Smart and Savvy: Best Practices for Owning a Weekend Home in Connecticut
How to Enjoy Your Getaway Without the Hassle
Let’s be honest—owning a weekend home in Connecticut’s scenic sweet spots (think east or west of New Haven, or tucked into the Connecticut River Valley) is a total dream. It’s your escape hatch from the city grind, a cozy place to unwind with friends and family, and yes — maybe even a smart investment. But like any dream, it works best when it comes with a plan. Here’s how to make the most of your weekend home without letting it become a second job.
Pick the Right Spot (You Already Did!)
You nailed it. The areas around Greater New Haven and the Connecticut River Valley are the perfect distance from NYC — about two hours give or take. That’s just far enough to feel like a true getaway, but close enough to make spontaneous weekend plans totally doable. Bonus: thanks to Metro-North and Amtrak, even your city friends who don’t drive can come visit — no car needed.
Know the Real Costs
There’s more to the price tag than the mortgage. Think property taxes, utilities, insurance (especially flood insurance if you're near water), and ongoing upkeep. And don’t forget the occasional big-ticket item like a new roof or septic service. Need help budgeting or finding the right insurance? I can connect you with pros who know this market inside and out.
You’ll Need Wheels
Even if your weekend home is right in a walkable town, a car is going to make life easier. And there's so much to explore in Connecticut. The good news? No battling for a parking spot in the city or paying outrageous garage fees. Just park your car (it does not have to be a Lamborghini) at one of the local train stations — east of New Haven, parking’s free; west of New Haven, it’s way cheaper than anything you'd pay in Manhattan.
Don't Let Guilt Take the Wheel
It’s tempting to feel like you have to use your weekend home every single weekend. Don’t fall into that trap. City weekends can be lovely too! Here’s my pro tip: at the start of the year, pick your 39 “yes weekends” (including a few long ones and longer vacations). The other 13? Let friends or family use the place, or rent it out on Airbnb or VRBO.
Two things that help:
- Install a WiFi-enabled keypad lock that lets you update entry codes remotely.
- Designate a lockable closet or cabinet for anything you don’t want to share.
Keep It Easy and Breezy
When it comes to furnishing, think “simple, durable, and comfortable.” Go for easy-care fabrics, skip the clutter, and opt for furniture that pulls double duty (like ottomans with storage or sofa beds for guests). This is your retreat, not a showroom.
Stay Safe and Sound
Since weekend homes are often vacant during the week, smart security is a must. Install motion-sensing cameras, leak detectors, and a smart thermostat to keep things in check remotely. A local caretaker or trustworthy neighbor can be a huge help too. Pro move: Schedule snow removal or yard maintenance even when you’re not there — your home will look cared for and you’ll avoid headaches.
Low Maintenance, High Enjoyment
Choose landscaping that’s happy to be left alone — think native plants, gravel paths, and hardy shrubs. Inside, use finishes that clean up easily. And if you'd rather skip the mop and duster, line up a cleaning service for pre- and post-visit refreshes.
Stock Up on the Essentials
Leave a stash of phone, tablet, and laptop chargers at your weekend home so you’re never caught with 2% battery and no backup.
Be a Neighbor, Not a Stranger
Even if you’re only there part-time, it pays to be friendly. Introduce yourself, wave hello, and keep things neighborly. If anything ever goes wrong — or you just need a local recommendation — you’ll be glad you made the effort.
Turn a Profit (If You Want To)
Thinking about renting it out to offset costs? That’s totally doable. Just make sure to follow local rules, grab the right permits, and work with a reliable cleaner or property manager to keep things running smoothly.
Your Getaway Should Feel Like One
Bottom line: your weekend home should bring more joy than stress. With a little planning, some smart tech, and a few good habits, your second home can become your favorite place to relax, recharge, and make memories that last.
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.
