
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| Sold by David Mayhew - beachfront with western views, enjoy nightly sunsets - $662,000 |
By buying early, you’re locking in today’s prices and opening up possibilities for how you might live tomorrow.
Thinking about a second or weekend home in Connecticut? I'm here to help. The search for a home is more than a transaction—it’s a journey, and I’d be honored to take it with you. Let's start with a visit. Hop on the train at Grand Central Station and two hours later I'll meet you in New Haven for an area tour. There's no better way to start.
Let’s talk.
